What are lipids?

 Lipids are heterogeneous group of compounds including fats, oils, steroids,

waxes, some vitamins and hormones, that are related more by their
physical than by their chemical properties.
 They have the common property of being:

Lipids 


Relatively insoluble in water
Soluble in non-polar solvents such as ether and chloroform

FATIMA MARIZ ALMENARIO-GAMMAD

ASSISTANT PROFESSOR II

Lipids are amphipathic molecules that Lipids are amphipathic molecules that
can be: can be:

 Major components of biological membranes  Thermal insulators in the subcutaneous tissues and
 Membranes define the basic unit of life (cell) and subcellular components in around certain organs
eukaryotes
 Electrical insulators allowing rapid propagation of
 Major form of stored energy in biological systems depolarization waves along myelinated nerves
 Complete oxidation of lipids generate lots of energy (more than what sugars  Provide shape and contour to the body
can provide)
 Hormones
 Used in signal transduction (communication) between cells
 Overview of Biological Lipids

 Fatty acids are the basic building blocks of complex lipids

 Lipids include:
 Waxes: Esters of fatty acids
 Triacylglycerols: membrane precursors, energy storage
 Glycerophospholipids: membrane components
 Sphingolipids: brain lipids, membrane components
 Steroids: cholesterol, bile salts, steroid hormones

Fatty acids: building blocks of lipids

 Composed of a carboxylic acid “head group” and a long

hydrocarbon “tail”. The tail generally contains an even
number of carbon atoms.
 Hydrocarbon tail can be saturated or unsaturated
 Saturated fatty acid do not contain double bonds while
unsaturated fatty acids contain double bonds
The common fatty acids found in biological systems

PRACTICE
Fatty acids in natural lipids have several
1. Linoleic acid is an omega-______ acid, as well as a delta-_______ acid.
characteristics

 They are usually straight chain carboxylic acids (no branching).

 The size of F.As range 10-20 carbons
2. There are two ways to count on a fatty acid, delta and omega. Using both  F.As usually have even number of carbon atoms including carbonyl carbon
methods, classify arachidonic acid.
 F.As can be saturated (no double bonds)or unsaturated contain one or more
double bonds and found in cis configuration

3. Draw the structure of alpha-linolenic acid (C18:3, -3).

 Fatty acids in natural lipids have several
characteristics
Nutrition and Fatty Acids

 The presence of double bond and the length of F.A chain in membrane  Essential fatty acids: linoleic and α-linoleic fatty acids; must be obtained
lipids partly explain the fluidity of biological membranes from plants
 Human body can synthesis all F.As except two (linoleic acid , linolenic  “Good fats” high in polyunsaturated fats. Typical foods include vegetable
acid) which are polyunsaturated F.As that contain 18 C atom, it must be oils, like olive, canola, sunflower, and other plant sources
obtained from the diet they are called Essential F.As: A fatty acid needed
 “Bad fats” high in saturated fats. Example include coconut and palm oils
by the body but not synthesized within the body ,it distributed in plants and
fish oils  “Really bad fats” trans- fatty acids, result from partial hydrogenation of
vegetable oils. Margarine has trans fatty acids. Difficult to metabolize, lead
 In body ,both acids are used to produce hormone like substances that
to increased cholesterol levels in the blood
regulate a wide range of functions and characteristic including blood
pressure, blood clotting ,blood lipid level ,immune response to injury and
infections

Cis and Trans- Isomers in unsaturated

Cis and Trans Isomers
fatty acids

 Depending upon the orientation of the radicals around

the axis of the double bond:
 Cis- if the radicals are on the same side of the double bond
 Trans- if the radicals are on the opposite side
 Oleic acid and elaidic acid have the same formula but
oleic acid is cis while elaidic acid is trans fatty acid
 Cis and Trans- Isomers in unsaturated
Significance of unsaturated fatty acids
fatty acids

 The hydrocarbon chains in saturated fatty acids are, fairly  Because of the kinks in the hydrocarbon tails, unsaturated fats cannot
straight and can pack closely together making these fats pack as closely together, making them liquid at room temperature
solid at room temperature  The membrane lipids, which must be fluid at all environmental
 Oils, mostly from plant sources, have some double bonds temperatures, are more unsaturated than storage lipids
between some of the carbons in the hydrocarbon tail,  Lipids in tissues that are subject to cooling. Example in hibernators or in the
causing bends or “kinks” in the shape of the molecules extremities of animals are more unsaturated
 Increase in the number of cis double bonds in a fatty  At higher temperatures, some bonds rotate, causing chain shortening,
acid leads to a variety of possible spatial configurations which explains why biomembranes become thinner with increase in
of the molecule- e.g. arachidonic acid with four cis temperature
double bonds has “kinks” or a U-shape  The carbon chains of saturated fatty acids form a zigzag pattern when
extended, as at low temperature

