LIPIDS

BCH 201-GENERAL BIOCHEMISTRY 1

Table of Contents

1.0 What are lipids

1.1 Biological roles of lipids

1.2 Classifications of lipids

1.3 Sources of lipids

1.4 Biological significance of lipids

1.5 Deficiency diseases of lipids

 LIPIDS
1.0 WHAT ARE LIPIDS
 Fats and lipids are an essential components of the homeostatic function of the human
body. Lipids contribute to some of the body’s most vital processes.
 Lipids are fatty, waxy, or oily compounds that are soluble in organic solvents such as
chloroform, carbon disulphide benzene, hot alcohol etc and insoluble in polar solvents
such as water.

 Lipids are a very important heterogonous group of organic substances which are widely
distributed throughout the plant and animal kingdom. In plant they are present in seeds,
nuts and fruits, while in animals they are stored in adipose tissues, bone marrow and
nervous tissues.
 Bloor [1947] defined lipids as “naturally occurring compound which are insoluble in
water, and soluble in one or more organic solvent such as benzene, chloroform, either
acetone the so called fat solvent on hydrolysis field fatty acids which are utilized by the
living organisms’’.

1.1 BIOLOGICAL ROLES OF LIPIDS

 Lipids have the common property of being relatively insoluble in water and soluble in
nonpolar solvents such as ether and chloroform.
 They are important dietary constituents not only because of their high energy value but
also because of the fat-soluble vitamins and the essential fatty acids contained in the fat
of natural foods. Fat is stored in adipose tissue, where it also serves as a thermal insulator
in the subcutaneous tissues and around certain organs.
 Nonpolar lipids act as electrical insulators, allowing rapid propagation of depolarization
waves along myelinated nerves.
 Combinations of lipid and protein (lipoproteins) are important cellular constituents,
occurring both in the cell membrane and in the mitochondria, and serving also as the
means of transporting lipids in the blood.
 Lipids are important in biological systems because they form the cell membrane, a
mechanical barrier that divides a cell from the external environment.
  Lipids also provide energy for life and several essential vitamins are lipids.
Lipids can be divided in two major classes, non-saponifiable lipids and saponifiable
lipids. A non-saponifiable lipid cannot be broken up into smaller molecules by
hydrolysis, which includes triglycerides, waxes, phospholipids, and sphingolipids.
Nonsaponifiable lipids include steroids, prostaglandins, and terpenes
A saponifiable lipid contains one or more ester groups allowing it to undergo hydrolysis
in the presence of an acid, base, or enzyme. Within these two major classes of lipids,
there are several specific types of lipids important to life, including fatty acids,
triglycerides, glycerophospholipids, sphingolipids, and steroids. Each of these categories
can be further broken down.
 Nonpolar lipids, such as triglycerides, are used for energy storage and fuel.
 Polar lipids, which can form a barrier with an external water environment, are used in
membranes. Polar lipids include glycerophospholipids and sphingolipids. Fatty acids are
important components of all of these lipids.

1.2 CLASSIFICATION OF LIPIDS

a. SIMPLE LIPIDS
Simple lipids are the esters of fatty acids with various alcohols. These can be further categorized
into fats and waxes. Fats are triesters of glycerol and fatty acids. A fat in the liquid state is called
oil. Waxes are the esters of fatty acids with long chain (higher mol.wt.) monohydric alcohols.

i. Fats

Fats are solids at room temperature. Chemically, fats are triglycerides since, three molecules of
fatty acids condense with one molecule of glycerol, e.g. three molecules of stearic acid are linked
to glycerol to yield glyceryl tristearate, a fat.
If all the three molecules of fatty acids are similar, the product is a simple glyceride. If fatty acids
molecules are different, it is called a mixed glyceride. Natural fats are largely composed of
mixed glycerides. Since these glycerides have no acid or basic groups, they are often called
natural fats. The melting point of fats depends upon the chain length and degree of saturation of
fatty acids. The melting points of fats are always higher than the solidification point, e.g.
tristearin melts at 72℃ but solidifies on cooling at 52℃ .

Fats develop unpleasant odor on aging, this is due to auto oxidation of fat. This is called
rancidification. The chemical changes that occur during rancidification are called rancidity.

