Biochemistry

Lipid
By Anika Bristy
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 Lipid
‘’Heterogeneous group of organic molecule relatively insoluble in water
but soluble in non polar organic solvents (alcohol, ether, benzene,
chloroform) etc.’’

• (Greek: lipos-fat)

• Many lipid molecules are amphipathic - they contain both polar

and nonpolar group.
• General chemical structure: glycerol + fatty acids
• Important dietary constituent.
• Building blocks of biological membranes.
• Energy reservoir of the cell and acts as fuel in the body.
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Lipid

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Lipid

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Lipid classification

Lipid

Simple lipids Complex lipids Derived lipids Miscellaneous

Fats & oils Glycolipids

Lipoproteins
Waxes
Phospholipids Sphingophospholipid

Glycerophospholipid

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Lipid classification

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Fatty acid

• The simplest lipids, are the fatty acids.

• Carboxylic acids containing a long hydrocarbon tail.

• Typically 12-20 carbon fatty acid (even number).

• Among the odd chain fatty acids, propionic acid (3C) and valeric acid (5C)
are well known.
• C16 & C18 fatty acids are the most common fatty acids in higher plants
and animals.
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Fatty acid

Occurrence:
✓ Mainly occur in the esterified form.
✓ They are also present as free (unesterified) fatty acids.
✓ Fatty acids of animal origin are much simpler in structure
in contrast to those of plant origin which often contain
groups such as epoxy, keto, hydroxy and cyclopentane
rings.

• Insoluble in water.
• Some contain double bonds, the number of double bonds in
fatty acids varies from 1 to 4 (usually), but in most bacteria it is
rarely more than 1.

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Fatty acid

Short-chain fatty acids

Fatty acids with aliphatic tails of five or
fewer carbons (e.g. butyric acid)

Medium-chain fatty acids

Fatty acids with aliphatic tails of 6 to 12
carbons, which can form medium-chain
triglycerides.

Long-chain fatty acids

Fatty acids with aliphatic tails of more than
13 carbons.

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Fatty acid (Classification)

Sea buckthorn
Palm tree

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Fatty acid (Classification)

1. Saturated fatty acid:

• Only single bond (C-C)
• Contain as many Hydrogen
atom as possible.
• Stearic acid, Palmitic acid.
• Dietary source: Beef, butter,
coconut oil etc.

Triglyceride with saturated fatty acid:

• Straight
• Closely packed
• Solid at room temperature
• Longer saturated fatty acid chain=
more solid
• Strong attraction between chains.
• High melting points.
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Fatty acid (Classification)
2. Unsaturated fatty acid:
• 1 or more double bond (C=C)
• Not saturated with Hydrogen
atom.
• Produces kink/twist in the chain.
• Oleic acid, arachidonic acid.

Triglyceride with unsaturated fatty acid:

• Nonlinear chains do not allow
molecules to pack closely.
• Liquid at room temperature
• Few interactions between chains.
• Low melting points.
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Fatty acid

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Unsaturated fatty acid (classification)
1.Mono-unsaturated fatty acid:
• 1 double bond (C=C)
• Oleic acid
• Dietary source: Olive oil, peanut oil
etc.
2.Poly-unsaturated fatty acid:
• Two or more double bonds (C=C)
• Arachidonic acid, Linoleic acid etc.
• Dietary source: corn oil, fatty fish
etc.

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Unsaturated fatty acid (classification)

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Unsaturated fatty acid (classification)

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Unsaturated fatty acid (classification)
1.Omega 3 fatty acid:
• Polyunsaturated fatty acid
• ALA (α-linolenic acid), EPA (Eicosapentaenoic acid) DHA (docosahexaenoic
acid), DPA
• ALA can be obtained only from diet. (Essential fatty acid)
• The human body can convert ALA to EPA & DHA insufficiently.

Marine sources
Produced by microalgae
Found in the tissues of fish
like salmon, and sardines.

Plant sources
Found in walnut,
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Unsaturated fatty acid (classification)

2.Omega-6 fatty acid:

• Polyunsaturated fatty acid
• Arachidonic acid, linoleic acid.
• Linoleic acid can be obtained only from diet. (Essential fatty acid)
• Human body can convert linoleic acid to arachidonic acid insufficiently.

