Lipids KKM220125
Lipids KKM220125
It contains C, H, O, sometimes N or
K
Lipid (TGL)
Droplets In
Adipose tissue
2. Structural components of biomembranes.
3. ThermalInsulator :
Provides insulation against changes in
external temperature.
4. Lipids
act as electric insulators
in neurons.
5. Act as metabolic regulators (steroid
hormones and prostaglandins).
6. Act as surfactants and prevents collapse of
lungs during expiration.
7. Lipids are used as detergents.
8. Lipids used in emulsification and intestinal
absorption of non polar nutrients like fatty
acids and fat soluble vitamins.
9. Associated with diseases such as
atherosclerosis, diabetes mellitus and obesity.
10. Gives shape and contour to the body.
Classification of lipids
Lipids are broadly classified into simple, complex, derived and
miscellaneous lipids, which are further subdivided into different groups
1. Simple lipids : Esters of fatty acids with alcohols. These are mainly of two
types
(a) Fats and oils (triacylglycerols) : These are esters of fatty acids with glycerol.
The difference between fat and oil is only physical. Thus, oil is a liquid while
fat is a solid at room temperature.
(b) Waxes : Esters of fatty acids (usually long chain) with alcohols other than
glycerol. These alcohols may be aliphatic or alicyclic. Cetyl alcohol is most
commonly found in waxes. Waxes are used in the preparation of candles,
lubricants, cosmetics, ointments, polishes etc.
2. Complex (or compound) lipids : These are esters of fatty acids with alcohols
containing additional groups such as phosphate, nitrogenous base,
carbohydrate, protein etc. They are further divided as follows
(a) Phospholipids : They contain phosphoric acid and frequently a nitrogenous
base. This is in addition to alcohol and fatty acids.
(i) Glycerophospholipids : These phospholipids contain glycerol as the alcohol
e.g., lecithin, cephalin.
(ii) Sphingophospholipids : Sphingosine is the alcohol in this group of
phospholipids e.g., sphingomyelin.
(b) Glycolipids : These lipids contain a fatty acid, carbohydrate and nitrogenous
base. The alcohol is sphingosine, hence they are also called as glycosphingolipids.
Glycerol and phosphate are absent e.g., cerebrosides, gangliosides.
(c) Lipoproteins : Macromolecular complexes of lipids with proteins.
(d) Other complex lipids : Sulfolipids, aminolipids and lipopolysaccharides are
among the other complex lipids.
3. Derived lipids : These are the derivatives obtained on the hydrolysis of group 1
and group 2 lipids which possess the characteristics of lipids. These include glycerol
and other alcohols, fatty acids, mono- and diacylglycerols, lipid (fat) soluble
vitamins, steroid hormones, hydrocarbons and ketone bodies.
4. Miscellaneous lipids : These include a large number of compounds possessing
the characteristics of lipids e.g., carotenoids, squalene, hydrocarbons such as
pentacosane (in bees wax), terpenes etc.
NEUTRAL LIPIDS : The lipids which are uncharged are referred to as neutral
lipids. These are mono-, di-, and triacylglycerols, cholesterol and cholesteryl esters.
FATTY ACIDS
Fatty acids are carboxylic acids with hydrocarbon side chain. They are the
simplest form of lipids.
Fatty acids mainly occur in the esterified form as major constituents of
various lipids. They are also present as free (unesterified) fatty acids.
Fatty acids of animal orgin are much simpler in structure in contrast to those of
plant origin which often contain groups such as epoxy, keto, hydroxy and
cyclopentane ring
Most of the fatty acids that occur in natural lipids are of even carbons (usually
14C – 20C). This is due to the fact that biosynthesis of fatty acids mainly
occurs with the sequential addition of 2 carbon units.
Both saturated and unsaturated fatty acids almost equally occur in the natural
lipids.
Fatty acids with one double bond are monounsaturated, and those with 2 or
more double bonds are collectively known as polyunsaturated fatty acids
(PUFA).
Nomenclature of fatty acids
The saturated fatty acids end with a suffix -anoic
(e.g., octanoic acid) while the unsaturated fatty
acids end with a suffix -enoic
Numbering of carbon atoms
The carbons adjacent to this (carboxyl C) are 2,
3, 4 and so on or alternately D, E, J and so on.
The terminal carbon containing methyl group is
known omega (Z) carbon.
There are other conventions of representing
the double bonds. '9 indicates that the double
bond is between 9 and 10 of the fatty acid.
9 represents the double bond position (9 and
10) from the end. Naturally occurring
unsaturated fatty acids belong to 9, 6 and
3 series.
ESSENTIAL FATTY ACIDS
The fatty acids that cannot be synthesized by the body and, therefore, should be
supplied in the diet are known as essential fatty acids (EFA). Chemically, they
are polyunsaturated fatty acids, namely linoleic acid (18 : 2; 9, 12) and
linolenic acid (18 : 3; 9, 12, 15).
