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Lipid: Structure & Classifications

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LIPID

Structure & Classifications


Introduction
 Lipids , a third major class of biomolecules –
molecules that do not form polymers

 Lipids – often defined as water insoluble organic


compounds found in biological systems.

- they have little or no affinity for water

- hydrophobic becausethey consist mostly of


hydrocarbons, which form nonpolar covalent
bonds
 Lipid functions:
Cell membrane structure – creates a
barrier for the cell, controls flow of
materials
Energy storage – fats stored in adipose
tissues
Hormone – communication between cells
Vitamins – assist in the regulation of
biological processes
Important families of lipids

Fats and oils Steroids


(Triglycerides)

Phospholipids
Fats
• Most familiar lipids
• Large molecules
• Not polymers
• Major function – energy storage
• Are made from :

Glycerol + Fatty acids = Fats


Glycerol

• is a three-carbon alcohol with a hydroxyl


group attached to each carbon
Fatty Acids
• consists of a carboxyl group attached to a
long carbon skeleton
• has long carbon – 16-18 carbon atoms in
length (form the hydrocarbon chain of fatty
acids)
Fatty acids

Saturated Fatty acids Unsaturated Fatty acids


-Has straight chain -Have 1 or more double
bonds
-No double bond
between the carbons -Have kink in its shape
atoms wherever a double bond
occur
Fig. 5-12a

Structural
formula of a
saturated fat
molecule

Stearic acid, a
saturated fatty
acid
(a) Saturated fat
Fig. 5-12b

Structural formula
of an unsaturated
fat molecule

Oleic acid, an
unsaturated
fatty acid
cis double
bond causes
(b) Unsaturated fat bending
• Fats made from saturated fatty acids are called
saturated fats - solid at room temperature
- most animal fats are saturated
- example : butter, bacon grease

• Fats made from unsaturated fatty acids are


called unsaturated fats or oils - liquid at room
temperature
- Plant fats and fish fats are usually unsaturated
- example : corn oil, olive oil
 Unsaturated fatty acids have lower melting
points than saturated fatty acids.

 Among the saturated fatty acid, as the


lengths of hydrocarbon tails (C-H-C)
increase, the melting points also increase
(more energy is required to disrupt the
interactions).
• A shorthand notation for identifying fatty acids uses two
numbers separated by a colon;
 First, refers to the number of carbon atoms in the fatty
acid.

 Second, refers to the number of carbon-carbon


double bonds, with their positions indicated as
superscripts following a Greek symbol, Δ.

Examples:
a) Palmitat is written as:
16:0 [ CH3(CH2)14COO- ]
• Essential fatty acids (EFAs)
- Fatty acid that cannot be synthesised in
the body – should be supplied in the diet
– e.g.: Linoleic acid, linolenic acids and
arachidonic acid
– All there fatty acids are necessary for the
formation of phospholipids (important
component for cell membrane)
– Also essential for normal development of the
brain and normal growth.
• Non essential fatty acids
- our body is able to synthesise them
Triacylglycerols
• (historically called triglycerides).
• Formed from condensation of 3 molecules
of fatty acids linked to one molecule of
alcohol (glycerol).
• Involving alcohol and acids, it is known as
esterification
• The bond between glycerol and fatty acids
– ester bonds
Fig. 5-11

Fatty acid
(palmitic acid)

Glycerol
(a) Dehydration reaction in the synthesis of a fat

Ester linkage

(b) Fat molecule (triacylglycerol)


Phospholipids
• Phospholipids have two fatty acids
attached to glycerol and a phosphate
group at the third position.
– The phosphate group carries a negative
charge.
– Additional smaller groups may be attached to
the phosphate group to form a variety of
phospholipids.
Fig. 5-13

Hydrophilic head

Choline

Phosphate

Glycerol
Hydrophobic tails

Fatty acids

Hydrophilic
head

Hydrophobic
tails

(a) Structural formula (b) Space-filling model (c) Phospholipid symbol


• When phospholipids are added to water,
they self-assemble into a bilayer, with the
hydrophobic tails pointing toward the interior
• The structure of phospholipids results in a
bilayer arrangement found in cell
membranes
• Phospholipids are the major component of
all cell membranes

Copyright © 2008 Pearson Education, Inc., publishing as Pearson Benjamin Cummings


Fig. 5-14

Hydrophilic WATER
head

Hydrophobic
tail WATER
Steroids
• are lipids characterized by a carbon skeleton
consisting of four fused rings
• contain four fused rings:
Three 6 carbon rings designated A, B & C.
One 5 carbon D ring.
• have different structures from other lipids
although they are insoluble in water and soluble
in organic solvents.
• have a basic four fuse rings hydrocarbon
structure with different functional side chains.
Steroids
Steroids

• Steroid cholesterol is an important component of


animal plasma membranes and helps to
maintain the fluidity of cell membrane.

• Cholesterol is actually a sterol – it has OH group


at C-3.

• Other steroids include stigmasterol (plant sterol),


ergosterol (fungi & yeast sterol), sodium cholate
(a bile salt) and mammalian steroid hormones.
Cholesterol

• Cholesterol often accumulates in lipid deposits (plaques)


on the walls of blood vessels.

• These plaques have been implicated in cardiovascular


disease, which can precipitate heart attacks or strokes.

• Most of the cholesterol in the blood are complexed with


protein and fatty acids to form low density lipoproteins
(LDL).

• High density lipoproteins (HDL) tends to carry excess


cholesterol to the liver to be processed.
Cholesterol

• When cholesterol exceeds the normal levels in


the body, they are deposited on the inner walls
of arteries.
• Artherosclerosis is a thickening of the
innerwalls of arteries due to deposits of
cholesterol, fibrous tissue and mineral salts
forming artheroma in the walls.
• This causes narrowing of the lumen and
reduced the blood supply to tissues which may
cause stroke or myocardial infarction (heart
attack).

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