Classification of Lipids Classification of Lipids

1. Simple Lipids: Esters of fatty acids with various fatty acids 3. Precursor and derived lipids: These include the following:
 Fats: Esters of fatty acids with glycerol. Oils are fats in liquid state ➢ Fatty acids
 Waxes: Esters of fatty acids with higher molecular weight monohydric alcohols ➢ Glycerol
2. Complex Lipids: Esters of fatty acids containing groups in addition to an alcohol and ➢ Steroids
fatty acids
 Phospholipids: Lipids containing, in addition to fatty acids and an alcohol, a phosphoric ➢ Other alcohols
acid residue. They frequently have nitrogen-containing bases and other substituents. ➢ Fatty aldehyde
Example are glycerophospholipids and sphingophospholipids
 Glycolipids (glycosphingolipids): Lipids containing fatty acid, sphingosisne, and ➢ Ketone bodies
carbohydrate ➢ Hydrocarbons- lipid-soluble vitamins and hormones
 Other complex lipids: Lipids such as sulfolipids and aminolipids. Lipoproteins may also be
placed in this category
Triglycerides Triglycerides

 Triglycerides are a storage form of fatty acids in mammals.

 Often when blood tests are done, they measure your triglycyeride levels.  Triglycerides are a combination of three
3 fatty acid molecules with a glycerol
 High triglyceride levels in the blood are a risk indicator for artherosclerosis. molecule.

*American Heart Association

21 22

Triglycerides Triglycerides

HO CH2
 For triglycerides, all three hydroxyls of the glycerol have a fatty acid
 Glycerol which is also called glycerin, is an residue attached to it.
alcohol with three hydroxyl groups. O
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2C O CH2
 As with the waxes, the fatty acids can react
with the hydroxyl groups to form esters. HO CH
O
 Since there are three hydroxyl groups, three
fatty acids can react to form three esters. CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2C O CH

HO CH2
glycerol O
CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2C O CH2
fatty acid glycerol
23 residues residue 24
 Triglycerides

 Just as with fatty acids, where the presence of cis double bonds lower the
melting points, triglycerides made from unsaturated fatty acids have lower
melting points than those made from saturated fatty acids.
 Triglycerides from animals tend to have a higher proportion of saturated fatty
acids.
• Most are solids at room temperature and are called fats.
• Examples include: butter, lard and bacon grease

 Triglycerides from plants tend to have a higher proportion of unsaturated fatty

acids.
• Most are liquids at room temperature and are called oils.
• Examples include: corn oil, canola oil, peanut oil and olive oil.
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Triglycerides Waxes

 Triglycerides as primarily used as a form of stored energy.  An ester of a long chain F.A. and long chain alcohol (13-32 carbon).Waxes
are insoluble in water and not as easily hydrolyzed as fat and oil ,they
 This is why when you eat more than you need to meet your energy requirements, the excess occur naturally in nature as protective coating on feathers, skin, fruits, and
energy is stored in the form of fat. Fat can store almost twice as much energy per gram as leaves.
carbohydrates and proteins

 In mammals the fats are stored in the adipose tissue

 Adipose tissue also functions to protect organs from shock and cold.

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Phosphoglycerides

Lecithin and cephalin are glycerophospholipids

 A complex lipid contains glycerol, F.As, phosphoric acid ,
 Abundant in brain and nerve tissues.
and an amino alcohol component.
 Found in egg yolk, wheat germ, and yeast.
 Phosphoglycerides are the major component of cell
membranes.

Sphingolipids

 A complex lipid contain sphingosine compound

(along-chain unsaturated amino alcohol ,an 18-
carbon alcohol) instead of glycerol, F.As,
phosphoric acid , and an amino alcohol
component. they found in cell membrane like:
sphingomyelin, glycolipid.
Sphingolipids Glycolipids

 A sphingolipid found in brain and nerve tissue and in protective myelin sheath that  A complex lipid contain a sphingosine ,F.A ,a carbohydrate (glucose or
surrounds nerves. It is a complex lipid contain a sphingosine, F.A, choline. There is an galactose)and often called cerebrosides because of their abundance in
amide bond between a fatty acid and sphingosine. brain tissues.

