II.

Lipids

• Long-term energy storage

• Generally insoluble in water
• Structural components of cells
(phospholipids)
• Cellular messengers (hormones)
 Chemistry of Lipids
• General formula of lipids: CnH2nO2
• Lipids are insoluble in water but are soluble in fat solvents (ether, chloroform, benzene)
• Biologically important fat-soluble and non-lipid substances are carotenoid pigment and
vitamins (vitamin A, D, E, and K)
• Based on the availability of fatty acids and other groups, lipids are classified as follows:
• Simple lipids
– Esters of fatty acids with alcohol
– Simplest alcohol available in fats is glycerol (a triglyceride alcohol)
– Triglycerides are common in nature
– e.g., fats, oils and waxes
– Waxes are esters of long chain fatty acid and long chain alcohols
• Compound lipids
– Contain an additional group along with fatty acids and alcohols
– e.g., phospholipids, glycolipids, lipoproteins
• Derived lipids
– Have isoprenoid structures
– Esters of hydrocarbon rings and long hydrocarbon side chains
– e.g., steroids, terpenes, carotenoids
Classification of lipids
 Classification based on structure
• Simple Lipids
– Constitute 98% of food and body fats
– Made up of three fatty acids attached to glycerol
– Mixed triglycerides which means that more than one type of fatty acid is
present in fat
– E.g. cooking oils and butter
• Compound Lipids
– Fats in which atleast one fatty acid is replaced by carbohydrate, protein
or phosphorous (fats + non-fat molecule)
– E.g. phospholipids, glycolipids, and lipoprotein
• Derived Lipids
– Breakdown products of fats and include diglycerides, monoglycerides,
glycerol, and fatty acids
• Sterols
– Not made up of fatty acids and glycerol but have a benzene ring structure
– Fat like substances include cholesterol and fat-soluble vitamins A, D, E,
and K.
Lipid Molecule
 Three membrane lipid types

Phospholipids Cholesterol Glycolipids

 Phospholipids
• Phosphatidylcholine
• Phosphatidylserine
• Phosphatidylethanolamine
• Sphingomyelin (serine replaces glycerol backbone)
• Phosphatidylinositol (one of the less common types)

Hydrophilic
(soluble)

Hydrophobic
(not soluble
= lipophilic)
 Cholesterol
• Up to 40% of mammalian cell membranes
• Small polar head makes it weakly amphipathic
Hydroxyl group
is a very small polar
(hydrophilic) head
Rigid steroid
hydrocarbon
ring structure

Flexible
Nonpolar
hydrocarbon
(hydrophobic)
chain
9
 Glycolipids
• Pattern of sugar residues is variable
• Always in outer leaflet of cell membrane, &
inner leaflet of organelles

Hydrophilic
(soluble)

