Professional Documents
Culture Documents
LIPIDS
Erick Awuoche
Introduction
■ Biological lipids are a chemically diverse group of compounds, the
common and defining feature of which is their insolubility in water.
■ The biological functions of the lipids are as diverse as their chemistry.
Fats and oils are the principal stored forms of energy in many
organisms.
■ Phospholipids and sterols are major structural elements of biological
membranes.
■ Other lipids, although present in relatively small quantities, play
crucial roles as enzyme cofactors, electron carriers, light absorbing
pigments, hydrophobic anchors for proteins, “chaperones” to help
membrane proteins fold, emulsifying agents in the digestive tract,
hormones, and intracellular messengers.
■ OCCURRENCE: Lipids are present in humans, animals, plants and
micro-organisms to some extent. Animal fat, egg yolk, butter and
cheese are lipids of animal origin, vegetable or cooking oils and
vanaspati are lipids are plant origin.
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:
– Energy content of fat is higher.
– 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. Fats serve as surfactants by reducing surface tension.
11. Eicosanoids which have profound biological actions are derived from the essential fatty acids.
12. Lipids present in myelinated nerves act as insulators for propagation of depolarization wave.
13. Some saturated fatty acids are anti-microbial and anti-fungal agents.
14. Lipids are an important group of antigens of parasites that cause filariasis, cysticercosis, leishmaniasis and
schistosomiasis in India and other Third World countries. Anti-lipid antibodies are found in the blood of
individuals affected with these diseases.
15. Some eicosanoids act as immuno modulators and mitogens.
16. Saturated free fatty acids (SFFAs) are pheromones of animals like tiger etc.
Chemical Nature of Lipids
■ Lipids are the group of greasy organic compounds, which are soluble
in organic solvents like chloroform, ether and benzene but insoluble
in water.
■ They are fats, waxes, compound lipids, steroids, fatty acids and fat
soluble vitamins.
■ A lipid is a fat-like substance but need not be a fatty acid always.
Classification of Lipids
■ Based on the composition lipids are classified into:
■ 1. Simple lipids,
■ 2. Compound lipids,
■ 3. Derived lipids.
Simple Lipids
■ They are esters of fatty acids with alcohols. Fats and waxes
are example for simple lipids.
■ An ester is formed when acid reacts with alcohol
PHYSICAL PROPERTIES OF
TRIGLYCERIDES
■ Pure fats have no colour, taste and odour.
■ 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.
■ Triglycerides containing asymmetric carbon atom are optically
active.
CHEMICAL PROPERTIES OF
FATS
1. 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. Vanaspati (dalda) is obtained from vegetable oils through
this process.
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 fatty acids of
triglycerides and forms lipid peroxides.
(a) Saponification of triglyceride
(b) Hydrogenation of fat
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.
Waxes
■ Structure: Waxes are esters of fatty acids with long chain alcohol. Examples:
– Lanolin or wool fat is a mixture of fatty acid esters of long chain alcohols
lanosterol and agnosterol.
– Cholesterol ester is wax present in the blood (lipoprotein) and cell
membranes.
– Bees wax is an ester of palmitic acid with myricyl alcohol.
Functions
■ 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.
■ Waxes act as water barrier for animals, birds and insects. Further wax is hard
in cold climate and soft in hot climate.
■ 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:
– Glycerophospholipids
– Sphingo lipids.
■ Compounds lipids are also divided into phospholipids and
glycolipids.
GLYCEROPHOSPHOLIPIDS
■ They are also called 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. Some glycerophospholipids are named
according to second alcohol or nitrogen base and they are
considered as derivatives of phosphatidic acid.
■ They are phosphatidyl choline, phosphatidyl serine,
phosphatidyl ethanolamine and phosphatidyl inositol. The
fatty acid combinations are different in each of these
phospholipids.
