LIPIDS

LIPIDS OR LIPINS OR LIPOIDS

 Lipids are a class of nonpolar molecules that include
 FATS,
 CHOLESTEROL,
 FATTY ACIDS,
 LIPID-SOLUBLE VITAMINS,
 WAXES,
 SOAPS,
 GLYCEROPHOSPHOLIPIDS,
 SPHINGOLIPIDS, and others.
 Lipids are found in the membranes of cells, the endoplasmic
reticulum, and in specialized fat storage cells called
adipocytes.
 Adipocytes are cells of the body involved in storage of fat.
MEDICAL AND BIOLOGICAL IMPORTANCE
1. Fat under skin serve as thermal insulator against cold.
2. Fat around kidney serve as padding against injury.
3. Fat serve as a source of energy for man like
carbohydrates.
4. Fat is an ideal form for storing energy in the human
body compared to carbohydrates and proteins because:
(a) Energy content of fat is higher.
(b) Only fat can be stored in a concentrated water free
form which is not possible with carbohydrates and
proteins
5. Lipids are structural components of cell membrane and
nervous tissue.
6. Some lipids serve as precursors for the synthesis of
complex molecules. For example, acetyl-CoA is used for
the synthesis of cholesterol.
7. Lipoproteins, which are complexes of lipids and
proteins are involved in the transport of lipids in the
blood and components of cell membrane.
8. Some lipids serve as hormones and fat soluble vitamins
are lipids.
9. Fats are essential for the absorption of fat soluble
vitamins.
10. Lipids present in myelinated nerves act as insulators
for propagation of depolarization wave.
12. Some saturated fatty acids are anti-microbial and anti-
fungal agents.
Components of cell membrane
 SUMMARY OF BIOLOGICAL ROLES OF LIPIDS
1. Food material. Lipids provide food, highly rich in calorific value. One gram
lipid produces 9.3 kilocalories of heat.
2. Food reserve. Lipids provide are insoluble in aqueous solutions and hence can
be stored readily in the body as a food reserve.
3. Structural component. Lipids are an important constituent of the cell
membrance.
4. Heat insulation. The fats are characterized for their high insulating capacity.
Great quantities of fat are deposited in the subcutaneous layers in aquatic
mammals such as whale and in animals living in cold climates.
5. Fatty acid absorption. Phospholipids play an important role in the absorption
and transportation of fatty acids.
6. Hormone synthesis. The sex hormones, adrenocorticoids, cholic acids and also
vitamin D are all synthesized from cholesterol, a steroidal
lipid.
7. Vitamin carriers. Lipids act as carriers of natural fat-soluble vitamins such as
vitamin A, D and E.
Various functions performed by lipids
(a)Fat. (b) Wax.
A European brown bear ready to Wax is a highly saturated lipid
hibernate. Fat is an efficient way to store that remains very firm at normal
energy. If this bear stored the same
outdoor temperatures. Its rigidity allows
amount of energy in carbohydrates instead
it to be used to form the strong but thin-
of fat, she probably would be unable to
walk!
walled hexagons of this honeycomb.
 Lipids
Simple Compound Derived
Lipids Lipids Lipids
 Classification of Lipids
Bloor (1943) has proposed the following classification
of lipids based on their chemical composition.

A. Simple lipids or Homolipids.

These are esters of fatty acid with various alcohols.

1. Fats and oils (triglycerides, triacylglycerols).

These are esters of fatty acids with glycerol.
A fat is solid at ordinary room temperature wheras an oil
is liquid.

2. Waxes. These are esters of fatty acids with high

molecular weight monohydroxy alcohols.
 B. Compound lipids or Heterolipids.
These are esters of fatty acids with alcohol and possess
additional group(s) also.
1. Phospholipids (phosphatids),
 These are compounds containing, in addition to fatty acids and
glycerol, a phosphoric acid, nitrogen bases and other
substituents.

