LIPIDS
Dr. Jyothilakshmi M
Lipids are one of the four major class of compounds found in living
organisms. The other compounds are carbohydrates, proteins and
nucleic acids. They are organic substances insoluble in water but soluble
in organic solvents.
Lipids are esters of fatty acids or substances capable of forming such
esters and are utilisable by living organisms
Lipids contain the elements C, H and O. Some lipids also contain P, N and S
Importance/functions of lipids
▪ Lipids play extremely important role in the normal functioning
of the cell.
▪ Component of cell membrane
▪ Storage compounds
▪ Plant – energy during germination
▪ Animals – stored in adipose tissue (triglycerides)
▪ Contain high calories
▪ Have fat soluble vitamins and essential fatty acids
▪ Neural tissues are rich in lipids
▪ Insulation against atmospheric cold
▪ Prevent loss of heat from the body
▪ Absorb mechanical impact and act as cushion to the body
▪ Help in rounding off the contours of the body
Classification of lipids
Simple lipids
• Neutral fats
• Waxes
Compound lipids
• Phospholipids
• Glycolipids
• Lipoproteins and others
Derived lipids
Compounds which are derived from lipids or precursors of lipids
• Prostaglandins, terpene, sterols, fatty acids, glycerol
Fatty acids
Organic compounds which contain carboxyl(-COOH) functional group are
called carboxylic acids. Their general formula is R-COOH where R is an
alkyl group.
Carboxylic acids are classified into monocarboxylic acids, dicarboxylic
acids, tricarboxylic acids etc according to the umber of carboxyl groups
present. The long chain mono carboxylic acids are called fatty acids
because many of them are obtained by the hydrolysis of animal fats or
vegetable oils. They may be saturated or unsaturated. A few are cyclic.
Most of the naturally occurring fatty acids are straight chain derivatives
and have an even number of carbon atoms.
∆series – numbering
starts from COOH
group
ω series numbering
starts from last CH3
group
Essential fatty acids (EFA)
Fatty acids that can not be synthesised by the body and hence must
be supplied in through diet
• Linoleic acid
• Linolenic acid
• Arachidonic acid
EFA required for Deficiency of EFA
Membrane structure and ❑ Phrynoderma (toad skin)
function ❑ Loss of hair
Transport of cholesterol ❑ Poor wound healing
Formation of lipoproteins
Prevention of fatty liver etc
Omega-3 fatty acids
The three main omega-3 fatty acids are alpha-linolenic acid (ALA),
eicosapentaenoic acid (EPA), and docosahexaenoic acid (DHA). ALA
is found mainly in plant oils such as flaxseed, soybean, and canola oils.
DHA and EPA are found in fish and other seafood.
Omega-3 fatty acids have been linked to many health benefits. In
particular, they may help promote brain and heart health, reduce
inflammation, and protect against several chronic conditions
Omega-3fatty acids are important components of the membranes that
surround each cell in body. DHA levels are especially high in retina (eye),
brain, and sperm cells. Some—but not all—research shows that people
who consume more omega-3s from food such as fish may have a lower risk
of developing Alzheimer’s disease, dementia, and other problems with
cognitive function. More study of the effects of omega-3s on the brain is
needed.
Eicosapentaenoic acid – C20 acid with five double bonds at 5,8,11,14 and 17
It is also a ω3 fatty acids
It also has the trivial name timnodonic acid. EPA is a polyunsaturated fatty
acid (PUFA) that acts as a precursor for prostaglandin-3
Docosahexaenoic acid (DHA) is an omega-3 fatty acid that is a primary
structural component of the human brain, cerebral cortex, skin, and
retina. It can be synthesized from alpha-linolenic acid or obtained
directly from maternal milk (breast milk), fatty fish, fish oil, or algae oil.
Its trivial name is cervonic acid. It has 22 carbons , 6 double bonds at
4,7,10,13,16,19
Polyunsaturated fatty acids (PUFA)
A fatty acid containing more than one double bond (C=C).
Polyunsaturated fats include omega-3 and omega-6 fats.
Monounsaturated fatty acids (MUFA) are fatty acids containing a single
double bond
Excessive consumption of saturated fatty acids (SFA) has been linked
with an increased risk of heart diseases and diabetes.
MUFAs and PUFAs on the other hand have significant health benefits
like,
❖ Increase in HDL cholesterol,
❖ Reducing LDL cholesterol, which is the bad cholesterol that
increase chances of a stroke or heart attack
❖ Can help reduce risk of coronary heart diseases
❖ Improving insulin sensitivity
❖ Can help to reduce the risk of diabetes
❖ MUFA and PUFA intake as per recommendation help in cell and
nerve maintenance and aid in digestion.
Trans fatty acids
Trans fatty acids (TFA) are unsaturated fatty acids that contain at least one
double bond in the trans configuration. The trans configuration
substantially alters the physical properties of the fatty acids
Trans fats occur naturally in meat and dairy products from ruminants due
to the action of bacteria in their rumen. For example, butter contains
about 3% trans fat. Natural versions exist only in a few isomeric forms.
But more trans fats are produced industrially especially during
hydrogenation of oils. Elaidic acid is the trans isomer of oleic acid
produced during hydrogenation of oil.
Hydrogenation causes the oil to become solid at room temperature. This
partially hydrogenated oil is inexpensive and less likely to spoil, so foods
made with it have a longer shelf life.
The manufactured form of trans fat can be found in a variety of food
products, including:
• Commercial baked goods, such as cakes, cookies and pies
• Microwave popcorn
• Frozen pizza
• Fried foods, including french fries, doughnuts and fried chicken
• Nondairy coffee creamer
• Stick margarine
Trans fat increases "bad" cholesterol and lowers "good" cholesterol.
