BIOCHEMISTRY

 “BIOS” means life = basically this is the study of the chemistry of LIFE
 the science concerned with the chemical basis of life
 chemical constituents of living cells and with the reactions and processes they undergo (when all
biochemical events or processes or reactions occur properly in a body = body/organism remains NORMAL;
any deviation or blockage = disease manifestation)
 a study of the compounds and processes associated with living organisms
 is the study of the composition of living matter & the changes which occur in it
 the science concerned with the chemical constituents of living cells & with the reactions & process they
undergo
 biomolecules/ micromolecules – molecules found in living organisms

 CELL – basic unit of life; is the structural & functional unit of biology; composed of protoplasm that would be
enclosed via a membrane with organelles; the PROTOPLASM OF A CELL would be composed of
BIOMOLECULES particularly proteins & nucleic acids

 BIOMOLECULES ARE DIVIDED INTO 2 (based on composition):

 Bio-inorganic – constituted water and trace elements (e.g. minerals: Na, K, Ca, Mg, Cu, Fe, Cl, HCO3,
PO4, SO4, Iodide, Fluoride)
 Bio-organic – Nucleic acids, proteins, carbohydrates, lipids

CELLS can be UNI or MULTIcellular organism

1. UNIcellular – example: bacteria or those that can from Kingdom Archaebacteria (prokaryotes)
2. MULTIcellular – examples: PLANT, HUMAN, ANIMAL, FUNGI, Kingdom Protista

CELLS that are grouped together with the same function & same characteristics will form tissues -> similar tissues
functioning with the same purpose will form ORGAN -> several organs group together -> ORGAN SYSTEM ->
emerged/connected organ systems = will form ORGANISM

 Molecular composition:
1. WATER – constitute the majority of the cell (70-75%)
2. Organic molecules (nucleic acid, protein, carbohydrate, lipid) – will constitute the remaining 25-30%
 NUCLEIC ACIDS – 7-10%
 PROTEINS – 10-20%
 CARBOHYDRATES – 2-5% - least % but majority of the food that we intake or the substances that we need
to sustain life -> WHY? –because carbohydrates will be the fuel or source of energy in a living
organisms/CONSUMABLE
 LIPIDS – 3%
3. Inorganic molecules (trace elements) – minute or very small amount as compared to other composition

 PARTS OF THE CELL:

1. Outermost membrane/ CELL MEMBRANE – composed of phospholipids, glycoprotein, cholesterol &
arachidonic acid
2. Nucleus – composed of nucleolus, nuclear membrane, & chromosomes (represented in the form of
chromatins –> chromatins will form CHROMOSOMES in cell division)
3. Organelles – Mitochondria, Lysosomes, Ribosomes, ER, Golgi Apparatus, Vacuole, Plastids, Cell Wall

I. CELL MEMRANE/ PLASMA MEMBRANE/ PLASMA LEMMA

 NOT SOLID BUT ACTUALLY FLUID-LIKE or SOMEWHAT OIL-LIKE (vegetable oil) in terms of its flexibility &
consistency because of CHOLESTEROL
 COMPOSED OF:
 o Phospholipids
 MAIN COMPONENT -> phospholipid bilayer (hydrophilic head & hydrophobic tail – the
outermost & innermost layer of a cell membrane are hydrophilic (water-loving heads)
and the tails are hydrophobic
 THE PHOSPHOLIPID BILAYER - CONTRIBUTES TO ITS SEMIPERMEABILITY
o Glycoprotein and glycolipids – both play a role in cell-signaling, cell attachment, & regulating the
immune system of the cell; are usually embedded in the cellular membrane
 GLYCOPROTEIN – important integral part of the cell membrane because it is responsible
with the cell-cell or intracellular interactions
 GLYCOLIPIDS – maintains the cell membrane stability and facilitates cellular recognition
o Cholesterol – plays an important role in the fluidity & consistency of the cell membrane so the
molecules in the cell membrane floats in an oil-like medium; the molecules of the cell can
actually move sideways
o Arachidonic acid – polyunsaturated fatty acid (PUFA) and 20 containing carbon containing fatty
acid with 4 double bonds (double bonds at position 5, 8, 11, 14)
 IMPORTANT STARTING MATERIAL for the synthesize of 2 important compounds -> prostaglandins &
leukotrienes
 The outermost structure of the cell that decides its contour is the cell membrane.
 SEMIPERMEABLE – controls the entry & exit of the substances in the cell
o MOSAIC FLUID MODEL – describes the structure of the cell membrane; refers to something that
contain many different parts (components: phospholipids, glycoprotein, cholesterol, &
arachidonic acid)

I. CELL MEMRANE/ PLASMA MEMBRANE/ PLASMA LEMMA – varies in terms of one organism to another; but the
cell membrane/wall protects these different organisms’ cell from mechanical and osmotic pressure

ORGANISMS MEMBRANE/ WALL STEROL PRESENT

Plants Cellulose (purely CHO) Phytosterol & Beta-Sitosterol
Bacteria Peptidoglycan – “peptid” means protein + “glycan” means CHO
-composed of alternating N-acetylglucosamine (NAG) and N-acetylmuramic acid
(NAM) residues connected by β-(1,4)-glycosidic bonds and cross-linked with short
polypeptide chain
Fungi Chitin (CHO particularly a heteropolysaccharide) Ergosterol

*Cell Membrane - bilayers, composed mainly of proteins & lipids

-contributing to the rigidity for barrier & protection of the cell and its components
-maintains osmotic pressure
Peripheral  Protein embedded outside cell membrane receptors
Integral  Protein embedded within cell membrane  ion-channel

II. Nucleus
 CONTROL center of the cell
 information center of eukaryotic cell because a PROKARYOTIC CELL DOES NOT POSSESSED A NUCLEUS
 it is mainly concentrated in the form of chromatins which are the chromosomes located
 *contains genetic material that manufacture nucleic acid
 COMPONENTS:
o Nuclear membrane or envelope – functions similarly like the cell membrane but rather than
protecting the cell & its constituents it protects the genetic materials contained in a nucleus;
 have nuclear pores that work as channels or passages by which the exchange of
materials between the nucleus and the rest of the cell occurs
o Nucleolus – found in the center of the nucleus
 SITE FOR RIBOSOMAL ASSEMBLY
  Referred as the nuclear matrix because this is where the DNA & RNA are synthesize
o Chromosomes – by-product of coiling of chromatins
 Only appear when the cell undergoes cellular division
 Would carry the genetic materials (DNA & proteins) needed for the genes or hereditary
information needed by the cell
 Mosquito – 6 chromosomes
 Frog – 26
 Dog – 78
 Turkey - 82

Mitosis Meiosis
 Cell Multiplication  Cell Division
 Cytoplasmic Division  Both Cytoplasmic & nuclear division occur
 Division of Nucleus into 2 nuclei  Sex Cells/ organelles
 Somatic Cells  Products: Haploid Daughter Cells
 Products: Diploid Daughter Cells o half of the total # of chromosome
o contain complete set of chromosome
o Ex: Human : 46 chromosomes (23 pairs) -22
somatic chromosomes -1 sex chromosome
Female: XX
Male: XY

Deficiency:
Aneuploidy –abnormalities in # of chromosomes
Trisomy 21/ Down’s Syndrome/ Mongoloids  by-product of an error during cell division referred as NON-
DISJUNCTION
 the disjunction results in an embryo with three copies of 21st chromosome instead of just 2
chromosomes/ 1 pair = fails to separate resulting to 47 chromosomes
* Y-linked chromosome – would result to hemophilia or the lacked of clotting factors that usually results to
excessive bleeding either forming hemophilia A or B

Excess:
* XXX – super-female, mentally retarded, short life span
*XXY - Klinefelter’s syndrome (male), biologically male but exert female –treats
Ex: Gynecomastia –enlargement of the breast
Hypogonadism small testicles, short-life span, mentally retarded

*Gold Fish - 90 chromosomes (45 pairs)

III. Organelles-*are structure with the specific shapes + specialized functions & are characteristic of eukaryotic cells
 contained within the cytoplasm (the cytoplasm have these organelles, numerous enzymes, proteins and
solutes that are suspended in the cytosol or the liquid portion of the cell)
 CYTOSOL – liquid portion of the cell will be the main site for glycolysis, HMP shunt (Hexose
Monophosphate), activation of amino acids, and fatty acid synthesis – affected during cell-division
 *CYTOSOL – where pentose phosphate pathway (PPP) is found
 a specialized subunit within a cell that has a specific function
 Mitochondria, Lysosomes, Ribosomes, ER, Golgi Apparatus, Vacuole, Plastids, Cell Wall

1. MITOCHONDRIA
 It has an inner and outer membrane which consists of proteins and phospholipids
 “CRISTAE” - folds in the inner membrane; the inner membrane is composed of cardiolipin (specific
phospholipid composition of the inner membrane)
  “KNOBS” – found in the cristae – these knobs contain the particular enzymes like ATP synthase that is
necessary for glycolysis or other metabolic processes that would lead to the generation of ATP
 “Powerhouse of the cell” – where the energy is produced -> ATP * ATP synthesis occurs in the inner
Mitochondria
 *location of the ETC (Electron Transport Kreb’s Cycle)
 * organ for respiration, redox reaction, glycolysis

2. LYSOSOMES - *containing digestive/ hydrolytic enzymes

 called as ‘SUICIDAL BAGS’ of the cell
 lysosomal enzymes digest the molecules like waste products, bacteria, other material brought into the cell
by phagocytosis (engulf -> cell-eating -> then lyse)
 play role in CELL DEATH -> 3 types of cell death:
o NECROSIS – referred as cell murder; once the cell undergo necrotic death it is damage due to oxygen
deficiency supply or ATP depletion
o ATROPHY – cell death due to absence of survival factors
o APOPTOSIS – program cell death
 If RBC does not reach the maturity cycle which is 120 days or defective organelles or dead cells =
lysosomes will engulf them

3. Peroxisomes/ MICROBODIES - *oxidizes amino acids, fatty acids & alcohols & use molecular oxygen to detoxify
harmful substances
 Are also small vesicles surrounded by a membrane
 Have 2 primarily functions:
o breakdown of fatty acids so FA can be used for membranes and fuel for respiration
o synthesize H2O2
 They contain enzymes for:
o H2O2 metabolism
o create H2O2 from reacting O compounds and H compounds
o convert H2O2 to a non-reactive species (catalase)
 WITHOUT PEROXISOMES there would be no way to produce peroxides and get rid of peroxides in the
body
 Also synthesize glycerophospholipids and eliminate ROS (reactive oxygen species)
 2 important enzymes present in peroxisomes:
o Peroxidase
o Catalase – digest H2O2 to become water and oxygen

Zellweger’s syndrome – MOST SEVERE FORM AMONG THESE SPECTRUM DISORDER

– associated with peroxisomes
-referred as CEREBROHEPATORENAL SYNDROME (brain esp. cerebral, liver & kidney esp. adrenal glands)
-rare congenital disorder characterized by the reduction or absence of a functional peroxisome in the cell of an
individual
-a family disorder belongs to Leukodystrophies
-shows reduction in the myelin levels -> damaging the white matters in the brain -> causing hypomyelination

NALD (Neonatal adrenoleukodystrophy) – medium severity

IRD (Infantile Refsum disease) – least severe in the Zellweger spectrum disorders

4. ENDOPLASMIC RETICULUM
 Rough E.R. – rough because of the bounded ribosomes
o are involved in protein synthesis w/c is mostly glycosylated
o Ribosomes are present
 Smooth E.R
 o Lipids synthesis
o Ribosomes are NOT present
 Associated degradation to ER:
o misfolding of proteins that would contribute to the development of parkinson’s disease
o unfolded protein response = down regulation that could result to alzheimer’s disease
o ER calcium homeostasis disturbed = ischemia
 *manufacturer & shipper
 *major function: Glycosylation
 *a membranous network in eukaryotic cells connecting the plasma membrane w/ the nuclear membrane
 *is a system of fluid-filled cisterns  site of acylglycerol synthesis

5. Golgi Apparatus/ PACKAGER - *storage site/ packaging counter of the cells

 are well developed in cells, which are involved in SECRETION
 involved in glycosylation and sulfation of proteins
 GLYCOSYLATION – is the processed of attachment of sugar to proteins
 *attachment of CHON in CHON products
 *storage of CHON -> undergo modification -> glycosylation

6. Ribosomes – responsible for protein synthesis especially in the translation process of the DNA or the *factory
sites of Protein synthesis
 Very small macromolecular complexes composed of rRNA and proteins responsible in protein synthesis
(translation) on mRNA templates
 CENTRAL DOGMA takes place in the ribosomes: DNA (replication) -> mRNA (transcription) -> CHON /protein
(translation)
 Prokayotes  70S (Sub-units: 50s & 30s)
Eukaryotes  80S (Sub-units: 60s & 40s)

Differentiation ANIMAL CELLS PLANT CELLS

Shape Round (irregular shape) Rectangular
Cell wall Absent (cell membrane) Present – maintains its rigidity;
composed of cellulose
Plastids None Present
Vacuole 1 or more 1

7. Vacuoles
 Water sac of the cell and gives it shape
 *storage tank of the cell
 *an intracellular inclusion
 in eukaryotic  surrounded by a plasma membrane
in prokaryotic  surrounded by proteinaceous membrane

8. Plastids – involve in the manufacture storage of food

 Different types of Plasmids
o Chloroplast – site of photosynthesis -> green pigmentation because it stores chlorophyll *performs
photosynthesis in photoautotrophic eukaryotes
o Chromoplast – all pigmented -> carotenoid pigments
o Geronplast – chloroplast that go with ageing process
o Leucoplast – non-pigmented, hence, colorless & usually found in most of the non-photosynthetic
parts of the plant like roots (e.g. starch, lipids, & proteins)

 ADDITIONAL NOTES
 Cetrosomes - helpers in cell division & involved in formation of the mitotic spindle
 Cytoplasm - found outside the nucleus
o where you can find organelles (organ-like structure), cytosol, & inclusions
o ▪in prokaryotic cell: everything inside the plasma membrane
o ▪in eukaryotic cell: everything inside the plasma membrane, & external to the nucleus
 Plasma Membrane  is the selectively permeable membrane enclosing the cytoplasm of a cell
 Cytosol - fluid/ liquid portion of cytoplasm  where glycolysis & PPP found
 Inclusion - include nutrients & cell products
 Cytoskeleton - microfilaments, intermediate filaments, & micortubules that provide support & movement for
eukaryotic cytoplasm
 Cytoplasmic Streaming - the movement of cytoplasm in a eukaryotic cell
 PLASMIDS - are small, extrachromosomal circular DNA molecules found in prokaryotes
o carry optional genes
o are circular DNA molecules
o are found in many rypes of bacteria
o replicate independently of the main chromosomes
o Each cell may contain several copies of plasmids
 Histones  are small basic proteins that participate in forming the nucleosomal structure of the chromatin
 Microsomes  where fatty elongation occurs
 Lysozyme  helps in the removal of damaged cell  contains a bactericidal agent such as lysozyme that kills
bacteria before it damages the cell

2 TYPES of CELL:
 PROKARYOTE – without nucleus & membrane-bound organelles but have cell membrane (which have in-
folding called mesosomes)
o MESOSOMES – site for DNA replication and enzymatic reaction in prokaryotic cell & if the prokaryotic
bacteria is photosynthetic it will have proteins & pigments to trap light & generate ATP
o Have chromatins but not enclosed and do not have nucleus
o First formed life on Earth
o Simpler forms and smaller than eukaryotes
o Have 3 basic shapes: round shaped or spherical (cocci), rod shaped (bacilli), helix shaped or coiled (spirilli)
o 70S (Sub-units: 50s & 30s)
o EXAMPLE: Protozoa -> BACTERIA from Archae
 EUKARYOTE – “EU” means true -> with true nucleus & with organelles such as Mitochondria, Lysosomes,
Ribosomes, ER, Golgi Apparatus
o 80S (Sub-units: 60s & 40s)
o EXAMPLES: Human, Animals, Fungi, Protist
 BIOMOLECULES

Carbohydrates – “hydrates of carbon” -> Molecule formula: Cn(H2O)n – believe before that for every one C there
would be 1 molecule of water so if 6C = 6H2O -> NOW, it was cleared that this formula is not applicable on all
types of CHO (only applicable to MONOsaccharide)
 Others referred it as sugars, amyloses, or glycans
 MOST wide-spread compound involved on the built up of biologic cells
 4 FUNCTIONS OF CHO in the body:
o Source of energy in all organisms (origin for ATP synthesis)
o Can store energy tho it is not their role (role of lipids) in the form of glycogen (stored form of energy
on animals & human) or starch (plants)
o Needed to build the other MACROmolecules (e.g. GLYCOlipids, GLYCOproteins)
o Comprised of one carbohydrate in the nucleic acid – deoxyribose & ribose
 Spares proteins and lipids for other uses – since it is the one being digest or consume to sustain metabolic
processes in the body
 *energy-giving
 *are aldehyde or ketone derivatives of polyhydric alcohol
 *defined as polyhydroxylated compounds w/ at least three carbon atoms that may or may not possess
carbonyl group
 Building blocks: Monosaccharides (connected by Glycosidic-bond)
 composed of three element: Carbon, Hydrogen, Oxygen (unless N-acetylated like N-acetyl glucosamine, N-
acetylmuramic acid, N-acetylgalactosamine but majority - CHO)

Lipids – form diverse group of compounds like fats, oils, hormones, membrane components, steroids
 can be unsaturated or saturated acid
o Saturated – CACACALAMYPASTAR (caproic – 6C, caprylic – 8C, capric – 10C)
o Unsaturated – e.g. 16 C + 1 double bond (16:1) = PALMITOLEIC ACID
 18C with 1 double bond = oleic acid
 18C with 2 double bonds = linoleic acid
 18C with 3 double bonds = linolenic acid – e.g. OMEGA-3 & 6
 20C with 4 double bonds = arachidonic acid
 FUNCTIONS:
o permanent storage of energy
o necessary for cell signaling
o acts as structural components (CHOLESTEROL)
o natural insulators
o protect or act as cushions of the organs in the body
 *are water-insoluble organic substances found in cells, which are soluble in non-polar solvents such as
chloroform, ether, methanol, hexane, & benzene
 *heterogenous group of compounds
 Building blocks: Fatty acids & glycerol (combine -> glycerol + 3 FA = triglyceride/triacylglyceride/TAG)
 composed of five element: Carbon, Hydrogen, Oxygen, Nitrogen, Phosphorus

Nucleic Acid – informational molecules for the store and transfer of genetic information: DNA & RNA
 *polymers of nucleotides
 *bind together with Phosphodiester Bond - connects successive monomer units through a phosphate residue
attached to hydroxyl on the 5’ carbon of one unit with the 3’ hydroxyl of the next.
 responsible for genetic information
 Phosphate Group - responsible or the acidic character on nucleic acid
 Carbon-2 - responsible for the difference between the two nucleic acid
 Building blocks: Nucleotide (composition of nucleotide: sugar, phosphate, nitrogenous base – purine or
pyrimidine base) IF (-) PHOSPHATE GROUP = nucleoside
 composed of five element: Carbon, Hydrogen, Oxygen, Nitrogen, Phosphorus

Protein – constituent 70% of the organic matter of the cell because it is structural component (e.g. tissues &
muscles, actin, myosin, hormones, enzymes, albumin)
 polymers of amino acids –Peptide Bonds
 polymers that are responsible for the metabolic capabilities & morphology of organisms
 very interesting because of their diverse functions
 are precipitated by Alcohol, Salts, Inorganic Salts
 Peptide Bonds -formed by dehydration
 Thyroxine - is aproten biopolymer
o is chemically 3,5,3’5’ –tetraiodothyronine
o is used as a precursor of Thyroid Hormone
 Building blocks: Amino acids (100+ AA discovered but only 20 are found in the human body & ONLY 10
ESSENTIAL AMINO ACIDS: PVT TIM HALL; essential because -> humans do not produce these amino acids so
we need to get them from the diet)
 ARGININE – only essential in children but if older = not needed
 composed of five element: Carbon, Hydrogen, Oxygen, Nitrogen, Phosphorus

1. Carbohydrates
 polyhydroxy compounds with aldehyde (ALDOSE), ketone (KETOSE), or an alcohol as acid functional group
 General formula: Cn(H2O)n
 Most abundant organic molecule in nature (cell wall of plants -> CHO)
 Source of energy:
o 1g lipids = 9 kcal
o 1g alcohol = 7 kcal
o 1g protein = 4 kcal
o 1g carbohydrates = 4 kcal
 FUNCTIONS:
o Storage form of fuel: starch in plants, glycogen in animals, & cellulose (fiber) for structural
component
 Glycogen – stored in muscles (primarily in muscles) & liver
o Structural element (e.g. GLYCOlipids, GLYCOproteins embedded in the cell membrane, structural
component for plants – “cellulose”
 HUMANS CANNOT DIGEST CELLULOSE BECAUSE WE DON’T HAVE THE ENZYME (CELLULASE) &
BECAUSE OF BETA-1,4 GLYCOSIDIC LINKAGE
 Glycoproteins/PROTEOGLYCANS – like glycosaminoglycans (GAGs) – hybrid of proteins or
peptides along with carbohydrates
 Glycosaminoglycans (GAGs)/Mucopolysaccharide –a heteropolysaccaride (have a sugar acid
 “GLYCO” either uronic or glucoronic acid & iduronic acid + amino sugar “AMINOGLYCAN” either
galactosamine or glucosamine (and usually N-acetylated amino sugar)
 ALL GAGs are considered proteoglycans except for HYALURONIC ACID or hyaluronan molecule
 HYALURONIC ACID – joint-lubricant
 CHONDROITIN – skeletal and joint-lubricant
 HEPARIN anti-coagulant
 In bacteria -> the present glycan is peptidoglycans; it can be used to differentiate one bacteria to
another because it retains the crystal violet dye

*Hyaluronic acid - ONLY ONE THAT DOESN’T HAVE SO4

 OTHER FUNCTIONS OF CHO:

o Lubricant of skeletal joints (Hyaluronic acid)
o Major component of bacterial cell walls (peptidoglycans) and soft cells coats in animal tissues
 EUKARYOTIC CELLS have the glycocalyx – external surface structure present in eukaryotic
 cells
o Provide adhesion between cells - e.g. Hormonal activation of cells, immune system mediation
through cytokines
 Glycoconjugate – glycoproteins and glycolipids that determines what enters and exit the cell
or MEMBRANE RECEPTORS
o Transport functions (biochemical transport) - e.g. Transferrin for Fe transport, Ceruloplasmin for Cu
Transport
o Confer biologic specificity on animal cell surface – e.g. blood types (different sugar components for
every types)

 BLOOD TYPE A – N-acetyl galactosamine

 BLOOD TYPE B – D-galactose
 BLOOD TYPE AB – N-acetyl galactosamine + D-galactose
 BLOOD TYPE O – no sugar present

o Supply precursors for synthesis of vital biologic substances – e.g. Enzymes, Hormones, Precursors of DNA,
RNA and ascorbic acid
 Hormones have CHO/sugar – specially FSH and TSH
 Enzyme – pancreatic enzyme

 BIOSYNTHESIS OF CHO

 The phosphoenolpyruvate being converted to Glucose-6-phosphate is a common carbohydrate pathway

in plants and animals
 Plants -> photosynthesis
GLUCONEOGENESIS (neo means new = new sources)– a process by which the CHO is generated from non-CHO
sources (e.g. pyruvate, glycerol, lactate, amino acid)
GLYCOLYSIS – glucose/carbohydrates is converted to pyruvate (2 pyruvate molecules to enter Kreb’s cycle)

Depends on the position of the carbonyl group:

-IF LOCATED IN THE TERMINAL CARBION = aldose
-MID CARBON (regardless if what position) = ketose

Erythrose – aldose (CH=O)

Ribulose – ketose (C=O)
BIOMOLECULES: CARBOHYDRATES

CLASSIFICATION OF CARBOHYDRATES

MONOSACCHARIDE
CRYSTALLINE -
usually sweet (e.g. sugar)
DISACCHARIDE (is also
classified as oligosaccharide)

OLIGOSACCHARIDE
FIBROUS –
usually tasteless (e.g. starch)
POLYSACCHARIDE
BIOMOLECULES: CARBOHYDRATES

MONOSACCHARIDE

• The simplest sugar; building block of

carbohydrates
• Contains 3-10 carbon atoms
• Can be classified according to:
o the number of carbon atoms
o the functional group present
(aldose/ketose)
o Ring structure formed
BIOMOLECULES: CARBOHYDRATES

MONOSACCHARIDE

• Monomers of CHO
• Colorless color crystalline that is freely
soluble in water & insoluble in non-polar
• are those carbohydrates that cannot be
hydrolyzed into simpler carbohydrates
• Naturally occurring sugar that contains 3-
10C (usually with 6C e.g. Glucose)
BIOMOLECULES: CARBOHYDRATES
Classification based on the # of carbon atoms
# of Carbons Category name Examples
3 Triose Glyceraldehyde
4 Tetrose Erythrose
5 Pentose Ribose,xylulose
6 Hexose Glucose, Fruc
Mann
7 Heptose Sedoheptulose
9 Nonose Neuraminic acid
42
BIOMOLECULES: CARBOHYDRATES

• Simplest aldose – Glutaraldehyde

BIOMOLECULES: CARBOHYDRATES

• Simplest ketose – Dihydroxyacetone

 BIOMOLECULES: CARBOHYDRATES
Based on the ring structure formed
• Monosaccharides containing 4 or more carbon atoms
tend to have cyclic structures.
• CYCLIC STRUCTURES – organic compounds that
resembles FURAN and PYRAN (e.g. furnose &
pyranose)
o Furanose – sugar containing 5C
o Pyranose – sugar containing 6C

In order to form the ring =

link w/ the other OH group
(at the penultimate C w/
carbonyl group)
MONOSACCHARIDE – all monosaccharide are REDUCING SUGARS
• 1,4 glycosidic bond - favored point of hydrolysis of sugars to
monosaccharides
I. Glucose – most abundant in nature
• ALDOHEXOSE – GLYCOLYSIS (major metabolite) = process
of converting glucose to pyruvate to generate ATP
• is the most important carbohydrate
• *is the major metabolic fuel of mammals (except
ruminant) & a universal fuel of the fetus
• *is stored in the liver as Glycogen
• present in Human Blood: 60 to 90 mg in 100 mL blood
• HIGH GLUCOSE = DM (insulin resistance + high blood sugar level)
• Other names:
• Blood sugar • Dextrose
• Physiologic sugar • Corn sugar
• Grape sugar • D-glucopyranose
MONOSACCHARIDE
II. Xylose
• KETOALDOSE
• Obtained by boiling the corn cobs with diluted acid to
hydrolyze xylan polymer
• Diluted acid + Xylose = xylan polymer
• Diagnostic agent for intestinal absorption
• Other name: WOOD SUGAR
 MONOSACCHARIDE
III. Fructose – sweetest sugar
• KETOHEXOSE (ketone)
• SOURCES:
o INVERT SUGAR = mixture of glucose & fructose from
sucrose by the application of heat and acid such as citric
acid and cream of tartar by the virtue of the enzyme
INVERTASE
o Present in sucrose
• CHEMICAL TEST - Seliwanoff’s Test = (+) RED (chem test
that identify sugars between aldose & ketose)
• Other names:
o Levulose
o Fruit Sugar
MONOSACCHARIDE
III. Galactose –
• ALDOHEXOSE (aldehyde)
• Comprised condition that cannot metabolized galactose =
accumulation of GALACTOSE in the blood= high galactose
in the blood (GALACTOSEMIA)
o Characterized by blindness & mental retardation
• CHEMICAL TEST: Mucic or Galactanic acid test - (+)
crystal formation with galactose and lactose
• C4 epimer of GLUCOSE
• Gal Glu
• Other names:
o Brain Sugar
 MONOSACCHARIDES

Rapidly absorbed in the small intestine

III. Mannose
• ALDOHEXOSE (aldehyde)
• Uses:
o Mannitol - Osmotic diuretic
• CHEMICAL TEST: Ozasone Test - (+) needle shaped
crystal
o Sunflower shaped - MALTOSE
o Powder puff shaped - LACTOSE
o Rhombic like GALACTOSE
• Ozasone Test – reducing sugars = forming ozazone crystals when
heated w/ excess phenylhydrazine - characterized by aldose/ketose
(OH group) near or of adjacent to the ketone group
• [O] reducing sugars + phenylhydrazine = (+) yellow to pale orange
ozasone crystals
• ALL SUGARS have soluble ozasone crystal EXCEPT for
MANNOSE
IV. Ribose
• ALDOPENTOSE (aldehyde)
• Important sugar for genetic formation
 BIOMOLECULES: CARBOHYDRATES
REDUCING PROPERTY

TEST REAGENT RESULT

FEHLINGS TEST Fehling’s A – Copper Sulfate (+) RED
Fehling’s B – Rochelle’s Salt

BENEDICT’S TEST Copper citrate (+) RED

TOLLEN’S TEST Silver nitrate (+) SILVER MIRROR

TROMMER’S TEST Alkaline solutions of copper (+) RED

sulfate
NYLANDER’S TEST Alkaline solution of bismuth (+) BLACK
subnitrate

BARFOED’S TEST Copper Oxide (+) RED

 CHEMICAL TESTS for REDUCING PROPERTY
1. Fehling‟s - (+) red color
• Determines the reducing property of sugar
2. Benedict‟s - (+) red color
• free aldehyde or ketose in the reducing sugar is reduce
(reduced by Copper nitrate) = cupric hydroxide in an
alkaline medium to form red color cuprous oxide
3. Tollen‟s or Silver Mirror Test – (+) silver mirror
• Used to distinguish sugars if ketone (not readily oxidized) or
aldehyde (readily oxidized)
4. Trommer‟s – (+) red color
• Involves in treating the sample with strong acid (H2SO4)
• Acid hydrolysis of a disaccharide = forming MONOSACC
then will be neutralized by the Trommer‟s reagent
5. Nylander’s – (+) black ppt
• Detects the presence of reducing sugars
• Glu/Fruc reduce -> will form oxybismuth nitrate -> bismuth under
alkaline condition
• NYLANDER‟S REAGENT = bismuth subnitrate or nitrate, K Na
Tartrate, & KOH
6. Barfoed‟s – (+) red color
• Detect the presence of monosaccharide especially reducing sugars (all
monosaccharides are reducing sugars)
• BARFOED‟S REAGENT: mixture of acetic acid & copper acetate
• Reagent + sample sugar (e.g. Glucose) + boil = (+) red copper oxide
ppt (hence, there is a presence of reducing sugar)
• If Disaccharide can be reducing sugar (e.g. Lactose & Maltose) or non
reducing (e.g. Sucrose) = negative result (except for MANNOSE &
LACTOSE)
o DISACCHARIDES have weaker reducing property
• When sugar [O] = ACID/ SUGAR ACID esp. aldose or
aldehyde = aldonic acid (product)
o when [R] = sugar alcohol
• Aldehydric C or Aldehyde carbonyl group = aldonic acid
• Primary terminal alcohol group [o] = uronic acid
• Aldehydric carbon or aldehyde carbonyl group [o] and primary
terminal alcohol group [o] = aldaric or saccharic acid
DISACCHARIDE/OLIGOSACCHARIDE – are also
considered as OLIGOSACCHARIDES
• Can be reducing (Maltose & Lactose) or NON-reducing (Sucrose)
• NON REDUCING SUGAR – OH group is not attached in the
anomeric C (e.g. Sucrose)
• Oligosaccharide or disaccharide [H] = MONOSACCHARIDES
• condensation products of two monosaccharide units + glycosidic
bonds
• Also formed via the dehydration reaction (removal of water
• *C12H22011

I. Sucrose – white sugar; standard to sweetness

• Other name:
o Table sugar
• Non reducing sugar
• GLU+ FRU
• C6H12O6 + C6H12O6 = C12H22O11
DISACCHARIDE/OLIGOSACCHARIDE

I. Sucrose – white sugar; standard to sweetness

• Other name:
o Table sugar
• Non reducing sugar
• GLU+ FRU
• USES:
o Important ingredient in SIMPLE SYRUP (85%
w/v)
o DEMULCENT – coat the surface to
prevent/protect the underlying cell from
irritation
• C6H12O6 + C6H12O6 = C12H22O11
II. Maltose
• Other names:
o Malt sugar
o Beer sugar
• Reducing sugar
• GLU+ GLU
• Product of partial hydrolysis of starach
• Formed via the diastatic fermentation of Barley
• Glycosidic bonds = link together through alpha-
1,4 glycosidic bonds
III. Trehalose
• Non reducing sugar
• GLU+ GLU
• Obtained from seaweeds, ergot, & yeast
• alpha- 1,1 glycosidic bonds
 CARBOHYDRATES

DISACCHARIDE
BIOMOLECULES: CARBOHYDRATES

DISACCHARIDE
IV. Lactose – the LEAST sweet of all sugar
• Other name:
o Milk sugar
• Reducing sugar
• GLU+ GAL
• SOURCES:
o Bos taurus (cow), goat, & carabao
• Lactose intolerance = people who do not possessed or
lack LACTASE enzyme
o Lactase- responsible for the metabolize of lactose
o Causing GI distress: bloating, diarrhea, loose
stools, vomiting, & producing gases
 OTHER DISACCHARIDES
1. Cellobiose – Glu + Glu
• Formed by enzymatic breakdown of cellulose
• Beta-1,4 glycosidic bond
• Disaccharide that the body cannot digest because
of:
o beta bonds (alpha = digestable, beta = harder to
digest specially the in long chains
o Lack of enzymes to digest
• Will cause GI distress (bloating & producing gas)
• Provides dietary fiber that is needed to stimulate the
contraction of intestine & helps pass the stool in the
digestive tract
 OTHER DISACCHARIDES
2. Sophorase – Glu + Glu
• From Sophora japonica (Leguminosae)
• Hydrolysis of sterioside
3. Primeverose – Glu + Xylose
• From the meadow wart
• Filipendula ulmaria (Rosaceae)
• Hydrolysis of spiralein
4. Lactulose – Fruc + Gal (alkaline rearrangement of lactose)
• poorly absorbed
• Bacteria in the colon metabolize the disaccharide to acetic and
lactic acids
• Osmotic laxative derived from LACTOSE
• BRANDS: Lilac, Movelax, Duphalac
• Treatment for: constipation & hepatic encephalopathy
 BIOMOLECULES: CARBOHYDRATES
OLIGOSACCHARIDE

SUGAR SUGAR UNITS

RAFFINOSE Gal + Glu + Fru
Glu + Glu + Glu
MALTOTRIOSE
Glu + Fru + Gal
SUCRALOSE
Glu + Glu + Fru
GENTIANOSE
 OLIGOSACCHARIDE – 3 to 10C

1. Raffinose - complex trisaccharide

• Found in beans, cabbage, broccoli, sprouts,
asparagus, other vegetables, & whole greens.
2. Maltotriose
• common oligosaccharide metabolite that is
found in urine after maltose ingestion
 OLIGOSACCHARIDE – 3 to 10C

3. Sucralose – 0 calorie artificial sweetener

• Common brand: Splenda sucralose
• 3 OH groups replaced by Cl in sugar
• Discovered in 1976 at the British College & later on
develop in the product of Splenda
• SPLENDA = sucralose + CHO (e.g. dextrose,
maltodextrin)

4. Gentianose – a plant metabolite

• A crystallizable sugar like substance from Gentian (plant)
with slightly sweetish taste)
BIOMOLECULES: CARBOHYDRATES

POLYSACCHARIDE

HOMOGLYCANS or HETEROGLYCAN or
homopolysaccharides heteropolysaccharides
(composed of several types of
monosaccharides)
1 component 2 or more component
Starch Gums
Glycogen Mucilage
Inulin
Dextran
Cellulose
 POLYSACCHARIDE

1. GLYCOSAN = combination of starch + glucose

• polysaccharides that yield glucose upon hydrolysis

2. FRUCTOSAN = present in inulin

• Polysaccharides that yields fructose upon
hydrolysis
BIOMOLECULES: CARBOHYDRATES
POLYSACCHARIDE
I. Starch – temporary storage for plants
COMPONENTS:
–amylose –amylopectin
• linear • Branching (every 25 units)
• composed of250 to 300
D- glucopyranose units • consists of 1000 or more
• linked by α -1, 4 glucose units
glucosidic bonds • α-1,4 linkages, α -1,6
• more soluble in water (branch)
than amylopectin
• Amylose + iodine = deep • amylopectin + iodine =
blue complex blue-violet or purple color
Alpha -amylase (α -1,4-glucan 4- glucanohydrolase)
• an enzyme present in pancreatic juice and saliva, hydrolyzes
starch by a random splitting of α -1,4-glycosidic linkages
• End products: Glucose, Maltose, & Amylopectin

ß- Amylase (α- 1,4-glucan maltohydrolase) – the enzymes

that the humans lack = causing the inability to metabolize
cellulose

• Produces its effect by removing maltose units from the

nonreducing ends of polysaccharide molecules.
• The end-product in the case of amylose is nearly pure
maltose
 POLYSACCHARIDE
II. Glycogen – major form of carbohydrate storage in
animals
• Stored in muscles (generates ATP for muscle contraction)
& liver (maintain the blood glucose during fasting &
exercise)
• α 1, 4 and α 1, 6 every 8-10 units
III. Cellulose - MOST ABUNDANT OF ALL CHO
• Not metabolized in the human body
• Made up of monosaccharide (Glucose) + disaccharide
(Cellobiose)
• In the addition of IODINE = NO COLOR (negative unlike
amylopectin & amylose)
• β 1, 4 glycosidic bond
 POLYSACCHARIDE

IV. Inulin
• Example of FRUCTOSAN
• Diagnostic agent for kidney fxn esp. used to measure the
Glomerular Filtration Rate (GFR)
• Filter only by the glomerular filtration and NEITHER
excreted nor reabsorb by the tubules
• Made up of fructose units that are linked by β 1, 2
glycosidic bond linkage
• water soluble
• Cannot be metabolized/hydrolyzed by the intestinal
enzymes
 POLYSACCHARIDE
V. Chitin
• Homopolymer of N-acetyl-B-D-glucosamine
o Glucosamine – monosaccharide derivative of glucose
• Aminated glucose
• Major constituent of the exoskeleton of the arthropods
• Present in the cell wall of fungi
• CHEMICAL FORMULA: C8H13O5N (complex CHO)
• Structure resembles CELLULOSE
• USES:
o ANIMALS: keep inner soft tissues safe from any sort of injuries &
acts as water type barrier against dehydration
o ARTHROPODS: defense mechanism against predation
o INDUSTRY: use as fertilizers, food additive in the form of
flavorants, emulsifying agent
o DIET: reduce the cholesterol efficiency or chole abs.
o Have antioxidant, anti-inflam, anti-coagulant, anti-DM, anti-CA,
anti-microbial & anti-hypertensive properties
 POLYSACCHARIDE
VI. Dextran
• Synthesize by sucrose by certain lactic bacteria
Leuconostoc mesenteroides & S. mutans
o – sucrose dextran
transglucosylase enzyme system
(dextran sucrase)
• Dental plaque is rich of dextran
• 10% solution = adjunct in the treatment of shock.
• Iron dextran inj.- hematinic preparation (sterile
colloidal solution containing ferric hydroxide)
• UNDER DEXTRAN
o Dextrin – sweetening agent
 VISUAL PROJECTIONS OF
CARBOHYDRATES

• There are three ways to present the structures

of carbohydrate:
o a Fischer Projection,
o Haworth Projection, and
o Conformational Formulas (most accurate
representation of sugar)
 A. FISCHER PROJECTION

• Developed by German chemist Emil Fischer in

the 1800s, when printing techniques could handle
only lines (not wedges)
• FISH BONE STRUCTURE & 2D STRUCTURE
A. FISCHER PROJECTION

• HORIZONTAL LINES =
represent the bond that
projects out of the plane
• VERTICAL LINES =
represent the bonds that
are extended back from
the plane
• C atoms are drawn
VERTICALLY so as to
depict the cyclic
structures of sugar
 D OR L SUGAR?

• D = rotate the plane polarized light CLOCKWISE or to the

right
• L = COUNTERCLOCKWISE or to the LEFT
 B. HAWORTH PROJECTION
• Developed by the English chemist WN Haworth
• Commonly used to show the stereochemistry of the
monosaccharide ring forms in 2D orientation
• More closely to depict the proper bond compare to
Fischer projection
• Same molecular formula
but different direction of H
& OH group in C1
o Alpha – below or
downwards
o Beta – above or
upwards
 ISOMER

Compounds with the same molecular formula

but with different structures.

There are 2 main classes:

1. Constitutional isomers
2. Stereoisomers/ Configurational isomers
 STEREOISOMER

• Also known as configurational isomers

• Compounds wherein the atoms are
connected in the same way, but differ in how
it‟s arranged in space.
• THE ONLY SUGAR WITH A SYMMETRICAL
CENTER IS DIHYDROXYACETONE
(smallest ketone)
 CHIRAL MOLECULES
• 4 different attachments one that has four
different groups attached to it. cannot be
superimposed on its mirror image
• - Any substance that has a chiral center
possess handedness
 OPTICAL ISOMERISM
1. ENANTIOMERS
• mirror image
• NONSUPERIMPOSABLE & MIRROR IMAGE
• Has chiral property

2. DIASTEREOMER
• differ in some stereocenter but are not mirror image
• NONSUPERIMPOSABLE & NOT MIRROR IMAGE
• Stereoisomers that are not enantiomers/mirror
images of each other.
ENANTIOMER
 EPIMER
• Diastereomers that differ ONLY in the
configuration at a single chiral carbon atom
 VAN‟T HOFF‟S RULE (2n)

• Compound with n chiral carbon has a maximum

of 2n possible isomers
• e.g. GLYCERALDEHYDE = 1 chiral C -> 2n =
2(1) =
2 stereoisomers
Glucose – 4 chiral C = 2(4) = 8 stereoisomers
 ANOMER
• Produced through mutarotation esp. when sugar esp. when the sugar is
suspended in aqueous solution producing alpha and beta forms of
sugar
• Occurs when sugar is in cyclic forms esp. in Haworth projection
• C1 = anomeric C (the only C that is bonded to TWO OXYGEN
MOLECULES)
• The only carbon in the molecule that is bonded to two oxygen atoms,
usually carbon.
1.The carbon on which this occurs is therefore called an anomeric
carbon.
REACTIONS OF MONOSACCHARIDES

1. Cyanohydrin formation
2. Ruff Degradation
3. Lobry de Bruyn Degradation
4. Osazone reaction
5. Oxidation reaction
6. Reduction recation
7. Phosphorylation
8. Glycoside formation
 CYANOHYDRIN FORMATION
• Also known as the „Kiliani Fischer‟ synthesis
• An organic chemical reaction by an aldehyde or ketone with
a cyanide anion or a nitrile to form a cyanohydrin
• used to lengthen or extend the sugar unit by adding another
sugar units
• Used in CHO chemistry as a chain extension e.g. for the
case of D-xylose
 RUFF DEGRADATION
• Removal of 1 carbon atom from molecule of an
aldose
• Ex. D-glucose (removing 1 C) to D-arabinose
• The terminal aldehyde group is converted to a
carboxylic acid group
LOBRY DE BRUYN Degradation

• Interconversion or transformation from

aldose to ketose or from ketose to aldose,
this process will then perform unsaturated
alcohol
 OSAZONE REACTION
• All sugar have soluble osazone except
MANNOSE = (hence, chem test used to detect
the presence of mannose (+) needle-shaped
• The carbonyl group of Aldose will be linked to
phenylhydrazine
• The product of the linkage is crystal called
OSAZONE.