2. Glycolipids (cerebrosides).
 These are the compounds of fatty acids with carbohydrates and
contain nitrogen but no phosphoric acid.
 The glycolipids also include certain structurally-related
compounds comprising the groups, gangliosides, sulfolipids and
sulfatids.
 C. Derived lipids.

These are the substances derived from simple

and compound lipids by hydrolysis.
These include
 fatty acids,
 alcohols, mono- and
 diglycerides,
steroids, terpenes and
carotenoids.
 Classification of Lipids
Simple Lipids
 They are esters of fatty acids with alcohols.
 Fats and waxes are example for simple lipids.
FATS (Triacylglycerols)
Fats are composed of glycerol esterified to three fatty
acids. All the three fatty acids can be same or different.
 Fats are derived from three primary sources:
(1) the diet;
(2) de novo biosynthesis, particularly in liver; and
(3) storage depots in adipocytes.
 Breakdown of fats by lipases yields fatty acids and
glycerol.
The carbon atoms of glycerol of triglycerides are indicated
with both Indo-Arabic numbers and Greek alphabets .
A. Simple triglyceride.
 If all the three fatty acids esterifed to glycerol are
same then it is called as simple triglyceride .
Example:
(a) Tripalmitin.
 Other names to tripalmitin are 1,2,3-tripalmityl
glycerol or α,β,α1-tripalmitin.
(b) Tristearin is another simple triglyceride.

B. Mixed triglyceride.
 If the three fatty acids esterified to glycerol are
different than it is called as mixed triglyceride
DIFFERENCE BETEEN ANIMAL AND PLANT FATS
Fatty acid composition of important animal and
plant fats
 Other Noteworthy Acyl Glycerols
1. Diacylglycerol
 In which 2 fatty acids are esterified to glycerol.
Example: 1,2-diacyglycerol and 1,3-diacylglycerol.
2. Monoacylglycerol
 In which one fatty acid is esterified with glycerol.
Example: 1-monoacylglycerol and 2-monoacylglycerol.
 Diacylglycerol and monoacylglycerol are called as
partial acyl glycerols.
 Mainly they are formed as intermediates during the
synthesis of triglycerides and during digestion of fat
 Functions of Triglycerides

They function as storage lipids in animals and in plants.

2. In man adipose tissue or fat tissue found under the skin, in the
abdominal cavity and in the mammary gland contain
triacylglycerols.
3. In other animals and plant cells also TGLs are found as tiny
droplets in cytosol.
4. The fat stored under the skin serve as energy store and as insulator
against cold.
5. Women have more fat than men.
6. In obese (fat) people, many kilograms of triacylglycerol is stored
under the skin.
7. The antarctic and arctic animals like seals and penguins appear
bloated because of high concentration of triglycerides in their
bodies.
PHYSICAL PROPERTIES OF TRIGLYCERIDES
1. Pure fats have no colour, taste and odour.
2. At room temperature, fat of plant origin remains oil because it
contains more unsaturated fatty acids where as animal fat remain
as solid, because it contains mostly saturated fatty acids.
3. Triglycerides containing asymmetric carbon atom are optically
active.
CHEMICAL PROPERTIES OF FATS
2. Saponification
 When fats are boiled with bases like KOH or NaOH glycerol and
salts of fatty acids are formed .
 This process is called as saponification.
 The salts of fatty acids act as soaps. Soaps are good cleansing
agents, germicides and detoxicants.
2. Hydrogenation
It converts unsaturated fatty acids of triglycerides into
saturated fatty acids.
Commercially hydrogenation is used to convert liquid
fats of plant origin to solid cooking fats which are known
as margarines.
 Since hydrogenation converts liquid fat to solid fat
it is also called as hardening.
 3. Lipid Peroxidation
 When natural fats are exposed to atmospheric
oxygen, they develop bad smell and taste.
 It is called as rancidity. Rancidity of fat develops
even on prolonged storing.
 It is due to formation of lipid peroxides.
 Atmospheric oxygen reacts with unsaturated fattly
acids of triglycerides and forms lipid
peroxides.
 Antioxidants
 Like vitamin E and ascorbic acid prevent peroxide
formation.
 They are added to food fats to improve storage
quality.
 In the body also lipid peroxides are formed.
 Free radicals mediate lipid peroxide formation in
the body.
 Diseases like cancer, diabetes, atherosclerosis are
due to the formation of lipid peroxides in the body.
 FATS – FACTS AND FANTASIES
Irrespective of the source, fat is the most concentrated form of
dietary energy.
While sugars (carbohydrates) and proteins provide
4 Calories (kilocalories) of energy per gram, fat of any type provides
9 Calories.