Industrial TFA poses severe effects on our health like cardiovascular
problems, stroke, insulin resistance, infertility in women, compromised
fetal development and cognitive decline. There are strict regulations for
limiting/removing the TFA content from food supply across the world.
Simple lipids – they consists of neutral fat and waxes
Neutral fat : They are esters of fatty acids with trihydric alcohol glycerol.
Hence called glycerides
Fatty acid
Glycerol
Some are solids at room temperature while others are liquids. Acyl
glycerols that are liquids at room temperature are called oils.
If all the three positions of glycerol are esterified with fatty acid then
they are called triglycerides or triacyl glycerol
Triglycerides
Esters of trihydric alcohol, glycerol with fatty acids
They are water insoluble, non-polar, hence called as Neutral fat
They serves as fuel reserves of animals
In humans triglycerides are stored in cytoplasm of adipose cells.
Naturally occurring oils and fats are mixtures of triglycerides
If all the three fatty acids in TG are same, they are known as simple TG
e.g. tripalmitin, triolein etc
If different FAs are esterified with the OH group of glycerol in TG, they
are called Mixed TGs
Properties of TAG
Hydrophobic in nature
Oils are TGs which contain higher proportion of shorter chain fatty acid
Oils are liquid at 20º C and are of plant origin
Fats contain mainly saturated long chain FAs and are of animal origin
Hydrolysis : Triacylglycerols undergo stepwise enzymatic hydrolysis
to finally liberate free fatty acids and glycerol. The process of
hydrolysis, catalysed by lipases is important for digestion of fat in
the gastrointestinal tract and fat mobilization from the adipose
tissues.
Soaps
Soaps are salts of fatty acids
Soaps are formed by the alkaline hydrolysis of fats and oils by sodium or
potassium hydroxide under reflux conditions
Saponification : The hydrolysis of triacylglycerols by alkali to produce
glycerol and soaps is known as saponification.
Triacylglycerol + 3 NaOH Glycerol + 3 R-COONa (soaps)
Rancidity is the term used to represent the deterioration of fats and oils
resulting in an unpleasant taste and/or odour. Fats containing
unsaturated fatty acids are more susceptible to rancidity. Rancidity
occurs when fats and oils are exposed to air, moisture, light, bacteria etc.
Mainly there are two types of rancidity.
Hydrolytic Rancidity - Hydrolytic rancidity occurs due to partial hydrolysis
of triacylglycerols. Oxidative Rancidity - Oxidative rancidity is due to
Antioxidants : The substances which can prevent the occurrence of
oxidative rancidity are known as antioxidants.
Lipid peroxidation in vivo : In the living cells, lipids undergo oxidation to
produce peroxides and free radicals which can damage the tissue. The
free radicals are believed to cause inflammatory diseases, ageing, cancer,
atherosclerosis etc
Cells possess antioxidants such as vitamin E, urate and superoxide
dismutase to prevent in vivo lipid peroxidation
Tests to check purity of fats and oils
Iodine number : It is defined as number of grams of iodine absorbed
by 100 g of fat or oil. Iodine number is useful to know the relative
unsaturation of fats, and is directly proportional to the content of
unsaturated fatty acids
Fat/oil Iodine number
• Coconut oil 7 — 10
• Butter 25 — 28
• Palm oil 45 — 55
• Olive oil 80 — 85
• Groundnut oil 85 — 100
• Cottonseed oil 100 — 110
• Sunflower oil 125 — 135
• Linseed oil 175 — 200
Saponification number : It is defined as the mg (number) of KOH
required to hydrolyse (saponify) one gram of fat or oil. Saponification
number is a measure of the average molecular size of the fatty acids
present. The value is higher for fats containing short chain fatty acids
• Human fat : 195–200
• Butter : 230–240
• Coconut oil : 250–260
Reichert-Meissl (RM) number : It is defined as the number of ml 0.1 N
KOH required to completely neutralize the soluble volatile fatty acids
distilled from 5 g fat. RM number is useful in testing the purity of butter
Acid number : It is defined as the number of mg of KOH required to
completely neutralize free fatty acids present in one gram fat or oil.
In normal circumstances, refined oils should be free from any free
fatty acids. Oils, on decomposition—due to chemical or bacterial
contamination—yield free fatty acids. Therefore, oils with increased
acid number are unsafe for human consumption.
Polenski Number
The number of ml of 0.1N KOH required to neutralize insoluble fatty
acids from 5g of fats or oils.
Waxes
Waxes are water insoluble solid esters of higher fatty acids with long
chain monohydroxylic fatty alcohols or with sterols. Free fatty acids,
alcohols and some hydrocarbons are also present mixed with ester.
They are soft and pliable when warm and hard when cold.
In nature waxes are seen in different forms,
▪ As insect secretions
▪ In vertebrates waxes are secreted by cutaneous glands as a
protective coating to keep the skin pliable, lubricated and water
proof
▪ As protective coating on feathers – birds especially waterfowl
secrete waxes in their preen glands to make their feathers water
repellent.
▪ Protective and shiny coating on the leaves and fruits of many plants
▪ Present on the exoskeleton of many insects
▪ Waxes serve as the chief storage form of fuel in planktons. Since
marine organisms whale, salmon, herring etc consume plankton in
large quantities waxes act as major food and storage lipids in them.
Plankton apparently use the biosynthesis of waxes to adjust their
buoyant density and thus their depth in the ocean. Whales and