Seen under the light microscope

Osazone of Glucosazone

Fructosazone

Galactosazone Maltosazone
 OXIDATION REACTION
• Oxidation means the addition of oxygen to a molecule or the
removal of hydrogen from a molecule.
• This will produce a sugar acid
• When a sugar has been oxidized = aldehydic carbon (an
aldehyde or an aldose) or aldehyde carbonyl group
• Further oxidized the aldehyde carbonyl group = aldonic acid
• If oxidized both the aldehydic C or aldehyde carbonyl group & as
well as the primary alcohol group = aldaric or saccharin acid
• Oxidize only the primary terminal OH group = uronic acid
• A sugar can be a reducing sugar if they can be OXIDIZE & yield
positive results of red ppt or a brick red ppt
• ALL SUGAR CAN BE A REDUCING SUGAR EXCEPT
SUCROSE
 REDUCTION REACTION
• Reduction means the addition of hydrogen to a
molecule or the removal of oxygen from a molecule
• Done either by catalytically like the presence of H &
catalysts or enzymatically
• If a sugar is reduced the resulting product is a
polyol/alditol/sugar alcohol
• E.g. Glucose – Sorbitol, Mannose – Mannitol
(osmotic diuretic), Fructose – mannitol or sorbitol
• Sugar alcohol are very useful intermediates e.g.
Glycerol (humectant & can be nitrated in the form of
Nitroglycerin which is used as anti-angina drug)
1. MANNITOL = isolated from Manna (Fraxinus
ornus from the family Olaeceae) Sorbitol or Glucitol
o From the reduction of MANNOSE = mannitol
o Used as laxative, osmotic diuretic, & diagnostic
aid
 REDUCTION REACTION
2. SORBITOL = also known as D-Glucitol or Glucitol; example of a hexitol
(6C)
o can be dehydrated to tetrahydropyrans & tetrahydrofurans compounds
o Can be obtained from the ripe berries of the mountainash (Sorbus
aucuparia of the family Rosaceae)
o Taste approx. half as sucrose
o Used as humectant & together with mannitol (sorbitol + mannitol
combination) for urologic irrigation
o Used as ingredient of toothpaste and chewing gums
• Sorbitans can be converted to detergents (SPANS & TWEENS used in
emulsifycation procedures) – can be dehydrated to 1,4,3,6 dianhydro-D-
sorbitol also known as isosorbide
• ISOSORBIDE when nitrated = ISDN & ISMN (isosorbide dinitrate &
mononitrate = use in the tx of angina)
3. GALACTITOL – derived from the reduction of galactose
• Contributes to the cataract formation which is associated with galactosemia
(can lead to blindness)
 PHOSPHORYLATION
• The hydroxyl groups of monosaccharide can react with
inorganic oxyacids to form inorganic esters.
• The phosphate formed from the phosphoric acid & various
monosaccharides are commonly encountered in the
biomolecules system
• NATURAL ENZYMES in the body that can catalyze the
esterification of the hemiacetal group particularly in the C1
and primary alcohol group at C6 of glucose to produce the
compound known as Glucose-1-PO4 & Glucose-6-PO4
 GLYCOSIDE FORMATION
• MOST WELL-KNOWN HEMIACETAL is GLUCOSE
• Hemiacetals can react to OH in acid solution to produce the
acetals
• The cyclic forms of monosaccharide (hemiacetal) will react
with alcohol to form acetals
• The general name for acetal is GLYCOSIDE
• Acetals are formed from cyclic monosaccharide by the
replacement of hemiacetal C OH groups (with another OR)
• Glucose named as Glucoside, if Galactose = galactoside
 AMINO SUGAR FORMATION
• If one of the hydroxyl groups of a monosaccharide is replaced
with an amino group, an amino sugar is produced.
• The amino group can replace the C2 hydroxyl group
• The amino sugars and their N-acetyl group are important
building blocks of polysaccharides that are usually found in
chitin (e.g. in the case of hyaluronic acid)
• The acetylated amino sugars like N-acetyl galactosamine is
present in the biological chemical markers of the blood/RBC
that can distinguish various blood types
Galactosamine Mannosamine
BIOMOLECULES: CARBOHYDRATES
GENERAL TESTS FOR CARBOHYDRATES
CHEMICAL TEST POSITIVE RESULT

Molisch Test (+) Purple Ring at the Junction

Anthrone Test (+) green/blue green color

Tauber‟s test (+) Cherry Red

Tauber‟s (+) Bright Reddish Purple

Aminoguanidine

Bial‟s Orcinol Test (+) Blue Green

 GENERAL TESTS for CHO
1. Molisch - (+) Purple Ring at the Junction
• General test for CHO – because it can be use to all types of
SUGAR
• Alpha-napthol reaction
2. Anthrone - (+) green/blue green color
• For pure fural derivatives (organic compound that is derived
from a variety of agricultural by-products (e.g. corncobs,
wheat bran, oats, soda)
• Came from the Latin word “furfur” which means bran
referring to its usual source
• From anthrone green to blue green color
 GENERAL TESTS for CHO
3. Tauber‟ sTest – (+) Cherry Red
• A color test for the identification of pentose sugar
• Will produce cherry red coloration when heated with
Benzidine solution in glacial acetic test

4. Tauber‟s Aminoguanidine – (+) Bright Reddish Purple

• Used together with Seliwanoff Test to identify aldose &
ketose
5. Bial‟s Orcinol Test – (+) Blue Green
• Used to distinguish between pentoses (blue green ppt) &
hexoses (muddy brown ppt)
 GENERAL TESTS FOR
CARBOHYDRATES
SELIWANOFF’S
FEHLING’S
TEST
TEST

MOORE’S
TOLLEN’S TEST
TEST
• SELIWANOFF‟S
o Test for aldose (faint red) and ketose (+) red)
• SILVER MIRROR TEST/TOLLEN‟S TEST
o Test for pentose & galactose
• KELLER-KILLIANI - (+) reddish brown layer at the junction of the 2 liquids
o Used in the phytochemical screening
o Test for deoxy sugars (sugars with OH group replace with H)
• Fehling‟s, Benedict‟s & Barfoed‟s – (+) brick red ppt
o Used for the reducing actions of sugars
• Moore‟s –
o Happens when the solution of reducing sugar is heated with an alkali
that turns yellow to orange then eventually brown liberating the odor of
a caramel
o This is due to the liberation of the aldehyde which polymerizes to form a
resinous substance known as the caramel = caramel like appearance
 LIPIDS ○ They are also responsible for dissolving
● Class of a heterogeneous group of compounds, fat-soluble vitamins.
which are more related by their physical than by their ○ Lipids aid in the digestion of the foods that
chemical properties. we take.
● They are other known as fats (solid) or oils (liquid). ● If there were be a deficiency or an imbalance,
● They are subjected to different chemical reactions: particularly on the metabolism of lipids, it will
○ Saponification - This is where fats are contribute to a particular disease or disorder.
boiled with strong bases: Potassium ○ Atherosclerosis for patients who suffers from
hydroxide and Sodium hydroxide, then obesity.
saponify.
○ Esterification FATTY ACIDS
○ Hydrogenation - Liquid fats or oils of plant ● Exists freely in the body in its unesterified form and
origin are subjected to solidification. It is also fatty acyl esters.
known as the process of hardening. For ● Consists of a hydrophobic hydrocarbon chain with a
example, Vegetable oils undergo terminal carboxyl group.
hydrogenation to become margarine and ● Not all lipids have fatty acids as their foundational
peanut oil to become peanut butter. structure or a basic unit, like steroids.
○ Rancidity - It is the staling of fats or oils due ● The longer the carbon chain, the more it becomes
to oxidation or hydrolysis. This is when insoluble in water.
fats or oils are exposed too much to air, ● TWO TYPES
moisture, light, or bacterial activity. It is ○ Essential - They are needed by the body but
responsible for the unpleasant smell of fats cannot synthesize it. Therefore, we need to
and oils. combine and take them into our daily food
● The structure of lipids is diverse that is why they are intake.
classified based on their physical properties rather ○ Non-essential - These are the fatty acids
than their chemical properties, which is usually the that can synthesize by our body. They are
standard way to classify compounds. still needed by the body.
● Lipids are also a source of energy, like carbohydrates. ○ The fatty acids that are usually present in our
They are in the form of stored energy so that when an body contain carbon 16-20.
individual is depleted of carbohydrates, Lipids will
then be metabolized to provide the necessary energy
SATURATED UNSATURATED
needed by our body. - They do not have a - They are those who have
● Hydrophobic in nature. They permit the partition of double bond in their at least one carbon-carbon
aqueous constituents or content of cells and structure. double bond.
subcellular structures.
● Cholesterol, a type of lipid, is an important part of the Butyric - 4 Oleic
cellular membrane. - 18 carbons:1 double bond
(delta 9)
● Prostaglandin and steroid hormones, which play a
major role in the control of the body’s homeostasis, Caproic - 6 Linoleic (Omega-6)
are derived from lipids.
● FUNCTIONS - 18 carbons: 2 double
○ REGULATORY: Certain hormones are bonds (delta 9,12)
dependent on lipids as their precursors,
Caprylic - 8 Linolenic (Omega-3)
specifically the steroid hormones.
○ Lipids serve as insulators for they regulate - 18 carbons:3 double bonds
the body temperature. (delta 9,12, 15)
○ They also protect the important organs of the
body. Capric - 10 Arachidonic
- 20 carbons:4 double bonds
 TYPES OF FATTY ACID CONFIGURATIONS
(delta 5, 8, 11, 15)
- It is an important part of
eicosanoids.

Lauric - 12

Myristic - 14

Palmitic - 16

Stearic - 18

Arachidic - 20

Lignoceric - 24
● Omega means terminal.
● Linolenic acid is named Omega-3 because you will
find a double bond on the third to the last carbon.
● Same with linoleic acid, but you will find the double
bond on the sixth to the last carbon.
● Delta (Δ) is usually used to designate the position of
double bonds when present in unsaturated fatty
acids.
● Other Important Fatty Acids
○ DHA (Docosahexaenoic acid)
○ EPA(Ecosapentaenoic acid)
■ They are both integral in the brain
and vision development of children.
● The saturated fatty acids can be further subdivided
based on their isomers:
○ Cis - same
○ Trans - opposite. They do not commonly
occur in nature. They are the by-product of
Hydrogenation.
● The orange lines signify the hydrophobic structures.
TYPES OF FATTY ACIDS ● Triacylglycerol has 3 fatty acids and 1 glycerol and a
Types of fatty acid Double Diagram carboxylic acid group of fatty acids are usually
bonds attached to the OH group of glycerol. This forms an
ester linkage. They are responsible for regulating
Saturated None body temperature or serve as an insulator of the body.
● Phospholipids are the most abundant type of lipids.
They are an integral part of the cell membrane and
Monounsaturated One give structural integrity To the membrane’s bilayer.
● Steroids are very hydrophobic and do not resemble
the structure of lipids at all. They are considered lipids
due to their hydrophobicity or insolubility in water.
Polyunsaturated Multiple ○ Cholesterol, being a steroid, serves as a
precursor to many compounds, particularly
hormones.
● Glycolipids are embedded in the cell membrane. They
also take part in cell recognition.

CHARACTERISTIC OF FATTY ACIDS

1. Fatty acids have low water solubility.
● The solubility of fatty acids in water
decreases as the carbon chain increases.
2. Melting points are influenced by both the carbon
chain and the degree of unsaturation.
● A higher melting point is expected of fatty
acids with a longer carbon chain. ● Through lipase, The fat is broken down into glycerol
● As the degree of unsaturation increases and fatty acids.
(The number of double bonds), the melting ● Glycerol can be further converted to
point decreases. glucose-3-phosphate by kinase. Then undergo
3. Saturated fatty acids are solid at room temperature isomerization, through the enzyme isomerase, to form
while unsaturated are liquid. glucose.
● Coconut oil is liquid at room temperature but ● Glucose will undergo glycolysis to form or produce
is considered a saturated fatty acid. ATP.
● Theobroma oil is solid at room temperature ● On the other hand, fatty acid will be converted into
but is considered an unsaturated fatty acid. Acetyl coenzyme A through beta-oxidation In the
mitochondria of the cell. This particular reaction
FATTY ACID SYNTHESIS usually produces by-products of ketone bodies:
○ Acetone
○ acetoacetic acid
○ beta-hydroxybutyric acid
● This is the reason why our mouth has a foul odor
because of the fatty acids being metabolized.
● Then it will enter the Krebs cycle which will generate
ATP.

PHYSICAL CONSTANTS
What are the different tests for lipids?
1. Acid Value or Acid number
● the number of milligrams of potassium
hydroxide required to neutralize the free fatty
● Fatty acid synthesis occurs in the cytosol. acids in 1 g of the substance.
● Acetyl coenzyme A, a by-product of decarboxylation ● It determines the free fatty acids in the oil.
of Pyruvic acid during the aerobic reaction, is the 2. Saponification Value
starting material for fatty acid synthesis. It is also ● the number of milligrams of potassium
important during the Krebs cycle and TCA cycle. hydroxide required to neutralize the free fatty
acids and saponify the esters contained in 1
LIPID METABOLISM g of the substance.
● It gives information as to the character of
fatty acids: The longer the carbon chain, the
less acid is liberated per gram of fat
hydrolyzed.
● A longer chain of fatty acids typically has a
lower saponification value Because of the
 few carboxylic acid groups that are needed
to be saponified. 2. COMPOUND LIPIDS
3. Iodine Number
● the number of grams of iodine absorbed, A. Phospholipids
under prescribed conditions, by 100 grams ● They are the most abundant type of lipids. They are
of the substance. an integral part of the cell membrane and neurons.
● It indicates the degree of unsaturation. The ● Chemical composition:
higher the iodine number, the higher the ○ Glycerol/Sphingosine (Platform molecule)
degree of unsaturation, ○ 1 or more Fatty acids
4. Other physical constants such as melting point, ○ Phosphate
specific gravity, and refractive index also served as ○ Organic molecule → Alcohol
identity, purity, and quality tests.
A.1 GLYCEROPHOSPHOLIPIDS
Classification of oils ● The glycerol and phosphate are attached to the fatty
● Drying oil is used for paintings. It has a high iodine acids. The organic molecule is attached to the
value (>120). phosphate
○ Linseed oil ● Chemical composition:
○ Cod liver oil ○ Glycerol
● Non-drying oil Is mostly saturated. Their iodine value ○ 2 Fatty acids
is <100. ○ Phosphate
○ Olive oil ○ Organic molecules → Alcohol (Choline,
○ Almond oil Ethanolamine, Serine)
● Semi-drying oil has an iodine value that ranges from ○ EXAMPLES:
100- 120. ■ Lecithin → Choline
○ Cottonseed oil ● It contains
○ Sesame oil phosphatidylcholine
(glycerol, fatty acids,
TYPES OF LIPIDS phosphate + choline).
1. SIMPLE LIPIDS ● Lecithin is an antioxidant
● Fats that treats memory
○ Esters of three fatty acids + disorders like Dementia
glycerol. and Alzheimer's.
○ It is also known as triglycerides. ● It is an emulsifying agent
● Wax For ice cream,
○ Esters of high molecular weight of mayonnaise, custard, etc.
fatty acids with a long chain of ● It is considered as the
alcohol. hemolyzing enzyme in
○ Bayberry wax, Carnauba wax snake and spider venom.
○ Lac wax, beeswax, spermaceti It causes blood clotting.
● Fats are lipids of animal origin. ● SOURCES: Soybean,
● Oils are lipids of plant origin. egg yolk, and brain
○ Jojoba oil came from plants tissues.
although its structure resembles ● The enzyme that
waxes due to its high molecular metabolizes lesson is
weight and long-chain alcohol. called lecithinase.
● Used for: ● Phosphatidylcholine is
○ Protection also present in the cell
○ Insulation membrane made by the
○ Energy
 liver but is not necessarily or glucose), and neuraminic acid (sialic acid / N-acetyl
an essential nutrient. neuraminic acid).
■ Cephaline → Ethanolamine ● It is a component of the brain's gray matter.
● Cefalin contains both ● They are commonly found in neuronal cells.
phosphatidylethanolamine ● It is composed of a glycosphingolipid due to the
and phosphatidylserine. hexose present in the structure.
● It is found in the liver, ● ↑ Ganglioside = TAY SACH’S DISEASE
tissues, and heart tissues. ○ It is considered an autosomal recessive
● Cephaline is also disorder and can be inherited.
associated with blood ○ The ganglioside accumulates excessively in
clotting. the nerve cells.
A.2 SPHINGOPHOSPHOLIPIDS ● GM2 GANGLIOSIDOSIS
● Chemical composition: ○ GM2 (Ganglioside, Monosialic acid, 2nd
○ Sphingosine monosialic ganglioside discovered).
○ 1 Fatty acid ○ It is a type of Tay Sach’s disease in which
○ Organic molecule → Alcohol (choline is the there is a deficiency of the enzyme called
usual alcohol present) beta-hexosaminidase, which is responsible
■ The choline present is in the form of for the biodegradation of gangliosides.
sphingomyelin, which is an ● HEXOSAMINIDASE-A DEFICIENCY
integral part of the myelin sheath ○ It is also known as sphingolipidosis.
that coats and insulates the brain ○ It is a type of Tay Sach’s disease In which
nerves. there is a deficiency in the degradation of
○ Niemann-Pick disease sphingolipids.
■ It is a disease where an enzyme B.2 CEREBROSIDE
called sphingomyelinase, which ● They are compounds that contain carbohydrates
digests sphingomyelin, is not (galactose is the most common sugar present or
present. Therefore, the glucose), one fatty acid (stearic acid - 18 carbons),
sphingomyelin accumulates and sphingosine, but no phosphoric acid or glycerol.
excessively in the body. ● It occurs and 7% of the dry mass of the brain.
■ It causes mental retardation, ● It is also a component of the myelin sheath nerves.
spasticity, and ataxia which ● It is discovered by Johann Tudichum.
eventually leads to death as early ● Lassaigne’s test Is used to detect the presence of
as the age of 3. cerebroside.
● ↑ Cerebroside = GAUCHER’S DISEASE
B. Sphingolipids ○ It is a lysosomal storage disorder wherein
● They have the same structure as the there is a deficiency of an enzyme called
sphingophospholipids but they differ in their glucocerebrosidase (gcase), which is
organic molecule. responsible for the digestion of cerebrosides.
● Chemical composition: Therefore, fat-laden Gaucher cells
○ Sphingosine accumulate and the bone marrow, liver, and
○ 1 Fatty acid spleen.
○ Phosphate ○ Beta-glucosidase leukocyte (BGL) test is
○ Organic molecule → Ceramide used to diagnose Gaucher’s disease.
○ Patients with Gaucher’s disease have low
B.1 GANGLIOSIDE enzymatic activity.
● They are compounds related to cerebrosides that B.3 CYTOLIPINS
contain sphingosine, long-chain fatty acids, hexoses ● They are compounds that contain fatty acids,
(usually, galactose is the most common sugar present sphingosine, glucose, and galactose.
● It is related to immunological properties.
 LIPOPROTEINS
They are usually the carriers of cholesterol throughout the
body.
Remember that the body synthesizes its cholesterol.

● Chylomicrons
○ They are produced in the intestines and
conduct fats to the liver, adipose tissues, and
skeletal muscles.
○ They have the least density and amount of
proteins but have high levels of triglycerides.
● VLDL
● It contains 2 cyclohexane, 1 cyclopentane, and 1
○ It delivers cholesterol to the blood vessels.
cyclohexene.
○ They are considered transitional between the
● It usually varies in position 17. If there is a hydroxyl
chylomicrons and LDL. It is denser than
group attached, it is considered testosterone. If
chylomicrons and has high triglyceride
there is a carbonyl group With alcohol attached, it is
levels.
called cortisone.
○ It is synthesized in the liver.
● Cardiac glycosides are a group of secondary
○ They are formed when the carbohydrate
constituents that contain the
intake is high.
cyclopentanoperhydrophenanthrene nucleus. They
○ The digestive enzyme is called lipoprotein
vary at the lactone ring attached in position 17.
lipase.
○ Two types of cardiac glycosides
● IDL
■ Cardenolides
○ It is rare in nature.
■ Bufadienolides
○ It is denser than VLDL but contains half the
amount of triglycerides the VLDL has.
I. STEROLS
● LDL (bad cholesterol)
● Plants have Sitosterol and sitostenol.
○ It delivers cholesterol to the blood vessels.
● Fungi have ergosterol.
○ It has low triglycerides level but has a high
● Soybeans contain stigmasterol, Which is considered
protein level. It can transport a higher
the Wulzen Anti-Stiffness Factor.
content of cholesterol from the liver
throughout the bloodstream.
A. Cholesterol
● HDL (good cholesterol)
● It is the counterpart of sterol in animals.
○ delivers cholesterol to the blood vessels but
● Approximately 1 gram of cholesterol is synthesized by
returns the excess to the liver.
the body every day.
○ It is the densest among the lipoproteins and
has the lowest Triglyceride levels. It also has
the highest protein levels among all
lipoproteins.

DISEASES RELATED
● Atherosclerosis is the build-up of plaques in the
inner walls of arteries.

STEROIDS
● Basic nucleus:
CYCLOPENTANOPERHYDROPENANTHRENE
RING
 (Increase bone density, Fat
distribution, Increased muscle
strength and mass, Red blood cell
production, Increased sexual drive,
Sperm production, Deepening of
the voice, Formation of adam's
apple, Production of pubic hairs).
● HYPOGONADISM - it is also
known as eunuchoidism. It is a
● 2 Acetyl CoA form Acetoacetyl CoA through the condition wherein the testes are not
enzyme thiolase. Acetoacetyl CoA then reacts with fully developed due to pituitary
HMG CoA synthase to form HMG CoA. It will be disorders, infections, and other
acted upon by HMG CoA reductase, forming underlying diseases. It is usually
mevalonic acid. Mevalonic acid will undergo certain treated by testosterone hormone
processes (kinases, condensation, isomerization) to replacement therapy via
form isoprenoids. The isoprenoids will undergo Injections, pellets, patches, or
isomerization to form squalene. Then it will undergo gels.
further oxidation to form a squalene-2,3 epoxide and B. Estrogen - include estradiol and others and
it will be further oxidized to form lanosterol. After, it is referred to as “female hormones”
will react to the enzyme because women have higher levels.
Lanosterol-14-alpha-demethylase to form ● Estradiol, Estrone, Estriol - can
cholesterol. be isolated from urine during
○ HMG CoA - also known as pregnancy and can be prepared
beta-hydroxy-beta-methyl-glutaryl CoA synthetically.
○ Statins inhibit HMG CoA reductase to ● Naturally occurring estrogen comes
prevent the production of cholesterol. from pregnant mare’s urine. They
○ Kinase - transfer phosphate into its exhibit carcinogenic properties
structure. when injected, especially if an
II. SEX HORMONES individual is subjected to mammary
● They are steroids that are released by gonads. They cancer.
affect the brain, genitals, and other organs. ● They are responsible for the
A. Androgens - They are a group of sex secondary female characteristics
hormones that include testosterone and (Menstrual cycle, Widening of the
others. Generally referred to as “male hips, Deposit of adipose tissues in
hormones” because men have higher levels the torso, area, Development of
than women. pubic hairs).
● The reason why men have the XY ● It is responsible for the
chromosomes is due to the development and maintenance of
Y-chromosome producing the SRY the uterus and vagina.
genes which are responsible for ● It aids in the pre-secretion of the
The production of primitive gonads, mammary glands.
that eventually develops into testes. ● It stimulates the growth hormone
● The testes are considered as the and is responsible for the uterine
sperm-producing organ. It also smooth muscles to enlarge during
produces testosterone. pregnancy.
● Testosterone further develops the C. Progesterone - makes the uterus for the
penis and scrotum. It is also implantation of a fertilized ovum and upholds
responsible for the development of the maintenance of pregnancy.
secondary male characteristics
 ● It is responsible for the thickening of ○ Vitamin D1 - Calciferol
the endometrium. ○ Vitamin D2 - ergocalciferol
● During pregnancy, the HCG ○ Vitamin D3 - cholecalciferol
(Human Chorionic Gonadotrophin) ● Function:
levels are increased. If HCG levels ○ Calcium absorption
are increased in men, it develops ○ It works with the parathyroid
into Testicular cancer. hormones to regulate calcium
● It is the active hormone of the levels.
corpus luteum. ○ It promotes bone mineralization,
● It is used to treat amenorrhea, therefore promoting bone
Dysmenorrhea, Endometriosis, development.
Functional uterine bleeding, ● Deficiency
Premenstrual tension, and habitual ○ Rickets in Child
abortion. ○ Osteomalacia in Adult
III. BILE ACIDS ○ If an individual is deficient in
● They are essential for the digestion of food, Vitamin D, bone problems may
especially for the solubilization of ingested arise.
fats. V. CORTICOSTEROIDS
● It is a lipid-emulsifying agent in the digestive ● Glucocorticoids regulate protein and carbohydrates
tract. metabolism.
● It converts 1/3 of the daily produced ○ Cortisone
cholesterol into bile acids. ○ Hydrocortisone
● It contains amino acids (either glycine or ● Mineralocorticoids
taurine) which makes the bile acids polar, ○ Deoxycorticosterone/desoxycortone
increasing their solubility in water. ○ Aldosterone
● They are synthesized and supplied in the
GLUCOCORTICOIDS MINERALOCORTICOIDS
small intestine.
● Cholecystokinin is the substance Secreted by Zona Secreted by Zona glomerulosa
responsible for the contraction of blood fasciculata of Adrenal gland. of Adrenal gland.
vessels to release bile acids.
Cortisone – NATURAL Aldosterone – Sodium (Na) and
ANTI-INFLAMMATORY Water Retention to restore
PRIMARY BILE ACID SECONDARY BILE ACID kidney functions especially if a
patient has a cortical deficiency.
Cholic Acid Lithocholic Acid

Chenodeoxycholic Acid Deoxycholic Acid EICOSANOIDS

● It came from the word “eikos” meaning 20.
● Primary bile acids are produced by the liver and
● All cells produce eicosanoids except the red blood
stored in the gall bladder.
cells.
● Secondary bile acids are produced by the
● Hormone-like.
production of microbes.
● Short half-life.
● It is responsible for inflammatory responses
IV. VITAMIN D
(prostaglandins).
● Fat-soluble vitamin
○ Characteristics of inflammation
● It is also known as the sunshine vitamin
■ Calor (heat)
because UV rays are needed to activate the
■ Dolor (pain)
25-hydroxy-cholecalciferol in the liver to
■ Rubor (redness)
be transported in the kidneys to produce
■ Tumor (swelling)
calcitriol.
● They regulate blood pressure (bradykinin) and induce
● Calcitriol is the active form of Vitamin D.
blood clotting (thromboxane).
● It also controls the reproductive functions (induction of ●
labor) and the regulation of the sleep-wake cycle.
● Linoleic acid acts as the precursor and is activated
by Phospholipase A2 to produce arachidonic acid.
Arachidonic acid acts upon cyclooxygenase to
form prostaglandins and thromboxane. While it
also acts with lipooxygenase to form leukotrienes.
○ Prostaglandins are responsible for
water-electrolyte balance and smooth
muscle contraction and relaxation.
■ Misoprostol (Cytotec) is an
oxytocic agent that triggers
prostaglandins.
○ Gastric acid secretion is regulated by
prostaglandins by inhibiting the gastric juices
and producing the protective mucus layer in
the stomach.
○ Thromboxane is produced by the blood
platelets and promotes platelet aggregation,
thus also promoting blood clotting.
○ Leukotrienes trigger chemotaxis or the
movement of an organism in response to a
chemical stimulus. They also cause
inflammation and platelet aggregation
especially during hypersensitivity reactions
or anaphylactic reactions.

CHEMICAL TESTS
TESTS

Salkowski Test Test for Cholesterol

Liebermann Burchard Test for Cholesterol

Osmic Test Test for prosthetic groups of

LIPIDS

Rosenheim’s test Test for CHOLINE

 LIPOPROTEINS
They are usually the carriers of cholesterol throughout the
body.
Remember that the body synthesizes its cholesterol.

● Chylomicrons
○ They are produced in the intestines and
conduct fats to the liver, adipose tissues, and
skeletal muscles.
○ They have the least density and amount of
proteins but have high levels of triglycerides.
● VLDL
● It contains 2 cyclohexane, 1 cyclopentane, and 1
○ It delivers cholesterol to the blood vessels.
cyclohexene.
○ They are considered transitional between the
● It usually varies in position 17. If there is a hydroxyl
chylomicrons and LDL. It is denser than
group attached, it is considered testosterone. If
chylomicrons and has high triglyceride
there is a carbonyl group With alcohol attached, it is
levels.
called cortisone.
○ It is synthesized in the liver.
● Cardiac glycosides are a group of secondary
○ They are formed when the carbohydrate
constituents that contain the
intake is high.
cyclopentanoperhydrophenanthrene nucleus. They
○ The digestive enzyme is called lipoprotein
vary at the lactone ring attached in position 17.
lipase.
○ Two types of cardiac glycosides
● IDL
■ Cardenolides
○ It is rare in nature.
■ Bufadienolides
○ It is denser than VLDL but contains half the
amount of triglycerides the VLDL has.
I. STEROLS
● LDL (bad cholesterol)
● Plants have Sitosterol and sitostenol.
○ It delivers cholesterol to the blood vessels.
● Fungi have ergosterol.
○ It has low triglycerides level but has a high
● Soybeans contain stigmasterol, Which is considered
protein level. It can transport a higher
the Wulzen Anti-Stiffness Factor.
content of cholesterol from the liver
throughout the bloodstream.
A. Cholesterol
● HDL (good cholesterol)
● It is the counterpart of sterol in animals.
○ delivers cholesterol to the blood vessels but
● Approximately 1 gram of cholesterol is synthesized by
returns the excess to the liver.
the body every day.
○ It is the densest among the lipoproteins and
has the lowest Triglyceride levels. It also has
the highest protein levels among all
lipoproteins.

DISEASES RELATED
● Atherosclerosis is the build-up of plaques in the
inner walls of arteries.

STEROIDS
● Basic nucleus:
CYCLOPENTANOPERHYDROPENANTHRENE
RING
 secondary male characteristics
(Increase bone density, Fat
distribution, Increased muscle
strength and mass, Red blood cell
production, Increased sexual drive,
Sperm production, Deepening of
the voice, Formation of adam's
apple, Production of pubic hairs).
● HYPOGONADISM - it is also
● 2 Acetyl CoA form Acetoacetyl CoA through the known as eunuchoidism. It is a
enzyme thiolase. Acetoacetyl CoA then reacts with condition wherein the testes are not
HMG CoA synthase to form HMG CoA. It will be fully developed due to pituitary
acted upon by HMG CoA reductase, forming disorders, infections, and other
mevalonic acid. Mevalonic acid will undergo certain underlying diseases. It is usually
processes (kinases, condensation, isomerization) to treated by testosterone hormone
form isoprenoids. The isoprenoids will undergo replacement therapy via
isomerization to form squalene. Then it will undergo Injections, pellets, patches, or
further oxidation to form a squalene-2,3 epoxide and gels.
it will be further oxidized to form lanosterol. After, it B. Estrogen - include estradiol and others and
will react to the enzyme is referred to as “female hormones”
Lanosterol-14-alpha-demethylase to form because women have higher levels.
cholesterol. ● Estradiol, Estrone, Estriol - can
○ HMG CoA - also known as be isolated from urine during
beta-hydroxy-beta-methyl-glutaryl CoA pregnancy and can be prepared
○ Statins inhibit HMG CoA reductase to synthetically.
prevent the production of cholesterol. ● Naturally occurring estrogen comes
○ Kinase - transfer phosphate into its from pregnant mare’s urine. They
structure. exhibit carcinogenic properties
II. SEX HORMONES when injected, especially if an
● They are steroids that are released by gonads. They individual is subjected to mammary
affect the brain, genitals, and other organs. cancer.
A. Androgens - They are a group of sex ● They are responsible for the
hormones that include testosterone and secondary female characteristics
others. Generally referred to as “male (Menstrual cycle, Widening of the
hormones” because men have higher levels hips, Deposit of adipose tissues in
than women. the torso, area, Development of
● The reason why men have the XY pubic hairs).
chromosomes is due to the ● It is responsible for the
Y-chromosome producing the SRY development and maintenance of
genes which are responsible for the uterus and vagina.
The production of primitive gonads, ● It aids in the pre-secretion of the
that eventually develops into testes. mammary glands.
● The testes are considered as the ● It stimulates the growth hormone
sperm-producing organ. It also and is responsible for the uterine
produces testosterone. smooth muscles to enlarge during
● Testosterone further develops the pregnancy.
penis and scrotum. It is also
responsible for the development of
 C. Progesterone - makes the uterus for the 25-hydroxy-cholecalciferol in the liver to
implantation of a fertilized ovum and upholds be transported in the kidneys to produce
the maintenance of pregnancy. calcitriol.
● It is responsible for the thickening of ● Calcitriol is the active form of Vitamin D.
the endometrium. ○ Vitamin D1 - Calciferol
● During pregnancy, the HCG ○ Vitamin D2 - ergocalciferol
(Human Chorionic Gonadotrophin) ○ Vitamin D3 - cholecalciferol
levels are increased. If HCG levels ● Function:
are increased in men, it develops ○ Calcium absorption
into Testicular cancer. ○ It works with the parathyroid
● It is the active hormone of the hormones to regulate calcium
corpus luteum. levels.
● It is used to treat amenorrhea, ○ It promotes bone mineralization,
Dysmenorrhea, Endometriosis, therefore promoting bone
Functional uterine bleeding, development.
Premenstrual tension, and habitual ● Deficiency
abortion. ○ Rickets in Child
III. BILE ACIDS ○ Osteomalacia in Adult
● They are essential for the digestion of food, ○ If an individual is deficient in
especially for the solubilization of ingested Vitamin D, bone problems may
fats. arise.
● It is a lipid-emulsifying agent in the digestive V. CORTICOSTEROIDS
tract. ● Glucocorticoids regulate protein and carbohydrates
● It converts 1/3 of the daily produced metabolism.
cholesterol into bile acids. ○ Cortisone
● It contains amino acids (either glycine or ○ Hydrocortisone
taurine) which makes the bile acids polar, ● Mineralocorticoids
increasing their solubility in water. ○ Deoxycorticosterone/desoxycortone
● They are synthesized and supplied in the ○ Aldosterone
small intestine.
GLUCOCORTICOIDS MINERALOCORTICOIDS
● Cholecystokinin is the substance
responsible for the contraction of blood Secreted by Zona Secreted by Zona glomerulosa
vessels to release bile acids. fasciculata of Adrenal gland. of Adrenal gland.

Cortisone – NATURAL Aldosterone – Sodium (Na) and

PRIMARY BILE ACID SECONDARY BILE ACID ANTI-INFLAMMATORY Water Retention to restore
kidney functions especially if a
Cholic Acid Lithocholic Acid patient has a cortical deficiency.
Chenodeoxycholic Acid Deoxycholic Acid
EICOSANOIDS
● Primary bile acids are produced by the liver and
● It came from the word “eikos” meaning 20.
stored in the gall bladder.
● All cells produce eicosanoids except the red blood
● Secondary bile acids are produced by the
cells.
production of microbes.
● Hormone-like.
● Short half-life.
IV. VITAMIN D
● It is responsible for inflammatory responses
● Fat-soluble vitamin
(prostaglandins).
● It is also known as the sunshine vitamin
○ Characteristics of inflammation
because UV rays are needed to activate the
■ Calor (heat)
 ■ Dolor (pain)
Liebermann Burchard Test for Cholesterol
■ Rubor (redness)
■ Tumor (swelling) Osmic Test Test for prosthetic groups of
● They regulate blood pressure (bradykinin) and induce LIPIDS
blood clotting (thromboxane).
● It also controls the reproductive functions (induction of Rosenheim’s test Test for CHOLINE
labor) and the regulation of the sleep-wake cycle.
● Linoleic acid acts as the precursor and is activated
by Phospholipase A2 to produce arachidonic acid.
Arachidonic acid acts upon cyclooxygenase to
form prostaglandins and thromboxane. While it
also acts with lipooxygenase to form leukotrienes.
○ Prostaglandins are responsible for
water-electrolyte balance and smooth
muscle contraction and relaxation.
■ Misoprostol (Cytotec) is an
oxytocic agent that triggers
prostaglandins.
○ Gastric acid secretion is regulated by
prostaglandins by inhibiting the gastric juices
and producing the protective mucus layer in
the stomach.
○ Thromboxane is produced by the blood
platelets and promotes platelet aggregation,
thus also promoting blood clotting.
○ Leukotrienes trigger chemotaxis or the
movement of an organism in response to a
chemical stimulus. They also cause
inflammation and platelet aggregation
especially during hypersensitivity reactions
or anaphylactic reactions.

CHEMICAL TESTS
TESTS

Salkowski Test Test for Cholesterol

PROTEINS
● complex, organic nitrogenous substances with very high molecular weights, found in all plant and animal cells, and consisting
largely or entirely of alpha-amino acids united in peptide linkage.
● “PROTEIOS” primary
● Very important to all living organisms
● Polymers of amino acid
Amino acids
➔ Basic units of proteins & usually joined together through a peptide bond.
➔ PEPTIDE BONDS ~ formed by dehydration
➔ There are 21 amino acids that we recognized as standard amino acids, though there are 700 amino acids known to us nowadays

BIOMEDICAL IMPORTANCE OF PROTEINS

1. Enzymatic catalysts
➔ Enzymes are actually proteins in nature; without enzymes we are not able to digest food
➔ Enzymes also involved in several metabolic pathways
2. Transport and storage
➔ Myoglobin ~ stores oxygen
➔ Hemoglobin ~ transports oxygen
3. Coordinated motion
➔ Actin ~ thin and moving filament
➔ Myosin ~ thick and stationary
4. Mechanical support
➔ Collagen ~ most abundant protein in the body
➔ Keratin ~ composition of our nails, hair...
5. Immune protection
➔ Gamma globulin
6. Generation and Transmission of Nerve
➔ Serotonin derived from Tryptophan
7. Control of Growth and Differentiation
8. Cell signalling
➔ Membrane receptors (insulin receptors)
9. Hormones
➔ Chemical messengers
◆ Insulin
◆ Growth hormone/Somatropin
10. Proteins are one of the major components of biological membranes

CLASSIFICATION OF PROTEINS
● Classification Based on Composition, Physical and Chemical Properties of the Protein, Based on Biofunction
○ Simple Proteins (Based on Composition) made of Amino Acids only;
■ Albumin ~ soluble in water also in dilute aqueous solution; it coagulates
■ Globulin ~ insoluble in h2o but soluble in aq. Solution; coagulable
■ Glutelin ~ soluble in acids and alkaline
➔ Grass family
➔ Oryzenin (rice has incomplete source of protein)
◆ Complete sources comes from any meat
◆ Complete protein ~ it can provide all the essential amino acids
◆ Milk (usually from animals)= complete protein
◆ Limiting amino acid
◆ Gelatin = x tryptophan
■ Prolamin ~ glutelin from Wheat
■ Albuminoid or Scleroprotein ~ Collagen, Elastin, Keratin
■ Histone ~ basic protein; component of DNA
 ■ Protamine ~ Salmon & Sturin in Fish Sperm; simplest protein
○ Conjugated Proteins (Based on Composition) simple proteins + a conjugate (prosthetic groups: the non-amino acid
portion of conjugated protein)
■ Nucleoprotein
■ Glycoprotein
■ Phosphoprotein
■ Chromoprotein
■ Lipoproteins
■ Metalloproteins
○ Derived Proteins (Based on Composition)
■ Primary derived: denatured proteins
■ Secondary derived: formed from progressive hydrolysis of protein
● Classification Based on the Shape and Certain Physical Characteristics of the Protein
○ Fibrous proteins ~ elongated protein, usually tough and water-insoluble. Polypeptide chain arranged in tightly parallel
fibers and sheets.
■ Collagen
■ Keratin
■ Elastin
○ Globular proteins ~ usually circular
● CLASSIFICATION BASED ON BIOLOGIC FUNCTIONS
○ Enzymes ~ most important class of proteins.
■ Acts as biological catalysts
○Storage Proteins ~ serve as nutrient stores
■ Ferritin, Ovalbumin (eggs)
○ Regulatory Proteins
○ Structural Proteins ~ forms as organism structure
■ Keratin
■ Elastin
■ Collagen
○ Protective Proteins
■ Antibodies: combine with/to foreign proteins which gain access to the bloodstream that help fight in infection
■ Fibrinogen & Thrombin: necessary in blood coagulation
○ Transport Proteins ~ have transport function
○ Contractile or Motile Proteins ~ essential elements in contractile and motile system
■ Actin and Myosin: serve as the major elements in the contractile system in the muscle
PROTEIN STRUCTURES
● Primary structure: sequence of AA
○ Sickle cell anemia: is caused by a genetic defect in blood hemoglobin(sticky) whereby Valine is substituted for
Glutamic Acid at only one position in a chain of 146 amino acids
● Secondary structure:twisting and folding
○ refers to how segments of the protein chain are oriented into a regular pattern refers to the spatial
arrangements of amino acid residues close to one another in the linear sequence of a polypeptide chain
○ H-bond
○ Alpha helix
○ Beta pleated sheet
● Tertiary structure
○ the way in which an entire protein molecule is coiled or folded into its specific three- dimensional shape
○ due to interaction of R-group
○ the overall arrangement & interrelationship of various regions or domains, & individual amino acid residues of
a single polypeptide chain
● Quaternary structure
○ in which the individual polypeptide chains for each other in the native conformation of an oligomeric proteins
 ○ 2 or more subunits/ domains
○ arrangement of polypeptide chains in
○ relation to one another in multi-chained protein

PRIONS

HUNTINGTON’S DISEASE: condition that stops parts of the brain working properly over time.