There is no such thing as low-calorie fat. Thus, by replacing fats of

animal origin like `ghee' and butter with vegetable oils like
groundnut, sunflower, mustard, palm oil or any other, weight
cannot be reduced.
For weight reduction, the only rule is to eat less and
exercise more.
Despite the same Calorie content, the nutritional quality
of different fats does differ.
Nutritionally, polyunsaturated fatty acids (PUFAs) are
considered superior.

While the human body can synthesize saturated fatty

acids (SFAs) and monounsaturated fatty acids (MUFAs), it
cannot synthesize the polyunsaturated fatty acids (PUFAs)
and hence PUFAs are referred to as essential fatty acids
(EFAs).

Fats of animal origin (lard (fat), cream, butter and ‘ghee’)

are saturated whereas vegetable oils, except coconut, have
varying degree of unsaturation.

Fish oils too are unsaturated and have long-chain-

length fatty acids.
 It is long known that saturated fats raise blood
cholesterol level whereas unsaturated fats lower
blood cholesterol and also ensure a more favourable
ratio of ‘good’ to ‘bad’ cholesterol.

 It is for this reason that the vegetable oils such as

groundnut, mustard, rice bran, sunflower, etc
(except coconut oil, which is saturated) are regarded
to be healthy, rather health-friendly fats.

 Therefore, these are prescribed for those

suffering with high levels of blood cholesterol or
those suffering from coronary artery disease.
Waxes
Waxes are esters of fatty acids with long chain
alcohol.
Examples:
(a) Lanolin or wool fat is a mixture of fatty acid
esters of long chain alcohols lanosterol and
agnosterol.
(b) Cholesterol ester is wax present in the blood
(lipoprotein) and cell membranes.
(c) Bees wax is an ester of palmitic acid with
myricyl alcohol.
 Functions of Waxes

1. Waxes serve as protective coatings on skin, fur and

feathers of animals, birds and on fruit and leaves of plants.
 Shiny appearance of fruits and leaves is due to waxes.

2. Waxes act as water barrier for animals, birds and insects.

 Wax is hard in cold climate and soft in hot climate.

3. Since wool is a wax woollen clothing provides protection

against cold. Marine organisms use wax as source of
energy.
 COMPOUND LIPIDS

 They are esters of fatty acids with alcohol containing

nitrogenous bases and additional
groups. Based on alcohol compounds lipids are
subdivided into
(a) Glycerophospholipids
(b) Sphingo lipids.
 Compounds lipids are also
divided into phospholipids
and glycolipids
Types of glycerolipids and sphingolipids.
Classification of compound lipids
 GLYCEROPHOSPHOLIPIDS OR PHOSPHOLIPIDS

 They contain two molecules of fatty acids

esterified to first and second hydroxyl groups of
glycerol.
 The third hydroxyl group of glycerol is
esterified to phosphoric acid.
 Further a nitrogen base or second alcohol is
also esterified to phosphoric acid.
 Glycerophospholipid without second alcohol is
known as phosphatidic acid .
 They are
 phosphatidyl choline,
 phosphatidylserine,
 phosphatidyl ethanolamine and
 phosphatidyl inositol.
 The fatty acid combinations are different in each
of these phospholipids.
 Phosphatidylcholine
Lecithins (likithosG = yolk)
 They are widely distributed in nature.
 Various oil seeds like soybean and the yeasts are
important sources from plant world.
 In animals, the glandular and nervous tissues are
rich in these lipids.
 Function
It is the major phospholipid of cell membrane. It is
also present in egg yolk and lipoproteins

The lecithins are required for the normal

transport and utilization of other lipids.