Fats which are liquid at room temperature are called oils. Oils are also esters of fatty acids and
glycerol, but the fatty acids found in oils are unsaturated fatty acids. The unsaturated fatty acids
have one or more double bonds. They have low melting point and are insoluble in water.
Hydrolysis of fats with alkali or enzymes lipase yields fatty acids and glycerol. When the fats are
hydrolyzed with alkali, the few fatty acids react with alkali to form salts. These salts are soaps
and this process is called saponification.

ii. Waxes

Waxes are another class of simple lipids. These are the esters of fatty acids with high molecular
weight alcohol. Waxes contain one molecule of fatty acids and one molecule of alcohol. The
bees wax, the fatty acid constituent is a smaller chain acid, palmitic acid and [16 ℃ ] and alcohol
is myristic palmitate. Ambretolide found in the seeds of abelmoschus esculentus is a hay hydro
nil acid and is responsible for the characteristic smell of the seed. Being highly insoluble in water
and having no double bonds in their hydrocarbon chains, waxes are chemically insert. And very
resistant to atmospheric condition also not digested by the fat splitting enzymes. They can be
split slowly with hot alcoholic KOH, however. They also have higher melting point. They serve
as protective coating on fruits and leaves. They play on important role in provide water barrier
for insects, birds and animals. They are used in furniture polishing.

A. Fatty Acids

Fatty acids are obtained from the hydrolysis of fats. Since all the fats contain glycerol, their
properties differ according to the nature of fatty acids present in them. A fatty acid can be
defined as an organic acid that occurs in a natural triglyceride and is a monocarboxylic acid
ranging in chain length from C 4 to about 24 carbon atoms. A few have branched chain or contain
hydromel group or have a cyclic chain at the end. Fatty acids that occur in natural fats usually
contain an even number of carbon atoms, one carboxylic group and are straight chain derivatives.
On the basis of presence or absence of double bonds, fatty acids may be classified into two main
classes-

i. Saturated fatty acids) (saturated with hydrogen

ii. Unsaturated fatty acids
i. Saturated fatty acids

The fatty acids which do not contain any double bond are called saturated fatty acids. The
general formula is C n H 2 n+1 COOH e.g. Butyric acid C 3 (CH 2) COOH. The most abundant
saturated fatty acids in nature are palmitic acid (C 18) and stearic acid (C 16). The saturated
fatty acids are straight chain acids. In addition to these straight chain acids, there are some
branched chain acids, with odd or even number of carbon atoms.eg. Isopalmitic acid, anti-
isopalmitic acid and tuberculostearic acid.

ii. Unsaturated fatty acids

The fatty acids which contain one or more double bonds are called unsaturated fatty acids.
On the basis of number of double bonds, the unsaturated fatty acids may be divided into two
groups

a) Monosaturated fatty acids: - having one double bond e.g. crotonic acid, oleic acid,
palmitoleic acid, nervonic acid etc.
b) Polyunsaturated fatty acids:-having more than one double bonds e.g. linoliec acid,
eleostearic acid etc.
In most of the monosaturated fatty acids there is a single bond lying between carbon
atoms 9 and 10. This is designated as ∆ 9 . The symbol ∆ with the superscript number
nine (9) indicates the positions of the double bond. When there are more than one double
bond (polyunsaturated fatty acids), the additional bonds occur between the ∆ 9 double
bond and the methyl terminal end of the chain. The symbol 18:3 signifies that there are
three double bonds and symbol ∆ 9 ,12 ,15 signifies that the position of double bonds are
between carbon atom 9 and 10, 12 and 13 and 15 and 16. Presences of double bonds in
the fatty acids lower their melting point considerably. Most plant fats contain unsaturated
fatty acids as oleic acid and linoleic acid and hence they are liquid at room temperature.
Contrary to this animal fats have more of saturated fatty acids and hence solid at room
temperature.
 Essential and Non-Essential Fatty Acids

i. Essential fatty acids: The fatty acids which cannot be synthesized by human body but are
essential for the normal maintenance of the body are called essential fatty acids .These
fatty acids must be included in our diet. Three polyunsaturated fatty acids, linoleic acid,
linolenic acid and arachidonic acid are the essential fatty acids.
ii. Non-essential fatty acid: These are the fatty acids which can be synthesized by our body.
Thus they need not be included in our diet. They are unsaturated fatty acids and are
synthesized from their corresponding saturated fatty acids by introducing a single
bond .e.g. palmitoleic acid and oleic acid.
 b. COMPOUND LIPIDS
Compound lipids contain some additional groups or elements besides fatty acids are alcohol. The
addition group may contain phosphorus, nitrogen, sulphur or it may be a protein. Compound
lipids can be categorized into the following: Phospholipids, Glycolipids, Other compound lipids.

I. Phospholipids

Phospholipids are those compound lipids which contain a phosphorus atom. Phospholipids are
wide spread in bacteria, animal and plant tissues and their general structures are quiet similar.
These have been termed as amphipathic and compound since they process both polar and non
polar function.