Creutzfeldt-Jakob Disease: a degenerative brain disorder that leads to dementia and, ultimately, death. Creutzfeldt-Jakob disease symptoms
can be similar to those of other dementia-like brain disorders, such as Alzheimer's disease.
➔ Spongiform in human

Kuru Disease: It is caused by an infectious protein (prion) found in contaminated human brain tissue. Kuru is found among people from New
Guinea who practiced a form of cannibalism in which they ate the brains of dead people as part of a funeral ritual.

Fatal Familial Insomnia: inability to sleep

Chaperons: protein helps in the folding of other proteins. (heat-shock proteins, chaperonin)

Heat shock protein 60 (HSP60) is a highly conserved protein abundantly expressed in both prokaryotic and eukaryotic cells.
➔ To isolate uncoated proteins

Hsp70 proteins are central components of the cellular network of molecular chaperones and folding catalysts. They assist a large variety of
protein folding processes in the cell by transient association of their substrate binding domain with short hydrophobic peptide segments within
their substrate proteins.
➔ Coating catalysts
➔ Prevent aggregation

Denaturation of proteins
● Destroy the higher structural levels of protein (particularly tertiary structure)
Renaturation of proteins
● The recovery of the protein from its denatured state.
 47

Amino Acids - Impairment in human seleno proteins have been implicated

– Building blocks of proteins in the manifestation or development of Neumorigenesis and
– Relatively simple building block molecules from which proteins are built Tetare Sclerosis
– All proteins are constructed from the 20 same sets of amino acids that are - It would also be associated to selenium deficiency,
covalently linked in characteristic sequences cardiomyopathy, or also referred to as Keshan Disease: a
– Each amino acid has distinctive side chain that differentiated them with fatal cardiomyopathy or abnormality of the cardiac muscles
each other and responsible for their chemical individuality because of selenium deficiency, usually it affects children
– Regarded as alphabets of proteins so whatever the characteristic of amino and women of child bearing age.
acids found in proteins have an impact on the function of protein itself
– There are 20 standard/ primary/normal amino acids that we refer to All amino acids have trivial or common names. In some cases, it is derived from
distinguish from other kinds of amino acids present in living organisms but the source from which they were first isolated:
not in proteins  Asparagine
– There are also non-standard amino acids, they are amino acid residues that – First amino acid to be discovered
have been chemically modified after being incorporated to a polypeptide – Found in asparagus in 1806
and occur in living organisms but not on proteins; >700 amino acids are  Glutamate
known to man – First isolated from wheat gluten
Example of Non-Standard Amino acids are:  Tyrosine
• Peptidyl proline converted to 4-hydroxyproline – First isolated from cheese
• Lysine converted to 5-hyroxylysine – Name is derived from the Greek “tyros” meaning “cheese”
• Peptidyl glutamate converted to gamma carboxylglutamate  Glycine
• Methylation, acetylation, and phosphorylation of other amino-acyl – Greek “glykos” means “sweet”
residues – So, named because of its sweet taste
**such modifications are extension of the biologic diversity of proteins to
alter their solubilities, stability and interaction with other proteins Functions of Amino Acids
i. Building blocks of proteins
General Structure ii. Precursor of various substances
o Amino acids have Central Carbon/ Alpha a. Glycine – heme (glycine + succinyl coA), purine,
Carbon to which the other groups attach to; creatine (a tripeptide containing glycine, arginine and methionine)
o Hydrogen atom which completes the four b. Glutamic acid – GABA (Gamma Amino Butyric Acid; an important
bonds or groups needed for each carbon natural tranquilizer)
atom; c. Phenylalanine and Tyrosine – thyroxine (thyroid hormone),
o Amino Group who contributes to the epinephrine (adrenaline hormone), melanin (pigment responsible for
alkalinity or basicity of amino acids; our complexion), dopamine, norepinephrine
o Acidic Carboxylic Group; and d. Tryptophan – niacin (vitamin B3), serotonin (a neurotransmitter),
o Distinctive Side Chain that characterizes and classifies amino acids to be melatonin (hormone that induces sleep & regulates circadian rhythm),
different from the others. indole & skatole (responsible for odor of stool)
– Common/ Alpha amino acids they have a primary amino group & a carboxylic e. Lysine – carnitine
acid group as substituents of the same alpha carbon atom; commonly found f. Histidine – Histamine
in the human body g. Lysine and Methionine – Carnitine
– In Beta amino acids, amino group are attached to the beta carbon; not found iii. Source of energy
in the human body • 1 gram of Carbohydrates = 4 calories
• 1gram of Fats = 9 calories
• 1 gram of Protein = 4 calories
iv. Special amino acids as components of certain types of proteins.
• Hydroxyproline & hydroxylysine
– Collagen
- a structural protein, so it needs to be strong; Made up of glycine
(most abundant component) and X&Y amino acids (can be
hydroxyproline/ hydroxylysine/ proline)
- Vitamin C/ Ascorbic Acid also helps in the formation, so if you do
not have this, you cannot synthesize hydroxyproline &
hydroxylysine and you will have a collagen that is abnormal and
such occurrence may happen among your blood vessels, they will
become fragile and it will be an early sign of vitamin C deficiency
like in patients who suffer from epistaxis or nose bleeding
• N-Methyllysine – Found in Myosin (contractile protein in muscles)
• Gamma-Carboxyglutamic Acid – Prothrombin (a clotting factor): this
requires vitamin K
• Desmosine – Derivative of Lysine; Found in Elastin
• N-Acetyllysine – Found in Histones that are associated with
Essential Non-Essential chromosomes
Needed by the Needed still by the v. Phosphorylation and Dephosphorylation of Serine, Threonine and Tyrosine
body but the body but the body play a major role in activation and inactivation of enzymes.
body itself can synthesize them E.g. Enzymes activated by phosphorylation like glycogen phosphorylase
cannot which is needed in glycogenolysis OR Enzymes activated in
synthesize them dephosphorylation/ removal of phosphate group like glycogen synthetase
Histidine Alanine vi. Some amino acids or their derivatives act as Chemical Messengers (e.g.
Isoleucine Arginine GABA, serotonin)
Leucine Asparagine vii. Several amino acids act as Metabolic Intermediates (e.g. Arg, citrulline,
Lysine Aspartic acid ornithine – urea cycle)
Methionine Cysteine viii. Hormones can be derived from amino acids
Phenylalanine Glutamic acid ix. Both D- and L-amino acids are present in polypeptide antibiotics elaborated
Threonine Glutamine by microorganisms.
Tryptophan Glycine
Valine Proline Classification of Amino Acids Based on Polarity
Serine A. Amino Acids with NonPolar or Hydrophobic R Groups
Tyrosine – Referred to as Neutral amino acids containing hydrocarbon R groups (no
Selenocysteine  +/-- charge)
- Instead of Sulfur being attached to the structure – Interact poorly with water; do not dissolve in water; water fearing
of cysteine, Selenium replaced it; – Play an important role maintaining the 3- dimensional structure of
- A rare amino acid inserted into polypeptides proteins.
during translation through post synthetic modification Two Types of Hydrocarbon Side Chains:
- Significantly noted to be present at the active site of several 1. Aromatic
human enzymes particularly those that catalyzes redox a. Phenylalanine * Benzene Ring
reactions like in enzymes thioredoxine, glutathione b. Tryptophan *Indole Ring: borderline member, for it can interact
peroxidase, iodimase through the hydrogen bond of the amino group in its side chain (R
group)
 48

2. Aliphatic
a. Glycine: simplest because it only has Hydrogen as side chain, do
not have chiral carbon
b. Alanine: only straight chain aliphatic (methyl group SC)
c. Valine:
d. Leucine
e. Isoleucine
f. Methionine
g. Proline: referred as Helix Breaker because its R group is not only
attached to alpha carbon but also to its side chain amino group, that’s
why it is somewhat cyclic in structure/ appearance; also referred as Test for Reagent Positive Result
Imino Acid because of the imine formed by the cyclic structure. Proteins
 (Almost all amino acids have chiral carbons, because of this chirality, they Biuret Test 1% NaOH & Copper Violet Color
exhibit ability to cause optical rotation (either dextro or levo) or can for sulfate
enantiomers or isomers. Exception is glycine.) Ninhydrin Test Ninhydrin reagent • Purple
(Ruhemann’s
purple) –free
amino group
• Yellow –
Imino acids
• Specific test
for proline
Xanthoproteic HNO3 & 40% NaOH Yellow colorspecific test
Test for tyrosine, tryptophan,
phenylalanine
Millon’s Test Hg dissolved in HNO3 Yellow color specific test
for tyrosine
Hopkin’s-Cole Glyoxylic in glacial acetic Purple color on the
Test acid & H2SO4 surface, indole, specific
test for tyrosine
Nitroprusside Nitroprusside in alkaline Red colorspecific test for
Test solution cysteine
Sakaguchi Test NaOH, α-naphthol & Red color specific test
Bromine solution for arginine

NUCLEIC ACIDS
B. Polar Amino Acids – Polymers of individual nucleotide monomer (CHONP)
Amino Acids with UNCHARGED POLAR R Groups – DNA- deoxyribonucleic acid, found in the nucleus of the cell whom is
responsible for carrying genetic information
- They are polar because of the hydrogen bonds/ soluble
– RNA- ribonucleic acid, found in the cytoplasm of the cell and is responsible
in water
for the synthesis of protein
1. Hydroxyl-containing Amino Groups: OH
a. Serine – Are responsible for making new cells, and has the ability for cells to make
new proteins
b. Threonine
c. Tyrosine – Very important factor of nucleic acids is CHO or sugar, also has a
2. Amide (CONH2) Derivatives of Glutamate and Aspartate nitrogenous base and also a phosphate group
a. Glutamine
Nucleotides
b. Asparagine
3. Other: Fundamental components:
a. Cysteine phosphate group is responsible for the acidic property of nucleotides

• Nitrogenous base
– Purines
– Guanine
– adenine

– Pyrimidines
o Only cytosine and thymine are found on the DNA
o while uracil is found on our RNA
Amino Acids with POSITIVELY CHARGED POLAR R Groups (Basic Amino
Acids)

• Pentose Sugar
Difference: Carbon 2 only difference is the presence of a hydroxylgroup

-Arginine GUANIDO GROUP

Amino Acids with NEGATIVELY CHARGED POLAR R Groups (Acidic
Amino Acids) 2 carboxylic groups
 49

Deoxyribonucleic Acid - According to Watson and Crick model of DNA where the model look like
– Double Strand acid forming helical shape , DNA molecules forming double Helix stands
– Sugar: Deoxyribose that are held together by hydrogen bonds
– Are usually coiled around histones to form chromosomes - Complementarity of nucleic acid bases which means a group of DNA
– Nitrogenous Base: or RNA that bonds together
• Purine: Guanine, Adenine
• Pyrimidine: Cytosine, Thymine

Ribonucleic Acid
– Single Strand
– SUGAR: Ribose
– Nitrogenous Base:
• Purine: Guanine, Adenine
• Pyrimidine: Cytosine, Uracil

Nucleoside
– named by changing the nitrogen base ending to -osine for purines and –
idine for pyrimidines.

Complementarity
• Adenine and Thymine
• Cytosine and Guanine
Nucleoside Phosphate • Adenine and uracil (RNA)
– named using the name of the nucleoside followed by 5’-monophosphate. • Hydrogen bonds
• # purines = # of pyrimidines A+G=C+T

Hydrogen Bonded Base Pairs

N-Base + Sugar Nucleoside Nucleotide

Adenine Ribose Adenosine Adenosine
Phosphate
Guanine Ribose Guanosine Guanosine
Phosphate
Cytosine Ribose Cytidine Cytidine
Phosphate (C=G) MINORGROOVE- 3 hydrogen bonds (A=T)
Uracil Ribose Uridine Uridine MAJORGROOVE- 2 hydrogen bonds
Phosphate
Thymine Ribose Thymidine Thymidine Antiparallelism
Phosphate In the chains, each end of the helix contains the 5' end of one
strand(PHOSPHATE) and the 3' end of the other(HYDROXYL).

Guanosine 5’-monophosphate
(GMP)

Structural Organization
• 1o sequence of the nucleotide
• 2o helical structure: Stabilized by H – bond • Primary structure sequence of the nucleotides
• 3o Structure: supercoiling • Secondary structure helical structure stabilized by H bond
• Tertiary structure supercoiling
Primary Structure of Nucleic Acids • Denaturation involves the breaking of many of the weak linkages, or
bonds (e.g., hydrogen bonds), within a protein molecule that are
responsible for the highly ordered structure of the protein in its natural
(native) state. ... The denaturation of many proteins, such as egg white, is
irreversible.
• Renaturation in molecular biology refers to the reconstruction of a protein
or nucleic acid (such as DNA) to their original form especially after
denaturation. This process is therefore the inverse of denaturation. In
denaturation, the proteins or nucleic acids lose their native biomolecular
structure.
 Primary structure that holds or connects one nucleic acid from Degeneracy of The Genetic Code
another it’s called phosphodiester bond, on position three of the – several codons may code for the same amino acid.
sugar – 1 Amino Acid = 6 Codons
Example of RNA Structure – Denaturation
The primary structure of RNA, – Renaturation
– Is a single strand of nucleotides with bases A, C, G, and U.
– Is linked by phosophodiester bonds between ribose and phosphate. DNA Forms
Z- unique left – handed helical structure
DNA counterclockwise
B- most common / most right -
DNA abundant handed
A- dehydrated B – DNA form double
DNA helices
clockwise

SECONDARY STRUCTURE OF NUCLEIC ACIDS

 50

Primase Synthesizes an RNA primer to begin the elongation

process.

DNA polymerase
– removes the RNA Primer
– Pol I: implicated in DNA repair; has both 5'- > 3' (Polymerase) activity and
3'- > 5' (Proofreading) exonuclease activity.
– Pol II: involved in replication of damaged DNA; has 3'- > 5' exonuclease
Central Dogma activity.
– Pol III: the main polymerase in bacteria (elongates in DNA replication); has
3'- >5' exonuclease proofreading ability.

Topoisomerases
• Central dogma states that DNA replicates itself and makes RNA in the – Real axis so the supercoiling of the double stranded DNA while being
process called transcription while RNA makes proteins in the process of unwind by helicase or rna polymerase
translation – Modify the newly synthesize DNA
• Reverse transcription refers to RNA being able to modify DNA – Topoisomerase type II
• Central dogma is stated by Francis Crick in 1957 and was published in – Ex. DNA gyrase  Target by Quinolones
1958
DNA Synthesis DNA SYNTHESIS
Conservative - One parent strand and one daughter strength appear in the final product
- New DNA it’s made by using the original DNA as a template
Dispersive
- The strands separate in a certain region
Semiconservative
- Basis for the new strand line up on the parent strand according to the rules
REPLICATION for watson and Crick base pairing
- Conservative 2 parent strand stay together and two daughter strands stay
Enzymes in volved in DNA replication:
together
Helicase (unwinds the DNA double helix)
Gyrase (relieves the buildup of torque during unwinding) - Dispersive parent and daughter strands are paired together
Primase (lays down RNA primers)
TRANSCRIPTION
DNA polymerase III (main DNA synthesis enzyme)
DNA polymerase I (replaces RNA primers with DNA) • Synthesis of RNA from DNA
Ligase (fills in the gaps) • Produces the three basic types of RNA:
Step 1: Initiation o Messenger RNA
Unwinding of the double helix: - Template of protein synthesis
- Carrier of codons
o Ribosomal RNA
- Site of protein synthesis
o Transfer RNA
- Contains anti – codon
** messenger RNA and transfer RNA work together to form proteins
Step 2: Priming - Synthesis of hnRNA
- Editing to yield mRNA molecule
- 1. Initiation is the beginning of transcription. It occurs when the enzyme
RNA polymerase binds to a region of a gene called the promoter. This
signals the DNA to unwind so the enzyme can ‘‘read’’ the bases in one of
the DNA strands. The enzyme is now ready to make a strand of mRNA
Step 3: Elongation with a complementary sequence of bases.
Polymerization - 2. Elongation is the addition of nucleotides to the mRNA strand. RNA
Assembly of 2 new strands of DNA: Leading (carries the strands in a three polymerase reads the unwound DNA strand and builds the mRNA
to five direction) & Lagging Strand (has spaces or unfilled spaces, carries the molecule, using complementary base pairs. There is a brief time during
strands in a five to three direction) this process when the newly formed RNA is bound to the unwound DNA.
Replication fork is a portion of the DNA that remains unwinded During this process, an adenine (A) in the DNA binds to an uracil (U) in
the RNA.
Step 4: Termination (removes the DNA primer and fill the gaps called ozaki - 3. Termination is the ending of transcription, and occurs when RNA
fragments) polymerase crosses a stop (termination) sequence in the gene. The
mRNA strand is complete, and it detaches from DNA.
FOLLOWED BY ANOTHER STEP CALLED HETEROGENOUS NUCLEAR
RNA (hnRNA) in becoming mRNA
Involves a process called RNA splicing/ALTERNATIVE SPLICING is a
process in molecular biology where a newly-made precursor messenger
RNA (pre-mRNA) transcript is transformed into a mature messenger RNA
Step 5: Proofreading and Correction (DNA ligase is involved ) (mRNA). It works by removing introns (non-coding regions of RNA) and
so joining together exons (coding regions).
TRANSLATION
Translation is the process of translating the sequence of a messenger RNA
(mRNA) molecule to a sequence of amino acids during protein synthesis. The
genetic code describes the relationship between the sequence of base pairs in
a gene and the corresponding amino acid sequence that it encodes
- Involves rRNA also known as ribosomes, has 4rRNA(65%) which has 80
proteins (35%)
- There are actually 64 possible codes and these codon’s would each have
a specific amino acid in accordance to the genetic code
- Initiation For translation to begin, the start codon (5’AUG) must be
recognised. This codon is specific to the amino acid methionine, which is
nearly always the first amino acid in a polypeptide chain. At the 5’ cap of
mRNA, the small 40s subunit of the ribosome binds. Subsequently, the
larger 60s subunit binds to complete the initiation complex. The next step
Key Enzymes in DNA replication: (elongation) can now commence.
Helicase Cleaves and unwinds short sections of DNA ahead - Elongation The ribosome has two tRNA binding sites; the P site which
of the replication fork. holds the peptide chain and the A site which accepts the tRNA. While
DNA Serves 3 different functions: Methionine-tRNA occupies the P site, the aminoacyl-tRNA that is
Polymerase 1. Adds new nucleotides to 3’ end of elongating strand. complementary to the next codon binds to the A site, using energy yielded
2. Dismantles RNA primer. (I) from the hydrolysis of GTP. Methionine moves from the P site to the A site
3. Proofreads base pairings (III) to bond to a new amino acid there, starting the growth of the peptide. The
DNA Ligase Catalyzes the formation of phosphate bridges between tRNA molecule in the P site no longer has an attached amino acid, so
nucleotides to join Okazaki Fragments leaves the ribosome. The ribosome then translocates along the mRNA
molecule to the next codon, again using energy yielded from the
 51

hydrolysis of GTP. Now, the growing peptide lies at the P site and the A - Purine replaces pyrimidine
site is open for the binding of the next aminoacyl-tRNA, and the cycle - Results of point mutations
continues. The polypeptide chain is built up in the direction from the N Silence: Codon containing the changed base codes for the same amino acid
terminal (methionine) to the C terminal (the final amino acid).
- Termination, One of the three stop codons enters the A site. No tRNA
molecules bind to these codons, so the peptide and tRNA in the P site
become hydrolysed releasing the polypeptide into the cytoplasm. The Missense: Codon containing the changed base codes for the diff amino acid
small and large subunits of the ribosome dissociate, ready for the next
round of translation.
Nonsense: Codon containing the changed base codes for STOP codon

FRAMESHIFT MUTATIONS
- where one or more bases is added or removed.
- Can be caused by an aromatic compound inserting between bases in
stacked DNA. This is called intercalation
- Insertion
- Deletion mutations

DISEASES
Xeroderma No Exonuclease; Inability to repair tissue
Pigmentosa damage
Sickle Cell Anemia Valine replaces Glutamic acid
Thalassemia Nonsense Mutation; Insufficient production of Hg
Fanconi’s Anemia Short stature, aplastic anemia, induced by
mitomycin C
Fanconi’s Proximal Tubule is Impaired
Syndrome
Lesch Nyhan Deficiency in HGPRT (Hypoxanthine- Guanine
Syndrome Phosphoribosyl Transferase)
Note: HANGGANG DETO LANG NAGDISCUSS SI MAAM DEKO LANG
ALAM KUNG KASAMA SA BABA!!!! – nagMAMAHAL KIARA MAÑALAC
tRNA
NA MAGANDA
Each tRNA
- has a triplet called an anticodon that complements a codon on mRNA.
- bonds to a specific amino acid at the acceptor stem. METABOLIC PATHWAYS

METABOLISM
sum total of all chemical reactions in order to maintain life

CATABOLISM ANABOLISM
BREAKING DOWN BUILDING UP
Complex --> Simple Simple --> Complex
Energy Producing Energy Requiring

LEORA GEROA
(+) OXYGEN (-) OXYGEN
EXONS (-) HYDROGEN (+) HYDROGEN
- The informational DNA segments that make up genes CATABOLISM ANABOLISM
INTRONS
- are the noncoding regions of the polypeptide. During processing (splicing), NAD 
the introns are removed and exons soliced together to yield the final mRNA FAD 

MUTATIONS
POINT MUTATIONS
Transitional Mutation
- Purine replaces another purine
- Pyrimidine replaces another Pyrimidine
Eg. 5 – bromouracil
• Thymine analog
• Replace thymine in DNA

Glycolysis/ Embden Meyerhoff Pathway

Glucose + Lysis  Glucose breakdown

– 2 – aminopyrine
• Can replace adenine or guanine in DNA
• Cause bone marrow toxicity

Transversional Mutation
 52

1. Glycolysis 6-8 ATP

2. Intermediate 6 ATP
pathway 24 ATP
3. Kreb’sCycle
TOTAL 36-38 ATP

ELECTRON TRANSPORT CHAIN

 Flavin adenine dinucleotide, or FADH2
 Nicotinamide adenine dinucleotide NADH
 NADH is a product of both the glycolysis and Krebs cycles
 FADH2 is only produced in Krebs cycle

What will happen to NADH?

Oxidative Phorphorylation
1. Glycerol Phosphate Shuttle (Brain and Skeletal Muscle)

2. Malate-Aspartate (Heart, Liver and Kidneys)

INHIBITOR SITE EFFECT

Cyanide Cytochrome Blocks transfer of electrons to
Oxidase oxygen. Blocks at site III.
Antimycin Electron transfer All intermediates before and
from cyt b to cyt including cyt a will be in the reduced
c1 state; all intermediates after and
Substrate Level Oxidative
including cyt c1 will be in the oxidized
Phosphorylation Phosphorylation
state. Blocks at site II.
2 Used 2 NADH Rotenone NADH-CoQ Blocks Oxidation of NADH (site I).
4 Produced X 3 or 2 Reductase NADH will become reduced;
2 ATP 4 - 6 ATP Substrates such as succinate that
enter via FADH will be oxidized and
Intermediate Reaction make 2 ATPs/mol.
Oligomycin ADP Blocks phosphorylation of ADP.
Phosphorylation Does not inhibit uncoupled
oxidations.
Atractyloside ADP-ATP Inhibits entry of ADP into
& Transporter mitochondria and ATP export. Stops
Bongkrekate electron transport because of lack of
ADP. Inside, all ADP is converted to
ATP.

SECONDARY PATHWAY FOR GLUCOSE METABOLISM

o Hexose Monophosphate Shunt/PPP
• NADH
• Ribose – 5 – Phosphate
o Glucose Glucoronic Pathway
Acetyl CoA will now enter the Mitochondria for Kreb’s Cycle • D – glucuronate
• L – ascorbic acid
KREB’S CYCLE

Steps of Glycogenesis

Oxidation of 3 9
NADH ATP
Oxidation of 1 2
FADH ATP
Oxidation of1 1
GTP ATP
12 ATP
12 ATP X 2 = 24 ATP Steps of Glycogenolysis

Summary
Process Number of ATP
Produced
 53

Glycogen Storage Diseases

Type Other Name Clinical
Features
O GSD 0 Muscle cramp
I Von Gierke Liver Damage
II Pompe disease Cardiac
Damage
III Forbes-Cori Liver Damage
disease
IV Andersen Liver Damage
disease
V McArdle Muscle
disease Damage
VI Hers disease Liver Damage
VII Tarui disease Muscle
Damage
 METABOLIC PATHWAY
METABOLISM - sum total of all chemical reactions in order to maintain life
 TYPES OF METABOLISM/CLASSIFIED INTO CATABOLISM OR ANABOLISM
o CATABOLISM – “Cut” – Break down of complex molecules to simple molecules producing energy
 PRODUCES ENERGY  ENERGY-PRODUCING
 Also allows molecules in the diet
 e.g.  Break down of proteins to amino acids
 Glycogen broken down into glucose
 Triglycerides breaking up into fatty acids
o ANABOLISM – Building up of simple molecules to complex molecules requiring energy
 Energy requiring  requires energy for building up complex molecules  but does not
produce energy
 Opposite of Catabolism
 E.g. Amino acids  Proteins
Glucose  Glycogen
Fatty acids  Triglycerides
o AMPHIBOLIC – is a combination of Catabolism and Anabolism; used to describe a specific
biologic pathway that involves the two types of metabolism (Catabolism and Anabolism)
 E.g.  Kreb’s Cycle or The Citric Acid Cycle
Cellular respiration (because the mere fact that we are breathing, that is how we
convert food into energy using water and oxygen)

DIFFERENT PROCESS UNDER METABOLISM

OXIDATION (the loss of e-  becoming more +) REDUCTION (the gain of e-  MORE -)
 LeORA  OIL (Oxidation is Loss - Electron)  GeROA RIG (Reduction is Gain - Electron)
(Reducing agents  Substances that undergo Oxidizing agents  Subtances that undergo reduction;
oxidation; molecules or compounds that oxidizes other molecules or compounds that reduces other compounds
compounds or molecules) or molecules)
 (+) OXYGEN  (-) OXYGEN
 (-) HYDROGEN  (+) HYDROGEN
 CATABOLISM  ANABOLISM
NAD  Nicotinamide Adenine Dinucleotide
 A coenzyme found in all living things
 Nucleotides under NAD are joined together by phosphate groups
 Accepts only 1 hydrogen  NADH (reduced form)
 Source: Active form of Vitamin B3 (Niacinamide); it is the central component of the co-factor NAD

FAD  Flavin Adenine Dinucleotide

 Considered as a redox co-factor that is related to many metabolic reactions and exist in to redox
states
 Accepts 2 hydrogens  FADH2 (reduced form)
 Source: Vitamin B2  it is the central component of the co-factor FAD

Coenzyme A  Source: Vitamin B5 (Pantothenic Acid)  component of Coenzyme A

 Essential coenzyme in a variety of reactions that also sustain life
 Used specifically for chemical reaction that generates energy  usually energy from fats,
carbohydrates, or proteins

DIFFERENCE BETWEEN NAD & FAD  Difference when it comes to accepting the number of hydrogen
atoms  NAD = Accepts only 1 hydrogen  NADH (reduced form) & FAD = Accepts 2 hydrogens 
FADH2 (reduced form)

FATE OF GLUCOSE:

• Digestion of Carbohydrates – you begin to digest carbohydrates the minute the food enters the
mouth because the saliva secreted from your salivary gland, moistened the foods as it is chewed.
• Saliva is important in digestion of glucose because saliva releases an enzyme called amylase, which
begins the breakdown process of the sugars from carbohydrates.
• Ptyalin – is a starch hydrolyzing enzyme that is produced by the salivary glands, particularly from
salivary amylase  digest CHO  glucose  produces ATP
• ATPs – energy currency of the cell because it traps energy
• Excess glucose is converted into glycogen which is sometimes stored in fats and proteins.
 Remember for Catabolic Reactions: They also served to capture chemical energy in the form
of ATP, particularly from the degradation of the energy reach fuel molecules  Also allows
molecules in the diet  converted into building blocks that are needed for the synthesis of
complex molecules

FOUR MAJOR METABOLIC PATHWAYS

1. GLYCOLYSIS  LOCATION: OCCURS AT CYTOSOL

2. Intermediate reactions
3. Kreb’s cycle  location: occurs at the inside of mitochondrial membrane
4. ETC  location: occurs at the inside of mitochondrial membrane
 3 STAGES OF CATABOLISM:

Stage 1: Hydrolysis of the complex molecule

• In the first stage, the complex molecules are broken down into their component building blocks or
simple molecules (e.g. Proteins  Amino acids, Polysaccharides  Monosaccharides)

Stage 2: Conversion of the building blocks to simple intermediates (only few ATPs produced  much
more w/ stage 3)
• For the second stage, the diverse building blocks produces from stage 1 were further degraded to
Acetyl co-enzyme A and few other simple molecules.
• Some energy was captured as ATP but the amount was small compared with the energy that is
produce during the third stage of catabolism.

Stage 3: Oxidation of Acetyl CoA

• Also referred to tricarboxylic cycle or Kreb’s Cycle, which is the final common pathway in the
oxidation of fuel molecules that is also produce Acetyl CoA.
• Oxidation of Acetyl CoA will generates large amounts of ATP (24 ATPs) via oxidative
phosphorylation as electrons flows from NADH to FADH2.

FOUR MAJOR METABOLIC PATHWAYS

1. Glycolysis or “EMBDEN MEYERHOFF PATHWAY”  OCCURS IN CYTOSOL OF ALL CELLS

• Glucose + Lysis = Glucose breakdown = FINAL product  2 MOLECULES OF PYRUVATE

• Important for the entry of glucose into the cells  extrahepatic tissues via facilitated diffusion.
• In liver, the entry of glucose in cell is mainly also in the process of facilitated diffusion, which is
an insulin dependent.
• Facilitated diffusion – is a passive transport of the molecules across the cell membrane via a
specific transmembrane or what we call protein; there is an involvement of carriers (carrier
mediated).
• The most common type of glycolysis is “Embden Meyerhoff Pathway”, discovered by Gustav
Embden, Otto Meyerhof, and Jakub Karol Parnas
• Embden Meyerhoff Parnas Pathway – Produce ATP and 2 Pyruvic Acid
o It allows the metabolic use of glucose to generate ATPs and NADH, as well as the
biosynthetic precursors like pyruvate.
• Other pathways of Glycolysis: Entner-Doudoroff Pathway
• Two kinds of Glycolysis:
1. Aerobic – there is an involvement of oxygen that is used to convert glucose to pyruvate
(which are burned for energy and later on converted into fats via fatty acid synthesis) and
ATP  can undergo Kreb’s or ETC
2. Anaerobic – includes ATP production and recycle when it comes to NADH by making the
product lactate; therefore, the pyruvate product of glycolysis will be converted to lactate (in
the muscle)
 10 STEPS FOR THE PROCESS OF GLYCOLYSIS
–composed of 2 stages: Stage 1 (Step 1-5): Preparatory stage & Stage 2 (Step 6-10): Payoff phase
 For other references: Stage 1 (Step 1-4) & Stage 2 (Step 5-10)

GLYCOLYSIS
Step 1-3: ENERGY CONSUMING STAGE (AKA PREPARATORY PHASE)
• In these steps, it is called energy consuming because it will use ATP instead of producing ATP.

Step 1: PHOSPHORYLATION USING ATP (1st ATP consuming STEP or 1st priming reaction)
• Glucose ring is phosphorylated (addition of phosphate group to a molecule derived from ATP)
• 1 molecule of ATP consumed (ATPADP)
• Enzyme: Hexokinase (PURPOSE: responsible for the phosphorylation of glucose  Glucose 6-
PO4)
o Requires magnesium ion for its activity
o Kinase – enzymes that phosphorylates other molecules
• Product: Glucose 6-phosphate (Attachment of phosphate group at 6th carbon)

Step 2: ISOMERIZATION
• Formation of fructose 6-phosphate
• Enzyme: Phosphoglucose isomerase (PI) or Phosphohexose isomerase
• Rearrangement of Carbon-Oxygen bond (6-membered ring isomerizes to 5-membered ring)
o Conversion of an aldose to Ketose
• Carbon 1 of glucose is no longer part of the ring structure  became an external part of the
ring/ placed in the external portion
• Product: Fructose 6-phosphate

Step 3: PHOSPHORYLATION USING ATP (2nd ATP consuming STEP or 2nd priming reaction)
• Conversion of Fructose 6-phosphate to Fructose 1,6-biphosphate (FBP)
• 2nd molecule of ATP is consumed (needed in the addition of Phosphate to Fructose 6-phosphate
 PRODUCING Fructose-1,6-“BI”phosphate)
• Enzyme: Phosphofructokinase (PKF) – rate-limiting enzyme
o Requires magnesium ion for its activity
• At this point, glucose 6-phosphate and fructose 6-phosphate can enter other metabolic
pathways. But fructose 1, 6-bisphosphate can only enter glycolysis.
• PRODUCT: FRUCTOSE 1,6-BIPHOSPHATE
STEP 4-10: ENERGY GENERATING STAGE (MEANING: ATP IS BEING PRODUCED INSTEAD OF BEING USED
IN THE PROCESS) & CONVERSION TO PYRUVATE

Step 4: There would be a formation of cleavage that would later on produced the 2 triose PO4 especially
the Glyceraldehyde 3-PO4 & Dihydroxyacetone PO4

 ENZYME: aldolase – responsible to catalyze the cleavage of fructose-1,6-biphosphate (FBP) to

yield two 3 carbon molecules
From fructose-1,6-biphosphate = DHAP (Dihydroxyacetone PO4) & GAP (Glyceraldehyde 3-PO4) by the
virtue of ALDOLASE

PRODUCTS OF STEP 4:

1. GAP – can proceed to glycolytic pathway

2. DHAP – dif with GAP – need to undergo further reaction unlike GAP  further acted by the
enzyme triphosphate isomerase (TIM) to rearrange DHAP to become GAP (ketone to aldehyde)
 because accrdg. with the principle of glycolysis only aldehydes can proceed, so therefore,
conversion is needed  STEP 5: the conversion of DHAP to GAP to continue the process

SUMMARY OF STEP 4: produced two 3-carbon molecules (DHAP & GAP – trioses, 3C) but not yet fully
converted into pyruvate
PREPARATORY STAGE (STAGE 1) – STEPS 1-4
CONSUMING STAGE – STEPS 1-3
STEPS THAT NEEDED ATP: Phosphorylation procedures (Step 1 & 3)
STAGE 2: PAY-OFF PHASE

STEP 5: ISOMERIZATION OR THE FORMATION OF ANOTHER GLYCERALDEHYDE 3-PO4

 Convert DHAP (Dihydroxyacetone PO4) to GAP (Glyceraldehyde 3-PO4) acted by the enzyme
TIM (triphosphate isomerase)
 DHAP (acted by TIM)  GAP
 Other names of TIM: triose phosphate isomerase
 PRODUCT ON STEP 5: another GAP = 2 GAP that will enter STEP 6

TAKE NOTE: since the product of STEP 5 already produced TWO 3-carbon molecules the succeeding
steps 5-10 would also produce 2 products (final product of glycolysis – 2 pyruvate)

STEP 6: OXIDATION & PHOSPHORYLATION using Pi (inorganic PO4) = Formation of 1,3-biphospho

glycerate

2 MAIN EVENTS:
1.) 2 molecules of GAP is oxidized by the coenzyme NAD (Nicotinamide adenine dinucleotide)
2.) The molecule is also phosphorylated by the addition of a free PO4 group

 ENZYME USED FOR THIS PROCESS: Glyceraldehyde-3-phosphate dehydrogenase (GAPDH) –

1. GAPDH allows NAD to pull a hydrogen off GAP  reduced (NAD + H)  forming NADH 
from NAD to NADH  NADH

2. PO4 attacks the GAP molecule & release it from the enzyme to yield the final product:
1,3-biphosphoglycerate (example of a high energy PO4 group; (1st step that produces HIGH
ENERGY COMPOUND in glycolysis), NADH, & Hydrogen atom

PRODUCT OF STEP 6:

GAP + NAD + Pi  (REVERSIBLE) 1,3-biphosphoglycerate + NADH + Hydrogen atom


STEP 7: PHOSPHORYLATION OF ADP (Formation of phosphoglycerate) = ATP PRODUCING STEP

 1,3-biphosphoglycerate - example of a high energy PO4 group  energy used in the

formation of ADP to ATP
 From 1,3-biphosphoglycerate converted to 3- phosphoglycerate
 ENZYME USED IN STEP 7: Phosphoglycerokinase (KINASE because of the process
phosphorylation)
 Loss of PO4 group from the starting material (SM: 1,3-biphosphoglycerate  “bi” PO4
meaning have two PO4 = instead of adding another PO4  in step 7 there would be
reduction of PO4  loss of PO4 group)
 The PO4 is transferred (“kinase” enzyme) to a molecule of ADP that yields the first ATP in
GYLCOLYSIS
 STEPS 1 & 3: used the ATP  2 ATP ; STEP 7: produced the ATP  2 molecules of 1,3-
biphosphoglycerate 2 ATP
 CONDITION: since we used 2 ATP for steps 1 & 3 so cancel out = 2 ATP produced in STEP 7
because we need to “pay off” leaving as a net balance of: 0 ATP

STEP 8: ISOMERIZATION or the FORMATION OF 3-PHOSPHOGLYCERATE

 Since “isomerization” – there would be rearrangement of the position of the phosphate

groupn on the 3-phosphoglycerate molecule (transfer the PO4 from C3 position to C2)
 ENZYME: phosphoglycerate mutase (PGM) or phosphoglyceromutase (when we say mutase
enzyme it would catalyzes the transfer of a functional group ffrom one position to another)
 PRODUCT OF STEP 8: 3-phosphoglycerate  2- phosphoglycerate

STEP 9: DEHYDRATION OR THE FORMATION OF PHOSPHOENOL PYRUVATE (high energy rich

compound aside from step 6; 2nd step that produces HIGH ENERGY COMPOUND in glycolysis)

 Conversion of two 2-phosphoglycerate to two phosphoenol pyruvate (PEP)

 ENZYME: ENOLASE or phosphopyruvate hydratase
 PRODUCT: PEP (PHOSPHOENOL PYRUVATE)

STEP 10: PHOSPHORYLATION OF ADP OR THE FORMATION OF PYRUVATE (2nd ATP-PRODUCING STEP)

 Last step in the glycolysis

 Convert the 2 PEP to two molecules of pyruvate
 ENZYME responsible for the conversion: pyruvate kinase
 transfer of PO4 group; the PO4 group attached to the 2C of PEP is transferred to the
molecule of ADP (get PO4 group from PEP  ADP  ATP)
 PRODUCT: since 2 pyruvate = 2 ATP molecules; net balance: 2 ATPs (no pay-off this time)

SUMMARY:

 Consumed 2 ATPs & generated 4 ATPs (from step 7 & 10)

 Step 1 &3 (energy-consuming steps) 7 & 10 (energy-producing/generate steps) – ATP related
processes
 STEP 1 = Glucose  Glucose-6-PO4
  STEP 3 = Fructose-6-PO4  Fructose-1,6-biphosphate (FBP)
 STEP 7 = 2 (1,3-biphosphoglycerate)  2 (3-phosphoglycerate)
 STEP 10 = 2 PEP (phosphoenol pyruvate)  2 pyruvate
 STEP 1 & 3 = -2 ATPs  STEP 7 & 10  4 ATPs  +2 ATPs

Glycolysis - 1 GLU = 2 PYRUVATE OR PYRUVIC ACID = ATPs

What will happen to NADH?

