Lipid and Membranes

By :

Zarith Afzan bt Zainal

 Lipids may be defined as compound which
are :

Insoluble in water
Soluble in nonpolar organic solvent like

Benzene
Chloroform
Ether
Hot alcohol
acetone
Function of Lipids
Storage form of energy (triglycerides)

Structural components of biomembranes

(phospholipids and cholesterol)

Providing insulation against changes in

external temperature (subcutaneous fat).
 Giving shape and contour to the body

Protecting internal organs by providing a

cushioning effect (pads of fat).

Metabolic regulators (steroid hormones

and prostaglandins)
 Acting as surfactants, detergents and
emulsiying agents (amphipathic lipids)

Acting as electric insulators in neurons

Helping in absorption of fat soluble

vitamins (A, D, E and K)

Adding taste and palatability to food.

Clinical applications

Excessive fat deposits cause obesity.

Truncal obesity is an important risk factor for
heart attack.

Abnormality in cholesterol and lipoprotein

metabolism leads to artherosclerosis and
cardiovascular diseases.
 In diabetes mellitus, the metabolisms of
fatty acids and lipoproteins are deranged,
leading to ketosis.
Classification of lipids
1. Simple Lipids

They are esters of fatty acids with glycerol or

other higher alcohols.

They are subclassified as

a. Triacyl glycerol or Triglycerides or neutral fat
b. Waxes
2. Compound Lipids

They are fatty acids esterified with alcohol; but

in addition they contain other groups.
Depending on these extra groups, they are
subclassified as:

A. Phospholipids, containing phosphoric acid:

i. Nitrogen containing glycerophosphatides:
Lecithin (phosphatidyl choline)
Cephalin (phosphatidyl ethanol amine)
Phosphatidyl serine
 ii. Non-nitrogen containing
glycerophosphatides

Phosphatidyl inositol
Phosphatidyl glycerol
Diphosphatidyl glycerol (cardiolipin)

iii. Plasmalogen, containing long chain alcohol

Choline plasmalogen
Ethanolamine plasmalogen
 iv. Phopho sphingosides, containing sphingosine
Sphingomyelin

B. Non-phosphorylated lipids
i. Glycosphingolipids (carbohydrate)
Cerebrosides (ceramide monohexosides)
Globosides (ceramide oligosaccharides)
Gangliosides (having N-acetyl neuraminic acid)

ii. Sulpholipids or sulfatides

Sulphated cerebrosides
Sulphated globosides
Sulphated gangliosides
3. Derived Lipids

They are compounds which are derived from

lipids or precursors of lipids e.g.:
Fatty acids
Steroids
Prostaglandins
Leukotrienes
Terpenes
Dolichols
4. Lipids Complexed to Other Compounds

Proteolipids
Lipoproteins
Fatty Acids
 Fatty acids id the most common
component of lipids in the body.

In nature, free fatty acids are present only

in very small quantity.

In the human body, free fatty acids are

formed only during metabolism.
 Fatty acids are aliphatic carboxylic acids
and have the general structure formula

R---COOH

COOH (carboxylic group) represents the

functional group.

Depending on the R group (the

hydrocarbon chain), the fatty acids may
vary.
Saturated Fatty Acids
They have the general structural formula

CH3-(CH2)n-COOH

They are named by adding the suffix

anoic after the hydrocarbon with the
same number of carbon atoms.
 The two carbon acetic acid and 4 carbon
butyric acid are important metabolic
intermediate.

C16 palmitic and C18 stearic acid are most

abundant in body fat.
 Human body fat contains :

50% Oleic acid

25% palmitic acid
10% linolenic acid
5% stearic acid
Unsaturated Fatty Acids
They are named by adding the suffix
enoic after the systematic name.

They are similar to saturated fatty acids in

the reaction to carboxylic group.

They also show the presence of the double

bond.
Polyunsaturated fatty acids (PUFA)

Linoleic acid (18C, 2 double bonds)

Linolenic acid (18C, 3 double bonds)
Arachidonic acid (20C, 4 double bonds)
Timnodonic acid
Clupanodonic acid
Cervonic acid
 Linoleic, linolenic and arachidonic acid are
present in large quantities in vegetable
oils such as sunflower oil.

They are the only fatty acids which cannot

be synthesized in the body.

They have to be provided in the food;

hence, they are essential fatty acids.
 Timnodonic and cervonic acids are seen in
fish oils. They are important for
development of human brain.

Normal dietry allowance of PUFA is 2-3%

of total calories.
 Deficiency of PUFA:

Acanthosis
Hyperkeratosis
Acrodermatitis
Hypercholesterolemia
Functions of PUFA
They are used for esterification and
excretion of cholesterol.