Animal sources
Found in fish, meat, eggs.

Arachidonic Acid

Plant source.
Found in safflower, corn
and soyabean oil.
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Unsaturated fatty acid (classification)

3. Omega 9 fatty acid:

• Monounsaturated fatty acid
• Example-Oleic acid.
• Human body can synthesize them.
• Dietary source: canola oil, almonds, olive oil etc.

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Essential fatty acids

Three polyunsaturated fatty acids, linoleic acid, linolenic acid

and arachidonic acid are called “essential fatty acids.

• They cannot be synthesized in the body.

• They must be provided in the diet.
• Lack of essential fatty acid in the diet can produce growth
retardation and other deficiency manifestation symptoms.
• Linoleic acid is most important as, arachidonic acid can be
synthesized from linoleic acid by a three stage reaction by
addition of acetyl-CoA.
• Biologically arachidonic acid is very important as it is precursor
from which prostaglandins and leukotrienes are synthesized in the
body.

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 Cis & Trans Fatty acid

1. Cis-fatty acid: 2. Trans-fatty acid:

• Functional group in the same • Functional group in the opposite
side of the double bond. side of the double bond.
(Cis configuration) (trans-configuration)
• Usually bends. • Chain is more straight and easier
• Doesn’t pack tightly together. to pack tightly.
• Liquid at room temperature. • Solid at room temperature.
• Found in nature. • Mostly Produced artificially. 21
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• Cooking oil, vegetable oil. • Margarine.
Dietary sources

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Practice Time

Label the diagram.

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Practice Time

Label the configuration of Oleic acid.

(Cis/trans/saturated/unsaturated)

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Practice Time

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Lipid: Daily intake

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Metabolism of dietary Lipid

Processing of dietary
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X in the stomach 27
Metabolism of dietary Lipid

STEP 1: Emulsification of fat droplets by bile salts

STEP 2: Hydrolysis of TG in emulsified fat droplets into fatty acid &
monoglycerides.
STEP3: Dissolving of fatty acid & monoglyceride into micelle to produce
mixed micelle.
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Metabolism of dietary Lipid

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Metabolism of dietary Lipid

The digestion of dietary lipids begins in the stomach and continues in the small
intestine. The hydrophobic nature of lipids require that the dietary lipids those
that contain long-chain fatty acids be emulsified for efficient degradation.
Triacylglycerols (TAG) obtained from milk contain short- to medium-chain length
fatty acids that can be degraded in the stomach by the acid lipases (lingual lipase
and gastric lipase).
Cholesteryl esters (CE), phospholipids (PL), and TG containing LCFAs are degraded
in the small intestine by enzymes secreted by the pancreas.
The dietary lipids are emulsified in the small intestine using peristaltic action, and
bile salts. The products resulting from enzymatic degradation of dietary lipid are
monoacylglycerol, unesterified cholesterol, and free fatty acids. These compounds
form mixed micelles that facilitate the absorption of dietary lipids by intestinal
mucosal cells (enterocytes).
These cells resynthesize TG, cholesterol, and phospholipid, and also synthesize
protein; all of which are then assembled into chylomicrons. These serum
lipoprotein particles are released into the lymph, which carries them to the blood.
Thus, dietary
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Metabolism of dietary Lipid

Adipose Tissue

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Metabolism of dietary lipid

1. Fate of free fatty acids:

The free fatty acids derived from hydrolysis of triacylglycerol may directly enter
adjacent cells or adipocytes. Alternatively, the free fatty acids may be transported
in the blood in association with serum albumin until are taken up by cells. The
cells can oxidize the fatty acids to produce energy.
Adipocytes can also re-esterify free fatty acids to produce triacylglycerol
molecules.

2. Fate of glycerol:
Glycerol that is released from triacylglycerol used almost exclusively by the liver
to produce glycerol 3-phosphate, which can enter glycolysis.