 In their absence, accumulation of lipids occurs in

the liver to as much as 30% against a normal value of
3-4%, giving rise to a condition called “fatty liver”.

This fatty infiltration may lead to fibrotic changes,

characteristic of the liver disease cirrhosis.
 Phosphotidyl ethanolamine
It is closely associated with lecithins in animal
tissues & identified from soybean oil.

These are similar in structure to the lecithins

except that the choline is replaced by ethanolamine.

In which second alcohol ethanolamine is esterified

to phosphoric acid of phosphatidic acid .
 Phosphatidyl serine
 In which aminoacid serine is esterified to
phosphoric acid of phosphatidic acid .

 Phosphatidyl ethanolamine and phosphatidyl

serine are called as cephalins and
aminophospholipids.
 Phosphatidyl Inositol
 In which polyol inositol is esterified to phosphoric acid of
phosphatidic acid .
Functions
1. Cephalins are major component of cell membrane, lipoproteins
and nervous tissue.
2. Phosphatidyl inositol is also a component of cell membrane.
 phosphorylated phosphatidyl inositol (PIP2) and inositol
triphosphate (IP3) are involved in signal transduction.
 Other Noteworthy Phospholipids
1. Dipalmitoyl Lecithin
(a) Structure.
 Two molecules of palmitic acid are esterified to 1st and 2nd carbon
atoms of glycerol. A phosphocoline is esterified to the third hydroxyl
group.
(b) Function.
 It is secreted in alveoli of lungs. It is involved in the maintenance of
shape of alveoli. It acts as surfactant (surface active agent) in the
lungs.
 It prevents the collapse of alveoli due to high surface tension of water
by reducing surface tension of water.
 It is synthesized only after 34 weeks of gestation.
Medical importance
 Its deficiency in the lungs of premature infants causes respiratory
distress syndrome (RDS) which accounts for 20% mortality in
premature infants.
 2. Cardiolipin
(a) Structure.
 It is a double glycerophospholipid.
(b) Function.
 It is present in inner mitochondrial membrane.
 It is also present in heart muscle.
 It has immunological properties and used in the
diagnosis of syphilis.
 3. Lysophospholipids

(a) Structure.
 They are derivatives of glycerophospholipids.
 They contain only one acyl group instead of two acyl
groups.

(b) Function.
 They account for 1-2% of phospholipids in living systems.
 They are formed from phospholipids by the action of
enzymes and formed during biosynthesis of phospholipids.
 Lysolecithin is a component of cobra venom and a
strong hemolysing agent.
 4. Plasmalogens
(a) Structure.
 They are also glycero phospholipids. These compounds contain
unsaturated fatty alcohol in place of fatty acid at the C-1 position.
Usually nitrogen bases are choline, serine and ethanolamine .
(b) Function.
They are found in brain, heart and muscle.
 Plasmlogen content is more in cancer cells.
 Platelet activating factor, which causes aggregation of
platelets is a plasmalogen.
 SPHINGOLIPIDS
 They contain fatty acid long chain amino alcohol
sphingosine and bases or additional groups. They are
subdivided into
1. Sphingomyelins
2. Glycolipids.
 The “backbone” is sphingosine rather than glycerol.
 SPHINGOMYELINS
Functions
1. They are simple and most abundant sphingolipids.
2. They are present in most of animal membranes.
3. Myelin sheath of nerve cells is rich in sphingomyelins.
4. Grey matter also contain sphingomyelins.
 Niemann-Pick disease
It is due to defective sphingomyelinase.
So, sphingomyelin accumulates in liver and spleen.
Spleen and liver are enlarged.
sphingomyelins are stored in
the brain in large quantities.
Usually occurs in infancy and
causes death in few months
 GLYCOLIPIDS
They are subdivided into: 1. Cerebrosides and 2. Gangliosides.

