LIPIDS

Lipids are the heterogeneous group of naturally occurring organic substances characterized by their insolubility
in water and soluble in organic solvents like other chloroform, benzene, alcohol etc.
The hydrophobic character is due to the presence of large amount of hydrocarbons in their structure. Lipids are
very diverse in nature and are found in all plants and animals. It includes fats, oils phospholipids, steroids,
pigments etc.
Biological importance of lipids:-
1. Lipids are the important dietary constituents, not only because of their high calorific value but also
because of fat soluble vitamins and essential fatty acids contained in the foods.
2. It serves as an efficient source of energy and is stored in the adipose tissue. 1 gm of fat yields 9 k cal of
energy where as 1 gm of carbohydrate yields 4 k cal of energy.
3. Lipids are characterized by their high insulating capacity. Layers of fat serve to protect vital organs of the
body. Subcutaneous fat serve as insulator to protect from heat loss. Lipids act as an electrical insulators
allowing rapid propagation of nerve impulses along myelinated nerve fibers.
4. Lipids are the major structural components of the membrane of all cells and cell organelles.
5. Lipids and lipid derivatives acts as vitamins, pigments and antioxidants.
6. Lipids and protein complexes (lipoproteins) are the important means of lipid transportation in the blood.
7. Polyunsaturated fatty acids are the source of prostaglandins which possess diverse physiological functions.
8. Bile acids being lipids facilitates emulsification of other lipids during digestion.
9. Cholesterol, a steroid lipid is the source of steroid hormones such as sex hormones and adrenocorticoid
hormones.
Classification: Based on the composition and nature of product obtained on hydrolysis, lipids are broadly
classified into 3 types: simple lipids, complex lipids and derived lipids.
SIMPLE LIPIDS: These are esters of fatty acids with alcohols. Fats and oils are complex mixtures of simple
and mixed triglycerols whose fatty acid composition vary with the organism that produced them. Fat is solid
and oil is liquid at room temperature. Plant oils are rich in unsaturated fatty acid residues and hence liquid
in nature. Animal fats usually contains higher amount of saturated fatty acid residues and hence solid in
nature.
Waxes: These are the esters of fatty acids with long chain monohydroxy alcohols. Ex: Bees wax
COMPLEX LIPIDS: These are the esters of fatty acids with alcohols in combination with additional
compounds. On hydrolysis, they give fatty acids, alcohols and additional groups like phosphoric acid, sugar
units etc. These are the amphipathic molecules composed of either 1, 2 diacyl glycerol or N-acyl sphingosine
(ceramide) linked to the polar head group, i,e., either a carbohydrate or a phosphate ester.
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 Phospholipids: There are two types.
1. Glycerophospholipids or phosphoglycerides. It contains 2 fatty acid molecules esterified to C1 and C2
hydroxyl group of glycerol. The C3 hydroxyl group forms ester linkage with phosphoric acid which in turn
is esterified to an alcohol derivative. Depending on the type of group attached to the parent molecule, they
are of different forms.
2. Sphingophospholipids: These lipids contain sphingosine (2-amino, 1.3 dihydroxy octadeca 4-ene),
instead of glycerol along with a molecule of fatty acid, phosphoric acid and choline. Ex: sphingomyelin.
Glycolipids: There are two types.
1. Sphingoglycolipids: It is the major form of sphingolipids. Most sphingolipids are sphingoglycolipids.
They contain sphingosine, long chain fatty acids and carbohydrate units. The principal classes are
cerebrosides (ceramide monosaccharides), sulfatides (ceramide monosaccharide sulfates) globosides
(neutral ceramide oligosaccharides) and gangliosides (sialic acid containing ceramide
oligosaccharides). The carbohydrate unit is glycosidically attached to the N-acyl sphingosine, at its C1 OH
group.
2. Glyceroglycolipid: When the C3 OH of glycerolipid attaches to a C1 OH of a carbohydrate, it is called
glyceroglycolipid.
Lipoproteins: are the complex formed by combination of various lipids with proteins. They are the transport
vehicles for lipids in blood plasma ex: chylomicrons, very low density lipoproteins, low density lipoproteins and
high density lipoproteins.
DERIVED LIPIDS: Derived lipids are the substances formed by the hydrolysis of simple and compound lipids.
They do not contain an ester linkage, It includes fatty acids, alcohols, hydrocarbons, carotenoids, vitamin A,
vitamin D, Vitamin E, Vitamin K, terpenes etc.
Fatty acids: Fatty acids are the carboxylic acids with hydrophilic head (carboxylic group) and a hydrophobic tail
(hydrocarbon chain). They are rarely free in nature but rather occur in esterified form as the major component of
various lipids.
The fatty acids which occur in natural fats are straight chain compounds with an even number of carbon atoms.
They may be saturated or unsaturated. Fatty acids with odd number of carbon atoms, branched chain acids and
cyclic acids occur rarely. Fatty acids contain 4-30 carbon atoms. Most of the fatty acids contain 16, 18, 20 carbon
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atoms.
Nomenclature: The systematic nomenclature is based on Genevan system. According to this system the fatty acid
is named after the hydrocarbon with the same number of carbon atoms with the suffix “oic acid” written in place
of last latter “e” in the name of hydrocarbon. Ex. Butane (butanoic acid). The name of saturated fatty acid end
with the suffix “anoic acid” and those of unsaturated fatty acid end with the suffix “enoic acid”
Ex: Octanoic acid (saturated, 8C), Octadecaenoic acid (unsaturated, 18 C).
In addition to the systematic names, fatty acids have common names (trivial name) which are widely used.
Numbering of carbon atoms: It starts from carboxyl carbon, and the adjacent carbon atoms are numbered as 2, 3,
4 and so on. The terminal carbon containing methyl group is known as ω (omega) end of the fatty acid.
Depending on the length of the carbon atom chain, fatty acids are categorized into 3 groups-
Short chain fatty acids (4- 6c), Medium chain fatty acids (8-14 c) and Long chain fatty acids (16-24c)
Short hand representation of fatty acids: The general rule is to write 1) no of carbon atoms 2) no. of double
bonds 3) position of the first carbon of the double bond counting from the carboxylic end.
Ex: Oleic acid, 18 carbon atom, 1 double bond between C 9 and C10 can be written as 18:1:9