 Oxidative phosphorylation –
o a biochemical process by which ATP is synthesized from ADP (ADP  ATP)
o the result of the transfer of electrons & H+ ions from NADH or FADH2 (Flavin adenine
dinucleotide) to Oxygen through to the electron carrier involved in that electron transport
chain producing ATP
o metabolic pathway wherein the cell used this enzymes to oxidize the nutrients, thereby,
releasing energy which is used to reform ATP
o IN THE EUKARYOTES:
 Oxidative phosphorylation takes place inside the mitochodria (because the inner
mitochondrial membrane lack NADH transporter & the NADH is produced in the cytosol)
 NADH: produced in the cytosol, therefore, it cannot DIRECTLY enter the mitochondrial
matrix. But the 2 electrons of NADH can enter the mitochondrial matrix from the cytosol
by using the substrate shuttles
 NADH cannot easily enter the mitochondrial matrix because 1.) NADH is produced from
CYTOSOL, 2.) the mitochondria have the barrier that separate the inner membrane to
 the intermembrane space (outside portion of the mitochondria) so the 2 electrons of
NADH is transported from the cytosol to the matrix using the substrate shuttle
(transport chains)
o EXAMPLES OF SUBSTRATE SHUTTLES:
1. Glycerol PO4 shuttle (brain & skeletal muscles) – 2 electrons are transferred from
NADH to dihydroxyacetone PO4 (DHAP) with the help of the enzyme
glycerophoshate dehydrogenase. Therefore, under glycerol PO4 shuttle it results in
the synthesis of 2 ATPs for every cytosolic NADH synthesized.
2. Malate-Aspartate shuttle (heart, liver, & kidneys) – produces NADH instead of
FADH2 (unlike in GPS – enters the mitochondrial membrane then oxidized and
converted to FADH2; for every 1 FADH2 = 2 ATPs but for NADH = 3 ATPs)
 Produces NADH in the mitochondrial matrix therefore it yields 3 ATPs per
each cytosolic NADH oxidized by the enzyme malate dehydrogenase.
UNDER GLYCOLYSIS:

1. Substrate Level Phosphorylation or the Embden Meyerhof Pathway (10 steps glycolysis) = 2 ATP
used – 4 ATP produced = 2 ATP
2. Oxidative Phosphorylation = 2 NADH (1 NADH electron that enters the mitochondrial membrane
yields 3 ATP via the MALATE ASPARTATE SHUTTLE x 2) = 6 ATPs or 2 NADH (1 NADH electron
that enters the mitochondrial membrane yields23 ATP via the GLYCEROL PO4 SHUTTLE x 2) = 4
ATPs
o 4-6 ATPs

DIFFERENTIATION OF SUBSTRATE LEVEL PHOSPHORYLATION W/ OXIDATIVE PHOSPHOLYRATION

SUBSTRATE LEVEL PHOSPHORYLATION OXIDATIVE PHOSPHOLYRATION
1. No middle man – happens when ADP is 1. Have middle men – in the form of NADH &
converted to ATP by the direct transfer of PO4 ETC to produce the ATP
group
2. DIRECT PROCESS  DIRECT TRANSFER – the 2. The phosphate comes from a pool of
phosphate group is donated & transfer from a inorganic PO4 instead of directly from
phosphorylated intermediate in contrast to OP another molecule. (The energy needed to
which have aids to produce ATP (e.g. step 7: phosphorylate ADP comes from a proton
from 1,3-biphosphoglycerate  1 PO4 group gradient together with ETC & NADH)
transfer to  ADP  ATP yielded
3. LOCATION: cytoplasm 3. LOCATION: inner mitochondrial membrane

INTERMEDIATE REACTION (after GLYCOLYSIS the product: 2 pyruvic acid or pyruvate)

2 PYRUVIC ACID would undergo two reactions:

1. Aerobic reaction – would undergo oxidative decarboxylation of pyruvate

o ENZYME: pyruvate dehydrogenase complex
o PRODUCT: 2 molecules of Acetyl CoA that would enter Citric acid cycle or Kreb’s Cycle
o Acetyl CoA product  ready for Kreb’s cycle & Fatty Acid synthesis
o Meaning to say if it enters KREB’s CYCLE = it undergoes the OXIDATIVE DECARBOXYLATION
o PRODUCES 2 Acetyl CoA = 2 NADH = 2x3 = 6 ATPs

2. Anaerobic reaction (without the presence of OXYGEN) – the pyruvic acid/pyruvate  lactic acid
o ENZYME: lactate dehydrogenase
o PRODUCT: lactic acid
o When lactic acid is produced in the body during intense exercise the lactate accumulates in
the muscles causing a drop in the intracellular pH & potentially would result to MUSCLE
CRAMPS. Hence, present in muscle fatigued.
o If diffuses in the blood stream it can be used by the liver to make glucose
o If there is a level of lactate/elevated concentration especially in the plasma = LACTIC
ACIDOSIS
THE 2 MOLECULES OF PYRUVIC ACID THAT ENTER THE AEROBIC REACTION (UNDERGOING THE
OXIDATIVE DECARBOXYLATION) WOULD RESULT TO TWO ACETYL CoA  ACETYL CoA WILL NOW ENTER
THE MITOCHONDRIA FOR KREB’S CYCLE

KREB’S CYCLE/TCA (TRICARBOXYLIC CYLE)/ CITRIC ACID CYCLE:

o COMPOSED OF 8 STEPS
o named after Hans Adolf Krebs
o final pathway where the oxidative catabolism of CHO, amino acids, & FA converge their carbon
skeletons being converted to CO2
o it occurs in the INSIDE THE MITOCHONDRIA & this is in close proximity to the Electron Transport
Chain (ETC)  which later on oxidize the co-enzyme NADH & FADH2 (produced by the Kreb’s
cycle)
o example of an AEROBIC PATHWAY because Kreb’s cycle requires OXYGEN
o series of chemical reaction that are used by all aerobic organism  used to generate energy
through the oxidation of acetate (the product Acetyl CoA was from the 2 pyruvate produced
after the glycolysis) that is derived from CHO, fats & CHON to be converted to CO2 & chemical
energy in the form of ATP
o PURPOSE: burn the Acetyl CoA that is made from fats, glucose, & proteins to be able to make
the ATPs incorporation with the oxidative phosphorylation
o GOAL: to produce CO2

STEP 1: FORMATION OF CITRATE & the process involved is CONDENSATION

 ACETYL CoA – major fuel for Kreb’s cycle; the MAIN SOURCE of ACETYL CoA is oxidative
decarboxylation of pyruvate
 Acetyl CoA  will undergo Kreb’s Cycle  BY THE PROCESS OF CONDENSATION  will donate
acetyl group to the 4 carbon OXALOACETATE by the enzyme citrate synthase  forming the
PRODUCT: CITRATE (6 CARBON achiral compound)
STEP 2: FORMATION OF ISOCITRATE through the process of ISOMERIZATION

 Citrate is isomerized to ISOCITRATE

 CITRATE with the aid of the ENZYME: Aconitase by the process of dehydration  producing CIS-
ACONITASE with the aid again of the ENZYME: Aconitase by the process of hydration  ISOCITRATE
(A CHIRAL COMPOUND; from citrate a achiral cmpd  under isomerization  isocitrate A CHIRAL
COMPOUND)

STEP 3: OXIDATION OF THE ISOCITRATE & FORMATION OF CO2 by the processes of oxidation &
carboxylation (1st STEP TO PRODUCE NADH & CO2)

 Isocitrate is oxidized & decarboxylated by isocitrate dehydrogenase to alpha-ketoglutarate

producing NADH & CO2
 Isocitrate acted upon the isocitrate dehydrogenase  NAD is converted to its reduced form: NADH
(NAD  NADH + H+)  producing oxalosuccinate (H+  CO2)  alpha-ketoglutarate

STEP 4: OXIDATION OF ALPHA-KETOGLUTARATE & FORMATION OF CO2 by the processes of oxidation &
carboxylation (2nd STEP TO PRODUCE NADH & CO2)

 alpha-ketoglutarate is oxidatively decarboxylated to succinyl CoA by alpha-ketoglutarate

dehydrogenase complex (enzyme very similar to pyruvate dehydrogenase & activated by CALCIUM,
inhibited by NADH & succinyl CoA)
 alpha-ketoglutarate + NAD + H+ + CoA-SH aided by the enzyme alpha-ketoglutarate dehydrogenase
complex producing  succinyl CoA + NADH + CO2 + H+

STEP 5: THIOESTER BOND CLEAVAGE in succinyl CoA & PHOSPHORYLATION of GDP (substrate level
phosphorylation example) = (STEP PRODUCING GTP)

 Succinyl CoA is cleaved by succinyl thiokinase or succinyl CoA synthetase producing the products:
succinate & GTP (Guanosine triphosphate)
 Succinyl CoA acted by the enzyme succinyl CoA synthetase  forming succinyl phosphate then
acted again by the enzyme succinyl CoA synthetase  SUCCINATE
o Succinyl CoA releases energy, which is trapped by the formation of GTP (GDP  GTP)
o GTP function: similar to ATP which is to store energy in the form of a high energy phosphate
bond

STEP 6-8: is a sequence of functional group changes

STEP 6: OXIDATION OF SUCCINATE = (STEP PRODUCING FADH2)

 Succinate is oxidized to FUMARATE by succinate dehydrogenase producing FADH2 (FADH2 = 2 ATPs
& if NADH = 3 ATPs)
 Succinate aided by succinate dehydrogenase  FUMARATE + FADH2 (FAD is reduced to FADH2)

STEP 7: HYDRATION OF FUMARATE

 Fumarate is hydrated by MALATE by fumarase

STEP 8: OXIDATION OF L-MALATE to REGENERATE OXALOACETATE (in the end it goes back to its
/generate to its starting point: OXALOACETATE) = (3rd STEP TO PRODUCE NADH)

 Malate is oxidized to oxaloacetate by malate dehydrogenase producing NADH ‘

IN SUMMARY of ONE ROUND OF KREB’S CYCLE:

(***NOTE 1 NADP = 3 ATPs; 1 FADH2 = 2 ATPs; GTP = 1 ATP)

3 NADH (STEP 3,4 & 8) = 3x3 = 9 ATPs
1 FADH2 (STEP 6) = 1x2 = 2 ATPs
1 GTP (STEP 5) = 1 ATP
-----------------------------------------------
12 ATPs per cycle x 2 because we have 2 pyruvates that will enter the cycle, SO A TOTAL OF: 24 ATPs
WHOLE KREB’s CYCLE: 24 ATPs
1 CYCLE: 12 ATPs

*GDP/GTP binding protein activity is regulated by the binding & hydrolysis of GTP. These proteins are
crucial for signal transduction events resulting in cell division, cytoskeleton management, & sensory
perception.

SUMMARY
PROCESS NO. of ATP PRODUCED
1. Glycolysis (SUBSTRATE LEVEL SUBSTRATE LEVEL PHOSPHORYLATION – 2 ATPs
PHOSPHORYLATION & OXIDATIVE OXIDATIVE PHOSPHOLYRATION – 4-6 ATPs
PHOSPHOLYRATION) TOTAL OF 6-8 ATP
2. Intermediate pathway 2 Acetyl CoA = 2 NADH = 2x3 = 6 ATPs
6 ATP
3. KREB’S CYCLE 24 ATP
TOTAL: 36-38 ATP
ELECTRON TRANSPORT CHAIN /ECT
 Electrons usually are not floating around the space particularly in the mitochondria they are stuck in
some atoms or others  consequence: when one thing losses ELECTRON something else must gain
them (OXIDATION & REDUCTION = a simultaneous process; if one molecule is oxidized other will be
reduced in simultaneous procedure or vice versa)
 Every oxidation of something must be coupled to the reduction of something else. So the molecule
or atom that loses an electron has been oxidized & the one that gains them reduced (ViLeORA &
VdGeROA).
 Oxidants/ oxidizing agents = molecules or compounds that oxidizes other compounds or molecules
(undergone REDUCTION or being reduced in the process)
Reductants/ reducing agent = molecules or compounds that reduces other compounds or molecules
(undergone OXIDATION or being oxidized in the process)
 EXAMPLES: Pyruvate  reduced to  lactate
Lactate  oxidized to  pyruvate
NADH (reduced form)  oxidized to  NAD
NAD reduced to NADH
Pyruvate & NAD = oxidizing agent
NADH & lactate = reducing agent
 As the fuel molecules are oxidized the electrons that have been lose are used to make NADH &
FADH2
 FUNCTION OF ETC & Oxidative Phosphorylation is to take these molecules (NADH &FADH2) &
transfer them to oxygen making ATP in the process
 LOCATION: inner mitochondrial membrane
 Flavin adenine dinucleotide or FADH2 (reduced form or the addition of H+  original form: FAD ;
FADH2 = 2 ATPs)
 Nicotinamide adenine dinucleotide or NADH (reduced form or the addition of H+  original form:
NAD; NADH = 3 ATPs)
 NADH is a product of both the glycolysis & Kreb’s cycle
 FADH2 is only produced in Kreb’s cycle
 Intermembrane space – outside the mitochondria
 Mitochondrial matrix – inside surroundings of mitochondria; e.g. have protons that will be pumped
from the inner mitochondrial membrane out to the intermembrane space through the complexes
particularly 1, 3 & 4 while complex 2 does not DIRECT promote proton pumping but it does promote
pumping through complex 3 & 4
 COMPLEXES 1,3 & 4: can directly pump protons from the matrix to the intermembrane while
complex 2 not direct  but it does promote pumping through complex 3 & 4
 EVERY TIME PROTON PUMPING OCCURS = requires ENERGY (so these complexes get these energy
by transferring electrons through a series of coupled reactions = that’s why they are called ETC bcs
these chains have connection from these complexes starting from complex 1-2-3-4.
 The inner mitochondrial membrane has enzymes & electron carriers needed for ETC. So, within this
membrane there are 4 distinct CHON complexes containing some of the molecules that are needed
for electron transport chain:
o Complex 1: NADH-coenzyme Q reductase (inhibited rotenone which is a rat poison)
 Largest protein complex
 Contains 40 sub-units including FMN (Flavin mononucleotide) or FeSP (Iron sulfur
protein)
 Received electrons coming from NADH (from sugar metabolism  will go to ETC  will
deposit 2 high energy electron to COMPLEX 1)
 When these small electrons pass through complex 1: will pass through a long chain of
redox centers (sub-units)  and when it final exit the complex 1  it will donate the 2
electrons to a co-enzyme Q molecule that will transfer it to complex 3
 COMPLEX 1  co-enzyme Q molecule will transfer 2 electrons to  COMPLEX 3
 STEP 1: interaction of NADH with FMN will oxidized the NADH  NAD & passes 2 H+ & 2
electrons to the FMN which is also reduced to FMN2 (FMN  FMN2)
 Last step: re-conversion of FeSP
 the COENZYME Q comes from a QUINONE molecules containing 10 isoprene units
attached to the quinone units
o Complex 2: Succinate-coenzyme Q reductase
 PURPOSE: process the FADH2 from the citric acid cycle/Kreb’s cycle
 The reaction of electrons when entering the complex 2 is almost the same with
complex 1
 Smaller than complex 1 & have 4 sub-units including 2 FeSP (Iron sulfur protein)
 The 2 electrons that come from complex 1 will not enter complex 2  these electrons
will be directly aided by CON-ENZYME Q & transport it to complex 3
 Almost the same with complex 1; the only difference is  high energy molecules will
enter but instead of NADH  FADH2 will enter
 Like complex 1 the electrons will pass through the redox centers (sub-units) inside
complex 2  and when it final exit the complex 2  donating them to CO-ENZYME Q 
co-enzyme Q molecule will transfer it to complex 3
 o Complex 3: Coenzyme Q- Cytochrome C reductase (inhibited by Antimycin A)
 Has 11 different sub-units & also includes FeSP (Iron sulfur protein) & cytochromes
(heme containing protein which reversible oxidation & reduction of an iron atom occur)
 The electron will enter complex 3  and will pass through redox centers before
reaching the cytochrome C  cytochrome C will then carry electrons from complex 3 to
complex 4
o Complex 4: Cytochrome C oxidase (inhibited by cyanide & CO)
 Has 13 sub-units including 2 cytochromes (the cytochrome present is in C oxidase)
 When the electron enters the complex 3  the ETC ends here, where the 4 electron
converts a molecule to oxygen converts to 2 molecules of water
 PRESENCE OF OXYGEN IS IMPORTANT IN THE ETC especially in the complex 4  because oxygen
will serve as the final acceptor of electrons in the last complex  therefore in the ABSENCE of
OXYGEN ETC comes to a halt & the ATP synthesis will also stop
 The electron transfer at the three classic sites of phosphorylation particularly complex 1, 2, & 3 
the protons are pumped out the mitochondria to cytoplasm. So this proton pumping makes the
mitochondria ALKALINE
 F1FO ATPase enzyme that would allow the protons back to the mitochondria (from the
intermembrane space back to  the inner mitochondrial matrix)
 INHIBITORS THAT CAN BLOCK THE FLOW OF ELECTRONS AT THE SPECIFIC SITE & CAN ALSO INHIBIT
THE ELECTRON FLOW & ATP SYNTHESIS:
o ROTENONE  block the electron flow at complex 1
o Antimycin A  complex 3
o cyanide & CO  complex 4
 SUMMARY
PURPOSE OF 4 COMPLEXES: when protons are being produced from matrix to the intermembrane
space ENERGY is needed  to produce this energy  these protein complexes will transport
electrons that will also be the source of their energy:
o starting from COMPLEX 1 with 40 sub-units  2 electrons will enter (from the NADH) 
will pass through to the redox centers  exit the complex 1  donate the electrons to
coenzyme Q  Co-enzyme Q will then transport the 2 electrons to  COMPLEX 3
o COMPLEX 2 (composed of 4 sub-units)  also similar to complex 1 however MUCH
SMALLER THAN THE COMPLEX 1 & the electrons will be coming from FADH2 instead of
NADH  electrons will enter complex 2  pass through to the redox centers  exit the
complex 1  donate the electrons to coenzyme Q  Co-enzyme Q will then transport the 2
electrons to  COMPLEX 3
o COMPLEX 3 (composed of 11 sub-units) electron will enter complex 3  and will pass
through redox centers before reaching the cytochrome C  cytochrome C will then carry
electrons from complex 3 to complex 4
o COMPLEX 4 (composed of 13 sub-units)  electron enters the complex 3  the ETC ends
here, where the 4 electron converts a molecule to oxygen converts to 2 molecules of water
 FINAL PRODUCT FOR ETC: WATER
 SECONDARY PATHWAY FOR GLUCOSE METABOLISM

1. Hexose Monophosphate Shunt (HMP shunt or pathway)/ Pentose Phosphate Pathway (PPP)/
Phosphogluconate Pathway
 NADH – needed for the biosynthesizes of fatty acid (particularly NADPH)  NADPH is a reducing
agent that is reserve for biosynthetic pathway particularly the FA synthesis  hence, HMP shunt
is called upon when reducing equivalents & fatty acids synthesis is turned on
o primarily the regulation is through the supply & demand of NADPH at the same time
o NADPH is also used to keep the cellular & mitochondria glutathione in the reduced form
through the action of the enzyme  glutathione reductase
 Ribose-5-PO4 – used for the synthesize of nucleic acids (particularly D-ribose); C5 sugar for the
RNA & DNA synthesis
2. Glucose Glucoronic Pathway/GLUCORONIC ACID PATHWAY (alternative oxidative pathway for
glucose)
 This concerned with the synthesize of glucoronic acid, pentoses & vitamin c/ascorbic acid
 D-glucuronate – serve as detoxifying agent for foreign organic compound
 L-ascorbic acid – Vitamin C
 Quantitatively a minor route of glucose metabolism
 Involves the conversion of glucose-6-PO4 into glucoronic acid
 LIVER is the major tissue performing this function (ORGAN INVOLVED: LIVER)
 the enzymes involved are located in the CYTOSOL
 Glucoronic acid is a component of glycosaminoglycans (which is used in the detoxification of
non-polar toxic compounds e.g. bilirubin & steroid hormones)
 CLASSIFIED INTO 3 STAGES:
o Conversion of GLUCOSE-6-PO4 to UDP glucose
o Conversion of UDP glucose to UDP glucoronate
o Unused UDP glucoronate can be converted into pentose phosphate pathway  which
then can be connected to glycolysis through the non-oxidative phase of the HMP shunt
TERMS TO REMEMBER IN CHO METABOLISM:

 GLYCOGENESIS  glycogen is synthesized from molecules of the alpha-D-glucose

o LOCATION: CYTOSOL
o Requires energy supplied by ATP as well as UTP (uridine triphosphate)
o While the excess insulin will promote the glucose conversion into glycogen (stored form of
glucose in the liver & muscle cells)
 GLYCOGENOLYSIS  opposite of glycogenesis; breakdown or the degradation of glycogen
o Degradative pathway that mobilizes the stored glycogen in the liver & skeletal muscle
o Not a reversal of synthetic actions instead it has separate sets of cytosolic enzymes that is
required
o When epinephrine & glucagon react with CHON coupled receptors  can stimulate the
GLYCOGENOLYSIS  elevation of BLOOD SUGAR LEVELS that is needed to provide energy
for exercising muscles
o while the insulin  inhibit or with inhibitory action because the main function of insulin is to
increase the storage of glucose in the form of glycogen
 GLUCONEOGENESIS  sugar is derived from other sources aside from glycogen  COMES FROM
NON-CARBOHYDRATE SUBSTRATE e.g. glycerol, lactate, & other glucogenic amino acid (common
sources of glucose from the process of gluconeogenesis)
 GLYCOGENESIS  conversion of glucose to glycogen (composed of alpha 1,4-D glucose with its
branches that are attached by alpha-1,6 linkages)
 Liver glycogen is used to maintain blood glucose during fasting & exercise
 Muscle glycogen is used to produced ATP for muscle contraction

 GLYCOGENOLYSIS  breakdown of glycogen to form glucose (“lysis”  breakdown)

 Glucose-6-phosphate in the muscle and glucose in the liver
 GLUCONEOGENESIS  synthesis of glucose from a
non-carbohydrate substance

GLYCOGEN STORAGE DISEASE 

-deficiency of a specific enzyme involved in the
metabolism of glycogen
-diseases wherein large amount of glycogen are
accumulated

TYPE 1 - VON GIERKE  a condition wherein the body cannot breakdown glycogen (since glycogen is the
stored form of glucose in muscles & liver)  normally this is broken down every time the body needs
energy
 Occurs when the body lacks the enzyme phosphatase that releases glucose from glycogen 
causing abnormal amounts of glycogen to tissues  leading to LOW BLOOD SUGAR LEVEL
TYPE 7 – TARUI DISEASE  also known as phosphofructokinase deficiency or the glycogen storage
disease type 7
DIGESTION OF THE DIETARY LIPIDS  occurs starting from the stomach then continues to the SI (small
intestine) UNLIKE IN CHO that starts with the MOUTH
 Since LIPIDS have hydrophobic nature  dietary lipids especially those containing long chain
fatty acids must be emulsified in the SMALL INTESTINE by the peristaltic action & presence of
BILE SALTS (which serves as a detergent that will act as surfactant) for efficient degradation like
for example:
o TAG (obtained from milk that contain short to medium chain of FA that can be degraded
in the stomach by the enzymes lactases or lingual lipase & the gastric lipase
o Cholesteryl esters phospholipids & TAGs are degraded in the SI particularly with the
enzymes secreted by the pancreas (most important enzymes produced by the pancreas:
phospholipase A2, pancreatic lipase, & cholesteryl esterases)
  BETA-OXIDATION occurs in the mitochondria
 THE PRODUCTS OF BETA-OXIDATION ARE KETONE BODIES  KETONE BODIES that are formed
from fat metabolism are responsible for breath odor when undergoing keto diet (or not eating)
 e.g. of ketone bodies Acetone, acetoacetic acid & BHA
 PRODUCT OF BETA-OXIDATION OF FATTY ACIDS  ketone bodies e.g. Acetone, acetoacetic acid
& BHA

 4 steps are involved in BETA-OXIDATION

 STEP 1: Once the FA has been transported to the mitochondrial matrix via the carnitine pathway 
STEP2: beta oxidation of the fatty acyl-CoA (occurs in the mitochondria)
 PHARMACOGNOSY

Pharmacognosy – formed from two Greek words  pharmakon (drug) and gnosis/gignosco (study)
 First coined by J.A. Schmidt; Venia; 1811. Introduced by C.A. Seydler in his work Analecta Pharmacognostica
(1815)
 Difference of PCOG to PCOL 
o PCOG  study of drugs particularly those derived from NATURAL RESOURCES (plants)
o PCOL  study of all information about drugs (drugs whether from natural or synthetic resources)
 Covered all information on medicines from natural sources:
o Plants
o Animals
o Microorgnisms
o Inorganic source
 an applied science that deals with the biologic, biochemical, economic of natural drugs and their constituents
DRUG/SUBSTANCE NATURAL SOURCE Scientific name of the source
Insulin Animal source Bos Taurus (bovine; cattle;cow)
Sus domesticus (pig; swine)
Digoxin Plant source Digitalis lanata  DIGOXIN
Digitalis purpurea  DIGITOXIN
Penicillin Microorganism Penicillium notatum (mold)
Morphine Plant source Papaver somniferum (opium poppy)
Urokinase Animal source Human urine
Sambong Plant source Blumea balsamifera
Colchicine Plant source Colchicum autumnale or Crocus
autoimmale (Autumn crocus)
Erythromycin Microorganism Streptomyces erythreus
Bacitracin Microorganism Bacillus subtilis  discovered from a
wound of a 7-year-old-girl named Tracy
Conjugated estrogen Animal source Urine of mare (horse  Equus caballus)

 embraces the knowledge of:

o HISTORY  e.g. ”Cinchona” plant  first identified and named after the wife of the Viceroy of Peru
named “Ana” from Cinchon = CINCHONA
o DISTRIBUTION  e.g. Clay tablets of Babylonians, Paper scrolls of Egyptians  although these are not
“plants” majority of the knowledge now a days regarding plants have been documented in these clay
tabs and scrolls that are used by the Babylonians & Egyptians
o Cultivation, Collection, Selection, & Preparation

HISTORY
Hippocrates Father of Modern Medicine  paved the way to modern
medicine knowledge that sickness can be cured if addressed the
abnormality or problem in the body
Aristotle Focus his studies on ANIMALS
PARACELSUS  Philippus Aureolus Theoprastus Focus his studies on PLANTS  Father of Botany
Bombastus von Hohenheim
CONTRIBUTORS BOOK/Manuscript/Encyclopedia/Compilations
Pedanios Dioscorides De material medica libri crinque
Christianus Aenotheus Seydler Analecta Pharmacognostica  introduced the term
Pharmacognosy (1815)
Claudius Galen Antidotaria and Receptaria
Johann Adam Schimdt Lehrbuch der Materia medica  first mentioned the term
 pharmacognosy in a book; first coined the term 1811
India Vedas  alternative forms of medicine e.g. Ayurveda
China  Emperor Shen Nung Pen T’sao  compilation of drugs based on hierarchy:
 Emperor drug – most potent
 Ministry – average potency
 SERVANT – least potent; almost inactive

**NOTE: De material medica libri crinque of Pedanios Dioscorides  has a significant contribution in the field of
pharmacognosy as it has a detailed explanation of the morphology, description or writings of the characteristics &
uses, drawings & illustrations of plant source.

MIDDLE AGES  19TH CENTURY (1800-1900s): AGE OF INNOVATION AND CHEMISTRY (from plant source to
active ingr)
 From finding new medicaments from vast world of plants to finding the active constituent/constituents that
accounted for their pharmacologic properties
 before antiquity people heavily relied on “PLANTS” (plant parts/species) as the sources for drugs  in the 19
th

century they identified/isolated the MAIN ingredients/constituents which were responsible for the effects

PERSON WHO ISOLATED SUBSTANCE/S ISOLATED & INDICATION

Joseph Caventou – French Pharmacist  Quinine  anti-malarial
 Caffeine (Coffea arabica)  CNS stimulant
Pierre Robiquet – French Pharmacist  Codeine  an opioid structure so innately has analgesic property but have
more significant antitussive property (because of the addition of methyl
group or methoxy group in the SAR rendering it with minimal analgesic &
more antitussive property  L-codeine isomer)
Friedrich Serturner – German  Morphine  for mild to severe pain
Pharmacist  prototype of opioid analgesics
Rudolf Brandes - German Pharmacist  Hyoscyamine  anticholinergic; managing spasms bcs of its anticholi
property
 Noscapine  antitussive
Rudolf Brandes + Philipp Geiner -  Atropine  anticholinergic
German Pharmacists
Johannes Buchner – German Salicin  anti-inflammatory, analgesic, antipyretic bcs it is the parent
Pharmacist compound of ASA/aspirin
 Nicotine  smoking deterrent for nicotine withdrawal symptoms
Carl Koller – American Surgeon  Cocaine  anesthetic
 under sched II so does not have much of significant
benefits & its additive property outweigh the risk
Albert Hoffman  LSD  Lysergic Acid Diethylamide
 MOST SPECIFIC PSYCHOTOMIMETIC AGENT = highly potent
& not safe for ingestion
 under sched I: have high potential for abuse & has no
currently accepted pharmaceutical treatment
** Johannes Buchner a German Pharmacist isolated salicin  from WILLOW BARK/TREE  Salix purpurea

DEFINITION OF TERMS:
 ACTIVE CONSTITUENTS responsible for the therapeutic or the substances with the pharmacologic activity
o TWO CLASSIFICATIONS:
 Pure or single chemical entity  glycosides, terpenoids, steroids, alkaloids, peptides
 Mixtures of principles  gums, fixed oils, fats, volatile oils, and resin combinations
 SUBSTANCES CLASSIFICATION
Lavender oil (Lavandula angustifolia) Mixture  a volatile oil (have FA, glycerol, ester)
Senna Single  glycoside (anthraquinone)
Coconut oil Mixture
Psyllium Mixture  a fiber composed of CHO
Morphine Single  alkaloid

 INERT CONSTITUENTS  inactive ingredient or excipients

PLANTS USE/S
Cellulose  homoglycan composed of purely CHO  PLANTS: Cell wall  Structural constituent
glucose  Pharmaceutical: adsorbent, thickening agent
Suberin, lignin, cutin  PLANTS: Rigidity, protective barriers or protection to control
the respiration or evaporation of constituents
Starch  PLANTS: Storage
Albumin  Pharmaceutical: to maintain osmotic pressure
Coloring agent
ANIMALS – majority from CHON USE/S
Keratin
Chitin  homoglycan (NAG & NAM)  Cell wall of fungi & backbone in invertebrates
 Structural constituent
Muscle fiber
Connective tissue
Collagen  Structural constituent of human skin
Glycogen  Storage form in animals
 Glycogen  Glucose = Glycogenolysis (breakdown of
glycogen to glucose-1-PO4
 Secondary plant substances – constituents that are extracted, crystallized and purified for therapeutic use.
o 3 PRINCIPAL FACTORS that influence the secondary plant substances:
 1. Heredity (genetic composition)
 e.g. Digitalis purpurea and D. lanata  almost same family, same appearance but difference
species
 induced or affect both the qualitative and quantitative changes or characteristics of
secondary constituents that’s why  GUIDELINES FOR COLLECTING & HARVESTING of a
particular plant parts (e.g. leaves or flowers) for extraction, & purification should be MATURE
already because if young/bloomed = low levels of secondary constituents
 2. Ontogeny (stage of development)  prefer: mature plant parts
 3. Environment  produce variations in secondary plant
 Preferably: DRY WEATHER with MINIMUM HUMIDITY
 For digitalis  afternoon (dry weather)
 MAJORITY: MORNING
 Volatile oil containing plants  do not harvest during summer (low volatile oil constituent)
 Flowers of plant  dry weather & during the morning
 Mesnstruum – solvent that have been used to soaked the plant constituent part to be able to extract the
secondary plant constituent
 Marc – undissolved portion of the drug that remains after the extraction process
 Extract – the particular portion that have been removed from the marc
 Graphic Source & Habitat:
 o Indigenous – plants growing in their native countries
o Naturalized – plant grown in a foreign land or in a locality other than their native countries
 E.g. Datura stramonium – indigenously from Europe but have been produced in the US or have been
introduced into US from Europe  have been naturalized
 Ethnobotany – it is a broad term referring to the study of plants by humans
 Ethnomedicine – it refers to the use of plants by humans as medicine
 Traditional medicine – it is the sum total of all non-mainstream medical practices, usually excluding so called
“western medicine”
 Pharmacopeia – is a book containing directions for the identification of samples and the preparation of
compound medicines
o Authorized by the government or pharmaceutical or medical societies (e.g. USP NF, British, Japan, India
Pharmacopeia)
 Drug Biosynthesis or biogenesis – study of biochemical pathways leading to the formation of secondary
constituents used as drugs (e.g. Glucose  glycolysis  acetyl CoA  Acetogenins, Terpenes, Steroids or AA
 CHON and nucleic acids  alkaloid)

 Extractives (derivatives) – this term deals with the principle constituents that found in natural substance by
many methods like extraction, distillation, percolation  DISSOLVED portion
 Natural product – is a chemical compound or substance produced by a living organism found in a nature that
usually has a pharmacological or biological activity for use in pharmaceutical drug discovery & drug design
o Can be:
 Entire organism (plant, animal, organism)
 Part of an organism (a leaf or flower of a plant, an isolated gland or other organ of an animal)
 An extract or an exudate of an organism
 Isolated pure compounds

TYPES OF DRUGS DERIVED FROM PLANTS:

 Herbal drugs, derived from specific parts of a medicinal plant
 Compounds isolated from nature
 Nutraceuticals, or “functional food”

VALUE OF NATURAL PRODUCTS – compounds from natural sources play a significant roles in modern medicine 
even with the advent of new technology today to come up with other means to have other sources but we still
value or rely on plants being sources of medicines:
1. They provide a number of extremely useful drugs that are difficult, if not possible, to produce
commercially by synthetic means.
2. Natural sources also supply basic compounds that may be modified slightly render them more effective to
less toxic  e.g. Morphine from P. somniferum  modification: to synthesize other drugs to become less
toxic or Fentanyl  becoming more active
3. Their utility as prototypes or models for synthetic drugs possessing physiologic activities similar to the
originals  e.g. Salicylic acid from salicin  is the prototype for ASA
4. Some natural products contain compounds that demonstrate little or no activity themselves but which
can be modified by chemical or biological methods to produce potent drugs not easily obtained by other
methods  e.g. Baccatin III have no used as a drug or not potent  have activity in the body but of no
pharmaceutical use  extract Baccatin III  isolate & modified to TAXOL from Taxus brevifolia or baccata

TAXONOMY – science of naming organisms as their correct integration to existing system of nomenclature

Papaver somniferum L.

 Genus  Papaver  a group of species, in this case poppies, which are closely related
 Species  sleep-producing; differentiate P. somniferum from the rest of the strains of Papaver
 L.  Linae; indicates the botanist who provided the first scientific description of the species and who
assigned the botanical name
 Family  Papaveraceae (a group of genera sharing certain traits)

DEFINITON OF TERMS:
 Crude drugs – are vegetable or animal drugs that consist of natural substances that have undergone only
the processes of collection and drying
 PREPARATION OF CRUDE DRUGS:
1. Collection TIME is very important for collection
2. Harvesting  proper harvesting
 Collecting & harvesting  is better in mechanical means than hand labor because it is more consistent
and fast in terms of duration
3. Drying  shelf-life rely of the crude drugs rely on this step, hence, removing efficiently the
moisture  if failed to there would be a problem with the final produt as moisture is a source of
microorganism  spoilage
4. Curing  modified drying method; uses nitrate & nitrite to cause drying
5. Garbling  the final step in the preparation of a crude drug. It consists of the removal of
extraneous matter, such as dirt or removal of unnecessary constituent present in the plant part
e.g. soil from the root crops
6. Packaging

STANDARD PACKAGING FOR DRUGS

DRUG PACKAGING MATERIAL
Aloe Goat skin
Colophony Kerosene tins
Asafoetida Well closed container
Senna, Vinca Pressed & baled
MOLECULAR PHARMACOGNOSY  a science dealing with the study of classification, identification, cultivation,
and protection of crude drugs and production of effective elements at molecular level
 Study objects  animal sources & herbal drugs

EVALUATION OF CRUDE DRUGS:

1. Organoleptic – evaluation by means of organs of sense and includes the macroscopic appearance of the
drugs, its odor and taste, occasionally the sound or snap of its fracture, and the fell of the drug to the
touch (highlighted by 5 senses  sight, taste, odor, hear, & feel)

BIOLOGIC ASSAY – assay on living animals as well as on intact or exercised organs often indicate the strength
of the drug or its preparations
 3 MAIN TYPES OF BIOLOGICAL ASSAY METHODS:
o Toxic
o Symptomatic
o Tissue methods

TEST ANIMALS
ANIMALS TESTS
Mice Phenol coefficient  measuring of the disinfecting power or assessing the anti-
infective activity of local anti-infectives that have been newly discovered in the ratio
dilution of phenol to elicit the same potency as to the drug
Turtles Cardiovascular drugs
Rabbits Insulin, tubocurarine
Rats Corticotrophin injection, Vasopressin
Cat Glucagon
Chicken Oxytocin
Pigeon Digoxin

2. Chemical Test – best method of determining the official potency; very reliable test of arriving of
concentration that constituent present in crude drug

TESTS (+) RESULT

Anthraquinone glycosides Borntrager’s test Pink-red color in the ammoniacal (lower) layer
Saponin glycosides Froth test Honey comb froth – 2-3 cm of rise of froth or
Capillary Tube test bubble formation
Hemolysis test
Cardiac glycosides Liebermann-Burchard test Green color
Kedde test Violet
Keller-Killiani test Reddish brown
Cyanophere glycoside  Guignard test Red coloration
cyanogenic

COLOR REACTION TEST

Halphen’s test Cottonseed oil
Baudouin test Sesame oil
Millon’s Olive oil

SPECIFIC CHEMICAL TESTS

Van Urk’s reagent Ergot
Vitali’s test Tropane
Murexide test Purine bases
Lead acetate Gums
 3. Microscopic
4. Physical

ANALYSIS OF VEGETABLE AND ANIMAL DRUGS (some adulterate or unintentional adulterate crude drugs so we
need to analyse)
 Analytical Pharmacognosy  detection of purity of crude drugs
 Purity  depends on the absence of foreign matter  very important because the presence of foreign
matter will affect the physiochemical property (e.g. BP) & quality of the crude drugs
 Quality  sum total of the absence of the characteristics that would make up a product. External and
internal characteristics

ADULTERATION – debasement of an article. While performing chemical test, ADULTERATION can be determined:
CAUSES:
 Erroneous adulteration caused by sharing of similar features or characteristics of the product or absence
of distinguishable characters
 Intentional substitution of high value material by inexpensive substances
 Misuse caused by sharing of similar common names
 Historical use of local substitutes

CONDITIONS OF ADULTERATION
Inferiority Sub standard
Spoilage Due to attack of microorganisms  DRYING – is important as it may contribute to
spoilage
Deterioration Impairment in quality of drug
Admixture Addition of one article to another through ignorance, carelessness or an accident
Sophistication Intentional or deliberate kind of adulteration e.g. intentional admixture, &
substitution
Substitution When an entirely different article is sold or use in place of one required
 CLASSIFICATION OF DRUGS
1. According to morphology  if from leaves, seeds, flowers, root crops
2. According to taxonomy  family
3. According to their therapeutic application  indication
4. According to their chemical constituents  majority of plant classification specifically the secondary
constituents e.g. gums, resin, terpenes, VO

ACCORDING TO THEIR MORPHOLOGY

FLOWER  modified shoot meant for production of seeds (e.g. rose, saffron, pyrethrum; flower buds – clove)

1. Calyx (collective term for all the sepals)  represented

by sepals (petal-like but color green flower), outermost whorl &
generally green
2. Corolla (collective term for all the petals)  represented
by petals, second whorl, & either white or bright colored  bright
colored to attract the pollinators
3. Gynoecium  collectively it would be the carpel or pistil,
third circle, & female part
 Stigma – what receives whatever brought bu the
pollinators passed through the style
 Style
 Ovary
4. Androecium  collectively it would be the stamen, fourth
circle, & male part

The picture provided is considered as a complete flower (both have female and male counterparts) e.g. Gumamela
while an incomplete flower  only one female or male part

BARKS
INDICATION
Cascara (Cascara sagrada) cathartic
Cinnamon (dried cinnamon bark) flavorant
Willow (Salix purpurea) ASA; antipyretic, anti-inflam, analgesis
Cinchona antimalarial agents
Sassafras (dried root bark) flavorant

SHAPES OF BARKS – may duffer based on the method adopted for its
preparation, types of incision, or made to extract or get the bark
1. Flat  when bark is removed from large tree or dried under
pressure e.g. QUILLAJA, ARJUNA
2. Curved  when bark is removed from small branches and the
soft tissues shrink & concave in the inner side e.g. CASSIA & WILD
BERRIES
3. Recurved  when bark is removed from small branches and
the soft tissues shrink & concave in the outside the bark e.g. KUCHI
4. Channelled  the shrinkage of the tissue is to a greater
extent  too much shrinkage of tissues = deep turf e.g. ASHOKA,
CASSIA, Cinchona ledgeriana
5. Quill  when one edge of the bark covers the other e.g.
CASCARA, CINNAMON
 6. Double quill  both edges of the barks are rolled independently e.g. JAVA
7. Compound quill  one quill of the bark id put inside the other quill, handmade shape of the bark e.g.
CINNAMON

3 LAYERS OF BARK

Cork
Cork-cambium  layer after the cork or phellem
 eventually produces cork cells; “phello””gen”
 will generate phellem

Collectively the layers of the bark is called PERIDERM

WOODS – the tissues produced by camdium on inner side

TWO TYPES OF WOOD (Commercially)

1. Heart wood or duramen  innermost central region of
dicot stem or root
 Non-functioning
 non-living
 dark coulored – due to tannins, pigments, gums, and resins
 gives mechanical support  what makes them rigid
 e.g. Sandal wood

2. Sapwood or laburnum – outer region of the wood

 Function: conducts water and food material to plant
 lighter in color
 e.g. Quassia

UNDERGROUND STRUCTURES
1. Rhizome Grow horizontally under the soil E.g. Ginger, turmeric, rhubarb, male fern, orris
2. Tuber – usually store Swollen underground structures E.g. potato, jalap, aconite, dioscorea (kamote)
starch for plant
3. Bulb – middle part not Specialized underground shoot Ex. Garlic, onion, squill
the whole/entire shoot
4. Corm Underground modification of stems E.g. Saffron and colchicum

ACCORDING TO THEIR MORPHOLOGY

PART OF PLANT DRUGS
Seeds Linseed, nutmeg, nux, vomica, mustard
Entire plant or organism Ephedra, cannabis, cochineal, cantharides
Gums Acacia
Latices - dagta Opium, papaya
Dried juices Aloe
Extracts Catechu, agar, gelatin
Leaves Coca, senna, digitalis
Fruits Lemon, fennel, coriander, dried unripe - pepper
 ACCORDING TO TAXONOMY
 Taxonomic Classification – consider the natural relationship or phylogeny among plants and animals

CLASS ORDER FAMILY DRUGS

Angiospermae

SUB CLASS:
Monocotyledonae Graminae (Poaceae) Rice, wheat, maize
Liliaceae Aloe, colchicum
Zingeberaceae Cardamom, turmeric
Dicotyledonae Rutales Rutaceae Buchu, orange, lemon peel
Rosales Rosaceae Wild cherry, almond, rose oil
Leguminosae Glycyrhiza, senna, tamarind
Umbelliflorae Umbelliferae/ Apiaceae (cremocrap fruits) Asafoetida, caraway, fennel
Contortae Apocynaceae Rauwolfia, vinca
Tubiflorae Solanaceae/ Asteridae (cymose flowers) Belladona, datura, capsicum