3. Fate of the remaining chylomicron components:

After most of triacylglycerol has been removed, the chylomicron (which contain
cholesteryl esters, phospholipids, apolipoprotein and some triacylglycerol) bind
to receptors on the liver and are then engulfed.
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 Lipid metabolism: Lipolysis
Lipolysis is the metabolic pathway through which lipid triglycerides are
hydrolyzed into a glycerol and three fatty acids to provide energy during fasting
or exercise, and usually occurs in fat adipocytes.

GAP

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 Lipid metabolism: (β)-oxidation

The breakdown of fatty acids, called fatty acid oxidation or beta (β)-
oxidation, in which fatty acids are converted into fatty acetyl CoA
molecules.
• It begins in the cytoplasm.

• The newly formed acetyl

CoA enters the Krebs cycle GAP

and is used to produce ATP

in the same way as acetyl
CoA derived from pyruvate.

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 Lipid metabolism: Ketogenesis

Ketogenesis is a metabolic pathway that produces ketone bodies,

which provide an alternative form of energy for the body.

• If excessive acetyl CoA is

created from the oxidation of
fatty acids & the Krebs cycle is
overloaded, the acetyl CoA is GAP
diverted to create ketone
bodies.

• Ketones serve as fuel source in

times of prolonged starvation
or when patients suffer from
uncontrolled diabetes.

• This reaction occurs in the

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mitochondria of liver cells.
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Lipid metabolism: Ketone body oxidation

When glucose is limited, ketone bodies can be oxidized to produce

acetyl CoA to be used in the Krebs cycle to generate energy.

GAP

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 Lipogenesis

Lipogenesis is the metabolic process through which acetyl-CoA is

converted to triglyceride for storage in fat. When glucose levels are
plentiful, the excess acetyl CoA generated by glycolysis can be
converted into fatty acids, triglycerides, cholesterol etc.

This process takes place

in cytoplasm of
adipocytes (fat cells)
and hepatocytes (liver
cells).

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Lipid metabolism: Lipolysis

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Lipid function (Structural lipid)

Fluid mosaic model:

The cell membrane consists of a continuous, fluid, double layer of phospholipids.
Proteins either are embedded in the bilayer or associated with either the
cytoplasmic or extracellular face. Carbohydrates are linked to the proteins
(glycoproteins) or lipids (glycolipids) only on the extracellular side. The
phospholipid profiles of the cytoplasmic and extracellular layers differ.
Cholesterol, in varying amounts depending on the cell type, lies within the
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membrane serving to stabilize it.
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Lipid function (Storage of energy)

Triacylglycerol or Triglycerides are the storage lipids.

Fatty acids in non esterified form, i.e. as free (unesterified) fatty acids are released
from triacylglycerols during fasting to provide a source of energy and to form
the structural components for cells.
Dietary fatty acids of short and medium chain size are oxidized rapidly in tissues
as a source of ‘fuel”.
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Lipid function (Storage of energy)

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Lipid function (precursor of hormone)

Polyunsaturated fatty acids (Arachidonic acid) are the precursors for the
synthesis of eicosanoids (C20 compounds), such as prostaglandins, thromboxane,
and leukotrienes.

Prostaglandins:
• regulates the synthesis of the intracellular messenger cAMP.
• elevate body temperature and cause inflammation and pain.
• stimulate contraction of the smooth muscle of the uterus during
menstruation and labor
• Stimulate endothelial cell to release Nitric oxide (vasodilator).

Thromboxane:
• act in the formation of blood clots & the reduction of blood flow
to the site of a clot.

Leukotriene:
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Lipid function (Thermal insulation)

Layers of subcutaneous fat under the skin also help in insulation and
protection from cold. Fat is a poor conductor of heat. It conducts heat
slowly, and therefore it assists to maintain the optimum temperature in
vertebrates.

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Lipid function (Chemical messenger)

As lipids are small molecules insoluble in water, they are excellent

candidates for signaling. E.g; Testosterone.
The signaling lipids, in their esterified form can infiltrate membranes and
are transported to carry signals to other cells. These may bind to certain
proteins as well and are inactive until they reach the site of action and
encounter the appropriate receptor.
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Lipid function (Fat soluble vitamins)

The "fat-soluble" vitamins (A, D, E and K) are essential nutrients with

numerous functions.

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 THANK YOU

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