Arachidonic acid (20 : 4; 5, 8, 11, 14) becomes essential, if its precursor
linoleic acid is not provided in the diet in sufficient amounts.
Linoleic acid and linolenic acid are essential since humans lack the enzymes
that can introduce double bonds beyond carbons 9 to 10
Essential fatty acids are required for the membrane structure and function,
transport of cholesterol, formation of lipoproteins, prevention of fatty liver etc.
They are also needed for the synthesis of another important group of
compounds, namely eicosanoids
1. Simple Lipids
Esters of fatty acids with various alcohols.
a. Fats :esters of fatty acids with
glycerol.
eg: triglycerides
b. Waxes: esters of fatty acids with
higher molecular weight monohydric
alcohols.
eg: beeswax
TRIACYLGLYCEROLS
(TRIGLYCERIDES)
O
H2C OH 3 fatty acids O
H2C O C - R1
OH + O HO - C - R1 O
HC
= HC O C - R2 +3H20
H2C OH HO - C - R2 O O
glycerol H2C O C - R3
HO - C - R3
triacylglycerol
© 2009 Cengage - Wadsworth
At 20°C, triglycerides
can be classified as
fats or oils
Solid = fats
Liquid = oil
Triacylglycerols of plants, in general, have higher content of
unsaturated fatty acids compared to that of animals.
Fats as stored fuel : Triacylglycerols are the most abundant
group of lipids that primarily function as fuel reserves of
animals. The fat reserve of normal humans (men 20%,women
25% by weight) is sufficient to meet the body’s caloric
requirements for 2-3 months.
a. Phospholipids:
b. Glycolipids:
c. Other Complex Lipids:
COMPOUND LIPIDS
Esters of fatty acids with various alcohols
along with an additional group.
4. Phospholipids are essential for the synthesis of different lipoproteins, and thus
participate in the transport of lipids.
5. Accumulation of fat in liver (fatty liver) can be prevented by phospholipids, hence they
are regarded as lipotropic factors.
Gangliosides : These are predominantly found in ganglions and are the most
complex form of glycosphingolipids. They are the derivatives of cerebrosides
and contain one or more molecules of N-acetylneuraminic acid (NANA), the
most important sialic acid.
The most important gangliosides present in the brain are GM1, GM2, GD, and
GT
The ganglioside, GM2 that accumulates in Tay-Sachs disease a rare inherited
condition that mainly affects babies and young children
1. Cerebrosides
2. Sulfatides
Types of
Glycolipids
3. Globosides
4. Gangliosides
LIPOPROTEINS
Lipoproteins are molecular complexes that consist of lipids and proteins
(conjugated proteins). They function as transport vehicles for
lipids in blood plasma. Lipoproteins deliver the lipid components (cholesterol,
triacylglycerol etc.) to various tissues for utilization
A lipoprotein basically consists of a neutral lipid core (with triacylglycerol
and/or cholesteryl ester) surrounded by a coat shell of phospholipids,
apoproteins and cholesterol. The polar portions (amphiphilic) of
phospholipids and cholesterol are exposed on the surface of lipoproteins so
that lipoprotein is soluble in aqueous solution.
1. Chylomicrons : They are synthesized in the intestine and transport exogenous
(dietary) triacylglycerol to various tissues. They consist of
highest (99%) quantity of lipid and lowest (1%) concentration of protein. The
chylomicrons are the least in density and the largest in size, among
the lipoproteins.
2. Very low density lipoproteins (VLDL) :
They are produced in liver and intestine and are responsible for the transport of
endogenously synthesized triacylglycerols.
3. Low density lipoproteins (LDL) : They are formed from VLDL in the blood
circulation. They transport cholesterol from liver to other tissues.
4. High density lipoproteins (HDL) : They are mostly synthesized in liver. Three
different fractions of HDL (1, 2 and 3) can be identified by ultracentrifugation. HDL
particles transport cholesterol from peripheral tissues to liver (reverse cholesterol
transport).
5. Free fatty acids—albumin : Free fatty acids in the circulation are in a bound form to
albumin. Each molecule of albumin can hold about 20-30 molecules of free fatty acids.
This lipoprotein cannot be separated by electrophoresis.
Electrophoresis of plasma (serum) lipoproteins
STEROIDS
Lipids containing Cyclo Pentano Perhydro Phenanthrene (CPPP)
ring
It consists of a phenanthrene nucleus (rings A, B and C) to which a
cyclopentane ring (D) is attached.
STEROLS
17
3 5
6
CHOLESTEROL
Chemical Properties
1. Undergoes rapid oxidation to form cholestenones.
2. Hydroxyl group forms esters with acids to form
Cholesterol Esters (cholesterol acetate, palmitate
and propionates)
3. Presence of double bond gives hydrogenation
reactions (similar to unsaturated fatty acids).
4. Colour reactions: LIEBERMANN BURCHARD,
SALKOWSKY, ZAKS.
Cholesterol (Greek : chole–bile) was first isolated from bile.
Cholesterol literally means ‘solid alcohol from bile.