Cerebrosides
Structure
They contain sphingosine, fatty acid and sugar. The
combination of sphingosine and fatty acid is called as
ceramide.
 Cerebrosides differ in the type of sugar, usually they are
named according to the sugar present.
 If the sugar is galactose then that cerebroside is called
as galactocerebroside and if the sugar is glucose then it
is glucocerebroside
 In some cerebrosides, sulfate is attached to sugar then
they are called as sulfatides or sulfolipids.
Function
 Cerebrosides occur in large amounts in white matter
of brain and in myelin sheath of nerves.
 Some cerebrosides are present in non-neural tissue.
 Gaucher's
disease

 Deficiency of β-glucosidase.
 Accumulation of glucocerebrosides in liver
and spleen.
 Enlarged liver and spleen.
GANGLIOSIDES
Structure
They are highly complex sphingolipids. They contain ceramide,
oligosaccharide and sialic acid.

Functions
1. They are abundant in grey matter of brain.
2. They are also found in non-nerval tissues.
3. They are components of hormone receptors.
4. They also function as receptors for toxins of cholera, influenza
and tetanus.
5. They are also involved in
cell-cell recognition,
growth, differentiation and
carcinogenesis.
 Tay−Sachs disease
 Hexosaminidase A is deficiency.
 Degrades GM2 gangliosides.
 Deficiency leads to accumulation of these in brain
and nerves.
 Symptoms are related to nervous systems. They are
mental defects, neurological disturbances and
blindness.
 This is the oldest medically described lipid storage
disease or lipidosis.
 It is a common hereditary disorder.
 When both parents are carrier, their children are
likely to develop Tay-Sachs disease even though
the parents show no symptoms of the disease.

 Tay–Sachs disease can be diagnosed during fetal

development.

 Amniotic fluid is obtained by amniocentesis and

assayed for
-N-acetylgalactosaminidase activity.
 DERIVED LIPIDS
They are formed from simple and compound lipids by hydrolysis.
They are fatty acids, steroids, glycerol and retinol.

Fatty Acids (CH3-CH2-CH2-(CH2)n-COOH)

They are acids derived from fats. They are monocarboxylic

acids containing long hydrocarbon side chain.
(a) Saturated fatty acids
In which hydrocarbon side chain is saturated (no double
bonds).
-CH2-CH2-CH2-
(b) Unsaturated fatty acids
In which hydrocarbon side chain is unsaturated (one or more
double bonds are present).
-CH2-CH=CH-CH2
 Fatty acids are also divided based on hydrocarbon chain length.

1. Short chain fatty acids Fatty acids containing less than

six carbon atoms (<6)
2. Medium chain fatty acids - 6-12 carbon atoms.
3. Long chain fatty acids -13-20 carbon atoms.
4. Very long chain fatty acids - 22-30 carbon atoms.

55
 Cis-trans isomerism
Because of the double bonds, unsaturated fatty acids
exhibit cis-trans isomerism.
 In the cis isomer bulky groups are located on the
same side of double bond where as in trans isomer
they are on the opposite side of double bond .
 All the naturally occurring unsaturated fatty
acids are cis-isomers.
Function
Cis and trans isomers are not interchangeable in
cells.
Only cis isomers can fit into cell membrane
because of bend at double bond.
56
57
 Nomenclature of Fatty Acids
 Saturated fatty acids
Saturated fatty acids have both trivial names and
systematic names.
Systematic name (Consist of two parts)
1. Name of hydrocarbon chain forms first
part.
2. ‘oic’ substituted in place of ‘e’ of
hydrocarbon name forms second part.
 Example, systematic name for a saturated fatty acid
containing 8 carbon atoms i.e.,
(octane + oic + acid) —→ octanoic acid.
Usually saturated fatty acids end as anoic acids.
58
In a fatty acid, the carbon atoms are numbered
from the carboxyl carbon.
The carbon atom adjacent to the carboxyl
carbon is known as the α-carbon.
 Carbon atom adjacent to the α-carbon atom is
known as β carbon atom and so on.
The end methyl carbon is called as ω-carbon