FAMILY NAME OTHER NAME EXAMPLES

Asteraceae Compositae Sunflower family
Mugwort
Milk thistle  Silimarin
Arecaceae Palmae Betel nut  Areca catechu
Coconut  Cocos nucifera
Caesalpinaceae Cassia fistula, golden shower tree
Apiaceae Umbelliferae Cremocrap fruits, anise
Asteridae Solanaceae Cymose flower, capsules and berries,
nightshade
Lamiaceae Labiatae Mint, peppermint and bilabiate flowers
Rutaceae Citrus fruits
Poaceae Graminae Grains
Fabaceae Leguminosae Legume

FAMILIES EXAMPLES
Citrus family Calamansi
Mint family Peppermint, spearmint, thyme
Sunflower family Mugwort, milk thistle
Palm family Betel nut, coconut
Nightshade family – Solanaceous alkaloid Belladona,, hyoscyamus, datura
Grains family Corn, rice, wheat
Legumes family Sitaw, bataw, patani
Ranunculaceae Aconitum, helleborus  glycoside containing specifically cardiac glycoside
Papaveraceae Saguinaria
Crassulaceae Sub family of Fabaceae (Legumes family)
Apocynacea Apocynum cannabinum –family with anti-cancer property
 ACCORDING TO THEIR THERAPEUTIC APPLICATION

Miotics – Physostigmine, Pilocarpine

Mydriatics – Atropine
Irritant laxative  irritating the lining of the stomach triggering defecation  e.g. castor oil (irritating by the virtue of the
secreted RICINOLEIC ACID), anthraquinone glycoside
Bulk-forming  adsorb water to form bulk to trigger defecation  e.g. gums, cellulose derivatives
Osmotic  attract water increasing the flow of water into intestine producing soften or easier to pass stools  e.g. lactulose
Carbohydrates – “hydrates of carbon” -> Molecule formula: Cn(H2O)n – believe before that for every one C there
would be 1 molecule of water so if 6C = 6H2O -> NOW, it was cleared that this formula is not applicable on all
types of CHO (only applicable to MONOsaccharide)
 building blocks: Monosaccharides (connected by Glycosidic-bond)
 composed of three element: Carbon, Hydrogen, Oxygen (unless N-acetylated like N-acetyl glucosamine, N-
acetylmuramic acid, N-acetylgalactosamine but majority - CHO)
 polyhydroxy compounds with aldehyde (ALDOSE), ketone (KETOSE), or an alcohol as acid functional group
 General formula: Cn(H2O)n
 Others referred it as sugars, amyloses, or glycans
 MOST wide-spread compound involved on the built up of biologic cells
 4 FUNCTIONS OF CHO in the body:
o Source of energy in all organisms (origin for ATP synthesis)
o Can store energy tho it is not their role (role of lipids) in the form of glycogen (stored form of energy
on animals & human) or starch (plants)
o Needed to build the other MACROmolecules (e.g. GLYCOlipids, GLYCOproteins)
o Comprised of one carbohydrate in the nucleic acid – deoxyribose & ribose

2 TYPES OF PHOTOSYNTHETIC REACTIONS IN GREEN PLANTS

PHOTOSYNTHESIS REACTION: CO2 + H2O by the aid of sunlight  glucose (or sucrose) + O2

1. Light reactions  that actually convert electromagnetic energy into chemical potential
 CO2 + H2O by the aid of sunlight  glucose (or sucrose) + O2
 light dependent (sunlight is needed for light reaction)
 LIGHT  source of light: sunlight  in the presence of the PHOTONS
 Once sunlight or the PHOTONS in the sunlight hit the chlorophyll = the electrons in the chlorophyll
get excited = PHOTOEXCITATION or PHOTO OXIDATION
 Photons from the sunlight + chlorophyll (electrons) = PHOTOEXCITATION  then these electrons will
be converted into something that the plants can use or as a source of energy/chemical energy in the
form of ATP & NADPH
 LIGHT REACTION: CONVERSION OF LIGHT ENERGY TO CHEMICAL ENERGY (electrons are converted to
ATPs & NADPH)
 LOCATION: thylakoid membrane
 PRODUCTS: ATP, NADPH, & O2 (the typical PHOTOSYNTHETIC REACTION)

2. Dark reactions/CALVIN CYCLE  consist of the enzymatic reactions that utilize the energy from the light
reactions to fix the carbon dioxide into sugar.
 2H2O + CO2 + light  (CH2O)n + H2O + O2
 Light independent  the source of energy instead of sunlight (photons) is the product derived from
the light reaction (no need for the sunlight/photons of the sunlight)
 Source of energy: Chemical energy (NADPH + ATP)  to stimulate the CALVIN CYCLE
 INPUT: CARBON DIOXIDE + 2H2O + chemical energy from the light reaction =  (CH2O)n + H2O + O2
 PRIMARY USE: Fixed CO2 into sugar
 LOCATION: stroma
 PRODUCT: GLUCOSE (mainly) – SUGAR UNIT
FOR CALVIN CYCLE  SUCROSE
  CALVIN CYCLE  input: 3 molecules of CO2 and product: GAP that will undergo to the production of sugar
 FINAL PRODUCT: sugar
 The first sugar formed during photosynthesis and also a main transport material  SUCROSE
 What type of reaction is responsible for the fixing or reducing of CARBON DIOXIDE into sugar  Dark
reaction or Calvin cycle (Mnemonics  “Ang itim ni Calvin parang carbon dioxide ”  ang cylinder ng CO2
tank ay gray)

CLASSIFICATION OF CARBOHYDRATES
MONOSACCHARIDE (one types of  CRYSTALLINE - usually sweet (e.g. sugar)
sugar) • The simplest sugar; building block of carbohydrates
• Contains 3-10 carbon atoms
• are those carbohydrates that cannot be hydrolyzed into simpler carbohydrates
DISACCHARIDE (is also classified as  CRYSTALLINE - usually sweet (e.g. sugar)
oligosaccharide)
OLIGOSACCHARIDE (2-10 sugar units)  FIBROUS – usually tasteless (e.g. starch)
 When hydrolyzed  MONOSACCHARIDES
POLYSACCHARIDE (10 or more)  FIBROUS – usually tasteless (e.g. starch)
 When hydrolyzed  MONOSACCHARIDES

MONOSACCHARIDES  Monomers of CHO and colorless color crystalline that is freely soluble in water & insoluble
in non-polar
 Ways to name/Nomenclature of monosaccharides: 1. Multiplier prefixes or based on the number of C, 2. With
used of suffixes –ose (ALDOSE) & -ulose (KETOSE), 3. With used of prefixes aldo (aldehyde) & keto (ketone)
Classification based on the # of carbon atoms
# of Carbons Category name Examples
3 Triose Glyceraldehyde, Dihydroxyacetone
4 Tetrose Erythrose
5 Pentose Ribose, Xylulose
6 Hexose Glucose, Fructose, Mannose
7 Heptose Sedoheptulose

 TRIOSES & TETROSE  never at free state

 PENTOSES  product of the hydrolysis of hemicelluloses, gums, & mucilages
 HEXOSES  MOST IMPORTANT monosaccharides found in plants and the first detectable sugars synthesize
by plants
 MONOSACCHARIDES  are ALL REDUCING SUGARS (1,4 glycosidic bond - favored point of hydrolysis of sugars to monosaccharides)
• Monosaccharides containing 4 or more carbon atoms tend to have cyclic structures.
• CYCLIC STRUCTURES – organic compounds that resembles FURAN and PYRAN (e.g. furnose & pyranose)
o Furanose – sugar containing 5C
o Pyranose – sugar containing 6C
Glucose SYNONYMS:  is the most important carbohydrate
Blood sugar  Most abundant form: Beta-D-GLUCOSE
Physiologic sugar  Reducing sugar LABORATORY or IDENTIFICATION TEST: Benedict’s test  tests the urine
Grape sugar sample for the presence of glucose
Dextrose  USES: nutrient (most important)  main ingredient in parenteral (DEXTROSE) especially for
Corn sugar unconscious patients
D-glucopyranose  SOURCES: grapes or fruits, and obtained in the enzymatic hydrolysis of starch (because
starch is a polysaccharide & made up of GLUCOSE units)
Crystalline  From rigorous purification of high-conversion hydrolysates
dextrose
Liquid glucose  Product obtained by the incomplete hydrolysis of starch
Galactose SYNONYM:  CHEMICAL TEST: Mucic or Galactanic acid test - (+) crystal formation with galactose and
Brain sugar lactose
 C4 epimer of glucose
 Sugar that is most absorbed/ RAPIDLY ABSORBED in the small intestine
 Person with deficiency of enzymes that breakdown galactose  Comprised condition that
cannot metabolized galactose = GALACTOSEMIA  genetic condition with ENZYME
DEFIENCY
 Cannot breakdown properly = accumulation of GALACTOSE in the blood = high galactose in
the blood (GALACTOSEMIA)  will be toxic to the liver (one of the common symptoms of
galactosemia  JAUNDICE), & BRAIN DAMAGE
 That’s why we should not give MILK (primarily with LACTOSE (glucose + galac) formulation
 cannot metabolized  will lead to infant diarrhea (HIGH MORTALITY RATE)
Mannose  C2 epimer of glucose
 Ozasone Test – reducing sugars = forming ozazone crystals when heated w/ excess
phenylhydrazine - characterized by aldose/ketose (OH group) near or of adjacent to the
ketone group
Fructose SYNONYMS: • SOURCES:
(KETOhexose) – Levulose o Sweet fruits, honey
SWEETEST Fruit Sugar o INVERT SUGAR or inversion of aqueous solutions of sucrose = mixture of glucose
SUGAR & fructose from sucrose by the application of heat and acid such as citric acid and
cream of tartar by the virtue of the enzyme INVERTASE
o obtained from enzymatically prepared high-fructose syrup
o from the hydrolysis of inulin (example of a FRUCTOSAN; fructosan = is composed
of fructose units [H] = fructose)
• CHEMICAL TEST - Seliwanoff’s Test = (+) RED (chem test that identify sugars between
aldose & ketose)
• USES: food substitute for diabetic people, beneficial to diabetic acidosis, ingredient in
infant feeding formulations, ingredient for fructose injection, fructose & NaCl injection
(these are liquid nutrient and electrolyte nutrients or reflenishers (IM, SQ)
Xylose – SYNONYM: wood • SOURCE: Obtained by boiling the corncobs or straws with diluted acid to hydrolyze xylan
(KETOaldose) sugar polymer
• USE: Diagnostic agent for intestinal absorption  high extent of absorption in intestine =
completely absorb in the systemic circulation/ body  excreted in the urine:
o Normal = xylose is PRESENT in the urine (since it has been absorbed & excreted)
o WHEN NOT PRESENT = intestinal malabsorption
 SOURCES SYNONYMS
Sugar cane Sucrose  Table sugar, invert sugar, cane sugar, beet sugar
Barley Maltose  malt sugar, beer sugar
Grapes D-glucose  dextrose, blood sugar
Found in fungi (ergot or yeast) Trehalose
Honey Fructose levulose, fruit sugar

SUGAR PREPARATION
Dextrates • From controlled enzymatic hydrolysis of starch
• USES: diluent in direct compressible drugs, substitute for sucrose in syrups,
tablet binders, and coating agent
Liquid glucose • Usually prepared by controlled acid hydrolysis of corn starch
• Product obtained by the incomplete hydrolysis of starch
• USES: tablet binders, base in oral solution and syrups
Crystalline dextrose • From rigorous purification of high-conversion hydrolysates
High fructose sweeteners • Prepared by controlled enzymatic isomerization of glucose
• e.g.  HFCS (High Fructose Corn syrup --. Composed of 90% fructose available
commercially)  one of the main causes of OBESITY EPIDEMIC IN US

MONOSACCHARIDES  PRODUCTS CONTAINING GLUCOSE

Calcium gluconate • considered as the calcium salt of gluconic acid
• Gluconic acid is obtained from the oxidation of dextrose with chlorine and
bromine or by fermentation
• USE: since it is made up of Ca  electrolyte replenisher provide therapeutic
effect because of Ca  supply Ca
Calcium gluceptate and calcium • Ca salts of 7 & 5 carbon acids
levulinate • Prepared via a cyanohydrin intermediate, and levulinic acid & these products
• can also be obtained from sugar canes & starch by boiling with HCl
• USE: used parenterally to produce the therapeutic effect of Ca
Ferrous Gluconate • Ferrous salt of gluconic acid
• USE: hematinic agent  employed in iron deficiency anemia

DISACCHARIDES  Can be reducing (Maltose & Lactose) or NON-reducing (Sucrose)

• NON REDUCING SUGAR – OH group is not attached in the anomeric C (e.g. Sucrose)
• Oligosaccharide or disaccharide [H] = 2 MONOSACCHARIDES (yield 2 monosaccharides upon hydrolysis)
• BOND: Glycosidic bonds  connect the CHO units of di, oligo & polysaccharides  formed via the dehydration synthesize
(removal of water in the sugar = to form glycosidic bonds  glycosidic bonds is an example of an ether bond)
• condensation products of two monosaccharide units + glycosidic bonds = di, oligo & polysaccharides
• Also formed via the dehydration reaction (removal of water)
• *C12H22011
SUCROSE (Glu SYNONYM:  SOURCES:
+ Fru) Table sugar o MAIN SOURCE in Ph  sugar cane (Saccharum officinarum) of Poaceae
o sugar beets (Beta vulgaris) Chenopodiaceae
o sugar maple (Acer saccharum) Aceraceae
 upon hydrolysis it will form  INVERT SUGAR (when sucrose has been hydrolyzed and the units of
glucose and fructose have been separated)
 ***Preparation:
1. Sugar Cane Juice is boiled w/ Lime  Lime  basic compound  neutralize plant acids 
coagulate albumins
 **Saccharose  is almost universally distributes sugar in green leaves & in stems
 **Invert Sugar  is darker & sweeter than sucrose
  USES:
o Drug delivery system  Important ingredient or pharmaceutical necessity in SIMPLE SYRUP NF
(85% w/v)
o DEMULCENT – a mucoprotective agent  coat the mucomembrane or surface to
prevent/protect/relieve the underlying cell/mucous membrane from irritation or inflammation;
provide a soothing film in the inflammed or irritated area
o Source of nutrient, common pharmaceutical sweetener (e.g. in troches, and lozenges)
o Also has bacteriostatic and preservative actions
 Glycosidic bonds = link together through alpha & beta - 1,2 glycosidic bond
Maltose SYNONYMS:  Product of partial hydrolysis of starch
(Glu + Glu) Malt sugar  The end product of the action of beta amylase on starch
Beer sugar  Formed via the diastatic fermentation of Barley
 Glycosidic bonds = link together through alpha- 1,4 glycosidic bond
Lactose SYNONYM:  LEAST sweet of all sugar
(Glu + Galac) Milk sugar  SOURCES:
o Cow’s milk is the fresh, unpasteurized or pasterurized milk of Bos taurus Linne (Fam.
Bovidae), without modification
 USES:
o Drug delivery system: principal pharmaceutical aid as tablet diluent
o Supply nutrients in the body
o Nutrient in infants food e.g. milk formulation
 Lactose intolerance = people who do not possessed or lack LACTASE enzyme
 Lactase- responsible for the metabolize of lactose
 Causing GI distress: bloating, diarrhea, loose stools, vomiting, & producing gases
Trehalose  Obtained from seaweeds, ergot, yeast & Rhodophyceae family
(Glu + Glu)  Glycosidic bonds = link together through alpha- 1,1 glycosidic bonds
Sophorose  From Sophora japonica (Leguminosae)
(Glu + Glu)  Can also be derived from the hydrolysis of sterioside  STERIOSIDE is a glycoside derived from the
plant Stevia (sweetener)
Primeverose  From the meadow wart or Filipendula ulmaria (Rosaceae)
(Glu + Xylose)  Can also be derived from the hydrolysis of spiralein
Cellobiose  Formed by enzymatic breakdown of cellulose
(Glu + Glu)  Glycosidic bonds = link together through beta-1,4 glycosidic bond
 Disaccharide that the body cannot digest because of:
o beta bonds (alpha = digestable, beta = harder to digest specially the in long chains)
o lack of enzymes to digest
 Will cause GI distress (bloating & producing gas)
 Provides dietary fiber that is needed to stimulate the contraction of intestine & helps pass the
stool in the digestive tract
Lactulose  Semisynthetic sugar prepared by alkaline rearrangement of lactose  if LACTOSE will be hydrolyze
(Fruc + Gal)  yields FRUCTOSE AND GALACTOSE CHO units
 poorly absorbed in the body  will reached the colon unchanged and the bacteria present in the
colon will metabolize the disaccharide to acetic and lactic acids
 Lactic acid & acetic acid  are examples of irritating acids  sufficient amount of these two
irritating acids will cause or stimulate  LAXATIVE EFFECT
 USES: Osmotic laxative derived from LACTOSE & decrease the blood ammonia concentration in
portal and systemic encephalopathy
 Treatment for: chronic constipation & hepatic encephalopathy
 BRANDS: Lilac, Movelax, Duphalac
 DISACCHARIDE SUGAR Definition
Fructofuranose • Cyclic form of levulose when it is present in oligosaccharide or polysaccharides
Sucrose or saccharose • The only disaccharide that occurs abundantly in the free state in plants
LACTOSE  MILK PRODUCTS
WHOLE MILK  have fatty globules  when it undergoes the process of CHURNING (process of the removal of fatty
globules)
 After churning we will produce 2 products:
o Butter  the collected fatty globules in the process of churning; the union of the fat globules
o Buttermilk  liquid left

BUTTERMILK  still have fatty globules left  if left upon standing  A FOAMY LAYER will be formed = CREAM (Fat
globules rise to the top upon standing or the foamy layer)

SKIMMED MILK (only have 0.1% of fat)  the milk after the separation of the CREAM
 Contain proteins: CASEIN & WHEY
o Casein + rennin (enzyme that coagulates casein) = precipitate forming COAGULUM or “coagulated casein”
 when coagulum is further treated with rennin  product after the proper treatment of the coagulum =
CHEESE
o COAGULUM + RENNIN = CHEESE
o Whey  liquid separated from the coagulum and is rich /contains lactose and inorganic salts

DISSACHARIDE SUGARS PRODUCT UPON HYDROLYSIS

Lactulose Fructose + Galactose
Lactose Glucose + Galactose
Sucrose Glucose + Fructose
Maltose, Trehalose, Cellobiose, Sophorose Glucose + Glucose
Primeverose Glucose + Xylose

TRISSACHARIDE SUGARS SUGAR UNITS SOURCE

Raffinose Gal + Glu + Fru Cottonseed
Maltotriose Glu + Glu + Glu
Sucralose Glu + Fru + Gal
Gentianose Glu + Glu + Fru Gentiana spp.
Melezitose Glu + Fru + Glu Manna from Larix
Planteose Glu + Fru + Gal Seeds of Psyllium spp
Rhamninose 2 Rhamnose + Glu Rhamnus infectoria
Manneotriose Gal + Gal + Glu Fraxinus ornus, Oleacea spp
Scillatriose Rhamnose + 2 Glu Glycoside of squill

TETRASACCHARIDES:
 Stachyose (2 Galactose + Glucose + Fructose) from the tubers of Stachys japonica, Lamiaceae
 PRODUCTS OF GLYCOLYTIC AND OXIDATIVE METABOLISM (Cherry juice, plant acids & alcohol)
1. Cherry juice or Succus cerasi  liquid expressed from the fresh, ripe fruit of Prunus cerasus Linne
(Rosaceae); contains NLT 1% malic acid
 Used in cherry syrup, flavored vehicle especially to those acidulous nature

2. Sugar alcohols  obtained from the reduction of sugar (from ALDEHYDE [R] to PRIMARY ALCOHOL)
 E.g. Dulcitol, mannitol, D-glucitol or sorbitol, galactitol, xylitol

ALCOHOL OR ETHANOL  is a liquid containing not less than 92.3% by o Brandy (from distillation of wine)  35-65%
weight, corresponding to 94.9% (ALMOST 95%) by alcohol content
volume, of ethanol at 15.56 degrees celsius o Whiskey (from fermented malted grain)
 we recognized the effect of alcohol in the body o Rum (from fermented molasses)
by the concentration:
o LOW CONCENTRATION  CNS stimulant **Molasses - is the residual dark colored syrup left
o HIGH CONCENTRATION  CNS depressant upon crystallization of sucrose.
**Diluted alcohol – 48.4 to 49.5 % ethanol at 15.56 **Wine- is sometime used medicinally as a mild
degrees C stimulant & tonic
**Distilled Spirits: (produced by Distillation) **Whiskey & Brandy - CNS Depressant
**from fermentation & distillation *In making Wine,
**70% = local anti-infectives  Tannin - acts as Clarifying Agent
 Yeast -acts as enzyme for fermentation
GALACTITOL  contributes to cataract formation which is
associated with galactosemia
 a hexahydric alcohol that is not absorbed from
the gastrointestinal tract
MANNITOL  isolated from manna Fraxinus ornus Linne (Fam.  ORALLY ADMINISTERED  Laxative effect
Oleaceae) obtained by reduction of mannose  PARENTERALLY  Osmotic diuretic
 Diagnostic agent for renal function  measures
the GFR highly extent or filtered by the GFR or
the kidneys but less on tubular/GI tract filtration
= can be measured in the urine
 usual diagnostic dose of Mannitol Injection:
200mg/kg body weight in a 15-25% solution IV in
3-5 minutes
SORBITOL OR D-GLUCITOL  ALDEHYDE (Glucose)  [R] PRIMARY ALCHOL  Taste sweet approximately half as sucrose
(Hexitol)  USES: humectant (prevent the loss of moisture)
 hexitol  that’s why  it is used as ingredient of
 obtained from the ripe berries of mountain ash toothpaste and chewing gums
(Sorbus aucuparia of the family Rosaceae)  together with mannitol (sorbitol + mannitol
combination) for urologic irrigation

3. PLANT ACIDS  when the functional group has been oxidized [O] = acid
**Sugar Acids  produce from the oxidation of Disaccahrides & Monosaccharides
(except sucrose)
**Aldonic Acid  produce from the oxidation of sugar’s aldehyde group (group 1)
CITRIC ACID  Isolated by Carl Wilhelm Scheele in lemon
 Tricarboxylic acid  important in TCA/Kreb’s cycle because it is the first intermediate being formed  named
after it
 USES:
o Useful in buffering systems
o Acidulant in effervescent formulations
**salt = Systemic Alkalinizer – Potassium Citrate (Acalka®)
**Anticoagulant – Citrated Tubes
LACTIC ACID  Main component of Lactacyd (feminine wash)  important to maintain the pH of the vagina  to prevent the
growth of microorganisms
 It is obtained by the lactic fermentation of sugar or is prepared synthetically
 USE: used as an acidulant, especially in infant feeding formulas
**substance accumulates in the muscle as a result of vigorous exercise
EXAMPLES OF DICARBOXYLIC ACIDS
OXALIC ACID  Ethanedioic acid
 CHEMICAL FORMULAS:
o Anhydrous  C2H2O4
o Dihydrate  C2H2O x 2H2O
 USE: Bleaching agent (e.g. in the laboratory for cleaning glassware to remove the stains)
 SHOULD NOT BE TAKEN ORALLY or INTERNALLY  TOXIC  can combine with the calcium ions in the body =
will form a crystal in the form of calcium oxalate (have a very low solubility  will precipitate in the kidneys
causing KIDNEY DAMAGE)
 E.g. of plant with high amount of oxalic acid  Taro (Colocasia esculenta)
**an organic acid found in fruits of Averboa balimbi
SUCCINIC ACID  Butanedioic acid
 CHEMICAL FORMULA: C4H6O4
MALIC ACID  2-hydroxybutanedioic acid
 CHEMICAL FORMULA: C4H6O5
 Very common on apples particularly on Malus domestica (have high amount of malic acid) hence, named
after it
TARTARIC ACID  Dihydroxybutanedioic acid
 CHEMICAL FORMULA: C4H6O6
 Obtained as a by-product of the wine industry (because during consumption  it is also the by-product)
 USE: Used as a substitute for citric acid in buffer systems and in effervescent formulations
 Denige’s Test – used to differentiate citric & tartaric acids (citrates & tartrates)
o Tartaric acid  EMERALD GREEN
o Citric acid  CARMINE RED
FUMARIC ACID  Ferrous fumarate  hematinic

DIFFERENCE IS IN THE LENGTH OF CARBONS

 POLYSACCHARIDES  polymers of monosaccharides (sugars)
 If it undergoes the hydrolysis  will yield several monosaccharides
 Linked together with the glycosidic (ether) linkages

HOMOGLYCANS or homopolysaccharides HETEROGLYCANS or heteropolysaccharides

1 component or yield only one type of monosacc unit 2 component/more or yield mixture or dif types of monosacc units
Starch, glycogen, inulin, & cellulose Gums, mucilages & glycosides

CLASSIFICATION BASED ON MONOMERS

HEXOSANS PENTOSANS
Polymers of hexose Polymers of pentose
E.g. E.g.
 Glucosan (made up of glucose)  starch, dextrin, glycogen,  Araban, xylan
cellulose (when [H] = glucose units)
 Fructosan (fructose)  Inulin
 Mannosan (mannose)  vegetable ivory

HOMOGLYCANS
1. Starch – temporary storage form of photosynthetic products (branching every 20-30 residues)
 SOURCES: Corn (Zea mays), potato (Solanum tuberosum), rice (Oryza sativa), and wheat (Triticum sativum)
**Unofficial Sources of Starch: - Arrow root (Maranta arundinacea)
 USES: ingredient in dusting powder, a tablet filler, binder (pregelatinized starch  slightly soluble - soluble in cold water)
and disintegrant in the form of SODIUM STARCH GLYCOLATE (a semi-synthetic material that is used as super disintegrant)
o Starch suspension – ANTIDOTE FOR IODINE POISONING
 COMPONENTS:
AMYLOSE – 25% of starch AMYLOPECTIN – 75% of starch (more abundant than AMYLOSE)
 linear  Branching (every 25 units)
 composed of 250 to 300 D- glucopyranose units  consists of 1000 or more glucose units
 linked by α -1, 4 glucosidic bonds  α-1,4 linkages, α -1,6 (branch)
 more soluble in water than amylopectin  amylopectin + iodine = blue-violet or purple color
 Amylose + iodine = deep blue complex

**Iodine Test confirmatory test for starch -->consists of a greater proportion of amylopectin than amylase
* Amylose - hydrolysis product of starch responsible for forming a dark complex w/ Iodine
* β –amylase -enzyme in pancreatic juice & saliva
* α -amylase - removes maltose units from the non-reducing ends of polysaccharide molecules - usually isolated from:
rhizome, fruit , & seed
**FORMS OF STARCH:
 *Starch paste – dispersing starch in cold water  boiled  granules swell & rupture  resulti
 *Pregelatinized Starch –all the granules have been ruptured in the presence of water  serve as plasma expander in 6%
concentration
 *Sodium Starch Glycolate – a semisynthetic sodium salt of carboxymethyl ether of starch – disintegrating agent in tablet
formation
 *Glutens – tacky proteins removed from corn & wheat in the preparation of starch
 Hetastarch – also known as hydroxyethyl starch  >90% amylopectin and water-soluble form
 6% solution = used as a plasma expander (increase the plasma in the blood resulting to the increase of blood volume =
hence, used for shock treatment especially hypovolemic shock (sudden drop in the blood levels/volumes caused by of
shock, by hemorrhage, burns, surgery, sepsis, or other trauma)
 adjunct therapy in treatment of shock, caused by hemorrhage, burns, surgery, sepsis, or other trauma
 2. Inulin or hydrous inulin  PRINCIPAL SOURCE: and chicory (succor or or blue dandelion root)  Chicorium intibus
 is a D-FRUCTOFURANOSE polymer whose residues are linked in linear fashion by β 1, 2 glycosidic bond linkage
 Diagnostic agent for kidney fxn esp. used to measure the Glomerular Filtration Rate (GFR) Filter only by the glomerular
filtration and NEITHER excreted nor reabsorb by the tubules  Cannot be metabolized/hydrolyzed by the intestinal
enzymes (same with mannitol)
 water soluble
 particularly abundant in taraxacum, inula (elecampne), lappa (burdock root), Echinacea (cone flower), and chicory (succor
or or blue dandelion root)

3. Dextran  is an α-1,6- link polyglucan

 Synthesize by sucrose by certain lactic bacteria Leuconostoc mesenteroides & S. mutans
 sucrose  acted upon the transglucosylase enzyme system (dextran sucrase) in Leuconostoc mesenteroides  dextran
 Dental plaque is rich of dextran
 10% solution = adjunct in the treatment of shock (hypovolemic shock)
 Iron dextran inj.- IV/IM hematinic preparation (sterile colloidal solution containing ferric hydroxide in complex with
partially hydrolyze dextran of low molecular weight and water for injection) and is also well used when oral iron preparations
are not well tolerated
 UNDER DEXTRAN
 Dextrin – sweetening agent

4. Glycogen – major form of carbohydrate storage in animals

 Stored in muscles (generates ATP for muscle contraction) & liver (maintain the blood glucose during fasting & exercise)
 α 1, 4 and α 1, 6 every 8-10 units
 example of a glucosan  [H]  will form glucose monosaccharides unit

5. Cellulose  MOST ABUNDANT OF ALL CHO

 STRUCTURAL ELEMENT  structural component of cell walls particularly in plants
 Not metabolized in the human body
 Made up of monosaccharide (Glucose) + disaccharide (Cellobiose)
 In the addition of IODINE = NO COLOR (negative unlike amylopectin & amylose)
 β 1, 4 glycosidic bond
 Purified cotton/absorbent cotton
 from the hair and seeds cultivated varieties of Gossypium hirsutum of Family Malvaceae
 MAIN SOURCE OF CELLULOSE & absorbent cotton
 USES: surgical dressing, mechanical protection to absorb blood, mucus, or pus, & to keep the bacteria from entering
the wounds
 Powdered cellulose  self-binding tablet diluent and disintegrating agent
 Microcrystalline cellulose  diluent in tablets

6. ***Chitin  structural polysaccharides in animals & fungi

 Major constituent of the exoskeleton of the arthropods
 homopolyglycan of N-acetylglucosamine
 structure resembles CELLULOSE but Galacturonic Acid - present in Chitin that cannot be found in cellulose

CELLULOSE DERIVATIVES USE/S

 Powdered cellulose Self-binding tablet diluent and disintegrating agent
 Cellulose acetate phthalate (CAP) Enteric coating
 Hydroxypropylcellulose Binder and film coating in tablet formulations
 Ethycellulose
 Methylcellulose Components of artificial tears  provides eye lubrication
 Hydroxyethylcellulose
 Hydroxypropyl methylcellulose
 Hydroxypropylmethylcellulose (HPMC) Most common suspending agent & used as an emulsifying agent
 Hydroxypropylmethylcellulose SUSPENDING AGENTS
 Methylcellulose
 Sodiumcarboxymethyl cellulose
 Oxidized cellulose and oxidized LOCAL HEMOSTATICS
regenerated cellulose
 Methylcellulose BULK LAXATIVE
 Sodiumcarboxymethyl cellulose
 PURIFIED RAYON  is a fibrous form of bleached, regenerated cellulose
 it is used as a surgical aid and may not contain more than 1.25% Titanium Dioxide
 PYROXYLIN/ Soluble guncotton/  used in the preparation of collodion and flexible collodion, topical protectants
Cellulose Trinitrate mixtures  obtained by the action of nitric & sulfuric acid in cotton
 DIFFERENCE BETWEEN COLLODION & FLEXIBLE COLLOIDION:
 Collodion = Pyroxylin + Ether/ Alcohol
 Flexible Collodion = Collodion + 3% Castor oil (used to provide flexibility) +
2% Camphor (provides watering proofing activities)  used as a topical
protectant or a surgical dressing

NOTES:
 Used as plasma volume expander  DEXTRAN AND HETASTARCH
 This enzyme affects the synthesis of amylose fraction of starch  TRANSGLYCOSYLASE

POLYSACCHARIDE BONDS
Alpha-1,4 glycosidic bonds Amylose, maltose, glycogen, amylopectin
Beta-1,4 glycosidic bonds CELLULOSE

1. APPLE
 Scientific name: Pyrus malus
 Family name: Rosaceae 5. MILK
 Constituent & use  MALIC ACID (ANTIOXIDANT)  Scientific name: Bos Taurus
 Chemical name: 2-hydroxybutanedioic acid  Family name: Bovidae
 Sugar component: Lactose
2. GRAPES  Synonym: Milk sugar
 Scientific name: Vitis vinifera  Milk formed in the mixture of coagulum and renin:
 Family name: Vitaceae CHEESE
 Constituent  Beta-D-GLUCOSE 
 SYNONYMS  Dextrose & blood sugar 6. HONEY
 Scientific name: Apis mellifera
3. POTATO  Family name: Apidae
 Scientific name: Solanum tuberosum  Sugar component: Fructose
 Family name: Solanaceae/Asteridae  Synonyms: Fruit sugar, & levulose
 Constituent  Starch
 Plant part used: TUBER

4. SUGAR CANE
 Scientific name: Saccharum officinarum
 Family name: Poaceae/Graminae
 Sugar component: SUCROSE
 Synonyms: Table sugar, beet, sugar, maple sugar
 HETEROGLYCANS  when [H] will form different kinds of monosaccharides units
GUMS & MUCILAGE
Gums Mucilages
 readily soluble in H2O  water soluble  form slimy masses in H2O  does not dissolve in water
 pathologic products  only produce when there is instead it forms a thick paste or slimy masses
injury (e.g. plant or tree injury = gums)  physiologic products (can be produced without injury 
hence, natural  can be produced naturally)

GUMS & MUCILAGE  used in pharmaceutical field as an inactive ingredient (e.g. when used in formulations  in
suspension a suspending agent, in emulsion an emulsifying agents)
 USES: ingredients in dental and other adhesives and bulk laxatives, tablet binders, emulsifiers, gelating agents,
suspending agents, stabilizers, & thickeners (since they form thick paste particularly the mucilage)

GUMS  natural plant hydrocolloids

 non-ionic – or anionic (Ca or Mg Salts) polysaccharides
 transluscent & amorphous substances
 swells when dispersed in water to form gels
 product of plat injury as a protective (a way for a plant to protect itself from injury)
 ***precipitated by alcohol & lead acetate

5 CATEGORIES BASED ON THE SOURCES

1. Shrubs and Tree exudates

2. Marine gums
3. Seed gums
4. Plant extracts
5. Microbial gums

1. SHRUBS AND TREE EXUDATES

SHRUBS AND TREE EXUDATES Synonym Botanical sources Constituent
1. Tragacanth Gum tragacanth, Astragalus gummifer  Bassorin – swelling property of
 derived from the Greek word Goat’s horn (Fam. Leguminosae)  Tragacanth
“tragos”  GOAT & “akantha”  horn Astragalus – milk bone  MAIN COMPONENT  60-70% present in
(which represent the curved shape of gummifer – gum bearing Tragacanth
the product  swells in the presence of water to form a
** most acid resistant hydrocolloid gel but does not dissolve
 USES: gelling agent & suspending agent
(5-6% conc)

 Tragacanthin also known as the

demethoxylated bassorin – composes the
30-40% (minor component) of the gum
which is more water soluble component

2. Acacia – low-viscosity Gum arabic or Acacia senegal  Arabin  arabin main sugar
 extensively used as thickening agent **Egyptian gum (Fam. Leguminosae) component: arabinose
and also for emulsification Arabin = complex mixture of Ca, Mg, K
 MOST COMMONLY USED salts of Arabic Acid swell in water
SUSPENDING AGENT IN PHARMACY
(low-viscosity but it is stable at pH
range of 2-10 + remains in solution at
alcohol concentration below 60%)
 CONC. (susp. agent): 33-35%
 **OTHER USES: Demulcent,
emollient, adhesive & binder
3. Ghatti gum  SUBSTITUTE FOR Indian gum Anogiessus latifolia (Fam.
ACACIA Combretaceae)
 USES: a very good emulsifier,
stabilizer, & a thickener, & binder for
compressed tablets
 Gives stable oil in water emulsion
 more viscous than acacia
4. Karaya gum Sterculia gum  Family  Sterculiaceae D-galacturonic acid and D-glucuronic acid
 Most unpleasant smelling gum (fetid derived from the  Sterculia urens,
odor of trees) Greek myth   S. villosa,
Least soluble among shrubs and tree “Sterculius”  S. tragantha
exudates gums means god of
 Forms a discontinuous type of feces (deity of Family  Bixaceae
mucilage manuring)  Cochlospermum
 USES: bulk laxative (COMPONENT OF gossypium
MOVICOL)  C. kunth

TRAGACANTH  the nature of the incision governs the shape of the final product
Vermiform tragacanth Tragacanth sorts Ribbon gum and flake gum
Source Natural injuries Natural injuries The better grade ccomes from transverse incisions made
with the knife in the main stem and older branches
Appearance Worm-like, twisted into coils Irregular tear shaped Ribbon-like, flaked
Color Yellowish brown Yellowish or brownish Clear (preferred grades
brown

TREES and EXUDATE Commercial grade:

TRAGACANTH No. 1  almost colorless and nearly translucent
No. 2 & 3 --. Have more color and opacity
GHATTI GUM OR INDIAN GUM Colorless (yellow  10 days, pin  weeks, brown  months color)
Characteristic odor and taste (e.g. acetic acid)

2. MARINE GUMS
BROWN SEAWEEDS  Sodium alginate or algin, Laminaria
RED ALGAE  Agar or Japanese Isinglas, carrageenan, Danish agar
MARINE GUMS Synonym Botanical sources Constituent
1. Algin (sodium alginate + alginic acid)  Extracted from BROWN  Major monosaccharide
SEAWEEDS by the use of component  Mannuronic acid
dilute alkali (oxidized form of mannose)
 Macrocystis pyrifera  Sodiumalginate  a mixture of
(Fam. Lessoniaceae) beta-D sodim salts of glucuronic
 Other sources: acid (Na-glucuronate) & sodium
o Class Phaeophyceae, salts of mannuronic acid (Na-
Ascophyllum, Ecklonia, mannuronate)
Laminaria, Nereocystis

 one of the component of Gaviscon (depends

on the DF):
-in powder  ALGINIC ACID
-in liquid  SODIUM ALGINATE (salt form of
algin)
 why there’s a difference between the DF?
bcs salt form is easily dissolved in liq. medium
 SODIUM ALGINATE & ALGINIC ACID = same
use  foaming agents (creating protective
foams in the lining of the esophagus in cases of
heart burn or GERD) in Gaviscon
2. Agar Japanese  Gelidium cartilagineum  2 major HIGHLY SULFATED
 USES: laxative, in the pharmaceutical Isinglas (Fam. Gelidiaceae) components:
necessity  suspending & emulsifier agent,  Gracilaria confervoides o Agarose  contains galactose
gelating agents especially for suppositories & (Fam. (abundant monosacc unit in
surgical lubricants, tablet excipient & Sphaerococcaneae) agarose)
disintegrant  Related to red algae o Agaropectin  higher sulfate
 COMMONLY USED IN microbiology (Class Rhodophyceae) content & contains glucuronic
particularly as a gel in bacteriologic culture acid
media
3. Carrageenan  Chordurs crispus (Linne)  Gelating agents
 Lambda  since it has phlogistic activities Stockhouse o Kappa-carrageenan
(can induce inflame)  employed in  Gigartia mamiliosa o Iota-carrageenan
carrageenan rat paw edema test (inj. (Goodenough and
carrageenan in the paws of rats = swell  apply Woodward) J Agardh  Thickener, phlogistic agent
the test drug to test the anti-inflam (Fam. Gigartinacea) (substance that can induce inflam)
property/reduce inflame = if reduced   Lambda-carrageenan (NON-
effective gelling agent of carrageenan, &
 used as in vivo testing for anti-inflam drugs have no stable helix)
**highly-sulfated polygalactans
**closely related hydrocolloids that are
obtained from various red algae ore sea weed
 **used in toothpaste
4. Furcellaran Danish agar  Furcellaria fastigiata 
(Furcellariaceae)

Chordurs crispus Gigartia mamiliosa

 Chrondrus or Irish moss  is an allusion to the  Gigartina  is an illusion to the fruit bodied that
cartilage like the character of the dry thallus apper elevated tubercles in the thallus

3. SEED GUMS  obtained from the husk or seed coat

SEED GUMS Synonym Botanical sources Constituent
1. Plantago seed Psyllium seed or Plantain  Plantago psyllium, P. indica Linne,  composed of arabinose,
 component of the product C- seed P. arenaria – Spanish or French galactose, galacturonic
lium Fibre (bulk laxative) psyllium seed acid, rhamnose, & xylose
 have thixotropic property  P. ovata – Forskal blonde psyllium
or Indian plantago seed (Fam.
Plantaginaceae)
 obtained from the husk or seed
coat especially in Spaghula 
dried seed
2. Quince seed Cydonium  Cydonia vulgaris (Fam. Rosaceae)
 have thixotropic property 
used as thixotropic agent in lotion
 3. Locust bean gum “Carob” pulp or St. John’s  Ceratonia siliqua Linne (Fam.  Galactomannan
 used as substitute for cocoa bread Leguminosae)
powder or chocolate because it
taste like chocolate
 OTHER USES: thickener &
stabilizer
4. Guar gum Guaran  Cyamopsis tetragonolobus (Fam.  Galactomannan alpha-D-
 USE: bulk laxative, thickening Leguminosae) galactose + Beta-D-
agent, tablet binder, & disintegrant mannose

4. MICROBIAL GUM  from microbial sources

Gums Source Remarks
Xanthan gum (Keltrol) Xanthomonas campestris  High-molecular-weight microbial gum pseudoplastic properties
 pseudoplastic flow  for toothpaste & ointment to hold/ retain shape,
& spread easily
 MOST FREQUENTLY SUSPENDING AGENT
 The exocellular gum is recovered from the fermentation broth by the
precipitation with isopropyl alcohol
Dextran Leuconostoc mesenteroides  Alpha-1,6-linked polyglucan
 10% solution can be used as an adjunct in the treatment of
shock/hypovolemic shock