In addition to phosphorus, phospholipids may also contain nitrogen as a key component. There
are various types of phospholipids including- lecithin, cephalins, plasmalogens,
phosphoinositides and phosphosphingosides.

a. Lecithin

Lecithin is widely distributed in nature. In animals it is found in liver, brain, nerve tissues,
sperm and egg yolk. In plant it is abundant in seeds and sprouts. On hydrolysis, lecithin yields
glycerol, fatty acids, phosphoric acid and nitrogenous base - choline. It is also called
phosphatidyl choline. The fatty acids commonly found in lecithin are palmitic, stearic, oleic,
linolenic and arachidonic acids. Lecithin is yellowish grey solid which is soluble in with soluble
in ether and alcohol but insoluble in acetone. On exposure to air they rapidly darken colour and
absorb water, forming dark grassy mass. Lecithins are broken down by the enzyme
lecithinase to lysolesithin which is present in venoms of bee and cobra. When injected into the
blood, lysolecithins cause rapid haemolysis of the red blood cells.

b. Cephalins

Cephalins are found in animal tissues in close association with lecithin. They are also found in
soya bean oil. The basic difference between cephalins and lecithin is the nature of nitrogenous
base. Cephalins contain ethanolamine in place of choline. The fatty acid components of
cephalins are stearic, oleic, linoleic and arachidonic acid. They are less soluble in alcohol then
lecithin.

c. Plamalogens

Plasmalogens are abundant in brain and muscles they are also found in the seeds of higher plants.
Structurally, they resemble lecithin and cephalins except in having an aldehyde group attached to
ex – carbon atoms of glycerol. They are soluble in all lipid solvents.
 d. Phosphoinositides

They are present in brain tissues and nervous tissues. They can be either mono or
diphosphoinositides. Monophosphoinositides contain hexahydric alcohol inositol. The name
lipoinosital was also proposed for them.

e. Phosphosphingosides

These lipids are abundant in lacking in plant and microorganisms. In these lipids glycerol is
replaced by an 18 carbon unsaturated amino alcohol called ‘sphingosine’. On hydrolysis they
yield fatty acids, phosphoric acid, choline and sphingosine.
 ii. Glycolipids

Glycolipids are compounds containing carbohydrates and high molecular sphingosine but no
phosphoric acid. These are of two types: Cerebrosides and Gangliosides.

a) Cerebrosides: They occur in large amount in brain and myelin sheath of nerves. The
structure of cerebrosides is somewhat similar to sphingomyelin. Here the fatty acid
ceramide is linked either to galactose or glucose.
b) Gangliosides: These are found in ganglion cells of nervous tissues and also in
parenchymatous tissues like spleen and RBCS, They are the most complex
glycosphingolipids. They are ceramides with attached oligosaccharides that include at
least one sialic acid residue.

Other compound lipids

 iii. Sulfolipids: Lipids containing sulfer, widely distributed in plant (localized in chloroplast)
and bacteria.
iv. Lipoprotein: They are the component of membranes found in the membranes of
mitochondria, ERL

The lipid component consists of triacylglycerol, phospholipids and cholesterol. The protein
components of lipoprotein have a relatively high portion of non polar acid residues.

There are five types of lipoproteins:

1. Chylomicrons, transport dietary lipids from intestine to peripheral tissues.

2. Very low density lipoproteins (VLDL), transport the lipids (endogenously synthesized)
mainly TG from liver to peripheral tissues).
3. Low density lipoproteins (LDL) ("bad" cholesterol), transport cholesterol from liver to
peripheral tissues.
4. High density lipoproteins (HDL) ("good" cholesterol), carry cholesterol from peripheral
tissues to liver.
5. Intermediate density lipoproteins (IDL).

Lipoproteins source and components and apolipoproteins.

Lipoprotein Source Main lipid Apolipoproteins

components
Chylomicrons Intestine Triacylglycerol A-I, A-II, A-IV, B
48, C-I, C-II, C-III,E
Chylomicron Chylomicrons Triacylglycerol, B-48, E
remnants phospholipids,
cholesterol
VLDL Liver (intestine) Triacylglycerol B-100,C-I,C-II,C-III
IDL VLDL Triacylglycerol, B-I00,E
 cholesterol
LDL VLDL Cholestreol B-100
HDL Liver, intestine, Phospholipids, A-I,A-II,A-IV,C-I,C-
VLDL, chylomicrons cholesterol II,C-111,D,E

c. DERIVED LIPIDS

Derived lipids are the product of hydrolysis of simple lipids and compound lipids and in addition
other lipid like compounds such as steroids, terpenes, fatty acids, alcohols, carotenoids, essential
oils etc.