Biological membrane

 Membranes performed two vital functions in living organisms :

 The external cell membrane: acts as a selective barrier between the living
cell and its environment.
 The internal membrane: surround some organelles ,creating cellular
compartments that have separate organization and functions.
 Lipid bilayer: A structure found in membranes, consisting of two sheets of
lipid molecules arranged so that the hydrophobic portions are facing each
other.
  Cell membranes contain lipid , protein and carbohydrates.
 Phosphoglycerides such as (lecithin, cephalin) and sphingomyelin,cholesterol are
lipids found in membranes.
 The lipids are organized in a bilayer in which the hydrophobic chains extend toward
the inside of bilayer and the hydrophilic groups(the phosphate groups and other
polar groups ) are oriented toward the outside, where they come in contact with
water, like the micelle.
 Membrane lipids usually contain unsaturated F.As chains that fit into bilayer more
loosely than do saturated F.As. This increases the flexibility or fluidity of the
membrane.

Terpenes

 Isoprenoids : Are a vast array of biomolecules that contain repeating five-carbon

structural units known as isoprene (methylbutadiene) units.The isoprenoids consist of
terpenes and steroids.
 Terpenes: They are linear or cyclic compounds formed by condensation of two or
more isoprene units and are found largely in the essential oils of plants (have been
used in perfumes and medicine), like vitamin A,K,E , carotenes , sequaline.
 Steroids Cholesterol

 They are completely different from the lipids, and  Most abundant lipid in human body (cellular membranes , myelin sheath,
defined: are compound contain four rings fused in brain, and nerve tissues) and has a rigid ring system and a short branched
a particular pattern (three six-membered rings and hydrocarbon tail.
a single five membered ring fused together).  Cholesterol is largely hydrophobic.But it has one polar group, a hydroxyl,
 Example is cholesterol making it amphipathic.
 Cholesterol inserts into bilayer membranes with its hydroxyl group oriented
toward the aqueous phase & its hydrophobic ring system adjacent to fatty
acid chains of phospholipids.
 The OH group of cholesterol forms hydrogen bonds with polar phospholipid
head groups.

Usually; saturated fat in diet cause high blood cholesterol level and
these consider risk factor of coronary heart diseases.
Cholesterol

 Cholesterol is a precursor for other important steroids including

:
 Bile salts
 Hormones
 Vitamin D HO
Cholesterol
 LDL (low-density lipoprotein), sometimes called
“bad” cholesterol, makes up most of your body’s cholesterol.
High levels of LDL cholesterol raise your risk for heart disease
and stroke.
 HDL (high-density lipoprotein), or “good” cholesterol, absorbs
cholesterol and carries it back to the liver. The liver then flushes
it from the body. High levels of HDL cholesterol can lower your
risk for heart disease and stroke. Cholesterol
in membrane
Bile salt Steroid Hormones

 It is a yellowish-brown or green liver secretion that is stored and concentrated in  Hormones are chemical messenger secreted by specific glands and carried by
the gallbladder. It is important in lipid digestion. the blood to a target tissue, where it triggers a particular response.
Adrenocorticoid Hormones:
Adrenal glands are small mounds of tissue located at the top of each kidney.The
outer layer of the gland , the adrenal cortex , produse a number of potent
steroid Hs., the adrenocorticoids are classified in to:
 Mineralocorticoids- regulate concentration of Na+ in body fluids (aldosterone)
 Glucocorticoids- enhance carbohydrate metabolism (cortisol)

Sex Hormones

 The tests and ovaries produce steroids that function as sex hormones,
which are responsible for secondary sex characteristics.
 Testes in the male produce sperm and male sex hormone (androgen)
 Ovaries in female produce estrogen and progesterone

aldosterone, which regulates electrolytes and water balance by the kidneys.

cortisone, a glucocorticoid, which increases blood glucose level and
stimulates the synthesis of glycogen in the liver
 Prostaglandins

 This group of compounds was given its name because the first
prostaglandins were identified from the secretion of the male prostate
gland , there are about 20 prostaglandins in a variety of tissues within both
male and female.
 Prostaglandin: A substance derived from unsaturated F.A with hormone
like effects on a number of body tissues and is a cyclic compound
synthesized in the body from the 20 carbon unsaturated F.A arachidonic
acid , like prostaglandin E 2 (PGE 2).

Clinically, PGs have many functions as stimulate blood clotting

,involved in every phase of reproductive process. Prostaglandins

 Produced by injured tissues

 Involved in pain, fever, and inflammation
 Not produced when anti-inflammatory drugs such
as aspirin inhibit their synthesis