Hydrophobic
(not soluble
= lipophilic)
 Sterols or Steroids
• Sterols or steroids contain 4 fused hydrocarbon rings called
cyclopentane perhydro phenanthrene rings and a long side chain
• Examples: Cholesterol (animals), stigmasterol (plants),
campesterol (plants), sitosterol (plants), ergosterol (plants)
• Cholesterol helps in absorption of fatty acids, sex hormones,
vitamin D and bile salts
• Excess of cholesterol in blood causes atherosclerosis
 Cholesterol
 Fat-like substance present in food
 Present in all cells of body and in large amounts in brain and
nerve tissues
 If consumed in excess it will cause cardiovascular diseases
 Normal blood cholesterol level for adults should be below
200 mg/100 mL blood
 Functions of cholesterol
Precursor of all steroid hormones (sex hormones)
Precursor of vitamin D,7-dehydrocholesterol which is present in skin
and gets converted to vitamin D upon UV irradiation
Required for formation of bile
Essential constituent of cell membranes
 Sources of cholesterol to human body
Synthesis in liver
Food rich in cholesterol (animal foods only – whole milk, butter,
ghee, cream, egg yolk, organ meat, shell fish)
 Lipoproteins
Lipid-protein complexes are called lipoproteins
Includes
Chylomicrons (Least amount of protein)
Very Low Density Lipoproteins (VLDL) (Low amount of
protein)
Low Density Lipoproteins (LDL) (Moderate amount of
protein)
High Density Lipoproteins (HDL) (Higher amount of
proteins)
LDL is the main carrier of cholesterol – increase in
LDL increases the risk of heart disease
HDL helps in lowering cholesterol levels
LDL/HDL ratio of less than 3 is desirable
 Lipoproteins
• Cholesterol is carried in the blood by molecules called lipoproteins.
– Low density lipoprotein (LDL)
• Often referred to as bad cholesterol
• LDL carries cholesterol from liver to cells
• If too much is carried, too much for the cells to use, there can be a
harmful buildup of LDL
• This lipoprotein can increase the risk of arterial disease if level is too
high
• Most human blood contains approximately 70% LDL – this may vary
depending on the person
– High density lipoprotein
• Often referred to as good cholesterol
• HDL prevents arterial disease
• HDL carries cholesterol away from cells and carry back to liver. In the
liver, cholesterol is either broken down or expelled from the body as
waste.
 Fatty acids
• Fatty acids are carboxylic acid with a chain of more than four carbon atoms ending
with COOH group
• Two types of fatty acids based on their availability
– Non-essential fatty acids: Fatty acids which can be synthesized in human body
– Essential fatty acids: Fatty acids which cannot be synthesized in human body
(linoleic, linolenic and arachidonic acid)
– Plants can synthesize all fatty acids
• Two types of fatty acids based on their structure
– Saturated fatty acids:
• they do not have double bonds, their melting point is high (e.g., palmitic
acid and stearic acid)
– Unsaturated fatty acids:
• They have one or more double bonds. Have low melting points.
• Oleic acid has one double bond, linoleic acid has 2 double bonds and
linolenic acid has 3 double bonds and arachidonic acid has 4 double bonds
• Fatty acids with more than one double bonds are called polyunsaturated
fatty acids (PUFA).
 Fatty acids
• Consists of chain of carbon atoms with methyl (CH3) group at
one end and carboxyl (COOH) group at other end
• Short chains or long chains (12 – 22 carbon units)
• Saturated fatty acid – single bonds between carbon atoms
– E.g. Stearic acid, Palmitic acid, Myristic acid, Butyric acid
• Unsaturated fatty acid – one or more double bonds between
carbon atoms
– Monounsaturated fatty acid – only one double bond
• E.g. Oleic acid – omega-9-fatty acid (grountnut oil, olive oil, corn oil)
– Polyunsaturated fatty acid – more than one double bonds
• E.g. Linoleic acid (2), Linolenic acid (3), Arachidonic acid (4) – groundnut
oil, soyabean oil, sesame oil, animal fats, tuna fish, salmon fish
– Higher the number of double bonds, higher the unstable the fat is
– Double bonds are highly reactive to oxygen and polyunsaturated
fat / oil becomes rancid (spoiled) soon
 Omega-3 and Omega-6 fatty acids
• Omega (w) is last letter of greek alphabet used by scientists to
name fatty acids
• End most double bonds are on 3rd and 6th carbon from methyl end
• Diet having right proportion of omega 3 and omega 6 fatty aids
helps in reducing blood cholesterol levels
• Omega-3 fatty acids
– Polyunsaturated fatty acids
– Olive oil, fish oil, mustard oil, soya bean, flax seed, fenugreek seeds,
mackerel, black gram, rajma, and green leafy vegetables
– 3rd carbon from the methyl end have double bond
– Linolenic acid (18:3 w3) – 18 carbon length, last double bond between
3rd and 4th carbon from the methyl / omega end (Soyabean oil, seasame
oil, butter)
– Eicosapentaenoic acid (EPA) (20:5 w3) – 20 carbon length, last double
bond between 3rd and 4th carbon from the methyl / omega end (fish oils)
– Eating 200-300 g of fish per week or 15-20 g of flax seeds daily meets
RDA (0.5-1.0 g/day of omega-3 fats)
 Omega-3 and Omega-6 fatty acids
• Omega-6 fatty acids
– Polyunsaturated fatty acids
– Safflower, sunflower, cottonseed, corn, sesame, and
groundnuts
– 6th carbon from the methyl end have double bond
– Linoleic acid (18:2 w6) – 18 carbon length, first double
bond between 6th and 7th carbon from the methyl / omega
end (safflower, sunflower, salmon, tuna, cottonseed,
corn, soyabean, groundnut)
– Arachidonic acid (20:4 w6) – 20 carbon length, first
double bond between 6th and 7th carbon from the methyl /
omega end (Animal fats, groundnut)
Omega-3 and Omega-6 fatty acids
 Biological Function of Lipids
• Lipids serve as the reservoir of energy because of the following
features:
• High energy content – the calorific value is 9 kcal/gm as
compared to carbohydrates which have calorific value of 4
kcal/gm
• Storage in concentrated or in water free state in the tissue as
compared to carbohydrates, which are highly hydrated and
cannot be stored in such concentrated form
• As structural component of cell membrane
• As transport form of various metabolic fuel
• As protective coating on the surface of many organs such as
kidney against injury
• To facilitate the absorption of the fat soluble vitamins (vitamins
A, D, E and K)