Saturated fatty acids: General formula: (CnH2n+1 COOH) ‘n’ represents number of carbon atom.

In animal fats, palmitic acid and stearic acids are very common in occurrence; other higher members of the
series are known to occur particularly in waxes. Lower member of fatty acids occurs in milk fat (Butyric acid).

Common No. of c atoms Systematic Structure Occurrence

name name
Butyric acid 4:0 Butanoic acid C3 H7 COOH Butter
Caproic acid 6:0 Hexanoic acid C5 H11 COOH Coconut and palm oil
Caprylic acid 8:0 Octanoic acid C7 H15 COOH Coconut and palm oil
Capric acid 10:0 Decanoic acid C9 H19 COOH Coconut and palm oil
Lauric acid 12:0 Dodecanoic acid C11 H23 COOH Lauril oil (plant oil)
Myristic acid 14: 0 Tetradecanoic acid C13 H27 COOH Butter and wool fats
Palmitic acid 16 :0 Hexadecanoic acid C15 H31 COOH Animal and plant lipids
Stearic acid 18 :0 Octadecanoic acid C17 H35 COOH Animal and plant lipids
Glycolipids, ground nut oil,
Arachidic acid 20 :0 Eicosanoic acid C19 H15 COOH
peanut oil
Lignoceric acid 24 :0 Tetraeicosanoic acid C23 H15 COOH Glycolipids