59
 Sources, trivial and systematic names of
saturated fatty acids
Unsaturated fatty acids
They have trivial names, systematic names,
and shorthand forms.
Systematic name
Like unsaturated fatty acids, the name of
hydrocarbon forms first part.
But ‘enoic’ substituted in place of ‘ne’ of
name of hydrocarbon in second part.

Number of double bonds are written before

‘enoic’ and symbol showing position of double
bonds and isomerism around double bond are
written between two parts or in the beginning.
61
Example
palmitoleic acid (trivial name) containing 16
carbon atoms and one double bond between 9
and 10 carbon atom is monoenoic acid or cis-9-
Hexadecaenoic acid.
Usually unsaturated fatty acids end as ‘enoic
acids’.

62
 Shorthand forms
Number of carbon atoms, number of double
bonds and location of double bonds of
unsaturated fatty acid are represented with
short form.
Example, palmitoleic acid is written as
16:1, Δ9 in shorthand form.
 First numeral indicates number of carbon
atoms, later number indicates number of
double bonds and Δ9 indicates position of
double bond.
63
Unsaturated fatty acids with their sources.
 ESSENTIAL FATTY ACIDS

They are not systhesized in the body.

So they must be obtained from diet.
 They are also called as (PUFA).
They are linoleic acid (LA), linolenic acid
(LNA) and arachidonic acid (AA).

Functions
1.Essential for the synthesis of eicosanoids.
2. Required for membrane lipids.
 Medical Importance of PUFA
Dietary essential fatty acids has blood
cholesterol lowering effect.
Deficiency status of essential fatty acids are
rare with normal diet.
However, deficiency causes dermatitis.
Lipid transport may be impaired.
Infants consuming formula diets are
susceptible to deficiency of essential fatty acids.
They may develop skin abnormalities.
66
 STEROIDS
 The steroids (stereosG = solid) are one of the most studied
classes of biological compounds and are often found in
association with fat
 All steroids may be considered as derivatives of a fused
and fully saturated ring system called
cyclopentanoperhydrophenanthrene or sterane.
 This system consists of 3 cyclohexane rings (A, B and
C) fused in nonlinear or phenanthrene manner and a
terminal cyclopentane ring (D).
67
 Steroids containing hydroxyl groups (hydroxy steroids)
are often referred to as sterols.
 The various sterols fall under 2 groups based on their
source :
 The animal sterols or zoosterols (cholesterol, cholestanol,
coprostanol).
 The plant sterols or phytosterols (ergosterol, stigmasterol,
spinasterol).
 A third group of sterols, which are obtained from fungi
including yeasts, is sometimes separately referred to as
mycosterols.

68
 CHOLESTEROL
In animal tissue, cholesterol is the major sterol.
It is found in bile (chol-bile).
(cholesterol literally means ‘solid alcohol from bile’).
In a normal 65 Kg adult, 200 gm of cholesterol
is present.
Brain is rich in cholesterol.
 It is also present in spinal cord and neurons.
Egg yolk is also rich in cholesterol.
 Functions
1.Cholesterol and its esters are important components of
cell membrane and lipoproteins.
2. Steroids with diverse physiological functions are derived
from cholesterol.
(a)Vitamin D: 7-dehydrocholesterol derived from
cholesterol is provitamin of vitamin D.
(b) Bile acids
They are required for the formation of bile salts.
(c) Hormones of adrenal cortex
-cortisol, corticosterone and aldosterone.
(d) Female sex hormones
-progesterone and estrogen
(e) Male sex hormones
-testosterone and androsterone
Steroids derived from cholesterol.
Testosterone,the male
sex hormone, is produced in
the testes.

