LIPIDS

Lipids
Lipids are
◦ biomolecules that contain fatty acids or a steroid
nucleus.
◦ soluble in organic solvents, but not in water.
◦ named for the Greek word lipos, which means “fat.”
◦ extracted from cells using nonpolar organic solvents.
◦ natural components of cell membranes, fat-soluble
vitamins, and steroid hormones.
Classification of Lipids
Types of Lipids
Lipids
There are 2 types of lipids;
◦those that contain the structural component of a
fatty acid; and

◦those that contain the structural component of a

four member steroid molecule.
 Types of Lipids
A. The lipids that contain fatty acids are( saponifiable lipids)
◦ waxes,
◦ fats and oils (triacylglycerols),
◦ glycerophospholipids, and
◦ prostaglandins.

B, The types of lipids that do not contain fatty acid chains

are steroids.( Non-saponifiable)
 Fatty Acids

© 2013 Pearson Education, Inc.

 Fatty Acids
Fatty acids
◦contain long-chain
hydrocarbons with a
carboxylic acid.
◦typically contain 12 to 18
carbon atoms.
◦are insoluble in water.
◦can be saturated or
unsaturated.
Fatty Acid Formulas
The formulas for fatty acids are written as
◦ condensed structural formulas.
◦ skeletal formulas.
Saturated Fatty Acids
Saturated fatty acids have
◦ only single C—C bonds.
◦ molecules that fit closely together in a
regular pattern.
◦ have properties similar to alkanes.
Saturated Fatty Acids
13
Monounsaturated Fatty Acids
Unsaturated fatty acids with one double bond
are called monounsaturated fatty acids.
Polyunsaturated Fatty Acids
Unsaturated fatty acids with more than one double bond
are called polyunsaturated fatty acids.
 Omega-3 and Omega-6 Fatty Acids
Fish and vegetable oils have high levels of unsaturated fats.
▪ In vegetable oils, they are mostly omega-6 with
the first at C6.

Linoleic acid

▪ In fish oils, they are mostly omega-3 with the first

at C3.
CH3─CH2─(CH═CH─CH2)3─(CH2)6─COOH
1 3
Linolenic acid
Omega-6 and Omega-3 Fatty Acids
Omega-3 Fatty Acids
Omega-3 fatty acids
◦lower the tendency of blood platelets to
stick together, thereby reducing the
possibility of blood clots.
◦can help reduce risk of heart disease.
◦are found in salmon, tuna, and herring.
Triglycerides
◦ Animal fats and vegetable oils are esters composed of three
molecules of a fatty acid connected to a glycerol molecule,
producing a structure called a triglyceride or a triacylglycerol:
General equation for the formation
of triglyceride
Formation of trygyceride
CHEMICAL PROPERTIES OF LIPIDS
II. Phosphoglycerides
◦ Phosphoglycerides are complex lipids that are major
components of cell membranes. Phosphoglycerides
and related compounds are also called phospholipids.

◦ They are compounds containing phosphoric acid in the

form of phosphatidic acid.
PHOSPHOLIPIDS
◦ formed by the combination of alcohol derivatives
with phosphatidic acid.
PHOSPHATIDIC ACID - parent compound of phospholipids

◦Formed when
glycerol reacts via
esterification with 2
fatty acids and one
phosphoric acid (
H3PO4)
 The amino alcohols
◦ Ethanolamine

Choline

Serine
Inositol
PHOSPHOLIPIDS
◦ formed by the combination of alcohol derivatives with phosphatidic acid.
Lecithins and Cephalins
◦Glycerophospholipids can be classified based
on the amino alcohol group attached to the
phosphatidic acid.

◦Two common types are lecithins (which

contain choline) and cephalins (which contain
ethanolamine)
◦Lecithins and cephalins are highly abundant in
brain and nerve tissues, and are also found in
egg yolks, wheat germ and yeast
Sphingolipids
◦ present in the coating of nerve axons
◦ Sphingolipidsare complex lipids that contain
sphingosine (backbone structure) instead of glycerol.
 Ceramide- parent structure of sphingolipids