Unsaturated fatty acids: These contain one or more double bonds in their structure. They may be classified
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 based on their degree of their unsaturation.
Monounsaturated fatty acids: These fatty acids contain single double bond within the hydrocarbon tail. Ex:
Oleic acid, double bond between C9 and C 10.
Polyunsaturated fatty acids: (PUFA): These fatty acids contain two or more double bonds in their hydrocarbon
chain.
1. dienoic aids : 2 double bonds: linoleic acid.
2. Trienoic aids: 3 double bonds: linolenic acid.
3. Tetraenoic acids: 4 double bonds: Arachidonic acid.
Most unsaturated fatty acids exists as cis isomers rather than stable trans forms. In animals additional double
bonds are introduced within the carbon chain leading to the production of three series of fatty acids known as ω3,
ω 6, ω 9 family respectively.
Oleic acid (18:1: 9) (octadecaenoic acid) (ω 9) (Natural fats).
Linoleic acid: (18:2:9, 12) (9, 12 octadecadienoic acid) (ω 6) (corn, peanut, soybean and plant oils).
Linolenic acid: (18:3:9, 12, 15) (9,12,15 octadecatrienoic acid) (ω-3) (linseed oil). Other important ω-3 fatty
acids include EPA (Eicosapentaenoic acid) and DHA (docosahexaenoic acid).
Arachidonic acid: (20:4:5, 8, 11, 14) (5, 8, 11, 14 eicosa tetraenoic acid) (ω 6) (ground nut oil, peanut oil, animal
phospholipid).
Essential fatty acids: The fatty acids which cannot be synthesized by our body and therefore supplied through
diet are called essential fatty acids. Linoleic and linolenic acids are essential fatty acids. Arachidonic acid
becomes essential only if precursor linoleic acid is not obtained through the diet. Human body can convert
stearic acid to oleic acid by inserting a single double bond. But our system is not capable to add up further double
bonds into the chain (due to lack of enzymes). Hence the body cannot synthesize, PUFA.
Properties of fatty acids:
 They are insoluble in water, but can be dispersed into micelles in dil NaOH / KOH which converts fatty
acids into soaps.
 These are amphipathic in nature, containing both hydrophilic and hydrophobic ends.
 The polar carboxyl group and non polar hydrophobic hydrocarbon chain enables emulsification.
 The melting point of fatty acids with even number of carbon atom increases regularly with increase in
chain length. The introduction of double bond causes fall in melting point.
Hence melting point of fatty acids increases with increase in chain length and decreases with the increase
in number of double bonds.
Phosphoglycerides: are the major groups of phospholipids that occur in biological membranes.
These are the esters of fatty acids with glycerol containing phosphoric group at C 3 and a nitrogen base, or an
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alcohol. The parent compound of this class is L phosphotidic acid. Phosphoglycerides containing different
nitrogen base or other groups are considered as the derivatives of phosphotidic acid.
Lecithin or phosphatidyl choline: These are the major component of cell membranes. It is more commonly
found in the outer portion of cell membrane. It consists of one glycerol molecule whose two hydroxyl groups
are esterified to 2 molecules of fatty acids while C3 has been esterified with phosphoric acid which in turn
attached to choline. Source: egg yolk or soybean.
Other examples are phosphatidyl ethanolamine, phosphatidyl serine (inner portion of cell membrane,
phosphatidyl inositol (cell signaling, membrane component), phosphatidyl glycerol (precursor of cardiolipins,
cardiolipins (rich in electron transport chain), plasmalogens (ether lipids).
Biological role of phosphoglycerides:
They are the structural components of the membranes and regulate membrane permeability. Phosphoglycerides
are essential for synthesis of different types of lipoproteins and thus participate in the transport of lipids through
circulation. It is an essential component of thromboplastin, a blood clotting factor. Thus it is one of the essential
components required for clotting process. It helps in the removal of cholesterol from the body by reverse
cholesterol transport. Phosphoglycerides in mitochonctrial membrane are responsible for maintaining the
conformation of electron transport chain components. It is involved in the signal transmission across the cell
membrane. It protects cells against damaging effects of singlet oxygen.
Sphingophospholipids: These types of phospholipids contain N-acyl sphingosine (ceramide) as its hydrophobic
tail.
Sphingomyelin (N-acyl sphingosine phosphocholine) is a sphingo-phospholipid and is an important structural
lipid of nerve cell membrane.
When the amino group in sphingosine is linked to fatty acid through an amide bond ceramide is formed. This is
the parent compound of sphingolipids. Alcoholic group of ceramide (C1) binds to phosphoryl choline via ester
bond to form sphingomyelin. It contains N-acyl sphingosine as its hydrophobic tail. Polar head contains
phosphoryl choline. Most prevalent acyl groups of sphingomyelin are palmitoyl (16:0) and stearoyl (18:0)
groups.
Importance: It is an important structural lipid of nerve cell membrane. It is present in myelin sheath found in
brain and nervous tissue.
Lipoproteins: Lipids and proteins associate non covalently to form complex lipids called lipoproteins, which
function in the blood plasma as transport vehicles for triacylglycerols and cholesterol.
Lipids such as phospholipids, triacylglycerols and cholesterol are sparingly soluble in water hence they are
transported by the circulation as components of Lipoproteins.
Lipoproteins are globular micelle like particles that consist of a non polar core of trglycerols and cholesteryl

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esters surrounded by an amphiphilic coating of proteins, phospholipids and cholesterol.
The protein potion of lipoprotein is called apolipoprotein. Different proportions are distributed in different
types of Lipoproteins. Generally apolipoprotein are water soluble and are weakly associated with the lipid
component. Cholesteroyl ester and triglycerol are present in a neutral core, surrounded by phospholipids,
apoproteins and cholesterol. The polar portion of phospholipid and cholesterol are exposed on the surface of
the lipoproteins and hence lipoporteins are soluble in aqueous solution.
Classification: Depending on their (size, composition and density) functional and physical properties,
lipoproteins have been classified into four categories
1) Chylomicrons 2) VLDL 3) LDL 4) HDL
Chylomicrons: Synthesized in the intestine and transport exogenous triglycerols from the intestine to the
liver, skeletal muscle and to the adipose tissue. It consist of high lipid and very low protein (<27) content and
rich in triglycerols. It has less density and larger in size.
Very low density lipoproleins (VLDL): They are produced in the liver and transport endogenous triglycerols
from the liver to other tissues.
Low density lipoproteins (LDL): They are formed from VLDL via blood circulation they predominantly
contain cholesterol and phospholipids. LDL transports cholesterol from liver to cells of the body. Increased
level of LDL in plasma leads to atherosclerosis and coronary thrombosis. LDL is therefore referred as the “Bad
cholesterol”
High density lipoproteins (HDL): Synthesized in liver. It is rich in proteins and phospholipids. They
transport cholesterol from peripheral tissue to liver for its utilization and excretion.
Increased level of HDL decreases the risk of atherosclerosis and coronary thrombosis hence HDL is referred is
good cholesterol. The transport of cholesterol from peripheral tissue, to the liver is called reverse cholesterol
transport.
Hence LDL is known as Bad cholesterol.
Liposomes are the circular bilayered lipids and are the vehicles to transport many substances within the cell and
for exocytosis and endocytosis. Micelles are the circular monolayer lipids in emulsification process. Bilayer
sheet are those present as a plasma membrane.

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