Estradiol,one of the female

sex hormones, is produced in
the ovaries and placenta.

Cortisol and aldosterone are

hormones synthesized in the
cortex of the adrenal gland;
they regulate glucose metabolism
and salt excretion, respectively.

Prednisolone and prednisone

are synthetic steroids used as
antiinflammatory agents. 72
Cholesterol is generally believed to be notorious as a
major cause of heart disease.

There are 2 types of cholesterol, the lowdensity

lipoprotein cholesterol. (LDL-C) and the high-density
lipoprotein cholesterol (HDL-C).

The LDL-C grows with intake of eggs and dairy

products and triggers heart trouble.

 However, in a study conducted by Dr. Ian Craig of the

Goteborg University,Sweden in the early 70s showed that
patients with heart trouble such as myocardial infarction
had low levels of HDL-C, as compared to other people.
73
 He pointed out that most of the preventive heart
attack studies have so far been aimed at lowering
the LDL-C levels through drugs and diet.
normal variations in diet made little difference in
HDL-C levels.
Also, HDL-C levels were generally found
higher in women than men.
Perhaps this is the reason why fewer women
than men have heart attacks.
incidence of heart disease may be lowered by
increasing the HDL-C level in heart patients.
74
“Cholesterol is the most highly decorated small
molecule in biology.

Thirteen Nobel Prizes have been awarded to scientists

who devoted major parts of their careers to cholesterol.

 Ever since it was isolated from gallstones in 1784,

cholesterol has exerted an almost hypnotic fascination
for scientists from the most diverse areas of science
and medicine

75
Fat and cholesterol content of some animal foods
76
2. Coprostanol ( = coprosterol).
 It occurs in feces and is produced in the intestine as a
result of bacterial action on the double bond of
cholesterol.
3. Cholestanol.
 It occurs as a minor constituent of the sterols of blood
and other tissues.

77
 C 24 Steroids or Bile acids
Bile acids are derived from cholesterol and aid in fat
digestion and absorption.
 Bile acid synthesis is the major metabolic end product of
cholesterol.
About 400 mg of bile acids are synthesised per day.
Bile acids are eliminated in the feces but, due to recycling,
only about 0.5g/day or less are eliminated in this way.
Example
 Cholic acid (25-60% of the total bile acids),
 Chenodeoxycholic acid (30- 50%) and
 Deoxycholic acid (5-25%).
78
Cholic acid and chenodeoxycholic acid are the
predominant bile acids in humans.
The bile acid deoxycholate is abundant in the bile of
some other mammals.
Conjugates of cholic acid with glycine and taurine
form salts called glycocholate and taurocholate.
Taurine is a by-product of cysteine metabolism.
Bile salts play important roles in emulsification of fat in
the digestion process.

79
 EICOSANOIDS
 They are derived from eicosapolyenoic fatty acid
like arachidonic acid.
 They are prostanoids, leukotrines (LTA)
and lipoxins (LX).
The prostanoids include
 Prostaglandins (PG),
 Prostacyclins (PGI) and
 Thromboxanes (TXA).

80
 Prostaglandins
Since they are initially found in prostate gland they are
named as prostaglandins.
But later they are identified in all cells and tissues except
erythrocytes.
Structures
Chemically prostaglandins are derivatives of a
20 carbon prostanoic acid.
Prostanoic acid is a cyclic compound with two side
chains.
The cyclic ring present in prostanoic acid is a
cyclopentane ring.
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Structural features common to
the biologically active
prostaglandins. These
compounds have 20 carbons

 There are some six or more types of prostaglandins.