Prostaglandins, thromboxanes and

leukotrienes are produced from
arachidonic acid.

PUFA are nutritionally essential; and are

called Essential Fatty Acids.
 Part of mitochondrial membranes. In
deficiency of PUFA, the efficiency of
biological oxidation is reduced.

PUFA will increase the fluidity of the

membrane. The membrane containing
PUFA are more prone for damage by free
radicals.
Prostaglandins (PGs)
PGs were isolated from prostate tissue.
But they are present in almost all tissue.

They are the most potent biologically

active substances.

As low as 1ng/ml of PG will cause smooth

muscle contraction.
Functions
cause constriction or dilation in vascular
smooth muscle cells.

cause aggregation or disaggregation

of platelets.

sensitize spinal neurons to pain.

 decrease intraocular pressure.

regulate inflammatory mediation.

regulate calcium movement.

 control hormone regulation.

control cell growth.

acts on thermoregulatory center

of hypothalamus to produce fever.

acts on mesangial cells in

the glomerulus of the kidney to
increase Glomerular filtration rate
Clinical Use
Synthetic prostaglandins are used :

To induce childbirth (parturition)

or abortion (PGE2 or PGF2, with or
without mifepristone, a progesterone
antagonist)

To prevent closure of patent ductu

arteriosus in newborns with particular cyanotic
heart defects (PGE1)
 To prevent and treat peptic ulcers (PGE)

As a vasodilator in severe Raynaud's

phenomenon or ischemia of a limb

In pulmonary hypertension

In treatment of glaucoma (as

in bimatoprost ophthalmic solution, a synthetic
prostamide analog with ocular hypotensive
activity)
 To treat erectile dysfunction or in penile
rehabilitation following surgery (PGE1
as alprostadil).

To treat egg binding in small birds

As an ingredient
in eyelash and eyebrow growth beauty
products due to side effects associated with
increased hair growth
Neutral Fats / Triacylglycerol (TAG)
They are also called triglycerides (TG).

Naturally occurring fats and oils are

mixtures of triglycerides.

Oils are liquid at 200C; they are

triglycerides which contain higher
proportion of unsaturated fatty acid.
 Oil are generally of plant origin.

Fats are solid at room temperature and

are mainly of animal origin.

When the constituent fatty acid have a

higher chain length and saturated, hard
fat is formed e.g., pig fat.
 Fats which are unsaturated fatty acids are
soft fats, e.g. :

Butter
Coconut oil

Triacyl glycerol molecules are:

Hydrophobic
Insoluble in water
 The triacyl glycerides are the storage form
of lipids in the adipose tissue.

In a 70kg normal person, body stores

contain about 11kg of tryacylglycerol.

The body can store unlimited quantities of

energy as TAG from adipose tissue,
leading to obesity.
Saponification

When triglycerides are hydrolysed by

alkali, the process is known as
saponification.

The products are glycerol and soaps.

 Saponification number is :

The number of miligrams of potassium

hydroxide required to saponify one gram of
fat.

Human fat has a saponification number of 194-

198
Butter has 210-230
Coconut oil has 253-262
 Rancidity of fat

Fat and oil have a tendency to become rancid.

The term rancidity refers to the appearance of

an unpleasant smell and taste for fat and oil.

Oxidative rancidity is the result of partial

oxidation of unsaturated fatty acids with the
resultant formation of epoxides & peroxides.
 Many natural fat and oil may contain anti-
oxidant (e.g. Vitamin E), which prevent the
occurrence of oxidative rancidity.

PUFA are more easily oxidised; so vegetable oil

having a high content of PUFA are usually
preserved with addition of anti-oxidant.
 Fat and oil are preferred cooking media.

Overheating and repeated heating would lean

to the formation and polymerisation of cyclic
hydrocarbon.

These will impart an unpleasant taste and

colour to the oil.
 Waxes

They are widespread in nature.

Form the secretion of insects, leaves and fruits

of plant e.g.

Lanolin or wool fat

Beeswax
Whalesperm oil
 They are esters of higher fatty acids.

Since they can take up water without

dissolving, they are used as the base for
the preparation of :

Cosmetic
Ointment
Polishes
Lubricant
Candle
Assignment 2
Discuss the functions of :

Phosphoglyceride
Sphingolipid
Glycolipid

Explain with diagram

Fluid mosaic model of membrane.

Deficiency of PUFA (Definition):

Acanthosis
Hyperkeratosis
Acrodermatitis
Hypercholesterolemia
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