◦formed when
sphingosine
connects with fatty
acid at the amino
group by means of
amide bond.
Sphingomyelins
Sphingomyelins, are abundant in the
◦white matter of the myelin sheath, a coating
surrounding the nerve.
◦cells that increase the speed of nerve impulses
and insulate and protect the nerve cells.
Sphingomyelin is the main component of
the myelin sheath of nerve cells
Multiple Sclerosis
In multiple sclerosis,
◦sphingomyelin is lost from the myelin
sheath, which protects the neurons in the
brain and spinal cord.
◦scars form on the neurons and impair the
transmission of nerve signals.
2. Glycolipids
◦Glycolipids are
sphingolipids that
contain carbo-
hydrates (usually
monosaccharides)
a.) cerebroside
A cerebroside is a
sphingolipid (ceramide)
with a monosaccharide
such as glucose or
galactose connected to
the no.1 hydroxyl group of
ceramine thru ß –
glycosidic bond.
◦ Occurs primarily in the
brain and nerve
synapse
 2.) ganglioside
◦Gangliosides have two or more
monosaccharides, usually glucose and
galactose
- they are abundant in the cell
membranes of neurons
- they act at the cell surface as receptors
for hormones
Abbreviations:
Glc: glucose;
Gal: galactose;
NeuNAc: N-acetylneuraminic acid;
GalNAc: N-acetylgalactosamine;
blue: fatty acid (16, 18, 22 or 24 C-atoms);
yellow: oligosaccharide;
green: sphingosine
Waxes
◦ Waxes are simple lipids contain a fatty acid joined to a
long-chain (12-32 carbons) alcohol:
◦Plants produce waxes on the surfaces of their
leaves, stems and fruits to prevent water loss
and protect against pests
◦Animals produce waxes on their fur or
feathers to provide a water-proof coating
(ducks, polar bears, etc.)
◦Waxes are used commercially to produce
many products, such as car wax, candles
and cosmetics Sebum, secreted by the
sebaceous glands of the skin, contains waxes
that help to keep skin soft and prevent
dehydration
Steroids
Non-saponifiable lipids
◦NON-SAPONIFIABLE LIPIDS - occur in
small amounts in cells and tissues but
they include many substances having
profound biological activity
◦A. Steroids
◦B. Terpenes
A.Steroids
Steroid molecules contain a
steroid nucleus with
◦ 3 cyclohexane rings,
◦ 1 cyclopentane ring,
◦ no fatty acids, and
◦ a total of four rings A, B, C, D.
The steroid nucleus is numbered
from the carbon atoms in ring A to
two methyl groups at 18 and 19.
a.)Cholesterol
Cholesterol
◦is the most important and abundant steroid in the
body.
◦is a sterol because it contains an oxygen atom as
a hydroxyl group, –OH on carbon 3.
◦has a double bond between carbon 5 and
carbon 6.
◦has methyl –CH3 groups, at carbon 10 and 13.
◦has a carbon chain at carbon 17.
Cholesterol

Cholesterol is a component of cellular membranes, myelin sheaths, and brain and nerve
tissues.
Cholesterol in the Body A normal, open
artery.
Cholesterol in the body
◦is obtained from meats,
milk, and eggs and
synthesized in the liver.
◦clogs arteries when high
levels form plaque.
An artery clogged by
cholesterol plaque
atherosclerosis
◦ There is apparently a correlation between high levels
of cholesterol in the blood and atherosclerosis.
 Learning Check
Match the components of the cholesterol molecule with
each of the following:
alkyl chain hydroxyl group
steroid nucleus methyl group

D
CH3 CH3
CH3
B
CH3
CH3

A
C
HO
b.) Bile Salts
◦are synthesized from cholesterol in the liver.
◦are stored in the gallbladder and secreted into
the small intestine.
◦have a polar and a nonpolar region.
◦help in the absorption of cholesterol into the
intestinal mucosa.
Sodium Glycocholate, a Bile Salt

Polar region

Nonpolar region
Gallstones
Gallstones are
◦ formed when large amounts of cholesterol accumulate
in the gallbladder.
◦ composed of almost 100% cholesterol, with some
calcium salts, fatty acids, and glycerophospholipids.
d.) Adrenal Corticosteroids
Adrenal corticosteroids are steroid hormones
produced by the adrenal glands located on the top
of each kidney and include
◦ aldosterone, which regulates electrolytes and water
balance by the kidneys;
◦ cortisol, released under stress to increase blood
sugar and regulate carbohydrate, fat, and protein
metabolism; and
◦ prednisone, a synthetic corticosteroid, derived from
cortisone, used for reducing inflammation, treating
asthma and rheumatoid arthritis.
 c.) Steroid Hormones
◦ Hormones act as
chemical messengers
◦ They are important in
control of many
biological functions
◦ They are secreted from
endocrine glands (and
placenta)
◦ They react with
receptors on cell
surfaces to trigger a
cascade response
◦ Usually control
metabolism at the
gene level
◦ Steroid hormones are
biosynthesized from
cholesterol
Adrenal Corticosteroids
B.) Terpenes
◦ consists of isoprene units ( 2-methyl-1,3- butadiene)
 Fat- soluble vitamins
◦VITAMIN A
◦VITAMIN D
◦VITAMIN E
◦VITAMIN K
VITAMIN A ◦ Vitamin a is an antioxidant in the
membranes of your cells where it
serves a protective function.
◦ Vitamin A is required by the eye for
vision, and it is also needed to
protect the rest of your body from
damaging effects of infection and
stress.

◦ Food Sources: Liver, fish, eggs,

bright yellow and orange fruits and
vegetables, dark green leafy
vegetables and broccoli
Vitamin D ◦ Vitamin D3
( Calcitriol)
◦ Vitamin D2
( calciferol)
◦Vitamin D, “the sunshine vitamin,” is necessary
for maintaining blood levels of calcium and
phosphorus for healthy teeth and bones.
Vitamin D also plays a vital role in immune
functions.

◦ Food Sources: Tuna, salmon and fortified milk

VITAMIN E – ALPHA TOCOPHEROL
◦ Vitamin E is a major part of your
protection from daily wear and tear. It
is the principal membrane antioxidant.

◦ Food Sources: Nuts such as almonds

and peanuts, vegetable oils such as
corn and sunflower and green leafy
vegetables.
spinach,
Vitamin k ◦ Vitamin K2 menaquinone

◦ Vitamin K1 (phylloquinone

◦ Vitamin K3 (menadione)
VITAMIN K
◦Vitamin K is a fat-soluble vitamin well known as an
essential factor for blood coagulation; however in
current research it has emerged
as a potential protector against osteoporosis,
cardiovascular disease, and possibly cancer.

◦ Food Sources: Green leafy vegetables, cauliflower,

cabbage, spinach, soybeans, and cereals