5. PLANT EXTRACT
Gums Source Remarks
Pectin Obtained from the dilute acid extract  Pectin is from the Greek and means congealed or curdled.  hence, used
 have of inner portion of the rind (skin) of in the preparation of jams
yellowish white citrus or from apple pomace  MW: ranges from 100,000 to 250,000
color that is also  CHIEF COMPONENT: methoxylated polygalacturonic acids
odorless & has a  Yields 74% of galacturonic acid  which is responsible for the gelling
mucilaginous and viscosity of the solution of pectins
taste  The main carbohydrate component is a linear 1,4-linked D-galacturonan
 completely  USES:
soluble in 20 o Classified as a protectant
parts of water & o Suspending agent
the solution is o Ingredient in many anti-diarrheal formulations (KAOLIN + PECTIN =
viscous KAOPECTATE) Kaopectate is an anti-diarrheal formulation
o As a colloid solution, it has the property of conjugating toxins and
enhancing the physiologic functions of the digestive tract through its
physical and chemical properties
 **intercellular cementing material
 **general term for a group of polysaccharides present on the primary cell
wall & intercellular cement
 **is precipitated from the solution by an excess of alcohol
 **is more stable in cold acid solution
 **Protopectase - attacks protopectin yielding soluble pectin
 **Exudate - natural product of plant injury
 PECTIN:
o Commercial pectin  contain sugars or organic acids
o Pharmaceutical pectin  is pure pectin to which no additions have been made
o Propectin  pectin in the fruit is found in an insoluble form & it is converted to the soluble form by heating the fruit with dilute
 acid
 DIFFERENT FORMS OF PECTIN:
o Protopectin  unripe fruits
o Soluble pectin  just ripe
o Pectic acid or pectinic acid  pectin present in overripe fruits

NOTES:
Used for treatment of gastric ulcer  Mastic gum
 Anti-diarrheal  Pectin
 gum component of Movicol  Karaya
 bulk forming laxatives  Seed gums
 phlogistic agent  Lambda carrageenan
 matrix for immunodiffusion, for electrophoresis chromatography, and gel in bacteriologic culture media 
AGAR
 a term referring to closely related hydrocolloids that are obtained from various red algae or seaweeds 
Carrageenan
 with pseudoplastic property (toothpaste and ointment)  Xanthan gum
 Purified CHO product obtained from the dilute acid extract of the inner portion of the rind of citrus fruits or
from apple pomace  Pectin
 A purified CHO product extracted from the brown seaweeds Macrocystic pyrifera by the use of dilure alkali 
Algin
 GLYCOSIDES

 Mixed acetals  in a sense that they yield one or more sugars among the product of hydrolysis
 SUFFIX  ends with –in
 COMPONENTS: glycone, aglycone/aglycon or genin

Glycone Aglycone (Genin)

Sugar component Non-sugar component
Common denominator Basis for classification
Inactive Therapeutically active
 IMPORTANCE: regulatory, protective, sanitary functions of plants, & therapeutic agents (some glycosides
employed as drugs)
 *(Beta) – only form of Glycoside that occurs in plants
 *are condensation product of sugar w/ various organic hydroxyl compounds
 *has beta-D-glucose as its most frequently occurring sugar
 *C, S, N; O – glycosides
”sugar ether” (R-O-R)
Ether Bond
 *Anthocyanins  pigments of flowers which is of Glycosidic character

CLASSIFICATION OF THE GLYCOSIDES BASED ON THE CHEMICAL NATURE OF THE AGLYCONE GROUP
 Cardioactive steroid group
 Anthraquinone group
 Saponin group
 Cyanophore group – cyanide group
 Glucosinolate or Isothiocyanate group
 Flavonol group
 Aldehyde group
 Phenol group
 Lactone

TESTS (+) RESULT

Anthraquinone glycosides Borntrager’s test Pink-red color in the ammoniacal (lower) layer
Saponin glycosides Froth test Honey comb froth – 2-3 cm of rise of froth or
Capillary Tube test bubble formation
Hemolysis test
Cardiac glycosides Liebermann-Burchard test Green color
Kedde test Violet
Keller-Killiani test Reddish brown
Cyanophere glycoside  Guignard test Red coloration
cyanogenic

1. Cardioglycoside steroid group

 MAJORITY ARE INOTROPIC AGENTS  produces an increase in the force of systolic contraction causing
increase cardiac output, increase renal blood flow, decrease cardiac filling pressure, decrease venous and
capillary pressure or decrease heart signs
 Related to the steroids  CPPP nucleus (cyclopentanoperhydrophenanthrene)
 Sugar component is attached on the 3 position of the CPPP nucleus
rd

 2 AGLYCONE:
 Cardenolides  5-membered ring
 Bufadienolides  (discovered from bufalin isolated from the skin of toad)  6-membered ring
 *CARDENOLIDES *BUFADIENOLIDES
More common Less common
From toad skin (Bufo spp.)
Optimum activity Less activity
C23 C24
Glycone: 2 deoxysugar
Test: Keller-Kellani test
Exert action on the cardiac muscles:
5-membered ring attached to the
CPPP nucleus = CARDENOLIDE
+ inotropic = inc. cardiac output
- choromotropic – dec. cardiac rate

MOA: Na-K-ATPase pump

USE: for HF

ADDITIONAL NOTES FROM THE MANOR REVIEWERS

 CARDIOGLYCOSIDES  have low margin of safety.
*Toxicity is more likely in the presence of Hypokalemia
 Test for Cardiac Glycosides: - Baljet’s Test, Legal’s Test & Keller-Keliani’s Test
 aglycone: steroidal  test: Lieberman- Bustard Test Salkowski Test

6-membered ring attached to the

CPPP nucleus = BUFADIENOLIDE

CARDIAC GLYCOSIDES
SYNONYMS BOTANICAL SOURCE CONSTITUENT/S REMARKS
DIGITALIS Foxglove D. purpurea  Digitoxin  before it MOST LIPID SOLUBLE
-Digitoxin provides longer was the DOC for CHF
DOA as an inotropic agent  Gitaloxin
than digoxin  not  Gitoxin
beneficial since these Grecian foxglove D. lanata (Fam. Polar, short-acting used
agents have narrow Scrophulariaceae)  Digoxin  nowadays: for rapid digitalization
therapeutic index & having DOC for CHF
them stay in the body =  Desacetyl lanatoside
would not be ideal (Desclanoside)  agent
-DIGOXIN INTOXICATION = used for rapid
common antidote: Digoxin digitalization
Immune Fab (DigiFab)
CONVALLARIA Lily of the Valley Convallaria majalis CONVALLOTOXIN – active Nowadays, FDA does not
(Fam. Liliaceae) component recommend the use of
CONVALLOTOXIN for
aged-related cardiac
complaints
APOCYNIUM  LITERALLY Black Indian Hemp, Apocynium cannabinum CYMARIN
translates to poisonous to Dog bane  named (Fam. Apocynaceae)
dogs this bcs it is VERY
POISONOUS to
animals esp. DOGS
ADONIS Pheasant’s eye Adonis vernalis (Fam.  ADONITOXIN  primary
Ranunculaceae) glycoside
 Cymarin, K-strophantin
CACTUS GRANDIFLORUS Night Blooming Selenicereus  a very rare plant &
Cereus grandiflorus(Fam. only blooms once a day
Cactaceae) (at night)
BLACK HELLEBORE Christmas rose Helleborus niger (Fam.  Hellebrin 3 VARIETIES:
Ranunculaceae)   Black  glycosidal
Relative to Adonis spp. cardiac stimulant
(inotropic)
 Green & white 
alkaloidal, cardiac
depressant
rd
STROPHANTHUS S. kombe & S. hispidus  K. strophantoside OUABAIN  3 most
(Fam. Aponacynaceae)  G. strophantin important glycoside
(OUABAIN)  OUABAIN available in the market
is used as an arrow (next to digoxin &
poison prior to discovery digitoxin)
as an important
glycoside made available
in the market
SQUILL Squill bulb Urginea maritime (Fam.  Scillaren-A  convert to  Scillarenin  USE:
Hyacinthaceae) scillarenin which is more expectorant
active  ITS RED VARIETY is
not used in the
pharmaceutical field
bcs of its toxicity so
it is employed as
rodenticide
ADELFA Oleander Nerium oleander (Fam.  Olleandrin  Genocide in Sri
Aponacynaceae) Lanka

**DIFFERENCES BETWEEN DIGITALIS

DIGOXIN DIGITOXIN DES-ACETYLLANATOSIDE
(DESLANOSIDE)
 Water-soluble  Lipophilic  Initial rapid loading of digitalis
 Easy to control in TDM  Completely absorbed  Digitalization
(therapeutic drug  most powerful glycoside for digitalis  DESLANOSIDE is more soluble
monitoring) most lipid-soluble of the cardiac than LANATOSIDE
 0.5-2 mg/ml glycoside used in therapeutics
 long half-life (increase for toxicity)
 1 digitoxigenin – aglycone
 3 digitoxone – glycone

2. ANTHRAQUINONE GLYCOSIDES
 Related to anthracene – in the sense that they usually possessed a three benzene structure
 USE: employed usually as stimulant cathartics
 Identification test: Borntrager’s test (red or pink coloration at the lower ammoniacal region) & SCHONTETEN’S
TEST (is often used for anthranols  (+) green flouroscence)
 derivatives are colored orange-red compounds
 Penicillium islandium (SOURCE)– produces these glycosides & is used to study these glycosides
 Upon hydrolysis, the aglycone portion consists of a di-, tri-, or tetrahydroxyanthraquinone
 Anthraquinols converted upon [O]  to Anthraquinones
 ANTHRAQUINONE GLYCOSIDES
SYNONYMS BOTANICAL SOURCE CONSTITUENT/S REMARKS
CASCARA Sacred bark Rhamnus purshiana (Fam.  Casanthranol  FOUND IN LANE’S PILLS
SAGRADA Rhamnaceae) or Buckthorn  Emodin – Cascarosides *has reduced
bark  Cascarosides A & B  based *Lane’s pills: Casanthrol
 (Rhamnus  is a on optical isomers of *cured with MgO x 1yr
classical term for barbaloin *Magnesium oxide – used to
buckthorn & purshiana  Cascarosides C & D  based treat Cascara Sagrada Extract
referring to the British on optimal isomers of to reduce its bitter taste.
botanist Frederick Pursh chrysaloin
who discovered this  2 types of anthracene
glycoside containing plant) compounds:
o NORMAL O – glycosides
(based on emodin) –
about 10-20%
o ALOIN LIKE C –
glycosides – about 80-
90% (e.g. barbaloin &
deoxbarbaloin
(chrysaloin)
FRANGULA Buckthorn bark Rhamnus fangula Frangulins A & B Component of OTC product
MOVICOL also contains
karaya (Karaya + Frangula =
MOVICOL)
ALOES  Sabila -Curacao Aloe: A. Aloin A  barbaloin  Pharmaceutical aid for
dried latex or barbadensis, A. vera Aloin B  isobarbaloin compound benzoin
juice of the -Cape Aloe: A. spicata, A. (Note: curacao aloe contains tincture
leave of: ferox, A. africana these cardiac glycosides as  Cathartic
Curacao aloe pharmaceutical aid for compd.  Aloe vera gel – for burn
Cape aloe benzoin tincture & cape aloe on abrasions and skin
the other hand contains these as irritation, inflame, &
cathartics) alopecia (since it has
*aloin  C-glycoside moisturizing & emollient
*aloe-emodin  O-glycoside properties)

RHUBARB  Rheum Rheum officinale (for  Rhein anthrones  causes

dried rhizome Chinese rhubarb rheum) drastic cathartic effects or
or root Himalayan rhubarb R. palmatum (chinese) activity & thus are not
Indian rhubarb R. emoid (Himalayan) employed as cathartics)
R. webbianum(indian)
SENNA Alexandria senna (broken leaves) of Cassia  Aloe-emodin or rhein –  Blue green  best
(Senokot) acutifolia sennosides grade, yellowish 
 employed as  Sennosides A & B – a pair of poorest
laxatives or Tinevelly senna (whole leaves) of Cassia stereoisomers dianthrone  Cultivated on wet lands
cathartics prep. angustifolia (Sennidin A & B) resembling rice paddies
 Sennosides C & D – dimeric *Sennoside is more potent
From the Fam. Fabaceae aglycone laxative than Cascara
Sagrada

CHYSAROBIN  mixture of neutral  Hot benzene  is used to  NOT A CATHARTIC (too

principles from Goa extratct 50-70% yield irritating to use), A
powder (Andira avaroba) chrysarobin from Goa KERATOLYTIC when
 powder dissolve in benzene
 KERATOLYTIC  for
psoriasis, trichophytosis,
& chronic eczema
DANTHRON or 1,8 -   A synthetic glycoside
CHRYSARIN dihydroxyanthraquinone for the natural
constituent of 1,6-
dihydroxyanthraquinone
is difficult to isolate
 USES:
 Cathartic
 It is an important
intermediate in the
manufacture of
anthralin and o alizarin
and indanthrene dye
stuff

3. Saponin glycosides  plants have this as a part of their immune system  acts as protectants for plants
whenever they are being ingested by insects, mollusks, cold-blooded animals, & snails (schistosomiasis)
 Form colloidal solutions in water that foam upon shaking  froth test (ID test + result  froth or bubble
formation)
 They have bitter, acrid taste and drugs containing them usually sternutatory and otherwise irritating to the
mucous membrane
 Destroy RBCs by hemolysis and are toxic especially to cold-blooded animals  but not toxic to humans, hence
ID tets: hemolysis test
 Widely distributed in the plant kingdom
 Toxic to insects and mollusks
 Used to control schistosomiasis & fish poison (but does not render the fish poisonous for human consumption
 hence, not poisonous to humans)
 SOURCE of ANTI-INFLAMMATORY AGENTS
 *aglycone .steroidal sapogenins:
o neutral or acidic
o Liebermann-Burchard’s test
o Precursor for Steroids Synthesis
 *two types based on their Sapogenins or aglycones:
-Neutral Saponin – are derivatives of steroids
-Acid Saponin – possess triterpenoid structures
 Saponin glycosides can either be: steroids or triterpenoids

2 CHEMICAL CLASSES OF SAPONINS

3.1. Steroids
o Diosgenin and botogenin  DIOSGENIN: anti-inflammatory & the most important plant steroids for
the partial synthesis of steroid hormones from the genus of Dioscorea  Mexicom vam (Dioscorea
floribunda)
o Hecogenin, manogenin & gitogenin from the species of Agave (A. cantalla)  Molluscicide
o Sitosterol from the crude vegetable oils
 SAPONIN GLYCOSIDES
SYNONYMS BOTANICAL SOURCE CONSTITUENT/S REMARKS
GLYCYRRHIZA Licorice root Glycyrrhiza glabra   MAIN GLYCOSIDE   Mask the taste of bitter
Spanish licorice Glycryrrhizin (Glycyrrhizic drugs
G. glabra Linne Var. acid)  50x as sweet as  Increase foaminess in
grandulifera  Russian sugar beer
licorice o USE: 1. Increases fluid &  Used in peptic ulcer &
Na retention & promotes K addison’s disease 
Fam: FABACEAE depletion froth produced by the
o C/I: patients with cardiac glycyrrhiza = protection
failure & HTN (since it can for ulceration
cause Na & H2O retention)

 Glycyrrhetic acid  aglycone

portion of glycyrrhizin 
ANTI-INFLAMMATORY
AGENT
DIOSCOREA Mexican yam D. floribunda  Dioscin (cardiac glycoside) Diosgenin  Best source of
 eventually converted to steroids
 DIOSGENIN Diosgenin Major precursor
of glucocorticoids, oral
Dioscorea spiculifora  Botogenin & diosgenin contraceptives & sex
(cultivated spp. of hormones
dioscorea)
GINSENG American ginseng Panax quinquefolius Linne  Ginsenosides  Tonic, stimulant,
 Panaxosides diuretic, and carminative
Asian ginseng Panax ginseng (Fam.  Chikusetsusaponins properties
Araliaceae)  Performance and
Ginsenoside Rg1  one of the endurance enhancer
major saponins (a triterpenoidal  In the Orient, it is used
ginseng) in the treatment of
anemia, diabetes,
insomnia, neurasthenia,
gastritis, & esp. sexual
impotence
(APHRODISIAC)
 Considered as an
adaptogenic agent 
reduces STRESS
Psidium guajava Fam. Myrtaceae  Vaginal wash after giving
birth & as an anti-
bacterial agent
Lupulin  Humulone (alpha-acids) &  USED in the
Lupulone (beta-acids)  manufacture of beer
mains compounds
responsible for the bitterness
of lupulin
Agave A. cantalla  Moluscicide
 4. Cyanogenic or Cyanophore glycosides  glycosides yielding hydrocyanic acid (HCN) as the by-product of
its hydrolysis by the beta-glucosidases
 cyanogenic = produce CN upon hydrolysis
 Beta-gucosidases  derivatives of mandelonitrite (nitrile of mandelic acid, or the cyanohydrin derivative of
benzaldehyde)
 Detected by GUIGNARD TEST
 Enzyme digesting cyanogenic  emulsin (collective enzyme which contains amygdalin & prunase that
hydrolyses the cyanogenic glycosides; **composite enzyme found in almonds; causes hydrolysis of beta-
glucoside)
 Usually cyanogenic glycosides  has amygdalin & prunasin as its primary glycoside present on them that will
eventually yield (R)-mandelonitrile as its aglycone portion
 Sambucus nigra (ELDERBERRY)  liberates (S)-mandelonitrile as it aglycone
 Amygdalin commonly found in Rosaceae family  e.g. bitter almonds, apricot, cherries, plum in kernels of
apricots
 Prunasin  wild cherry bark (Prunus serotina) wild cherry, linseed, & patani bean
 Other glycosides: laetrile, linamarin, & phaseolunatin
 STEPS IN HYDROLYSIS OF AMYGDALIN:
1. The molecule is hydrolyzed initially to liberate 1 molecule of glucose and 1 molecule of mandelonitrile
glucoside.
2. The second molecule of glucose is liberated with the formation of mandelonitrile.
3. The mandelonitrile then breaks down with the formation of benzaldehyde and hydrocyanic acid

Amygdalin  amygdalASE  glucose + prunasin

Prunasin  prunASE  glucose + mandelonitrile
Mandelonitrile (aglycone)  mandelonitrile lyase  benzaldehyde + HCN

ADDITIONAL NOTES FROM MANOR:

 Vitamin B17 (Amygadalin or Laetrile)  flavoring agent, anticancer claims,
& useful for SCA (sickle cell anemia)
 Amygdalin  MOST COMMON CYANOPHORE GLYCOSIDE
 SOURCES: – Cherry  Prunus serotina, Apricots  Prunus armeniaca, Almonds  Prunus amygdalus, Barley
 Hordeum vulgare

CYANOPHORE GLYCOSIDES
SYNONYMS BOTANICAL SOURCE CONSTITUENT/S REMARKS
WILD CHERRY Prunus virginia & wild Prunus serotina Ehrhart  Prunasin (D-  USES:
black cherry tree (Fam. Rosaceae) mandelonitrile o Flavored vehicle especially
glucoside) in cough remedies
 Scopoletin - resin o Sedative expectorant
APRICOT PITS Prunus armeniaca Linne.  Laetrile (-) –beta-
(Fam. Rosaceae) mandelonitrile 
beta-glucuronoside
 5. Isothiocyanate or Glucosinolates glycosides
 ENZYME (that acts upon or hydrolyses isothiocyanate glycosides): myrosinase
 Group of bound toxins, like cyanogenic glycosides
 MAJOR ROLE IN PLANTS: feeding deterrents against both insects & mammals because these glycosides are not
pleasant smelling or they contribute to the properties of some non-pleasant smelling plants
 Comes from the mustard family  Cruciferus plants (Brassicaceae family)
 DISTRIBUTION: Mustard family (Brassicaceae) which include: oilseeds (rapeseed), condiments (mustard &
horseradish), & vegetables (broccoli, cabbage, & trunips)
 Mustard family vegetables have been found to have anticarcinogenic properties
 Principle isothiocyanate glycoside would include  SINIGRIN, SINALBIN, & GLUCONAPIN

ISOTHIOCYANATE GLYCOSIDES
SYNONYMS BOTANICAL SOURCE CONSTITUENT/S REMARKS
GARLIC Ajos Allium sativum  Alliin (+) –S- allyl – L –  ALLICIN -- Responsible for
cysteine sulfoxide)  lachrymator factor of allium;
ALLICIN  ALJOENE taste and odor of garlic; & its
 Allicin  primary antibacterial &
glycoside antihyperlipidemic property
 ALJONE – responsible for the
anti-thrombotic property
 Derived from cysteine
MUSTARD  SINIGRIN  principal
constituent of isothiocyanate
White mustard Sinapis alba Brassica alba  SINALBIN  Acrinyl glycosides which is
Black mustard Sinapis nigra Brassica nigra isothiocyanate accompanied by the enzyme
Brown mustard  SINIGRIN  Allyl MYROSINASE
isothiocyanate  SINIGRIN/Allyl isothiocyanate/
Mustard volatile oil 
employed as a local irritant &
emetic, rubefacient, & vesicant
**Sinalbin  Myrosinase  Acrinyl
Isothiocyanate  pungent –tasting
oil & less volatile

6. Alcohol glycosides

ALCOHOL GLYCOSIDES
SYNONYMS BOTANICAL SOURCE CONSTITUENT/S REMARKS
WILLOW BARKS Prunus virginia & Salix purpurea & S.  SALICIN  SALICIN  anti-rheumatic agent &
wild black cherry fragilis  POPULIN natural forerunner of ASA
tree (Benzoylsalicin)  *Salicin  Saligenin + beta- D-glucose
= (salicin alcohol) produced by the
hydrolysis of Salicin by Emulsin
 *Salicin  Emulsin = Saligenin or
salicyl alcohol + beta-D-glucose

 POPULIN Poplar Bark (Populus spp.)

 7. Aldehyde glycosides
ALDEHYDE GLYCOSIDES
SYNONYMS BOTANICAL SOURCE CONSTITUENT/S REMARKS
VANNILA Mexican vanilla or Vanilla planifolia  Vanillin is  Flavoring agent
Vera Cruz methylprotocathechuic  Mexican vanilla  the best grade
Bourbon vanilla aldehyde vanilla present in the market
 Vanillin  chem.  Bourbon vanilla  specific variety that
Tahiti vanilla V. tahitensis (Fam. known as: 4-hydroxy-3- resembles Mexican vanilla
Orchidaceae) methoxybenzaldehyde  Tahiti vanilla  unpleasant in odor &
less suitable as flavorant
PINE TREES  Coniferin  Glycoside present in the cambium sap
of pine trees
LIGNIN  By-product the bulb industry
 MOST OF THE VANILLIN in commerce is
made from lignin
 ETHYL VANILLIN – a synthetic analog of
vanillin is also used as flavoring agent
 COMMERCIAL VARIETIES OF VANILLA
1. Mexican or Vera Cruz vanilla  best grade on the market
 the pods frequently attain the length of 30-35 cm

2. Bourbon vanilla  it resembles the Mexican variety but it is about two thirds as long, blacker in color, usually covered with sublimate
of needle shape vanillin crystals & possess a coumarin-like odor.

3. Tahiti vanilla  is the reddish-brown in color and about as long as the Mexican variety but sharply attenuated and twisted in lower
portion
 the variety is rendered less suitable for flavoring because the odor is somewhat unpleasant

4. Vanilla splits & cuts  represent the more mature fruits in which dehiscence has taken place
 they cut into short lengths  POOREST GRADE among vanilla varieties

8. Phenol glycosides  the aglycone portion is phenolic in character

PHENOL GLYCOSIDES
SYNONYMS BOTANICAL SOURCE CONSTITUENT/S REMARKS
UVA-URSI Bearberry Arctostaphylos uva-ursi  ARBUTIN MAIN  Antiseptic and astringent 
Fam. Ericaceae GLYCOSIDE in. uva-ursi urinary antiseptic
 *available in the form of herbal
teas
OTHER PHENOL  HESPERIDIN  from Citrus
GLYCOSIDES fruit
 PHLORIDIZIN  root bark of
Rosaceous plants
 BAPTISIN  Baptisia
 IRIDIN  Iris spp.
**POISON IVY & Rhus spp.  UROSHIOL  A non-volatile principle
OAK producing allergic symptoms
 cause delayed contact
dermatitis
9. Flavonols Glycosides  largest group among the naturally occurring phenolic compounds
 aglycone: Flavonoids
 EXAMPLES  Rutin, Hyperoside, Quercetin, & Vitexin
 CHALCONES  found in yellow flower pigment: rutin, & quercitin
 CHALCONES  these compounds are termed nitrogenous anthocyanins which are responsible for the bright
colorations of flowers & fruits of Cactaceae
 OTHER EXAMPLES:
o Anthocyanin  vascuolar pigment – red, purple, blu, & black
o Betalains  red, & yellow tyrosin-derived pigments
o Leucoanthocyanin  colorless
 CITRUS BIOFLAVANOIDS: hesperidin, hesperitin, naringenin
 Vitamin P – permeability factor  rutin + hespiridin  treat capillary fragility
 **common colds  are abundant in the ff plant families:
- Polygoneaceae
- Rutaceae
- Umbelliferae
 **Elin (Ulmus sp.) – Quercitin
 **Milk thistle (Sylibum marianum)
 hepatoprotectant (treatment of liver ailments)
 e.g. Silibium & Sylimarin
 **Ginkgo biloba (G. biloba)
 Ginkgolides, bilobalides
 a memory-enhancer
 has a drug-herb interaction w/ ASA

 Flavonol  containing a phenyl benzo-pyrone ring system

o A pyran with double bond  with phenyl + benzene + oxygen  OH = -ol = FLAVONOL
 Flavanone  no OH
 Anthocyanin  has benzopyran
 10. Lactone glycosides

LACTONE GLYCOSIDES
SYNONYMS BOTANICAL SOURCE CONSTITUENT/S REMARKS
TONKA BEANS Dipteryx odorata  COUMARIN  popular  Bishydroxycoumarin or dicoumarol
o **lactone of beta-  first oral anti-coagulant. The
**hydroxycinnamic usual dose is 200 to 300 mg initially,
acid then 25-200 mg once a day, as
o fragrant odor, bitter indicated by the PT (prothrombin
aromatic, burning time) determinations
taste  *Bishydroxycoumarin or
dicoumarol  improperly cured
leaves of sweet clover Melilotus
officinalis & first oral anticoagulant,
precursor of warfarin
CANTHARIDES Spanish flies, Cantharis vesicatoria  CANTHARIDIN   0.6-1.0% the chief vesicating
Russian flies, or Linne De Geer (Fam. vesicating principle principle of cantharides
Blistering flies Meloidae)  USES: irritant (urogenital tract
priapism), rubefacient, aphrodisiac,
warts removal (topical)
PSORALENS  Umbelliferae  Methoxalen, 8-  USES: repigmentation agent for
photosensitizing Methoxypsoralen or idiopathic vertigo (Leukoderma)
coumarins **Family: Rutaceae & xanthotoxin and for control of symptomatic
Apiaceae  Trioxalen control of severe, disabling
**Bishop’s Flowers – psoriasis
Ammi majus 
contains large amount
of bergapten &
xanthotoxin

OTHER LACTONE GLYCOSIDES:

SWEET VERNAL GRASS - Anthoxanthum odoratum Linne (Fam. Graminae)
SWEET CLOVER - Melilotus albus Mediscus & M. officinalis Linne Lamarck, (Fam. Leguminosae)
SWEET SCENTED BEDSTRAW - Galium triflorum Michaux, (Fam. Rubiaceae)
RED CLOVER - Trifolium pratense Linne (Fam. Leguminosae)

REVIEW FOR LACTONE GLYCOSIDES:

Coumarin  tonka beans USE OF LACTONE GLYCOSIDES
Skimmin  Japanese star anise Anti-cougulant Tonka beans
Aesculin  chestnut tree Aphrodisiac Cantharides (Blistering flies)
Daphnin  mezereum Antihelmintic Santonin
Fraxin  ash bark Antispasmodic Scoploletin
Scopolin  belladonna Repigmentation agent Psoralens  Methoxalen & trioxalen
Limethin  citrus fruits
Scopoletin  true camp tree
Santonin  Artemisia cina  formerly used as an antihelmintic
Cantharidin  blistering flies
Bishydroxycoumarin or dicoumarol  Melilotus officinalis
Viburnum

TANNINS WAS NOT INDICATED IN THE HANDOUTS  read about tannins on the manor handouts
 LIPIDS  consists of fixed oils, fats, and waxes
 Esters of long chain fatty acids and alcohols, or closely related derivatives
 Fats and fixed oils are obtained from either plants (olive oil, peanut oil) or animals (lard)
 Greasy, lighter than water, & compounds insoluble in water but soluble in organic solvent

ANOTHER WAY TO NAME LIPIS TRIGLYCERIDES (produced through esterification)

Triglycerides or Triacylglycerol

DID NOT EXPLAIN  pls refer in the biochemistry book (pp. 338 onwards)

LIPIDS  primary function is food (energy) STORAGE

 Fixed oils and fats differs only as to melting point
o Fatty or fixed oils  liquid at normal room temperature EXCEPT cocoa butter
o Fats  semi-solid or solid at ordinary temperature EXCEPT cod liver oil
o RATIONALE: if the lipids have unsat fats (double bonds)  LIQUID at RT, whereas, lipids with saturated fatty acid
containing are usually solid at RT

Fats Fixed Oils Waxes

esters of Fatty acids + esters of Fatty acids + glycerols esters of Fatty acids + High molecular
glycerols weight monohydric alcohol
Solid (except: Cod liver Liquid (except: Myristica Solid, Semisolid, Liquid
oil) theobroma oils)
Saturated Fatty Acids Unsaturated Fatty Acids Saturated, Unsaturated Fatty Acids
Animals Plants Plants, animals
Energy Storage Energy Storage Protection, etc
 1. FATTY ACIDS
TYPES OF FA IN DEPENDING IN THE DEGREE OF SATURATION
(DOUBLE BONDS):
Saturated or Unsaturated:
 Saturated = no double bonds/triple
 Monounsaturated = have at least one C-C bonds at
their structure
 Polysaturated = have multiple double bonds

 Unsaturated FA – can also be subdivided by isomers

whether cis (Hydrogens of the double bonds are on the same
side) or trans (opposite direction of the double bonds)
 Trans FA- do not usually occur in nature; by-product
of hydrogenation/hardening of oils

EXAMPLES OF SATURATED FA EXAMPLE OF MONOUNSATURATED FA

SHORT HAND ABBREVIATION FOR UNSATURATED FA: EXAMPLE OF POLYUNSATURATED FA

8:1 (∆ 3)  first number 8 = no. of C + 1 = no. of bonds
8:2 (∆ 3, 6)  3,6-octadienoic acid
DELTA sign usually used to designate the position of double
bond if present in FA structure
CLASSIFICATION OF FA PRESENT AS GLYCERIDES IN FOOD FATS
SATURATED FATTY ACIDS  BuCa CaCaLaMyPaStAr
Common name Systemic name Formula Common source
Butyric Butanoic CH3(CH2)2COOH Butterfat
Caproic Hexanoic CH3(CH2)4COOH Butterfat, coconut, & palm nut oils
Caprylic Octadenoic CH3(CH2)6COOH Butterfat, coconut, & palm nut oils
Capric Decanoic CH3(CH2)8COOH Butterfat, coconut, & palm nut oils
Lauric Dodecanoic CH3(CH2)10COOH Butterfat, coconut, & palm nut oils
Myristic Tetradecanoic CH3(CH2)12COOH coconut, & palm nut oils, most animals & plants fats
Palmitic Hexadecanoic CH3(CH2)14COOH Practically all animal & plant fats
Stearic Octadecanoic CH3(CH2)16COOH Animal fats and minor component of plant fats
Arachidic Eicosanoic CH3(CH2)18COOH Peanut oil

UNSATURATED FATTY ACIDS

A. Monoethenoic acids
Common name Systemic name Formula Common source
Oleic Cis 9-octadecenoic C17H33COOH Plant & animal fats
Elaidic Trans 9-octadecenoic C17H33COOH Animal fats
B. Diethenoic acids
Linoleic  OMEGA 6 9, 12- octadecadienoic C17H31COOH Peanut linseed, and cottonseed oils
C. Triethenoid acids
Linoleic  OMEGA 3 9, 12, 15- octadecatrienoic C17H29COOH Linseed & other seed oils
Eleostearic 9, 12, 13- octadecatrienoic C17H29COOH Peanut seed fats
Arachidic Eicosanoic CH3(CH2)18COOH Peanut oil
D. Tetraethenoid acids
Moroctic 4,8,12,15-octadecatetraenoic C17H27COOH Fish oils
Arachidonic 5,8,11,14-eicosatetraenoic C19H31COOH Traces in animal fats
 EFA (ESSENTIAL FATTY ACIDS)  omega 3 & 6 FAs
 Omega indicates the position of the first double bond from the methyl group
 The first point of saturation if next to the third C (Omega 3-FA)  Linolenic
 The first point of saturation if next to the sixth C (Omega 6-FA)  Linoleic
 Great significance on human nutrition and health issues
 Omega 3 & 6 = VITAMIN F

PROCESSES
 Hydrogenation  conversion of liquid oil to semisolid fats which are used as cooking fats and shortening (e.g.
margarine  hydrogenation product of peanut oil)
 Saponification  alkali catalyzed by hydrolysis of fats & fatty acids yielding soap.
 Hydrolysis  will yield alcohol and acids
 Oxidation  responsible for the randicity
 Heating oil  will produce acrolein

WHAT ARE THE DIFFERENT TESTS FOR LIPIDS? (PHYSICAL CONSTANTS THAT TELLS YOU WHAT LIPIDS DO YOU
HAVE)
1. Acid value – the number of milligrams of KOH required to neutralize the free FA in 1 g of the substance
 basically determines the amount of free FA in the oil

2. Saponification value – the number of milligrams of KOH required to neutralize the free FAs and saponify the
esters contained in 1g of the substance.
 gives information about the FA usually the longer the carbon chain the less acid is liberated per gram of fat
hydrolyzed
 Therefore, long chain FA = have lower saponification value since there are less carboxylic group to be
saponified
 Shorter carbon chain/ lower C atom = higher saponification value

3. Iodine Number – the number of grams of iodine absorbed, under prescribed conditions, by 100 g of
substance.
 indicates the degree of unsaturation; so the higher the IN = the higher the degree of unsaturation (more
double bonds)
 That’s the reason we have a classification in FIXED OILS:
o drying oils (usually used in painting since they dry faster & leaves on canvas) ; drying oil have high
iodine number usually above 120 (e.g. linseed oil, fish oil & cod liver oil; linseed oil is used for oil-
based painting)
o Non-drying oil – saturated & iodine number is less than 100 (e.g. olive & almond oil)
o Semi-drying oil – 100-120 iodine number (e.g. cotton seed oil & sesame oil).
 ANOTHER EXAMPLE:
IODINE NUMBERS OF TRIGLYCERIDES
Fatty acids # of DOUBLE BONDS IODINE #
Palmitoleic acid 1 95
Oleic acid 1 86
Linoleic acid 2 173
Linolenic acid 3 261
Arachidonic acid 4 320
* When exposed to air, drying oils undergo oxidation with the formation of a tough, hard film upon exposure to
air.
*The drying quality is caused by the presence of unsaturated fatty acids of a distinctive character, such as linoleic &
linolenic acids
 4. Other physical constants such as: melting point, specific gravity, and refractive index is also served as identity,
purity & quality tests.

Class of Lipids based on its ability to absorb OXYGEN FROM AIR

Drying >120 iodine Linseed oils, Fish oils, Cod-liver oils
Semi-drying 100-120 Cottonseed oils, Sesame oils
Non-drying <100 Olive oils, Almond oils

METHODS OF OBTAINING FIXED OILS OF VEGETABLE AND ANIMAL ORIGIN:

 Fixed oils and fats of vegetable origin are obtained by expression in hydraulic presses. Expression  hydraulic
presses (vegetable oils):
o Virgin oils or a cold-pressed oil  if the expression is carried out in a cold (processed w/out heat)
o Hot pressed oil  if the expression is carried out w/ heat
o Sometimes organic solvents are used for extraction of oils
o ** Rendering:
 for fats
 steamed, until fat melts & rises to the top
 separate the fat by decantation
 cleared by filtration
 bleached w/ ozone
o **Solvent Extraction  non-polar solvents are used

SATURATED FIXED OILS

SOURCE BOTANICAL SOURCE CONSTITUENTS REMARKS
COCONUT OIL Cocos nucifera (Fam. Lauric and myristic acids  Has the highest saponification value &
Arecaceae) lowest iodine value (because it is a
pure saturated FA)
 USES: shortening agent, source of
margarine or for frying fat, soap &
candle manufacture
 Endosperm  part of coconut made
into copra
PALM OIL Elaeis guineensis (Fam.  One of the world’s most widely
Arecaceae) consumed edible oils, next to soybean
oil
PALM KERNEL OIL Elaeis guineensis (Fam.
Arecaceae)

MONOUNSATURATED FIXED OILS

SYNONYMS BOTANICAL CONSTITUENT/S REMARKS
SOURCE
CASTOR OIL Ricinus communis 45-55% of fixed oil of 20%  Tri-ricinoleoylglycerol  cathartic effect
(Fam. protein substance  ** tririnolein = 1 glycerol + 3 ricinoleic
Euphoribiaceae)  (Globulin, albumin, acid  stimulant cathartic (can lead to
castor bean nucleoalbumin, dehydration & works primarily in the
glycoprotein & ricin) small intestines)
 RICIN  a toxic lectin;  Emollient plasticizer in flexible collodion
toxic principles; a  Hydrogenated castor oil  stiffening
poison agent
 Ricinoleic acid  is an ingredient in a
 vaginal jelly for restoration &
maintenance for vaginal acidity
 *aromatic castor oil = castor oil +
flavorant
 *hydrogenated castor oil = castor wax
(polish, cosmetics)
 *should not be used by pregnant
women because it may induce
premature labor
OLIVE OIL Sweet oil, Oil of Olea europea (Fam.  USE: Setting retardant for dental
Europe, Salad Oleaceae) cements and in the preparation of green
Oil soaps, plasters, and liniments
 *forms:
-virgin/ cold-pressed – w/out heat
-technical = from boiling H2O
-tournant – from fallen of decomposed
fruits
-sulfur – from solvent extraction, CS2
 *test for Olive Oil: Millon’s Test
PEANUT OIL Arachis oil Arachis hypogaea  45% fixed oil, 20%  Non-drying
(Fam. Fabaceae) protein, and thiamine  SOLVENT for IM injections
 **Contains: Oleic,  Official Fixed Oils for IM inj (CoCoPeaSe):
Linoleic Peanut Oils
Sesame Oils
Corn Oils
Cottonseed Oils
 Peanut oil cake  the residue upon
expression of the oil
RAPESEED OIL Canola oil Brassica  50% erucic acid
campestris, B.
juncea, and B.
napus (Fam.
Brassicaceae)

GRADES OF PURITY OF OLIVE OIL:

1. Virgin oil – obtained by gently pressing the peeled pulp with greater pressure
2. First class or first grade oil – is pressed from crushed pulp with less pressure
3. Second grade of edible oil is pressed from crushed pulp with greater pressure. Hand-picked olives are used, and the oil is obtained
promptly before decomposition produces fatty acids. Finally, the pukp, mixed with hot water, is pressed again.
4. Technical oil: or the pulp is extracted with CS2 (carbon disulfide) to obtain sulfur olive oil of inferior quality.
5. The fallen, decomposed or refused leaves that are allowed to ferment furnish a low grade “tournant oil” which contains large
amounts of free fatty acids.