i. Steroids

Steroids are the derivatives of cyclopentanoperhydrophenanthrene, a compound consisting of

four fused non planer rings. They are named as A, B, C and D. The rings A, B and C are
hexagons and are called cyclohexane rings while D is a pentagon and is called cyclopentane.

ii. Sterols

The steroids may have one or more alcoholic groups. The steroids having alcoholic groups are
called sterols. They are crystalline compounds and differ from alcohols in being solids that is the
reason they are called so. Steroids are widely distributed in plant, animals and microorganism.
They are found in cell membranes and other cellular component containing lipids. Unlike other
lipids, sterols cannot be saponified and by this process they can be separated from other lipids.
Ergosterol is present in food in small amount. It has been isolated from parasitic fungus
Claviceps pupurea (Ergon) growing on rye plants. Other plant sterols are spinasterol obtained
from spinach and cabbage, stigmasterol from coconut and soyabeans and sitosterol from cereal
seeds.

iii. Cholesterol

The best known animal sterol is cholesterol, which is a major component of animal plasma
membrane. It is classified as sterol because of its C30H group It is present in relatively high
concentration in nervous tissues and in bile. Cholesterol is a crystalline solid with rhombic
crystals and its solution is levorotatory. It has a high melting point.

In mammals, cholesterol is the metabolic precursor of steroid hormones – adrenocorticoids and

sexsteroids.

a. Adrenocorticoids

They are secreted by the adrenal cortex hormone contains – glucocorticoids, aldosterone,

cortisterone, desoxycortisterone adrenosterone and other mineral corticoids influence a wide

variety of vital functions.

b. Sex steroids
The testes secrete testosterone, andosterone and adrenosterone, while estrogens and progesterone

are secreted by the ovary. They affect sexual development and functions.

FIG 1.0: CLASSIFICATION OF LIPIDS

1.3 SOURCES OF LIPIDS

Lipids are widely distributed in plants and animals. Common sources of fatty acids are butter,
coconut oil, animal fats and some bacteria. Lecithin, a type of phospholipids is found in liver,
brain, nerve tissue, sperm and yolk sac in animals while in plants it is abundant in seeds and
sprouts. Similarly other phospholipids and glycolipids are also found in animal tissues like brain,
muscles and nervous tissues. Terpenes and carotinoids are types of derived lipids which are
exclusively of plant origin.

1.4 BIOLOGICAL SIGNIFICANCE OF LIPIDS

1. Rich source of energy: fats provide food of high calorific value (1g fat produces about 9.3 kilo
calories of heat).

2. As food reserve: Fats are stored in body as reserve food material, because these could be
readily stored in the body on account of insoluble character sticks. Triglycerides stored in
adipocytes (fat cells) of adipose tissue are the principal fat reserve.

3. As heat insulators: Fats deposited in the subcutaneous tissues act as insulators conserving
body heat.

4. Solvent: Lipids act as a solvent for fat soluble vitamins like vitamin A, D and E.

5. Structural constituents: Phospholipids, glycolipids and sterols are structural components of all
the membrane system of cell (i.e. cell membrane, nuclear membrane, membranes of the
endoplasmic reticulum etc.)

6. Fat transport: Phospholipids play an important role in the absorption and transportation of
fatty acids.

7. Hormone synthesis: Adrenocorticoids, sex hormones, vitamin D and cholic acids are
synthesized from cholesterol.

8. As shock absorber: The fat deposited around the visceral organs and underneath the skin acts
as cushion and absorbs mechanical shocks.

9. As electric insulators: Myelin sheath around medullated nerve fibres forms an electric
insulation.

10. Prostaglandins: They control local activities in the body.

11. Protective layers: Lipids form a protective waxy covering on the aerial parts of plants to
check loss of water by evaporation.

12. Thrombokinase: helps blood clotting.

13. Leukotrienes: a group of eicosanoid helps in respiration.

14. Some isoprenoids form insect hormones.

15. Some insoprenoids form volatile oil and pigments. Natural rubber is also an isoprenoid.
16. Glycolipids help in cell recognition.

17. Complex lipids form phospholipid bilayer of plasma membrane.

18. Steroid act as hormones and neurotransmitters in mammals.

1.5 DEFICIENCY DISEASES OF LIPIDS

The deficiency of lipids in human body causes dry, scaly skin, hair loss, loss of mensuration,
cold intolerance, power resistance to infection and bruising, poor growth, poor wound healing
and low body weight.