 They differ in the substituents on the cyclopentane ring.
 They are prostaglandin A(PGA), PGB, PGC, PGD,
PGE, PGF, PGG and PGH.
 Most widely distributed prostaglandins are PGA1, PGA2,
PGE1, PGE2, PGE3, PGF1, PGF2, PGF3.

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Prostacylins
Structure : They contain a second five-numbered ring
in addition to the one common to all prostaglandins.
Thromboxane
Structure : They are so named because they are
identified first in thrombocytes. They contain a six
numbered heterocyclic oxane ring .
Leukotriens and Lipoxins
Structure : They are found in leukocytes. They are
derivatives of arachidonic acid and contain no cyclic
ring. HydroPeroxyEicosaTetra Enoic acid derived from
arachidonic acid serves as precursor for leukotriens
and lipoxins.
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 FUNCTIONS OF EICOSANOIDS
They function as local hormones.
They act on several organs and produce physiological
as well as pharmacological effects.
1. Heart PGE class prostaglandins increases cardiac
output and myocardial contraction.
2. Blood vessels (PGE) maintain blood vessel tone and
arterial pressure.
3. Blood pressure PGA and PGE class lower blood
pressure.
So they may be useful as anti hypertensive agents.

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4. Brain PGE class produce sedation and
tranquilizing effect in cerebral cortex.
5. Kidney PGA and PGE class increases excretion
of Na+, K+ and CI-. They may increase urine
volume by increasing plasma flow.
6. Lungs PG dilate bronchi, so they are useful in the
treatment of asthma.
7. Nose PG relieve nasal congestion.
8. Stomach PG decreases acid secretion in stomach.
So they are useful in the treatment of peptic ulcers.

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9. Uterus PG induces contraction of uterine muscle.
They are used in the termination of pregnancy.
Prostaglandins also has role in fertility.
10. Metabolism Prostaglandins influences several
metabolism by altering cAMP level.
Example -they inhibit lipolysis in adipocyte by
increasing cAMP level.
11. PGE class are involved in inflammation.
12. Prostacylins inhibit platelet aggregation.
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13. Thromboxane's causes platelet aggregation
and clot formation.
14. Leukotriene's are involved in the regulation of
neutrophil and eosinophil function.
They act as mediators of immediate hyper
sensitivity reaction.
Lipoxins are vasoactive and immuno
regulatory substances.
15. Thromboxane A2 regulates acquired immunity.
It causes construction of smooth muscle cells.
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 LIPOPROTEINS
 They are lipid protein complexes found in plasma.
 They are non-covalent assemblies.
 The protein part of lipoprotein is called as apolipoprotein or
apoprotein.
 The apoprotein and lipids are held together by non-covalent
forces.
Structure
 Lipoprotein structure consist of non-polar lipid core surrounded
by apoproteins and more polar lipids.
 The outer apoprotein and polar lipid coat of lipoprotein solubilizes
these lipid rich particles in aqueous plasma.

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 Classification of Lipoproteins

1. Based on their density, the liporoteins are classified

into 4 classes.
The four classes of liporoteins can be separated by ultra
centrifugation.
Density of a lipoprotein is inversely related to the lipid
content.
The greater the lipid content, lower is the density.
1. Chylomicrons,
2. Very low density liporoteins (VLDL)
3. Low density liporoteins and (LDL)
4. High density lipoproteins (HDL)
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 Functions of Lipoproteins

They are involved in the transportation of lipids in the body.

1. Chylomicrons They transport dietary or exogenous triglycerides
from intestine to liver.
2. Very low density lipoproteins (VLDL)
They are involved in the transport of endogenous
triglycerides from liver to extra hepatic tissues.
3. Low density lipoproteins (LDL)
LDL is the major vehicle for the transport of cholesterol from liver
to extra hepatic tissues.
4. High density lipoproteins (HDL)
HDL is the major vehicle for the transport of cholesterol from extra
hepatic tissues to the liver.
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