SYNONYMS BOTANICAL SOURCE CONSTITUENT/S REMARKS

SESAME OIL Teel oil Sesamum indium  Sesamolin, sesamol  USE: effective synergist for
Benne oil (Fam. Pedaliaceae)  Sesamolin  Phenolic pyrethrum insecticides
Gingily oil constituent Confers stability  Test: Bauduin Test  (+) pink
 *Oleic, Linoleic, color w/ fuming HCl
 SOLVENT FOR IM INJ
COTTONSEED OIL Gossypium hirsutum  Glossypol  toxic principle;  USE: use against P. falcifarum
(Fam. Malvaceae) usually occurs in the and E. histolytica
 secretarial cavities of all parts  Test: Halphen Test / Bevan Test
of the plants but can be  SOLVENT FOR IM INJ
remove b the treatment of
alkalis
**linoleic, oleic, malwanic acid

SOYBEAN OIL – a Glycine soja (Fam.  Stigmasterol or also known  Stigmasterol  precursor in
drying oil, with an Fabaceae) as WULZEN ANTI-STIFFNESS the synthesis of progesterone
iodine value between FACTOR  Contains the enzyme LECITHIN
120-141 & is not  STIGMASTEROL  also  ingr. of parenteral nutrient
useful as cooking oil present in calabar bean  correct derange lipid &
 hence, the oil is cholesterol metabolism & for
used in the emulsions
manufacture of  SOYBEAN OIL  the usual
varnishes, insulators & source of lecithin
other products
SOYBEAN MEAL Flour sifted from   Used to detect urea nitrogen in
decorticated ground blood serum
seed of Glycine soja  SOYBEAN IS THE ONLY PLANT
THAT POSSESSED the enzyme:
urease  BUN test
ALMOND OIL Prunus amygdalus  contain oleic acid
(Fam. Rosaceae)
APRICOT KERNEL OIL Persic Oil P. armeniaca  similar to almond oil
PEACH KERNEL OIL Persic Oil P. persica  similar to almond oil

POLYUNSATURATED FATTY ACIDS (PUFA)

SYNONYMS BOTANICAL SOURCE CONSTITUENT/S REMARKS
CORN OIL corn (Zea mays) Linoleic, Oleic  Solvent for irradiated ergosterol, IM inj
 The oil-rich embryos (often called
germs) are separated by a FLOTATION
during the preparation of corn starch.
 Germ Oil  the residue upon
expression
SAFFLOWER OIL Carthamus tinctorius Linne
(Fam. Asteraceae)
SUNFLOWER Helianthus annuus Linne
(Fam. Asteraceae)
LINSEED OIL Flaxseed oil Linum usitatissimum Linne
(Fam. Linaceae)
COD LIVER OIL Gadus morhua Linne  THE ONLY OIL FROM ANIMALS (the rest
(Gadidae) are from PLANTS)
 A good source of Vit. A & D
Ethiodized oil  An iodine addition product of the ethyl
injection ester of the fatty acids of poppy seed oil
 RADIOPAQUE  & is used as a
diagnostic aid in hysterosalpingography
& lymphography
 DEFINITION LIPIDS
Lipid lowering found in sugar cane waste and leaves of alfalfa and wheat Policosanol
Drying fixed oil expressed from Carthamus tinctorius and is recommended for its cholesterol lowering properties Safflower oil
An antifungal with the MOA of gradually release of acetic acid Glyceryl triacetate
A substance obtained from Glycine soja which is used to control deranged lipid and cholesterol metabolism Lecithin
Milky fluid produced by the salivary glands of worker bees Royal jelly
Used for counteracting the effects of ageing and for the treatment of depression & dermatitis
A purified internal fat of the abdomen of the sheep, Ovis aries which is used as ointment base Suet (Prepared Suet NF
1950)

FATS & RELATED COMPOUNDS  contain a higher proportion of solid glycerides or saturated glycerides & yields
the largest calories per gram
1. Theobroma oil  cacao seed (Theobroma cacao)  THE ONLY FAT THAT IS LIQUID IN ROOM TEMP
 *“Food of the Gods”
 *Solid fixed oil
 *Oleopamitostearin
 *Cacao butter as suppository base
 *Breakfast cacao or prepared cacao powdered expressed marc.
 *a vegetable oil, solid at room temperature

2. Lanolin – hydrous wool fat  purified fat like substance from sheep wool (Ovis aries)
 have 25-30% H2O
 WATER ABSORBABLE ointment base

3. .Anhydrous  aka Wool Fat from Ovis aries

 NMT 0.25% H2O
 absorbable ointment base

4. Undecylenic acid  anti-fungal (Zn salts)  e.g. undecenoic acid used to treat athlete’s foot
 11:1  from the pyrolysis of castor oil (Ricimus communis)

5. Sodium Morrhuate  sodium salts of the fatty acids in cod-liver oil (Gaddus morrhua)
 Antisclerosing agent for varicose veins

6. Lard NF X (1955) SYNONYMES: Hogs lard, Manteca, Grasa

 ORIGIN: fatty matter of the abdomen of the hog Sus scrofa (Suidae)
 USE: ingredient in the preparation of ointment & cerates  emollient

**Cod Liver Oil  Cod fish (Gadus morrhuae) Liquid fat

 rich sources of oleovitamin A & D
 antirachitic
 an animal fat, liquid at room temperature

** Butterfat  Cow’s Milk (Bos taurus)

 Water-soluble B - growth promoting factor found in Butterfat

WAXES
 are esters resulting from condensation of high molecular weight, straight chain fatty acids & high molecular
weight, primary, straight chain alcohols  that’s why majority is solid or semi-solid at RT (exc. JOJOBA OIL 
liquid plant wax)
 have low iodine value  because the chains are mainly made up of single bonds (NO DEGREE OF UNSAT)
  IMPORTANCE OF WAXES IN PLANTS & ANIMALS: prevent water loss in plants & to water-proof animals
 *In plants: Epidermal walls of leaves & fruits (protect from entry & exit of water)
 *lipid used to control the consistency of creams & ointments  *Ointments; cosmetics; cerates

Animal Wax:
1. Spermacetti  head of spermwhale (Physeter macrocephalus) Fam. Physeteridae
 quality emollient & ingredient in cold creams
 ingredient in cold creams (now being substituted because of
endangerment) REPLACED BY CETYL ESTER WAX (synthetic spermacetti) or
cetyl alcohol

CETYL ALCOHOL – a mixture of solid alcohols consisting chiefly (NLT 90%) of cetyl alcohol
or 1-hexadecanol  an emulsifying agent and a stiffening agent

Insect wax:
1. Beeswax  from honeycomb of bees (Apis mellifera)
 Forms: White – bleached beeswax
Yellow – not bleached
 myricyl palmitate  main component

FORM SOURCE REMARKS

Beeswax/Yellow Apis mellifera (Fam. COMPONENTS:
wax Apidae) 1. myricyl palmitate – 72%
2. cerotic acid – 14%
3. hydrocarbons – 12%
4. moisture
5. pollen
6. propolis (bee glue)
USES:
-stiffening agent & ingredient to yellow ointment
-base for cerates & plasters
White wax Apis mellifera -BLEACHED BEESWAX
-Saponification cloud test  it is a rapid, reliable, and expensive
method of detecting the presence of certain adulterants of natural
beeswax
-USE: more employed pharmaceutically in ointments & cold creams
 because it is more aesthetically appealing

2. Lac wax

Plant Wax:
1. Jojoba Oil  liquid wax from the seed of Simmondsia chinensis Fam. Simmondsiaceae
 eicosenyl & docosenyl esters
 an emollient

2. Carnauba Wax  leaves of Copernicia prunifera

 myricyl cerotate
 candles, varnish, polish; substitute for beeswax

3. Bayberry waxy  myricyl cerotate

 PROSTAGLANDINS
 Are C20 lipid metabolites formed in the body form essential, unsaturated fatty acids in the diet
 Apparently, occur in all mammalian tissues, but they are present in low concentrations
 4 CLASSIFICATIONS: Prostaglandin A, B, E, & F

-derived from linoleic acid (omega-6) acted upon by phospholipase

A2  Arachidonic acid (precursor of LOX & COX)

*Regulate blood pressure (Bradykinin), induces blood clotting

(Thromboxane), & control also the productive fxns like induction
of labor, regulation of sleep-wake cycle
*COX – activated PG & TXA; LOX – Leukotrienes

PROSTAGLANDIN
SYNONYMS REMARKS
PGF2a Dinoprost Uterine stimulant
(15s)-Methyl PGF2a Carboprost IM injection
PGE2 Dinoprostone Vaginal suppository
PGE1 Alprostadil  USES: vasodilator, inhibits platelet aggregation,
and stimulates intestinal & uterine smooth muscle
 is used in the palliative therapy to maintain
temporarily neonates with patent ductus
arteriosus
 Secondary metabolites  important to know their characteristics
TANNINS
 abundant in TEAS
 non-crystalisable hydrocolloid mixture of polyphenols  hence , called POLYPHENOLIC COMPOUNDS
 Difficult to separate because they won’t crystallize (DO NOT CRYSTALLIZE)
 MOST IMPORTANT PROPERTY  have the ability to combine with other macromolecules  therefore, can precipitate
 Can precipitate: protein, pectin & cellulose  but since it can ppt CHON it is CARCINOGENIC particularly in teas 
when we open the tea bags you can see dried plant materials to be infused in hot water to get the content  have
tannins present in the form of tannic acid  TANNIC ACID is the CARCINOGENIC SUBSTANCE
 Parts: barks & stems (the usual and best source of tannins from plants)
 MAIN USE: astringent since it can ppt CHON  hence, used in facial wash (e.g. witch hazel)
 EXAMPLES OF polyphenolic compounds from Camellia sp.  catechin, kaempferol, myricetin, & quercetin

CLASSIFICATION OF TANNINS BASED ON GOLDBEATER’S SKIN TEST

 Goldbeater is derived from the intestine of the ox or ox skin  dipped in HCl then rinsed in water and lastly
soaked in tannin soln for 5 minutes  then wash again with water & treated with 1% FeSO4 soln)
 POSITIVE RESULT  brown & black (the color of leather)  WILL BE CLASSIFIED AS POSITIVE TANNING TEST
 “True tannin”
 NEGATIVE TANNING TEST  “pseudo” (fake) tannin

TRUE TANNINS PSEUDO TANNINS

 Have 2 types: hydrolysable & non-hydrolysable  Substance with low molecular weight than true tannins 
 NOTE: FeCl3 Test  general test for true tannins does not respond to gold beater’s test  hence, negative 
can ppt but not that much unlike true tannins

TRUE TANNINS (Difference between hydrolysable & non-hydrolysable)

HYDROLYSABLE/pyrogallol derivatives NON-HYDROLYSABLE/catechol derivatives/condensed/proanthocyanidins
 Soluble in water  Not soluble in water
 These are ester of sugars and phenolic acid molecules  Also known as catechol derivatives or condensed tannins (called
 COMPONENTS: gallic acid (phenolic acid) and glucose condensed tannins because it undergoes CONDENSATION or
(sugar)  linked or connected by ester bond POLYMERIZATION) or proanthocyanidins
 With DRY DISTILLATION will yield or converted to   Proanthocyanidins  because they consist of flavan-3-ol units linked
pyrogallol derivatives together by C-C bonds
 The hydrolysable tannins are soluble in water and their  WHEN FLAVANOLS  undergo condensation  will form NON-
solution produces blue color with ferric chloride  hydrolysable tannins
(FeCl3 test  blue-black color)  COMPOSITION: catechins & leucocyanidin
 Bromine water test  no precipitate are formed  With DRY DISTILLATION will yield  catechol derivatives
 Upon the (+) addition of hydrolytic agent  would be  Condensed tannins are also soluble in water and produces green color with
hydrolyzed and breaking of the ester bonds (bonds ferric chloride. (FeCl3 test  greenish black or brownish green)
connecting glucose and gallic acid)  Br water test  will form precipitate upon the reaction
 Hydrolysable tannins on heating with hydrochloric or  Upon the (+) addition of hydrolytic agent (e.g. acid or enzyme)  red
sulphuric acids yield = gallic acid and ellagic acid insoluble compound (PHLOBAPHENES)
 SOURCES of gallic & ellagic acid: Myrobalan (Terminalia  ANOTHER TEST for NON-hydrolysable  Matchstick test  GENERAL TEST
chebula  Combretaceae), Bahera (Terminalia belerica FOR CONDENSED TANNINS
 Combretaceae), Witch hazel (Hamamelidaceae)  Matchstick test  soaked the matchstick in the tannin solution  then
HCl  flame  (+) PINK
NOTES:
FeCl3 Test  general test for true tannins  to identify if hydrolysable or non-hydrolysable
Matchstick test  general test for non-hydrolysable tannins
 Phenolic Acids
-Gallic acids or
Ellagic acids

Gallotannins-
Ex: rhubarb, gall clove
Ellagitannins
Ex: Pomegranate,
eucalyptus

REVIEW
Hydrolyzable Non-hydrolyzable tannins
 They readily hydrolysed to yield phenolic acid and sugar  Derived from the condensation of 2 or more flavan-3-ols like
(gallic acid and glucose) catechin
 Gallic acid when heated result to formation of pyragallol  Derived from condensation of 2 or more flavan-3,4-diols like
 They no precipitate with bromine water TS leucocyanidin
 Pyragallol give soluble compounds with LEAD ACETATE  When treated with hydrolytic agents they form phlobaphenes
 With phenols esteried with glucose  Form green colored solution with FeCl3

CHEMICAL REACTIONS
REACTANTS POSITIVE RESULT
 Tannins + K ferrocyanide & ammonia Deep red
 Hydrolyzable + FeCl3 blue-black color
 Non-hydrolyzable + FeCl3 greenish black or brownish green
TAKE NOTE:
FeCl3 Test  general test for true tannins  to identify if hydrolysable or non-hydrolysable
Matchstick test  general test for non-hydrolysable tannins

USES OF TANNINS:
 PRIMARY USE: Astringent  since it can ppt CHON  hence, used in facial wash (e.g. witch hazel)
 Anti-microbial
 Used in the treatment of burns
 Converts animal hides to leather  important in the formation of leathers
 Preservative
 Antidote for alkaloidal poisoning  because it can ppt CHON it can also ppt the alkaloidal drugs 
decreasing the absorption of the alkaloidal poisoning = decreasing the alkaloid conc. = antidote
 UNIVERSAL ANTIDOTE: activated charcoal, magnesium oxide, and tannic acid (2:1:1)
 In labs  reagent for detection of proteins, alkaloids, heavy metals because of their precipitating properties.
 IMPORTANT SOURCES:
1. Nutgall  CHIEF SOURCE OF TANNING & DYING industries & formerly used in the manufacturing of ink
o INSECT: Cynips tinctora (wasp)
o PLANT (the nutgall itself): Quercus infectoria (Fabaceae)
o The C. tinctora (wasp)  will create a hole in the nutgall  lay their eggs or ova in there = important
in the formation of tannic acid
o MAJOR COMPONENT OF NUTGALL  Tannic acid
o Medicinal use of nutgall  astringent

2. Witch hazel: Hamamelis virgiana (Hamameliceae)

o major component  2-hexen-1-al
o USE: anti-hemorrhoidal products, treating insect bites, & stings
o 2-hexen-1-al  HAVE VOLATILE OIL however does not give off or confer pleasant or characteristic
odor
o Hamamelis virgiana is present in the Celeteque toner with witch hazel extract  used in the facial
wash since it has astringent property

VOLATILE OILS/ ETHEREAL OILS/ESSENTIAL OILS/Olii distillati/ Oleo Aethera

 Used in aroma therapy particularly peppermint oil, lavender oil
 Peppermint oil  stimulant to keep people awake
 Odorous principle found in various plant parts
 CHARACTERISTICS:
o Have characteristic odor,
o high refractive index (can bend light),
o optically active (can rotate the plane polarized light  D/L direction),
o immiscible in water but miscible in organic solvents (since lipophilic)
 USES:
o Aside from being used in perfumes  used as spices, condiment, flavorants, and odorants
o Spices & condiments  anise, clove, nutmeg
o Carminative  relieve flatulence or bloating
o perfumes
 DIFFERENCE BETWEEN VO to FIXED OIL  STAIN TEST: drop 1 in special paper  if evaporated = VO while FO
cannot evaporate and it will be the one leaving the stain
 Another difference  between FO & VO  when exposed to air & light the FO will oxidized and rancidify
while the VO instead of being rancid it will resinify
 CLASSIFICATIONS:
o Terpenoid derivatives  formed via acetate-mevalonic acid pathway (Human pathway for the formation
of sterol particularly cholesterol)
o Aromatic compounds  formed via the shikimic acid phenyl propanoid route
 Cinnamic acid and p-coumaric acid are the principal phenylpropanoid compounds derived from what amino
acids?  PHENYLALANINE & TYROSINE
 TERPENES  specific compound removed by distillation under reduced pressure from volatile oils like lemon
and orange to avoid deterioration and development of TEREBINTHENATE ODOR

VOLATILE OILS OCCURRENCES

Specialized secretory structures Families
1. Glandular hairs Lamiaceae/Labitae (mint)
2. Modified parenchymal cells Piperaceae (pepper)
3. Oil tubes or vitae Apiaceae/Umbelliferae (dillweed)
4. Lyzigenous or schizogenous passage Pinaceae(pine), Rutaceae (Rutaceae  Citrus fruits family e.g. lemon &
orange)
 Specialized secretory structures Volatile oils
1. Rhizome Orris oil
2. Dried root bark Sassafras oil
3. Dried bark Cinnamon oil
4. Heartwood Sandal wood oil, pine oil, creosote, juniper tar, pine tar
5. Leaves Tanglad oil, basil, citronella, buchu, cedar

PRACTICE QUESTION:
Which is INCORRECT about VO? ANSWER: B
a. They have high refractive index and mostly are optically active
b. They are usually colorless but on long standing they may oxidize and become rancid  resinify
c. They occur in specialized secretory structures
d. The chemical constituents of volatile oils are derived from either terpene or aromatic compounds

METHODS OF OBTAINING VO SAMPLE EXAMPLES

1. Distillation
 Water distillation employed to plant material that is Turpentines (Pinus palustris)
dried & not subject to injury by
boiling
Best suited for dried form of plants
 Steam or Direct steam distillation Fresh sample of drugs Peppermint & spearmint
o DIRECT STEAM DISTILLATION  employed
if the fresh plant drugs are used and
macerator of the plant is unnecessary
 Water & Steam distillation applied to either dried or fresh Cinnamon oil & clove oil
substances that may be injured by
boiling
Dried & fresh
 Destructive distillation  w/o the presence of AIR PRODUCTS  Empyrematic oil e.g. pine
(without the presence of H2O) tar (charcoal  Pinaceae,
Cupressiaceae)
2. Expression Decomposed before distillation Orange and lemon oil
 Ecuelle method  example of an expression method Common method used for citrus
and the general method in obtaining citrus oil fruits
 involves puncturing the oil glands by rolling the
fruits over a sharp projections (e.g. set of needles)
 piercing the oil glands usually located in the outer
part of the peel
3. Enfleurage  applicable to plant part containing Flowers
small amount of VO especially in flowers
 traditional, can be done even at home or
homemade
 formerly used extensively in the production of
perfumes and pomades (with the use of cold fat)
4. Solvent  Most modern production of VO by
the used of solvent system or different kinds of
solvent like benzene and petroleum ether (PET)
NOTES:
**Enzymatic hydrolysis  Sinigrin  myosin  allyl isothiocyanate (mustard VO)
**Clavenger apparatus  used to distill VO that is heavier than water and lighter than water
Eleoptene  hydrocarbon portion of the oil is liquid (e.g. eucalyptol, eugenol, methyl salicilate)
Stereoptene  oxidized hydrocarbon portion of oil usually solid (e.g. menthol, camphor, thymol, anethole)
Classification of VO (alcohol, aldehyde, ketone & ester VO)  depends on the presence of functional group and
suffix:
 suffix –ol like methol  ALCOHOL
 Camphor  KETONE (usually –one)
 Thymol  ALCOHOL
 Trans-anethole 
Classification of VOLATILE OILS
HYDROCARBON VOLATILE OILS  elements: hydrogen & carbon

1. Turpentine oil  Pinus palustris (Pinaceae)

 HC constituent or HV VO present  Pinene, terpene, & campene  PINENE MOST COMMON
 TURPENTINE OIL + NaOH = rectified turpentine oil
 RECTIFIED TURPENTINE OIL + nitric acid with alcohol = terpin hydrate or terpinol  not exactly HC VO
because it is converted into ALCOHOL (-ol)
 Turpentine oil is used as: COUNTERIRRITANT
 Rectified turpentine oil & terpin hydrate or terpinol are used as: EXPECTORANT

CYCLIC MONOTERPENE HYDROCARBON ACYCLIC MONOTERPENE HYDROCARBON

 Cymene  Myrcene
 Pinene  Ocimene
 Limonene  can produce CYMENE
 Sabinene

ALCOHOL VOLATILE OILS (-ol)

1.Linalool  OH VO that can be found in the ff:
 Basil leaves – Ocimum basilicum
 Coriander oil – Coriandrum sativum
o USE: flavorant & carminative
 Orange flower oil or neroli oil  distilled from the fresh flowers of Citrus aurantium
o USE: flavorant & perfume

2. Geraniol, Citronellol, nerol

 Rose oil (Otto of Rose)  Rosa damascene, Rosa alba, Rosa gallica

3. Menthol  OH VO present in peppermint oil

 Peppermint is derived from 2 sources:
o Natural  can rotate the polarized light to the left  LEVOROTATORY ACTIVITY
 SOURCES: Mentha piperita (American variety)
Mentha arvensis (Japanese)  have more amount of menthol than M. piperita
o Synthetic  racemic menthol is produced by hydrogenation of thymol (racemic mixture 
OPTICALLY INACTIVE  cannot rotate the plane polarized light)
 USES:
o Topical antipruritic agent
o Depressant effect on heart
o Counter irritant
o Carminative
o Stimulant

4. Cineol  OH VO found in cardamom oil (Elletaria cardamomum)

 USE of cardamom oil  flavorant & carminative

5. Borneol  OH VO found in juniper oil (Juniperus communis from the Fam. Cupressaceae)
  USE of borneol oil  flavorant & diuretic

6. Alpha terpinol  OH VO found in pine oil Pinus palustris (Pinaceae)

 USE of pine oil  disinfectant & deodorant and an ingredient of terpene hydrate elixir.

MONOCYCLIC ALCOHOL ACYCLIC ALCOHOL

 Menthol  Geraniol
 Terpinol or terpineol  Linalool
 Citronellol

DICYCLIC ALCOHOL  Borneol SESQUITERPINE  Zingiberol (ginger 

Zingiber officinale

ALDEHYDE VOLATILE OILS (-al)

Citral (combination of neral & geranial)  present in citronella oil, lemon peel, & lemon grass

1. Citronella oil or tanglad from Cymbopogon winterianus of Fam. Poaceae used as insect repellant
2. Orange oil  Citrus sinensis (Rutaceae)
o USE: flavorant
o Aldehyde present in orange oil  decanal
3. Lemon peel  Citrus limon
o USE: flavoring agent & stimulant
o Aldehyde present in lemon peel  citral (combination of neral & geranial)
4. Hammamelis water  distilled from witch hazel extract
o Steam distillation of dried dormant twigs of Hamamelis virginiana (Hamamelidaceae)
o major component  2-hexen-1-al
o USES: astringent in hemorrhoid preparation
o Hammamelis owes its astringent property to the secondary metabolite  TANNINS (since it has the
ability to constrict CHON)
5. Cinnamon oil  Cinnamomum cassia (Lauraceae)
o Also known as Saigon cinnamon, cassia cinnamon, ceylon cinnamon
o Steam distillation of the leaves and twigs of Cinnamomum cassia (Lauraceae)
o Cinnamaldehyde, cinnamic aldehyde, cinnamyl aldehyde  CHIEF CONSTITUENT
o USES: flavoring agent, carminative, has a characteristic odor or pungent odor, anti-septic
6. Mannitol  imparts sweetness of cinnamon
o USES: flavoring agent, pungent aromatic, antiseptic

KETONE VOLATILE OIL  MOST STABLE FORM OF VO & cannot be OXIDIZED

Ketone VO SOURCE USES
1. Camphor Cinnamomum camphora Natural antipruritic (0.1% - 3%)
Have (+) natural & (+) synthetic forms Counterirritant (up to 11%)
2. (+)Dextrorotatory carvone Caraway oil  Carum carvi (Umbelliferae) Flavor, carminative
3. (-)LEVOROTATORY carvone Spearmint Used in chewing gum industry, flavorant,
carminative
4. Diosphenol Buchu (Barostoma betulina) Diuretic especially in women with menstrual
problem
5. Thujone Wormwood oil (Absinthe oil)  Artemisia Counterirritant
absinthium
6. Thujone Cedar leaf oil  Thuja accidentalis Counterirritant
Fenchone
7. Thujone Sage  Mentha spicata Antiseptic & carminative visceral antispasmodic
 MONOCYCLIC KETONE DICYCLIC KETONE
 Menthone  Camphor
 Carvone  Fenchone
 Pulegone  Thujone
 Piperifone
 Diosphenol (crystalline ketone in buchu)

PHENOL VOLATILE OIL

1. Eugenol (4-allyl-2-methoxyphenol)
o Found on clove  Eugenia caryophyllus
o USES of eugenol from CLOVE OIL: toothache drops or toothache relive so it is considered as dental
analgesic particularly from the CLOVE OIL, carminative, flavorant, counterirritant, antiseptic, & used in
the production of vanillin
o Myrcia oil (Bay oil)  Pimenta racemosa  myrcia oil is primarily used in perfumes

2. Thymol (isopropyl m-cresol)

o USES of THYME OIL: antifungal, antiseptic
o SOURCES: from flowering plant  Thyme oil (Thymus vulgaris)
o OTHER SOURCES: Horsemint oil (Monarda punctata), Oswego tea oil (Monarda didyma), Ajowna oil
(Carum copticum), Trachyspermum amni
o Hydrogenation produces synthetic menthol (racemic)

3. Cardinene  from Juniper tar or Cade oil (Juniferus oxycedrus)

o USE OF JUNIPER TAR: local antieczematic drug, example of a empyrematic volatile oil

4. Guiacol, creosol  from creosote or beechwood creosote

o USE CREOSOTE: disinfectant

5. Cresol  from pine tar

o USES OF PINE TAR: local antieczematic, antipsoriasis, & expectorant

PHENOLIC ETHER VOLATILE OIL  used as condiments and source of spices

1. Anethole  phenolic ether VO present in:
o Anise  from dried ripe fruit of Pimpinella anisum
o Chinese anise (star anise)  from dried ripe fruit Illicium verum
 Major adulterants of star anise (that be a substitute to star anise): JAPANESE ANISE  which is not
used as a condiment because it produces a hallucinogenic effect
o Fennel  Foeniculum vulgare

2. Saffrole
o Sassafrase  Sassafras albidum (have saffrole & tannic acid)  used as a flavorant
o Nutmeg  Myristica fragrans  Nutmeg: a hallucinogenic drug which gained reputation among prison
inmates

OXIDE VOLATILE OILS

OXIDE SOURCES
 Cineole Eucalyptus  counterirritant, carminative, diaphoretic, & expectorant, Vicks vaporab = camphor,
methol, eucalyptus
 Cajuputol Cajeput  Melaleuca leucodendron (Myrtaceae)
 Components: cineole, terpineol, acetate
 USE: internally and externally as a stimulant treatment of several parasitic condition
 Eucalyptol Eucalyptus globulus
 Ascaridol Chenopodium ambrosiodes
 Cineole and terpin-4- Tea tree oil from Paperback Tree  dried leaves and branches of Melaleuca alternifolia (Myrtaceae)
ol USE: antiseptic, antifungal

ESTER VOLATILE OILS

ESTER REMARKS
 Methyl salicylate  Steam distillation of Gaultheria (hydrolysis of Gaultherin acted upon by the Gaultherase  Methyl
(combination of salicylate)
salicylic acid +  Synonyms: Betula oil, Gaultheria oil, WINTERGREEN OIL, & sweet birch oil
methanol)  USES: flavor for cascara sagrada fluidextract, local irritant, antiseptic, antirheumatic
 Has a delicate odor due to enanthic alcohol
 Lavender oil  Have Linalyl acetate
 From Lavandula angustifolia
 USE: perfumery
 Pine needle oil or  Bornyl acetate
Dwarf pine needle oil  Pinus mugo
 USE: perfumery
 Mustard oil  Allyisothiocyanate & acrinylisothiocyanate (but the ESTER VO OIL of Mustard oil is only 
Allyisothiocyanate)
 Under glycosides  from Brassica nigra (glycoside component  SINIGRIN) & Brassica alba
(SINALBIN)
 By the action of myrosinase enzyme  B. nigra is converted to the final product: Allyisothiocyanate
(VO component) and B. alba  acrinylisothiocyanate (NON-VO part of mustard oil)

VO  USED IN PERFUMERY
TOP notes MIDDLE notes BASE notes
High volatility and tenacity Intermediate volatility and tenacity Low volatility and tenacity
e.g. Lemon oil, lavender oil, & e.g. thyme oil, & rose oil e.g. ambergris, musk, & civet
anise (used as fixatives in perfume ambergris, musk, civet, &
vanilla)

Classification of volatile oils

Hydrocarbon
- limonene, turpentine

Ketone
- camphor, diosphenol, spearmint

Alcohol
- Cardamom, basil, menthol

Phenol
- thymol, eugenol

Oxide
- Ascaridol, eucalyptus
 RESINS
 Oxidation product of volatile oils or products of the oxidation of terpenes
 Hard, transparent or translucent and when heated they soften & melt
 Brittle, amorphous solids
 On evaporation = varnish-like film
 Burn = smoky flame  hence use in incense
 Complex mixtures of resins:
o Resin acids  contains a large amount diterpenoid oxyacids usually combining the properties of a
carboxylic acid & phenols
 Resinates  metallic salts of resins
 Glycoresin  sugar + resin acids
o Resin alcohols  resin + alcohol
o Resinotannols  complex alcohol with high MW
o Esters  acids + alcohols
o Resenes  HC  complex neutral + devoid of chemical properties
 Resin combinations:
o Oleoresin  combination of resin with volatile oil
o Oleo-gum resin  oleoresins (VO & resins) + gums
o Balsams  resinous mixtures but with an addition of acid like cinnamic acid, benzoic acid or both

TRUE RESINS  called true resins because they contain pure resins (they only contain resins)
TRUE RESINS SOURCE USES
1. Jalap Tuberous root of Exogonium purga or Cathartic, hydragogue, purgative
Ipomoea purga Purganol  drastic purgative
2. Rosin or colophony Pinus palustris o Stiffening agent in cerates, plasters, and ointment
o Adulterant of other resinous products
o Used in the manufacturing of paints, varnishes, paint
dryers
o Have abietic acid
3. Eriodictyon or yerba Eriodictyon californicum Stimulant, expectorant, Flavorant, disguise the bitter taste
santa of quinine
4. Kava or Kava kava Piper methysticum Skeletal muscle relaxant, & tranquilizer, utilize in the
preparation of intoxicating beverages
5. Mastic or Mastiche Piscata lentiscus Used to seal dental cavities
6. Manila copal Agathis alba Used for varnish
7. Podophyllum or American SOURCE: Podophyllum peltatum
Mandrake or Mayapple CONSTITUENTS:
(have another variety  Etoposide (lignin derivatives) Treatment of small lung cancer and testicular cancer
European mandrake  from
Mandragora officinale (an Podophyllin Anti-warts
alkaloid) Peltatin Laxative
Podophyllotoxin Etoposide & tenoposide (antimitotic)
Resin (Podophyllin & Peltatin) Purgative, paint in the treatment of soft venereal wart
8. Cannabis or Indian hemp SOURCE: Cannabis sativa
or Marijuana or Mary CONSTITUENTS:
Jane or Hemp THC  cannabinol & nabillone THC (tetrahydrocannabinol)  psychoactive substance
 Cannabinol  high amount in old & Cannabinol & nabillone constituents responsible for its
matured plants effect particularly the euphoric effect
Hemp fiber Rope
 Cannabichromene & cannabidiolic acid Cannabichromene & cannabidiolic acid  responsible for
its sedating principles
Resins present in C. sativa  Bhang or
Hashish

OLEORESINS (Volatile oil + resins)

OLEORESINS REMARKS USES
1. Balsam of copaiba  Since “balsam” are resins with cinnamic acid or benzoic  Diuretic
acid or requiring an aromatic cmpd in their structures  Expectorant
 Balsam of copaiba = no aromatic cmpd or cinnamic or  Laxative
benzoic in its  considered as not a true balsam  Genitourinary disinfectant
 From Copaifera officinalis
2. Capsicum or Cayenne  SOURCES: Capsicum anuum or C. frutescens from the Irritant (in the kidney), carminative,
Pepper Fam. Solanaceae rubefacient, condiment
 CONSTITUENT or the RESIN PART Capsaicin
3. Turpentine  SOURCE: P. palustris Counterirritant
4. White or Weymouth pine  P. strobus Expectorant
5. Ginger  SOURCE: Zingiber officinale Have antiseptic property (esp. ginger
 CONSTITUENTS: zingerone & shogaol  responsible for ale)  hence, used in mouthwash
the characteristic or pungent odor preparations

OLEOGUM RESINS (Volatile oil + resins + gum)

OLEOGUM RESINS REMARKS USES
1. Myrrh or “Ancient funeral spice”   SOURCE: Commiphora molmol Astringent  part of the product astring-
because back in ancient times Egyptians o-sol
used it as an embalming agent in the antiseptic activity
mummification process
2. Asafoetida or Devil’s dung, stinking gum,  SOURCES: Ferula asafeotida Antiflatulent
asant, food of the gods  “fetid”  the most unpleasant smelling
oleogum resins
3. Gamboge  not commonly used  SOURCE: Gamboge hanburyi Constipation, parasites
 Gambonium  pigment
4. Oliganum  Boswellia carterri  Formerly used as antileprosy in
China
 Used in incense
 Have anti-inflammatory property

BALSAMS  resins + aromatic compound like cinnamic acid ad benzoic acid

BALSAMS REMARKS USES
1. Peru balsam  SOURCE: Myroxylon pereirae  Used for skin disease
 Local protectant
 Antiseptic dressing for wounds
 Parasiticide
 Treats hemmorhoids
2. Compound benzoin tincture  COMPONENTS: Topical protectant, for the treatment of
o Aloe  not a balsam but considered as ingr. of wounds & sores
the cmpd benzoin tincture
o Benzoin  Stryrax benzoin
 o Storax  Liquidambar orientalis
o Tolu balsam  Myroxylon balsamum – tolu
balsam is used as a pleasant flavoring
specifically in medicinal syrups & perfumery

Oleoresin
- balsam of copalba, ginger

True resin
- cannabis, mandrake, rosin, mastic

Oleo-gum
- myrrh, gamboge
TERPENOIDS/ISOPRENOIDS

 Secondary metabolite that are synthesized by plants (e.g. marine organisms, or fungi)
 These are made up of building blocks: isoprene units (5 carbon molecules)
 Terpenoids are the natural product also known as isoprenoids
 Isopentanyl pyrophosphate  the most intermediate product in the biosynthesis pathway of terpenoid

1 isoprene unit = 5C
MONO  2 isoprene

Classification Isoprene units

Hemiterpene- one
Monoterpenoid- two
Sesquiterpenoid- three
Diterpenoid- four
Sesterterpenoid- five
Triterpenoid- six
Tetraterpenoid- eight

MONOTERPENOIDS
 Have 2 isoprene units
 Isolated from higher plant parts & marine organisms  can also be seen in the pheromonal secretions of
insects
 PATHWAY  formed via the acetate-mevalonic acid pathway
 From geranyl diphosphate
 EXAMPLES: volatile oils like camphor, menthol, & limonene

SESQUITERPENOID
 From farnesyl diphosphate
 3 isoprene units
 Widely distributed class  that’s why it is considered as the LARGEST CLASS OF TERPENOIDS
  PATHWAY  formed via the acetate-mevalonic acid pathway

SESQUITERPENOID
SESQUITERPENOIDS REMARKS USES
1. Artemissinin/Qinghaosu  SOURCE: Artemisia annua Antimalarial usually given with
 FORMS: Mefloquine
o Sodium artelinate & Sodium artesunate  water soluble form
and given orally or by IV inj
o Sodium artemether  most promising derivative; MOST
POTENT
2. Ginger  COMPONENTS:
o Bisabolene
o Zingiberol
o Zingiberene
 SOURCE: Zingiber officinale

3. Chamomile/ Ginseng of  Usually found in tea products When taken orally Anxiolytic
Europe  SOURCES: (lessening anxiety)  hence,
o German  Matricaria recutita usually taken at night 
o Roman  Chamaemelum nobile  most common & available as relaxant before sleeping
a tea
 One of the most popular herbs used in US
 CHAMAZULENE  main component of chamomile
4. Feverfew  SOURCE: Tanacetum parthenium Used as antipyretic
 MAIN CONSTITUENT  Partenolide (responsible for the
antipyretic effect of feverfew)
5. Valerian  SOURCE: Valeriana officinalis  Anxiolytic (lessening
 Have valerenic acid anxiety)  but it is used as
ingr of sleeping pills
 Sleep aid specifically in the
product: Sleepasil (have
the product Valerian,
Chamomile, & Melatonin)
 Also used in teas
NOTES:
Abscisic acid  essential plant hormone controlling growth and development
Lactones  with antimicrobial and antitumor activity

DITERPENOIDS
 have 4 isoprene units
 From the Geranyl geranyl diphosphate
 EXAMPLES:
1. Ginkgo – inhibit platelet aggregating factors (PAF)  therefore, considered as anticoagulant & used as
memory enhancer
o Have GINKGOLIDES  flavone glycoside of ginkgo biloba
2. Taxol  from Pacific yew Taxus brevifolia or Taxus baccata
o Source of the drug PACLITAXEL  for breast CA
3. Forskolin  anti-hypertensive
4. Gibberelins  are plant hormones that stimulate plant growth
5. Prodolactones  are plant inhibitors
 TRITERPENOIDS
 Have 6 isoprene units
 From squalene
 EXAMPLES:
1. Cucurbitacins  defense against herbivores; have a characteristic effect wherein they are poison and
toxic present in the family of Cucurbitaceae (e.g. pumpkin, cucumber, ampalaya)
2. Quassinoids  from Quassia amara & is used as anti-malarials
3. Saponins  toxic to cold blooded animals

TETRATERPENOIDS
 Have 8 isoprene units
 EXAMPLES:
1. Vitamin A  precursor is beta-carotene
o Major natural form of Vit. A: retinal
o Provitamin A: Beta-carotene or the precursor of Vit. A
o USE:
 Tretinoin (Retin-A)  used to treat acne vulgaris  TOPICAL
 Isotretinoin (Accutane)  For severe recalcitrant cystic acne  ORAL PILL

MEROTERPENOIDS
 Composed of isoprene and non-isoprenoid units
 EXAMPLES: ergot , quinine (an alkaloid containing a monoterpenoid unit), cannabinoids, phylloquinones
such as Vitamin K, and tocopherols such as Vitamin E

NOTES:
 CHICLE  polyisoprenoid consisting of a mixture of cis- & trans- C5 isoprenoids & obtained from
Manikara zapota. Used as a base for chewing gum.
 GERANYL PYROPHOSPHATE  serves as precursor of terpenes and is formed by condensation
of isopentanyl pyrophosphate and dimethylallyl pyrophosphate

Monoterpene
- Camphor, menthol
Diterpene
- ginkgo, taxol
Sesqui
- artemissinin, chamomile,
Feverfew, valerian
Triterpene
- Cucurbitacins, saponin
Meroterpene
- Vitamin K, quinine
 ALKALOIDS (-ine)

 Alka-like  hence, named alkaloids

 Bitter, basic, heterocyclic nitrogenous compounds
 Majority are physiologically active
 SOLUBILITY:
o Free alkaloids are insoluble or sparingly soluble in water
o Salts formed on reaction with acids are usually freely soluble  exception: Salts of
quinine (Quinine monosulfate) which is insoluble with water
o Salts of alkaloids that are among organic solvents  Lobeline, Apoatropine
hydrochloride which are soluble with CHCl3 (chloroform)
 All are solids except  Coniine, nicotine, sparteine (LIQUID alkaloids  lack oxygen in their
molecules)
 Form double salts with compounds of mercury, gold, platinum, and other heavy metals
 Families rich in alkaloids:
1. Apocynaceae (Dog bane family)  which is anti-neoplastic agents (anti-CA) in terms of
pharmacologic activity, e.g. VINCA ALKALOIDS
2. Rubiaceae (Coffee family, & bedstraw family)
3. Solanaceae (Nightshade family)
4. Papaveraceae (Poppy family)
 FAMILIES FREE FROM ALKALOIDS  Rosaceae (Rose family), Peppermint family (probably 
Lamiaceae/Labitae)
 DICOTYLEDONOUS ORDER FREE OF ALKALOIDS  Cucurbitales, Fagales, Salicales, & Oleales
 Amino acid precursors of alkaloids  Arginine, Hydroxyproline, Proline, & Tyrosine

Amino acid precursors ALKALOIDS

Phenylalanine Tropic acid fragment like hyoscine and hyoscyamine
Lysine, Tryptophan, Ornithine Atropine, Hyoscyamine, Nicotine
Other amino acids: Histidine, Anthranilic acid, & Aspartic acid

ADDITIONAL NOTES FROM MANOR:

 Basic nitrogenous compounds found in plants that are physiologically active
 Are group of organic substances of biologic origin which have different chemical structure but
have a heterocyclic N in common. (N  element responsible for the basic pharmacological
properties of alkaloids)
 Combine directly with acids to form salts
 Form highly soluble ppt with salts of heavy metals
 CHEMICAL FORMS:
o Free base  not soluble in water but soluble in non-polar solvent
o Alkaloidal salt  only soluble in water but not in non-polar solvent
o *free alkaloids  are sparingly soluble in water
 Physical forms:
o Solid-crystalline  amorphous
o Liquid: 1. Coniine  Poison hemlock (Comium maculatum) & execution of Socrates
2. Nicotine tobacco leaves (Nicotiana tabacum) & derivative of Pyrrolidine
3. Sparteine  Scotch Broom (Cytisus scoparius) & Lupin (Lupinus mutabilis)
  used for cardiac arrhythmias & also used as oxytocic
4. Levodopa  Horse bean (Vicia faba)
 Extraction of Alkaloids: Process A Acid-treated
Process B  Base-treated
ALKALOIDAL REAGENTS:
1. Mayer’s Reagent  Potassium mercuric iodide, cream ppt.
2. Nessler’s Reagent  Alkaline Potassium mercuric iodide, brown ppt.
3. Wagner’s Reagent  I2/ KI (iodine in potassium iodide), reddish brown ppt
4. Bouchard Reagent  I2/ KI, most sensitive
5. Dragendorf Reagent  Potassium Bismuth Iodide, reddish brown ppt
6. Marme’s Reagent  Potassium Cadmium Iodide
7. Valser’s Reagent  HgI2 (mercuric iodide), red ppt
8. Sonnencheim’s Reagent  Phosphomolybdic acid
9. Scheiber’s Reagent  Phosphotungstic acid
10. Gold Compunds
11. Tannic Acid
12. Hager’s Reagent  Saturated solution of picric acid
13. Murexide test  specific test for caffeine, purple color

Chemical Properties:

I. Nitrogen

Primary amines (R-NH2) - norepinephrine

Secondary amines (R2-NH)- ephedrine
Tertiary amines (R3-N) - Atropine
Quarternary ammonium salts (R4-N) -
tobucurarine

CLASSIFICATION BASED ON THE RING STRUCTURE OR NUCLEUS OF THE CHIEF ALKALOID GROUP IN THE PLANT DRUG
1. Pyridine & piperidine e.g. Lobeline, Nicotine, Arecholine, Coniine 2. Tropane  e.g. Atropine

3. Quinoline e.g. Quinine, Quinidine, Isoquinoline e.g. Papaverine, Tubocurarine,

Cinchonine, Cinchonidine Opium
4. Indole e.g. Ergometrine 5. Imidazole e.g. Pilocarpine

6. Purine e.g. Caffeine 7. Steroidal e.g. Solanum & Veratrum

alkaloids (have CPPP nucleus)

8. Alkaloidal amines  not alkaloids themselves  they do not have nitrogenous base but only amine but included since
they are alkaloidal in nature

