pharmacognosy

3rd stage/1stterm

Lipids
Part 1

Dr. Zahraa Shubber

Lec .10
 Lipids
The lipids are a heterogeneous group of compounds,
including fats, fixed oils, steroids, waxes, and related
compounds, which are related more by their physical than
by their chemical properties.
They have the common property of being relatively
insoluble in water and soluble in nonpolar solvents
such as ether and chloroform.
Lipids (fixed oils, fats, and waxes) are esters of long-
chain fatty acids and alcohols.

The chief difference between these substances is the

type of alcohol; in fixed oils and fats, glycerol
combines with the fatty acids; in waxes, the alcohol has
a higher molecular weight, e.g., cetyl alcohol.
Classification of lipids
1. Simple lipids: Esters of fatty acids with various
alcohols.
(a) Fats: Esters of fatty acids with glycerol. Oils are fats in
the liquid state.
(b) Waxes: Esters of fatty acids with higher molecular
weight monohydric alcohols.
2. Complex lipids: Esters of fatty acids containing groups
in addition to an alcohol and a fatty acid.
(a) Phospholipids: Lipids containing, in addition to fatty
acids and an alcohol, a phosphoric acid residue.
(b) Glycolipids (glycosphingolipids): Lipids containing a
fatty acid, sphingosine, and carbohydrate.
(c) Other complex lipids: Lipids such as sulfolipids and
aminolipids. Lipoproteins may also be placed in this
category.

3. Precursor and derived lipids: These include steroids,

lipid soluble vitamins, and hormones.
Fatty Acid
A fatty acid is a molecule characterized by the presence
of a carboxyl group attached to a long hydrocarbon chain.
Therefore these are molecules with a formula R–COOH
where R is a hydrocarbon chain.
The “tail” of a fatty acid is a long hydrocarbon chain,
making it hydrophobic.
 The “head” of the molecule is a carboxyl group which
is hydrophilic.
Fatty acids are the main component of soap, where their
tails are soluble in oily dirt and their heads are soluble in
water to emulsify and wash away the oily dirt.
 However, when the head end is attached to glycerol to
form a fat, that whole molecule is hydrophobic.
Saturated and unsaturated fatty acids

A. Saturated fatty acids do not have any double bonds.

 A fatty acid is saturated when every carbon atom in the
hydrocarbon chain is saturated with hydrogen.
Saturated fatty acids are solids at room temperature.
Animal fats are a source of saturated fatty acids.
Saturated fatty acid chain –CH2 – CH2 – CH2 –
B. Unsaturated fatty acids can have one or more double
bonds along its hydrocarbon chain.
A fatty acid with one double bond is called
monounsaturated.
 If it contains two or more double bonds, we say that the
fatty acid is polyunsaturated.
When double bonds are present, they are nearly always in
the cis rather than in the trans configuration.
The melting point of a fatty acid is influenced by the
number of double bonds that the molecule contains and
by the length of the hydrocarbon tail.
The more double bonds it contains, the lower the
melting point.
As the length of the tail increases, the melting point
increases.

Plants are the source of unsaturated fatty acids.

Unsaturated fatty acid chain –CH = CH – CH = CH –
Triacylglycerols
Triacylglycerols, also called triglycerides, are the
simplest of lipids composed of three fatty acids each in
ester linkage with a single glycerol molecule.
Those containing the same kind of fatty acid in all three
positions are called simple triacylglycerols.
Fats:
are mostly from animal sources, have all single
bonds between the carbons in their fatty acid
tails, thus all the carbons are also bonded to the
maximum number of hydrogens possible.
Fixed Oils:
are mostly from plant sources, have some double bonds
between some of the carbons in the hydrocarbon tail,
causing bends or “kinks” in the shape of the molecules.
 Because some of the carbons share double bonds, they
are not bonded to as many hydrogens as they could if
they were not double bonded to each other.
Therefore these oils are called unsaturated fats.
Because of the kinks in the hydrocarbon tails,
unsaturated fats (or oils) can’t pack as closely together,
making them liquid at room temperature.
In unsaturated fatty acids, there are two ways the pieces
of the hydrocarbon tail can be arranged around a C=C
double bond (cis and trans).
In cis bonds, the two pieces of the carbon chain on
either side of the double bond are either both “up” or
both “down,” such that both are on the same side of the
molecule.
 In trans bonds, the two pieces of the molecule are on
opposite sides of the double bond, that is, one “up” and
one “down” across from each other.
Naturally-occurring unsaturated vegetable oils have
almost all cis bonds, but using oil for frying causes some
of the cis bonds to convert to trans bonds.
Fixed oils and fats differ only as to melting point; those
that are liquid at normal temperatures are known as
fixed oils, whereas those that are semisolid or solid at
ordinary temperatures are known as fats.
Physical properties:
fixed oils and fats are insoluble in water, greasy to feel,
leave a permanent translucent stain on paper and do not
volatilize on exposure to air.
They are freely soluble in ether, chloroform, light
petroleum, but they are usually insoluble in alcohol (an
important exception being castor oil which dissolves in
3.5 volumes of alcohol 90%).
Vegetable oils and fats may occur in various parts of the
plants but as a general rules seeds contain larger
quantities of them than do other parts of the plants e.g.
cotton seed oil, linseed oil, sesame, castor beans seeds,
almond and others.
Biosynthesis of Lipids
Acetate first reacts with CoA, and the acetyl-CoA formed
is converted by reaction with carbon dioxide to
malonylCoA. This, in turn, reacts with an additional
molecule of acetyl-CoA to form a 5-carbon intermediate,
which undergoes reduction and elimination of carbon
dioxide to produce butyryl-CoA. Malonyl-CoA again
reacts with this compound to form a 7-carbon intermediate,
which is reduced to caproyl-CoA. Repetition of the
reaction results in a fatty acid containing an even number
of carbon atoms in its chain. Thus, the malonyl portion of
malonyl-CoA, a 3-carbon compound, is actually the source
of the 2-carbon biosynthetic units of the fatty acids.
Thank you