Phosphatidylcholine
■ Structure: It contains two fatty acids esterified to first and second hydroxyl group of
glycerol. The third hydroxyl is esterified to phosphoric acid to which second alcohol
choline is also esterified. Phosphatidylcholine is also called as lecithin. Lecithin
contains a saturated fatty acid at C-1 position and unsaturated fatty acid at C-2
position.
■ Function: It is the major phospholipid of cell membrane. It is also present in egg yolk
and lipoproteins.
■ Phosphotidyl ethanolamine
■ In which second alcohol ethanolamine is esterified to phosphoric acid of phosphatidic
acid.
■ Phosphatidyl serine: In which amino acid serine is esterified to phosphoric acid of
phosphatidic acid.
■ Phosphatidyl ethanolamine and phosphatidyl serine are called as cephalins and
amino phospholipids.
■ Phosphatidyl Inositol: In which polyol inositol is esterified to phosphoric acid of
phosphatidic acid.
■ Functions of Phosphatidyl Inositol
– Cephalins are major component of cell membrane, lipoproteins and nervous tissue.
– Phosphatidyl inositol is also a component of cell membrane. Further phosphorylated
phosphatidyl inositol (PIP2) and inositol triphosphate (IP3) are involved in signal
transduction.
Other Phospholipids
1. Dipalmitoyl Lecithin
■ 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.
■ 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 30 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
■ Structure. It is a double glycerophospholipid. It
contains two phosphatidic acids esterified to C-1 and C-
3 of glycerol.
■ 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
■ Structure. They are derivatives of glycerophospholipids.
They contain only one acyl group instead of two acyl
groups.
■ 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
■ Structure. They are also glycero phospholipids. These
compounds contain unsaturated fatty alcohol in place
of fatty acid at the C-1 position. Hence, the normal
ester linkage is replaced by ether linkage on the C-1
carbon of glycerol. Usually nitrogen bases are choline,
serine and ethanolamine.
■ 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.
SPHINGOMYELINS
■ Structure
■ In sphingomyelins, fatty acid is linked to sphingosine by an
amide bond and phosphoryl choline is esterified to C-1
hydroxyl of sphingosine.
■ Because of the phosphorous sphingomyelins are called as
sphingo phospholipids.
■ Functions
– They are simple and most abundant sphingolipids.
– They are present in most of animal membranes.
– Myelin sheath of nerve cells is rich in sphingomyelins.
– Grey matter also contain sphingomyelins.
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.
GANGLIOSIDES
■ Structure: They are highly complex sphingolipids. They contain ceramide,
oligosaccharide and sialic acid.
■ Functions
– They are abundant in grey matter of brain.
– They are also found in non-nerval tissues.
– They are components of hormone receptors.
– They also function as receptors for toxins of cholera, influenza and tetanus.
– They are also involved in cell-cell recognition, growth, differentiation and
carcinogenesis.
DERIVED LIPIDS
■ As the name implies they are formed from simple and compound lipids by
hydrolysis. They are fatty acids, steroids, glycerol and retinol.
Fatty Acids
■ They are acids derived from fats. They are monocarboxylic acids containing long
hydro carbon side chain. Based on the nature of hydrocarbon side chain, they are
divided into:
– A. Saturated fatty acids
– B. Unsaturated fatty acids
■ Saturated fatty acids: In which hydrocarbon side chain is saturated (no double
bonds).
■ Unsaturated fatty acids: In which hydrocarbon side chain is unsaturated (one or
more double bonds are present).
■ Fatty acids are also divided based on hydrocarbon chain length. They are
– Short chain fatty acids Fatty acids containing less than six carbon atoms.
– Medium chain fatty acids Fatty acids containing 6-12 carbon atoms.
– Long chain fatty acids In which hydrocarbon chain contains 13-20 carbon atoms.
– Very long chain fatty acids In which hydrocarbon chain contain 22-30 carbon
atoms.
■ Fatty acids of natural fats contain an even number of carbon atoms. Small
amounts of fatty acids with odd number of carbon atoms also occurs.
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.