PYRIDINE-PIPERIDINE ALKALOIDS  from amino acid Ornithine

ALKALOIDS Synonyms SOURCES Remarks
1. Coniine Poison Hemlock Comium maculatum  A popular state poison during ancient times for
execution of deaths sentence e.g. one & only,
let’s give it up for SOCRATES
2. Nicotine tobacco leaves Nicotiana tabaccum  CNS stimulant
 Smoking deterrent  to help a chain smoker to
Lobeline INDIAN tobacco Leaves Lobelia inflata stop smoking available in the form of patch, &
chewing gums
 Nicotine  (Nicorette®)
 Lobeline  (Bantron®)
3. Arecholine Betel or Piper nut, Areca catechu  Veterinary used  anti-helmintic
“nganga”  Arecholine  Stimulant masticatory, chewed
w/ lime & Piper/Betel leaves
 CNS stimulant,
 Catechin: Tannin, Carcinogen Potetial
 Arecha Tannin  is the carcinogenic
constituent found in “nganga” has been
linked to high rates of oral & esophageal
cancer
4. Ipil-ipil Leucaena  Veterinary used  anti-helmintic (used for
leucocephala Ascariasis)
 yields an alkaloid of the pyridine-piperidine
type.
 Tropane alkaloid esters of Tropic Acid & Tropane  from Amino Acid – Ornithine
SOLANACEOUS ALKALOIDS (Nightshade family)
ALKALOIDS Synonyms SOURCES Remarks
1. SCOPOLETIN & ATROPINE Deadly Belladona  Scopoletin (Beta-methyl aesculetin) 
Nightshade Atropa belladonna responsible for the flourescent substance in the
-CHIEF SOURCE OF ATROPINE: leaf
Duboisia (NOT BELLADONA   Atropine  an anticholinergic  when (+) baryta
bcs it have more hyoscine water then heated at 60 degrees C = will produce
than ATROPINE) tropine & tropic acid
o (-) hyocyamic  racemized  Atropine
o CLINICAL EFFECTS: Hyperthermia,
Antisialogogue, Mydriasis, & Constipation
o MNEMONICS FOR ANTICHOL: red as a beet,
dry as a bone, blind as a bat, mad as a hatter,
hot as a hare, and full as a flask, etc
o causes pupil dilation (mydriasis)
o discovered by R. Brandes
2. HYOSCINE/SCOPOLAMINE Datura sp.  Hyoscine/Scopolamine  the principal alkaloids
in all Datura species (e.g. Datura metel 
talumpunay or Angel’s trumphet, Datura
stramonium  Dimsonweed/Jamestown weed)
 Upon hydrolysis will yield tropic acid & scopolin
 Hydrobromide form is employed in preoperative
medication usually with papaveretum, 30-60
mins before the induction of anesthesia.
 Scopolamine or hyoscine: active employed for
motion sickness
 Hyoscine N-butylbromide: Antispasmodic
 is burned & inhaled for the relief of asthma
3. MANDRAGORINE Europian Mandragora  Free alkaloids also present in mandragora aside
Mandrake Mandragora from mandragorine: HYOSCINE/SCOPOLAMINE
officinarum  MANDRAGORINE  emetic
4. HYOSCYAMINE Hyoscyamus  Hyoscyamine  The product of esterification of
tropine with tropic acid
Henbane Hyoscyamus niger  Main alkaloid: Hyoscyamine, scopolamine
 Henbane  0.04% alkaloids
E. Hyoscyamus  E. Henbane  1.5% alkaloids
or Egyptian Hyoscyamus
Henbane muticus

5. Withania Withania somnifera  USE: sedative

 “somnolence”  ***commercial source of ATROPINE
6. Duboisia Duboisia  CHIEF SOURCE OF ATROPINE
myoporiodes  Eventhough atropine was named after
BELLADONA  but it has more HYOSCINE than
atropine
7. Pituri Datura hopwoodii  AUSTRALIAN TOBACCO
 TROPANE ALKALOIDS  COCA ALKALOID

1. Coca leaves
 Source: Huanuco-coca – Erythroxylon coca
 ALKALOID: Cocaine (methylbenzoylecgonine/benzoylmethylecgonine)
 Street name: crack, coke
 Multiple central, peripheral effects as well as the rewarding property  psychomotor stimulant,
euphoria (MOA: blockade of DOPAMINE REUPTAKE = inc. DOP  EUPHORIA)
 Has multiple central nervous actions  hence, that why it has an effective dose range as it has
strong abuse potential  COCAINE & its SALTS  Significant agents of abuse either by smoking,
sniffing, inhaling, or rapidly absorbed in the mucosa
 Because of the CNS stimulant of cocaine  used in depression, narcotic induced-sedation can be
counter-acted by cocaine
 local anesthetic
 component of Brompton’s Cocktail (BROMPTON’S COCKTAIL = Methadone/ Morphine + Cocaine HCl
+ Alcohol) analgesic for terminal cancer pain
 Free Basing  inhalation of the vapors of alkaloidal cocaine (VAPORS CAUSES THE PLEASURABLE
EFFECTS of cocaine: reduce fatigue, etc)

2. Truxillo coca (a variety of coca leaves; the alkaloid is still COCAINE)

 SOURCE: Erythoroxylon truxillense
 (DIVINE PLANT OF INCAS  stimulant that makes it possible for them to travel great distances
without being tired/fatigue/hungry)
 Cultivated for “coca chewing” and the manufacture of coca cola based soft drinks

NOTES (terminologies):
BENZOYLECGONINE  main metabolite of cocaine which may be identify in body fluids
ECGONINE  basic moiety of cocaine alkaloids
TROPINE  3-hydroxy derivative of tropane

REMEMBER: CP (cholinergic/para) AS (adre/sympa)

CORRECT ANSWER: abd (EXCEPT C)
 REVIEW
Australian tobacco Pituri
INDIAN tobacco Lobelia (Lobelia inflata)
Alkaloid: PYRIDINE-PIPERIDINE (Lobeline)
Jimson weed Dimsonweed/Jamestown weed (Datura stramonium)
Alkaloid: SOLANACEOUS tropane (HYOSCINE/SCOPOLAMINE)
Scopolamine Indication: Anti-motion sickness
Alkaloid: SOLANACEOUS ALKALOIDS/Nightshade family (Hyoscine)
European mandrake Mandragora (Mandragora officinarum)
Alkaloid: SOLANACEOUS ALKALOIDS/Nightshade family (Hyoscine)
Deadly nightshade Belladona (Atropa belladonna)

QUINOLINE ALKALOIDS (named base on Genus  Cinchona alkaloids)  from Amino Acid/PRECURSOR –Tryptophan

ALKALOIDS SOURCES Remarks

1. CINCHONA (Rubiaceae) Red  Cinchona succirubra  Studided by Pelletier & Caventous
Yellow  Cinchona calisaya  CINCHONINE & CINCHONIDINE  parenteral alkaloids
 NOTE: Usually all anti-  QUININE: Antimalarial, Toxic water
malarial o TEST: Thalleoquine reaction - used to identify quinine
(except: Quinidine  anti- o Has skeletal muscle relaxant effect  for it affects the
arrhythmic) distribution of Ca in the muscle fiber (used before for
 All cinchona alkaloids  the management of nocturnal recumbency leg cramps
CINCHONA bcs of its skeletal muscle relaxant effect)
TOXICITY/CINCHONISM o Quinine and all other cinchona alkaloids  have the
-Toxic reactions occurs at enzyme: OXIDASE (that’s why it THESE should not be
levels above 8 mg/ml. the expose to photo/light  will change color to brown
patient should be instructed o QUININE  flourescent characteristic; can emit
to notify the physicain if skin flourescence
rash, fever, unusual bleeding,  Quinidine: Antimalarial; ANTIARRHYTHMIC
or bruising, ringing in the o Prophylaxis of cardiac arrhythmias & tx of atrial fib
ears, or visual disturbance o Also has skeletal muscle relaxant effects  for it
occurs. affects the distribution of Ca in the bloodstream
–temporary hearing loss, o There are some cinchona alkaloids that manage
ringing in the ears (Tinnitus), arrhythmic or mimics the ANTIARRHYTHMIC property
impaired sight of Quinidine
o Cuprea  Cuprea Bark (Remijia purdieana) 
commercial source of quinidine
 Isoquinoline  PRECURSOR: Phenylalanine or
ALKALOIDS SOURCES Remarks
1. Opium alkaloids milky exudates of ripe  Opiates: natural-occuring opioids
-only legal source in India puppy seeds of o Morphine  most important opium alkaloid
-termed “Stone of Papaver somniferum  High amount when the latex is harvested after flowering
Immortality” by Paracelsus” from the unripe capsules of opium poppy
- Meconic acid  acid o Codeine (methylmorphine)  methylated morphine 
present in opium alkaloids prepared from morphine by Methylation
- Meconic acid reacts with  Obtained before flowering  if the latext is harvested early
FeCl3 to form  DEEP RED  MOST WIDELY USED OPIUM ALKALOID
COLOR (e.g. Wagner’s,  Antitussive agent
Dragendorf) o Noscapine/Norcotine  not narcotic/no narcotic property 
ANARCOTINE & only employed as antitussive
PREPARATIONS: o Papaverine  smooth muscle relaxant & when demethylated or
-Powdered opium  10- undergo demethylation  PAPAVEROLINE (demethylated
15% morphine & to make papaverine)
Dover’s powder o Thebaine

-Paregoric  camphorated  Opioids: compound that are on the opioid receptor (Synthetic
opium tincture Opioids):
o Heroine (diacetylmorphine)  prepared from morphine by
-Papaveretum BP Acetylation
components: Codeine,  Most lipid soluble
Morphine & Papaverine  SCHEDULE 1: no therapeutic action & only HIGHLY
ADDICTING  popular substance of abuse
- Laudanum (opium tincture) o Apomorphine (dehydrated morphine)  emetic & used in the tx
of Parkinson’s Disease
o Hydromorphone  prepared by reducing morphine in HCl
solution w/ hydrogen in the presence of a catalyst
o Hydrocodone
2. HYDRASTINE & GOLDEN SEAL   USES OF HYDRASTINE: astringent, used for the control of uterine
Berberine (Yellow Hydrastis canadensis hemorrhage in the inflammation of mucus membrane
alkaloid)  USUALLY ALKALOIDS ARE CRYSTALLINE IN STRUCTURE  SO
COLORLESS but  Berberine is a yellow alkaloid (colored alkaloid)
 USE OF BERBERINE  anti-protozoal
3. TUBOCURARINE CURARE  Types: Calabar  gourd/calabash, Tube  bamboo, Pot  clay pot
(bisbenzylisoquinoline) Strychnus toxifera  TUBOCURARINE USES:
Strychnus castelanaei -NON-DEPOLARIZING NEUROMUSCULAR BLOCKER
-CURARE also known as Chondrodendon -Skeletal muscle Relaxant  used to secure muscular relaxation
“South American Arrow tomentosum in surgical operation but not deep anesthesia
poison” -Control convulsion of strychnine & tetanus  Anticonvulsant
in Strychnine poisoning
-DIAGNOSTIC AID FOR MYASTHEMIA GRAVIS
o Standardized by the head drop test  rabbits
o SE: Anaphylactoid Reaction (Histamine Release, not IgE
Mediated)
 Mice  official test animal used to assay Curare Alkaloids by the
 “head drop” cross-over method.
4. Sanguinarine (RED)  SAGUINARIA or BLOOD  COPPER RED
another colored alkaloid ROOT  Sanguinaria  Leave a stain & used before as cough remedy
canadensis  USES: stimulant, expectorant, emetic
NOTE!!! 2 colored alkaloids
 HYDRASTINE &
SAGUINARINE
5. EMETINE  principal IPECAC  EMETINE  emetic, anti-amoebic, expectorant, antitumor
alkaloid Brazilian  Cephalis -Usual dose for ipecac particularly emetine  15 ml for the
PSYCHOTRINE ipecachuanha treatment of overdose/poisoning either for adult or children older
CEPHAELINE Panama  Cephaelis than 1 year old followed by 2 glasses of water
acuminate -EMETINE/IPECAC + 2 glasses of water  if the px does not undergo
emesis even after 20 mins  do a repeating dose once again
-EMETINE  used for the treatment of amebiasis in the route of
SQ/parenteral (if oral administration it would not undergo absorb in
the systemic circulation, hence, cannot target the causative agent
of amebiasis in the site of action; WOULD ONLY INDUCE VOMITING
AND WOULD NOT ELICIT SYSTEMIC EFFECT); IV = would not induce
vomiting + systemic activity
 Psychotrine  phenolic principal
 Cephaeline  alkaloids from ipecac
 Ipecac + HCl and KClO3 = yellow to red color
 PREPARATIONS:
o IPECAC + OPIUM = Dover’s powder (DIAPHORETIC)
o Ipecac fluidextract  14 times stronger, more potent than the
syrup form
o Ipecac Syrup: Emetic (previously for poisoning cases)

USES OF OPIUM ALKALOIDS

Narcotic analgesic Dilaudid, Morphine
Antitussive Hydrocodone
Codeine  present in cough syrup that’s why it was a substance of abuse on 19th century
o Devoid of analgesic activity but retained  antitussive & narcotic properties
Smooth muscle relaxant Papaverine
Antiperistaltic Laudanum (opium tincture)  deodorants
Paregoric (camphorated opium tincture)

Pyri-pipe- coniine, nicotine

Tropane - cocaine, atropine, hyoscine
Quinolone- cinchonine, cusparine, quinine
Isoquinolone-morphine, ipecac, goldenseal,
codeine
 APORPHINE alkaloids  reduced isoquinoline/naphthalene
1. BOLDINE  Peumus boldus (Monimiaceae)  (Mnemonics Hev’s edition: Peumus – Famous bold)

Indole Alkaloids – from Amino Acid (L-Tryptophan)

ALKALOIDS SOURCES Remarks
1. RESERPINE  major Rauwolfia (Apocynaceae) or  RESERPINE  Rauwolfia (selective 1 antagonist)  mgt.
RESCINNAMINE snakeroot (Rauwolfia against HTN
DESERPIDINE serpentina)  MOA: depletes the catecholamines at post synapse 
AJMALICINE  produced by prevents production of catecholamines
cell suspension culture R.  USES: hypotensive, antipsychotic or tranquilizer
reserpina  Reserpine (Serpasil®): Hypotensive Agent Adjunct in
psychotherapy
 RESCINNAMINE (3,4,5 trimethoxy cinnamic acid)  used
to manage mild HTN
 DESERPIDINE (Recanescin)  same use with reserpine
 AJMALICINE  anti-arrhythmic
 SE: Depression, Depletes Norepinephrine storage
 Root is used as Antihypertensive
2. VINCA ALKALOIDS Vinca rosea/minor,  Vincristine  ANTICA, but has the ADR: neurotoxic
(Aponacynaceae) Chichira or Madagascar  Has superior anti-tumor activity than Vinblastine
 ANTICANCER  ANTIMITOTIC periwinkle (Cataranthus  Vinblastine  treatment of generalized hodgkins disease
AGENTS roseus) and non hodgkins lymphoma
 Vinblastine, Vinleurosine,  MOA: exerts its antineoplastic action by interfering
Aniosidine, vincristine  with the polymerization of tubulin into microtubules
Antineoplastic, leukemia  Vinorelbine  semi-synthetic anhydrous derivative of 8-
 MOA: Arrest cell division of norvincristine
Metaphase or inhibit the  Has broader anti-CA activity & lower neurotoxicity
metaphase by inhibiting than Vincristine
microtubules
activities/synthesis

3. YOHIMBINE Pausinystalia yohimbe  USE: treat impotence

(Aponacineae)  Alpha 2-selective antagonist  SYMPHATOLYTIC AGENT
 Peripheral autonomic system acting agent  can
increase the cholinergic activity while dec. adrenergic
activity = hence, employed for treating impotence
4. ESERINE/PHYSOSTIGMIE CALABAR BEAN/ORDEAL  Reversible inhibitor of the cholinesterases
BEAN  MIOTIC
Physostigma venenosum  USE OF PHYSOSTIGMINE (Eserine): employed in the
treatment of glaucoma
 inhibitor of acetyl cholinesterase - acetylcholine
 for glaucoma miotic (increase outflow of aqueous
humor)
 DOC of Atropine Toxicity
 Toxicity: Cholinergic Crisis (DUMBELSS)
  Antidote: Atropine
5. STRYCHNINE NUX VOMICA  Strychnine: CNS stimulant  extremely toxic for it has
BRUCINE Strychnus nux vomica central stimulant & may cause tonic-clonic convulsion =
Strychnus ignatii – hence not use in humans but rather  RAT POISON or
St.Ignatius’ bean Vermin Killer
Strychnus nux vomica   *Strychnine Poisoning: Inhibits the Glycine receptors in
efficient to quench singlet oxygen the Spinal Cord
*Manifestations: Opistothomos Sardonic Smile (lacking of
the jew)
 Brucine USE: commercially use as alcohol denaturant
 LESS TOXIC THAN STRYCHNINE BUT IT IS EXTREMELY
BITTER  unfit for human consumption

6. ERGOTAMINE ERGOT 1. ERGOTAMINE  vasoconstrictor & alpha-adrenoceptor
ERGOSINE Rye Ergot that grows on rye antagonist
ERGOCRYSTINE (Secale cereal)  used to abort or prevent vascular HA (e.g. migraine, &
ERGOCRYPTINE Parasitic (grows on living)  cluster headaches)
(ALL water-INsoluble) Claviceps purpurea 2. ERGOSINE  ergolite chemical made on Claviceps
Saphrotic (grows on dead) purpurea
ERGONOVINE  water sol  Claviceps paspanii 3. ERGOCRYPTINE starting material for Bromocriptine
ERGOTOXINE  combination 4. ERGOTOXINE (Hydergine®)  composed of ergocomine,
DERIVATIVE  LSD ergocryptine, & ergocristine (pure substance isolated by
Barger and Carr)
 ERGOTISM or GANGRENOUS  vasorelaxant; hypotensive agents
ERGOTISM or ST. ANTHONY’s 5. ERGONOVINE (Ergometrine)  uterine stimulant &
FIRE a toxicity caused by WATER-SOLUBLE
ergot alkaloids  Oxytoxic Agent; Assist in Labor
-decrease the blood flow into  used to cause contractions in the uterus to treat heavy
extremities (gangrene) vaginal bleeding after child birth
6. Derivative: LSD (Lysergic Acid Diethylamide)  although
this pharmacologically alkaloid is sometimes referred as
peptide alkaloid class
 was discovered by A. Hoffman is considered as the
most active & most specific psychomimetic or
hallucinogen acid
 psychomimetic or sympathetic stimulation
 CAUSES fusion of senses, “bad trip”, fear, depression &
anxiety, confusion, nausea, tremors
7. ERGOT/INDOLE RELATED ALKALOID:
Ololioqui (Rivea corymbosa)  ALKALOID: (+) Lysergic
acid amide (Ergine)  A hallucinogenic drug used in
Mexico

Imidazole alkaloid/GLYOXALINE ALKALOIDS  from Amino Acid: Histidine

1. Pilocarpine (Pilucarpus jaborandi) & other sources: P. pennatifolius
 Cholinergic agent, hygroscopic & lactone of pilocarpic acid
 USES: for the mgt. of open-angle glaucoma, miotic, long term use  lens opacity
 STEROIDAL Alkaloids – have the CPPP nucleus  USUALLY FROM HELLEBORE
ALKALOIDS SOURCES Remarks
1. VERATRINE Green hellebore  American  Germidine, Germetrine  possess hypotensive property,
Hellebore (Veratrum viride) Insecticide

White Hellebore  European

2. PROVERATRINE Hellebore (Veratrum album)  Protoveratine A & B  hypotensive (cardiac depressant),
insecticide
WHITE & GREEN  alkaloid  not used clinically
BLACK HELLEBORE  glycoside
DUE TO THEIR TOXICITY (Green & White hellebore)  are only
employed as INSECTICIDES
OTHER STEROIDAL ALKALOIDAL GLYCOSIDES  abundant in Solanaceae & Liliaceae (with hemolytic properties)

1. Potato  A-solanine
2. Bitter-sweet property of S. dulcamara  Soladulcin
3. Tomato  Tomatin (Popular antioxidant & has antiseptic property)
4. Veratrum sp.  Rubijervine
5. Nitrogen analog of diogenin  Solasodine

Alkaloidal amines – non-heterocyclic alkaloids (derivatives of phenylethylamine, phenylalanine, or tyrosine)

ALKALOIDS SOURCES Remarks
1. COLCHICINE  cause the AUTUMN CROCUS/MEADOW  USES: for acute attacks of gout
doubling of chromosomes in SAFFRON (corm & seed) 
cell Colchicum automnale

2. EPHEDRINE EPHEDRA or Ma Huang  Have no clinical use  so employed as a dietary

(Ephedra sinica) supplement, & energy booster
Other souce: (Ephedra  Ephedrine SO4: used to combat HYPOTENSIVE STATE for
distachya) allergic disorders such as bronchial asthma,
mucotreatment, & nasal congestion
 USES: Sympathomimetic, Vasoconstrictor for
hypertension, Cardiac stimulant, Bronchodilator, Topical
Nasal Decongestant (OTC), Mydriasis
3. MESCALINE PEYOTE/MESCAL BUTTONS  Mescaline (a psychomimetics; hallucinogenic)  causes
(Lophophora williamsii) hallucination &euphoria
 Ingestion of MESCAL BUTTONS  may cause mydriasis &
unusual or bizarre color perception
 the subject may become drowsy & eventually sleeping 
as an effect of mescaline
 Mescarinic  hallucinogen
4. (-) CATHIONE ABYSSINIAN TEA (Khat plant)  Used to alleviate hunger and fatigue
(LEVOROTATORY from the leaves of (Catha  Cathinone  similar to amphetamine
CATHIONE) edulis)
 ALKALOIDAL AMINES  Tryptamine derivatives
EXAMPLES:

1. Gramine, Hordenine in Hordeum vulgare

2. Psilocybin in the Mexican mushroom Psylocbe semperviva  Psilocybin - hallucinogen; psychedelic
3. Serotonin
4. Bufotenine in number of plant and animal species

QUINOLIZIDINE ALKALOIDS  Lupin alkaloids (COMMONLY OCCURING IN FAMILY LEGUMINOSAE)

 Cystisine, Laburnine, Lupinine, Lupanine, Sparteine, Anagyrine

 Lupinine, Lupanine, & Sparteine  most toxic Qas in humans

PURINE ALKALOIDS  methylxanthines

-from different Amino Acids (glycine, glutamine, aspartic acid)
-Do not precipitate w/ alkaloidal reagent
-MOA: inhibit PDE (Phosphodiesterase)  inc. cAMP (Cyclic Adenosine
Monophosphate

ALKALOIDS SOURCES Remarks

1. Caffeine, theobromine, Cola  Kola Nuts (Cola  CNS stimulant
Kolacatechin nitida)
 Coffee Beans –release caffeine from Cholinergic Acid
2. Caffeine (1,3,7 – Coffee  Coffea 25rabica,  Volatile Oil containing caffeol is released  aroma at
trimethylxanthine) Coffea robusta, Coffea coffee
liberica  Caffeine (1,3,7 – trimethylxanthine)  is used w/
Ergotamine Tartrate to treat migraine headaches
 USES: CNS stimulant, Bronchodilator, Diuretics 
THEOPHYLLINE & THEOBROMINE (more popular
bronchodilating activity)
 GIVES PURPLE COLOR with MUREXIDE TEST
 DOC for obtaining a stimulating effect of the CNS
 does not react w/ or precipitate w/ Alkaloidal reagents
 COMPONENTS:
 Chlorogenic acid  condensation product of
caffeine acid and quinic acid & occurs in mate,
coffee, hops, elder flower & lime flower
 Decafenized: <0.08% caffeine  has higher price than
ordinary coffee
 CNS Stimulation  most potent effect of trimethyl
substitutions in position 1,3,7 of the xanthine molecule
 MOA: Inhibition of Phosphodiesterase enzyme
3. THEOPHYLLINE (1,3 – usually prepared by teas of  FORMS: Black  Rapid heat
dimethylxanthine) the leaves of Thea (Camelia Green  mild heat
sinensis) & black tea (though  ISOMER OF THEOBROMINE
usually caffeine is really what  USES: smooth muscle relaxant, bronchodiator in asthma
composed black teas) & COPD, diuretic, & have astringent property due to
tannin content
 Aminophylline = Theophilline + Diethylamine
4. THEOBROMINE (3,7 – Theobroma  cocoa seeds (  USES: smooth muscle relaxant, &diuretic
dimethylxanthine) Theobroma cacao)  Theobromine  is preferred over caffeine in the tx of
or can be synthetically cardiac edema & angina pectoris because it has little
prepared stimulant action on the CNS.
5. CAFFEINE, CATECHOLAMINES Guarana  dried paste of  USE: CNS stimulant, astringents
the seeds of Paullinia cupana
6. CAFFEINE, TANNINS Matē  Paraguay Tea (Ilex  USE: CNS stimulant, astringents
paraguariensis)

OTHER ALKALOIDS

1. Jatrorhizzine  From Coptis chinensis  prevent & treat metabolic disorders

2. Aconitine  TERPENOID ALKALOID derived from Wolfsbane root
3. ANTI-PROTOZOAL ALKALOIDS  Berberine, emetine, arecholine, quinine, conessine, crytolepine
 CONESSINE/ KURCHI BARK  Holarrhena pubescens (Aponacynaceae)
 TERPENES ANTI-PROTOZOAL  Artemissinin, Quassinoids
 QUINONES ANTI-PROTOZOAL  Lapachol, Plumbagin
 PHENOLIC CMPDS ANTI-PROTOZOAL  Lichochalcone A, Phloridzin

MUSHROOM POISONING
Rapid onset (Amanita muscaria) Delayed onset (Amanita phalloides, A. virosa)
 30 mins – 2 hrs after ingestion  First symptoms: 6-12 hrs after ingestion
 SYMPTOMS: stomach upset, hallucinations, disulfiram  Nausea and vomiting, hepatic & renal injury that inhibit
effects, nausea, vomiting, diarrhea, urinary urgency, RNA polymerase
sweating, salivation, bronchoconstriction

Sympathetic agonist- Ephedrine, cathinone indole- reserpine, yohimbine, physostigmine

Sympathetic antagonist- Yohimbine steroidal- veratrine, solanine
Cholinergic agonist- Physostigmine, pilocarpine purine- theobromine, caffeine, theophylline
Cholinergic antagonist- atropine, hyoscine alkaloidal amines- psilocybin, ephedrine,
colchicine, mescaline

Yohimbine
 ENZYMES (-ase)  Biological catalyst or have catalytic action

 Organic catalysts produced by living organisms

 Lifeless (parang ikaw)
 Colloids & are soluble in water
 Act best at temperature between 35 and 40 degrees celcius
 Activity is highly affected by the pH of the medium
 Highly selective (e.g. LOCK & KEY)
 RETIRE THE ENZYME ACTIVITIES: FORMALDEHYDE & FREE IODINE

 Consist of a protein and a NON-PROTEIN  CO-FACTOR (non-protein associated to enzyme)

o *substances that most enzymes requires for their activities
o COENZYME/ COSUBSTRATE  are cofactors dissociate from the enzymes Ex: Organic
Compounds derived from vitamins:
 *NAD+/ NADH (nicotinamide Adenine reduce form dinucleotide) B3
 *FAD+/FADH2  Flavin Adenine Dinucleotide
 *Pyridoxal –Pyridoxamine transferase (common cofactor of transferase)
o Prosthetic Group  Metal ions  Fe, Co. Mo. Mn, K, Mg, Se  cofactors that remain tightly
bound to the enzyme, often attached to proteins by a covalent bond.

 ZYMOGEN/PROENZYMES  inactive enzyme

o *the active site of the enzyme is masked by a small region on its peptide chain.
o *Proteases  secreted as inactive Zymogen
o *Pepsinogen  inactivated to pepsin by gastric acid (HCl) & by activated pepsin (autocatalysis)
o *Trypsinogen  in small intestines, precursor of trypsin  is activated by entropeptidase, which
is secreted by the duodenal epithelial cells
 Trypsin can then activate the following:
Chymotrypsingen to chymotrypsin
Proelastase to elastase
Procarboxypeptidase to carboxypeptidase
Proaminopeptidase to aminopeptidase

 APOENZYME  the protein component of an enzyme, to which the coenzyme attaches to form an
active enzyme
o *protein portion of an enzyme w/out a bound cofactor

 Holoenzyme  A COMPLETE ENZYME

o COFACTOR + APOENZYME
o *apoenzyme + bound cofactor (coenzyme/ metal)
o *active form of an enzyme

I. CARBOHYDRATES Amylolytic enzymes

Amylase  Salivary amylase  Ptyalin
 Pancreatic amylase  Amylopsin
 *Alpha-amylase  cleaves amylase to maltose & maltotriose
Invertase/Sucrase  Found in yeast and in intestinal juices
 Alcohol fermenting enzyme  aid in OH fermentation
  Add yeast  [invertase]  ALCOHOL
 Brings about the hydrolysis of sucrose forming glucose & fructose
(SUCROSE [invertase]  GLUCOSE & FRUCTOSE)
Zymase  Fermenting enzyme causing the conversion of monosaccharides into alcohol
& carbon dioxide (GLUCOSE [zymase]  OH + CO2)
Emulsin  Enzyme found in almonds, it causes the hydrolysis of beta-glucosides
 AMYGDALIN = benzaldehyde & HCN (guess what glycoside? paghindi mo
alam kulang ka sa aral) –sige na nga hmp “CYANOPHORE”
MYROSIN  Found in white white & black mustard
 It hydrolyses sinalbin, sinigrin & other glycosides (oh, glycoside ulit????) 
ISOTHIOCYANATE diba allyl/acylisothiocyanate yan????
II. Esterases (Lipase, pectase, steapsin, ureases) III. Proteolytic Enzymes (Pepsin, trypsin, rennin)

ADDITIONAL NOTES FROM MANOR:

 Renin  is a coagulating enzyme, which curdles the soluble casein in milk present in the mucous
membrane of the stomach in mammals
 Pepsin  is a proteolytic enzyme found in gastric juice  converts proteins into proteoses &
peptones (Ma’am corrected herself here pls don’t get confuse PEPSIN TALAGA YON look at the
arrow process)
 Trypsin  is formed by the action of enterokinase on trysinogen in the small intestines  converts
proteoses & peptones into polypeptides & amino acids
o is a proteolytic enzyme used for the debridement of necrotic, & pyogenic surface lesions
o enzyme that catalyze the hydrolysis of proteins
 Rennin  a proteinase which is found mostly in gastric juice of infants

ENZYMES REMARKS
Papain  Active proteolytic enzyme in gastric juice
 A mixture of proteolytic enzymes found in unripe fruits of PAPAya (dried & purified
latex of the fruit of Carica papaya)
 USES: Meat tenderizer, digestant, remove symptoms of episiotomy (surgical incision
of vulvu for obstetric purposes) &ingredient in cleansing solutions for soft contact
lenses
Chymopapain  USE: Employed in the treatment of herniated lumbar intervertebral disk
  *is injected in the nucleus pulposus to hydrolyze the noncollagenous polypeptides or
proteins, which maintain the tertiary structure of chondro mucuproten.
Bromelains  is a mixture of protein-digesting enzymes & milk-clotting enzymes from Ananas
comosus (Bromelicaceae), commonly known as Pineapple
 USE: adjunctive therapy to reduce inflammation and edema, &accelerate tissue repair
especially following episiotomy
Chymotrypsin  USE: for ophthalmic solution
Lactase  Hydrolyses LACTOSE
Hyaluronidase  SPREADING AGENT (used as a spreading & diffusing factor)
 Hyaluronidase (for Injection)  prepared from mammalian testis
Streptokinase  Fibrinolytic drug
Urokinase  Streptokinase  tx of pulmonary embolism, deep vein thrombosis, arterial
thrombisis, & embolism, arteriovenous cannula occlusion, & coronary artery
thrombosis
 Urokinase  is an enzyme isolated from human urine or from human kidney cells by
tissue culture technique
Fibrinolysin  Used primarily in the treatment of blood clots within the cardiovascular system,
exclusive of the thrombi of the coronary & cerebral arteries
Sutilains  From the bacterium Bacillus subtilis  used for the wound debridement
 are substances containing proteolyics enzymes, which are topically used as ointments
for wounds debridement
Collagenase  from the cultures of Clostridium histolyticum
L-aspariginase  from the cultures of E.coli

REVIEW FOR ENZYMES:

Papain- found in papaya
Bromelains- found in pineapple
L- aspariginase- from E. coli
Myrosin- from- mustard
Sutilains- from Bacillus subtilis
Urease- from soybean

VITAMINS  used as special dietary supplements

*Four General Categories in Which Vitamin Supplementation is indicated:
- Inadequate dietary intake
-Increased metabolic requirement
-Impaired intestinal absorption
-Iatrogenic situations
 VIT F  omega 3 & omega 6 (iniba ko lang term
baka mamali ka pa VITAMIN F, F for eFa)

Vit Q10  for CHF, angina & HTN

VITAMINS
1. VITAMIN C/ antiscorbutic vitamin
 USES: for IMMUNITY & WOUND HEALING
o formation of intercellular collagen, & healing of bone fractures
o metabolism of tyrosine
o may be administered w/ Ferrous Sulfate to prevent/ minimize the oxidation of ferrous to ferric
ions
 SOURCES: citrus fruits  GUAVA (rich in vit C  a fruit included in LUBISANTA)
 DEFICIENCY: sCurvy

2. VITAMIN A  was the first fat-soluble vitamin discovered

 USES: maintains the integrity of epithelial membranes & essential in the formation of rhodopsin &
the normal functioning of the retina
 SOURCES: ingested in precursor forms
o ANIMAL precursor: liver & eggs have retinyl esters
o PLANT precursors: carrot & spinach (contain PROVITAMIN A & BETA-CAROTENE)

Precursors  Provit A. & Beta-carotene

FINAL/ACTIVE FORM  Retinol (major natural form of Vitamin A)

*Retinoic Acid  structurally related to Vitamin A

*Beta-carotene  a precursor of vitamin A which does not occur In plants, but
in its place are compound that are converted into Vitamin A in the small animal
body
 DEFICIENCIES: Xerophthalmia (corneas are swollen & ulcerated), keratomalacia (soften & destructed
cornea), night blindness, & total blindness (pagkabulag sa pag-ibig pwede rin siguro)

3. VITAMIN D/Sunshine vitamin

 FORMS:
o Vitamin D1  Calciferol
o Vitamin D2  Ergocalciferol (plant steroid derived from Ergosterol )
o Vitamin D3  Cholecalciferol (animal species  may be formed by irradiation of 7-
dehydrocholesterol & resembles ergocalciferol in appearance & physical properties)
o Dihydrotachysterol  is a synthetic substance formed by the reduction of tachysterol  closely
related to ergosterol
o 7-Dehydrocholesterol  is converted to calciferol upon exposure to ultraviolet light
 DEFICIENCIES: Osteomalacia, weakness, rickets, & tetani (muscle spasm & pain)
 PROCESS:
1. D3 (Cholecalciferol)  [HYDROXYLATION]  25-HVT D3 or 25-
hydroxycholecalciferol
2. 25-HVT D3 or 25-hydroxycholecalciferol (the MAJOR STORAGE
FORM in liver together with dietary intake of D2 & D3)  will be
transported to KIDNEY
3. Upon transportation  [HYDROXYLATION]  Calcitriol
4. Calcitriol/1,25-diHVT D3/Sunshine vitamin/1,25-diHCC (ACTIVE
FORM OF Vit. D)

4. VITAMIN K
 SOURCES: green leafy vegetables
 USE: important in blood clotting
 FORMS:
o K1  Phytonadione
o K2  starting Ji Chang-wook char  Menaquinone
o K3  Menadione

VITAMINS DEFICIENCIES
A Xeropthalmia, Night blindness, keratomalacia
D Rickets, tetany
E Nerve damage
C sCurvy

5. VITAMIN B

5.1Vitamin B1 (Thiamine)  Appebon®

 *occur in greatest proportion in dried yeast
 *most rapidly reduced vitamin
 essential nutrient used by the body to convert food into energy & important in the metabolism of
ALCOHOL (kung mani ang pulutan niyo sa inuman oh may pangontra ka na sa Wernicke encepa kasi
rich in B1 yon ang galing ng mga Pinoy diba  common problem sa mga alcohol dependent  B1
deficient, wala share ko lang)
 DEFICIENCIES:
o Wernicke-Korsakoff syndrome  (“Wernicke encephalopathy”  lack of coordination,
“korsakoff-psychosis”  short term memory)
o Beri-beri  affected areas are heart and circulatory system  CV problems
o *Pernicious Anemia Vitamin

5.2. Vitamin B2  Riboflavin

 USE: source of FADH2/FADH  hence, important in the breakdown of fats, CHO, & CHON
 DEFICIENCIES:
 o Cheilosis  characteristics of cracks of the mouth
o Glossitis, & seborrheic dermatitis

5.3. VITAMIN B3  Niacin (naturally occurring pyridine derivative that prevents pellagra)
 USE: important in the energy metabolism  because source of: NADH, NAD
 *can be used in the management of hyperlipidemia  MOA: Inhibition of VLDL secretion
 DEFICIENCY: Pellagra
 MANIFESTATIONS OF PELLAGRA (3Ds):
- Dementia (CNS disorder)
- Diarrhea
- Dermatitis

5.4. VITAMIN B5  Pantothenic Acid

 Vitamin B + C
 serve as a precursor of coenzyme
 a cofactor for the metabolism of Carbohydrate, Lipid, & Protein
 DEFICIENCY:
o *Most distinctive deficiency symptom: -Paresthesia of the Extremities or “BURNING FOOT
SYNDROME” (burning sensation and aching sensation)

**ADDITIONAL NOTES FROM MANOR (hindi kita pinipilit basahin):

 Vitamin B6 (Pyridoxine)  required in the transfer of aminogroups & decarboxylase of amino acid
o must be supplemented in poisonings caused by Cycloserin & Isoniazid enhance Leveodopa
metabolism (periphery)  Levodopa Effect
o Deficiencies: - Hypochromic microcystis anemia
- Resemble Niacin & Riboflavin abnormalities
- Neurologic Abnormalities
o Tryptophan loading dose maybe used for its diagnosis
o was isolated in crystalline form by both Xeresztesy & Stevens

 Vitamin B9 (Folic Acid)  decrease the risk of neutral tube deffects

o Deficiency: Glossitis& Megaloblastic Anemia

 Vitamin B12  is the best supplement recommended for strict vegetarian

 Vitamin P (PERMEABLITY FACTOR refers to the mixture of RUTIN and HESPERIDIN)

BIOLOGICS
 *include immunizing biologics that are derivatives of animals: serums, antitoxins, globulins; or of
microscopic plant organisms; vaccines, toxins, toxoids, tuberculins.
 classified into two: Antigens & Antibodies
o Antibodies  is a material, which induces an immune response (IgA, IgD, IgE, IgG, IgM)
o Antigen  a material that provokes the immune response (usually a protein)
 *when introduced into the body causes the formation of antibodies.
 *Are specific, that is, they react specifically with the antigen that stimulated their production
 *Diagnostic Antigen  are employed to determine whether an individual has developed
hypersensitivity
Immunity
- innate
- acquired
(Passive/active)

Commonly present in ferns e.g.

Paco
 DIURETICS  Coffee, tea, juniper oil (Borneol), Buchu (diosphenol), Uva-ursi (Bearberry), Horsetail
 NUTRACEUTICALS which are used for the maintainance of eye health, are antioxidant and can fight
blue light
o Lutein  caretenoid (found in spinach, kale, etc.)
o Zeaxanthin  caretenoid alcohol gives color to paprika & corn

 ANTIHELMINTICS  Rottlerin from Kamala (Mallotus philippensis), Santonin, Ipil-ipil, Areca

 HEMOLYTIC AGENTS  Glycyrrhizin, Senegin, A-solanin, Tomatin

TOXIC/POISONOUS
CONSTITUENT

Oxalic
acid Use to COUNTER
BARBITURATE
POISONING
Traditional medicine

Karela Momordica charantia Control diabetes

St. john’s wort Hypericum perforatum Anti-depressant, anti-
inflammatory agent, reduce
plasma concentration of the
protease inhibitor indinavir
Neem Azodirachta indica Seed oil (margosa oil),
azadirachtin-active agent with
anti- feedant property

Hallucinogens

Common Name alkaloid

Lophophora williamsil Peyote cactus anhalonium Mescaline
Catha edulis Khant plant Cathinone
Rivea corymbosa Ololiuqui LSD
Psilocybe Mexicana Mushroom Psilocybin
Amanita Mushroom Muscarine
Myristica fragrans nutmeg Myristicin, elamine, saffrole
Hallucinogens:
INDIAN HEMP
- From Cannabis sativa Moraceae
- In America and Europe: marijuana
- In north Africa: Kief
- In south Africa: dagga
- Arabia and Egypt: hashish
THC: principal psychoactive constituent
Cannabidiol: has anticonvulsant and possible analgesic effects
Cannabichromene: enhance THC activity and has anti-fungal, antimicrobial, and anti-inflammatory
activity.
Natural Allergens
1. Pollen
2. Spores- commonly present in ferns E.g Paco
3. Rhus- poison ivy
- Rhus radicans
- URUSHIOL (component produce severe dermatitis)

Tetratogens Rodenticides
Ipil-ipil- Leucaena leucocephala Red Squill- Urginea maritima
Lupins- Lupinus sericeus Strychnine- Strychnos spp.
Constituents
Vellarin Gotu-kola Diuretic, blood purifier, treats
Centella asiatica leprosy, body strengtherner, and
revitalizer counterirritant
Capsaicin Cayenne pepper Counteriiritant
C. frutescens Diaphoretic
Ditamine Aus. Quinine Bark Antimalarial agent
Alstonia scholaris
Policosanol Alfalfa Decrease cholesterol production
Medicago sativa
Vetiver oil Kuskus oil, moras Insect repellant
Vetiveria zizaniodes
TOXIC/POISONOUS
Local Poisonous Plants CONSTITUENT
Saga-saga Jequirity bean Abrin
Tubing-bakod Purging-nut free Curcin
Gabi Taro Oxalic acid
Tangan-tangan Castor bean Ricin
Kamoteng kahoy Cassava Linamarin
Water hemlock Water dropwort cicutoxin

Source Constituents Use/s

Coccus cacti Carminic acid Red dye
- Cochineal insect
Cocculus indicus/ Anamirta Picrotoxin An analgesic
cocculus/ Amanita cocculus - Glycoside from fish
berries
Crocus sativus Crosin Golden yellow dye
- saffron - carotenoid dye