hormone like, help regulate blood pressure, clotting, and produce

pain and fever.

Triglyceride

Lipids
Lipids: are structurally heterogeneous group of substances of biological
origin that are insoluble in water but are soluble in non-polar organic
solvents.

Fatty acids: are mono-carboxylic acids (COOH) that contain long, unbranched hydro-carbon (CH2) chains generally 12-26 carbon atoms in
length. They are rarely found free in nature but rather occur mostly in
esterified form. They almost always contain an even number of carbon
atoms.

Fatty acids can be classified into Saturated or Unsaturated

F.Acids:

1-Saturated fatty acids: have a carbon chain in which all carboncarbon bonds are single bonds.
2- Unsaturated fatty acids:
a. Mono-unsaturated fatty acids: have a carbon chain in which
one carbon-carbon double bond is present.
b. Polyunsaturated fatty acids: have a carbon chain in which two
or more carbon-carbon double bond are present. Up to 6 double
bonds are found in biologically important unsaturated fatty acids.

Saturated Fatty Acids

un-branched hydro-carbon
(CH2) chains

single bonds

monocarboxyl
ic
acids

Unsaturated Fatty
Acids

18 Carbon Atoms

Double bound
Kink

un-branched
hydro-carbon
(CH2) chains

monocarboxylic
acids

Saturated F.A: Solid at R.T

Unsaturated F.A: liqui

Amphipathic: one end of the

molecule is hydrophilic and the
other is hydrophobic

Saturated Fatty Acids

Monounsaturated F. Acids

Polyunsaturated F. Acids

Saturated Fatty Acids

monounsaturated Fatty Acids

Omega-3 ,
Omega-6
Essential Fatty Acids

and

*An omega fatty acid, has two ends, designated as the methyl (CH3) end and
the carboxyl (COOH) end.

An Omega-3 fatty acids: is a polyunsaturated fatty acid with its endmost double
bond three carbons away from its methyl end. linolenic acids
An Omega-6 fatty acid: An Omega-6 fatty acids: is a polyunsaturated fatty acid
with its endmost double bond six carbons away from its methyl end. Linoleic

*Essential fatty acids: are fatty acids that are needed by the human body and

must be obtained from dietary sources because they cannot be synthesized

within the body from other substances. There are two essential fatty acids
linolenic acid (omega-3 acid) and linoleic acid (omega-6 acid). Both are 18carbon polyunsaturated fatty acids.
Both acids contribute to proper membrane structure. When linoleic acid is
missing from diet, the skin reddens and becomes irritated, infections and
dehydration are likely to occur, and the liver may develop abnormalities. If
the fatty acid is restored, then the conditions reverse themselves.
Infants are especially in need of linoleic acid (omega-6) for their growth.
Human breast milk has much higher percentage of it than cows milk.

methyl (CH3) end

carboxyl (COOH) end

Linoleic (omega6) and linolenic acids (Omega3) (18)are needed for

the synthesis of other longer-chain poly-unsaturated acids, including:
1- Arachidonic acid (20), the major precursor of Ecosanoids, (hormon like)
help regulate blood presure, clotting, and produce pain and fever.

2- Eicosapentaenoic acid (EPA) (20) and 3- Docosahexaenoic acid (DHA)

(22) are important constituents of the membranes of the brain and

are necessary for brain development. EPA and DHA are also active
in the retina of the eye.

Vegetable oils and meats provide omega acids and fish is a good source of
omega-3 acids. (Eat more fish).
Heart attack rate is much higher in USA (consume twice the amount of
omega-6)
The people of Greenland have prolonged bleeding time and a high incidence
of stroke. (consume twice the amount of omega-3)
-Take balanced food.
-(4-10 grams of omega-6

to

1 gram of omega-3)

Omega-3 and Omega-6

Essential Fatty Acids
16: 1
CH3
methyl end

and
9
9
9

6
12

(omega-6

acid)
(omega-3 acid).

(omega-6
acid)

6
19

16 13 10

22: 6

4,7,10,13,16,19

methyl
(CH3)
end

carboxyl (COOH) en

Fats function as energy reservoirs in animals

The fat content of normal humans allows them to survive starvation for 2 or 3 months
While human store of glycogen can supply only for one day but carbohydrates are quick
sources for metabolic energy because of water solubility
Fat stores: skin, abdominal cavity and mammary gland Triacylglycerols
Triacylglycerols function to insulate: protect the body from the outer
environments
Vegetable oils: are composed of Triacylglycerol with unsaturated fatty acids
liquid at
room tem.
Vegetable oils can be into solid by catalytic hydrogenation which reduce the double bonds
to single bonds.
* Exposure of the lipid rich food to oxygen for long time may spoil and the lipid is said to
be Rancid. Rancidity results from the cleavage of double bond in unsaturated F.
A that
produce aldehyde and carboxylic acid(butyric acid) with low M.wt bad smell

Fatty acids
Physical and Chemical properties

-Solubility: the (hydrophobic) non-polar hydrocarbon chain

account for the poor solubility of F.As in water.
* Carboxyl group is (Hydrophilic) polar and this account for
the slight solubility of short chain fatty acids in water.
*The longer the fatty acids and fewer the double bonds, the
lower is
the solubility in water.
-Melting point: depends on chain length, the degree of
unsaturation.
- Double bonds disrupt intermolecular packing and there fore
lower melting temperature.
- Saturated F.As are solids at R.Temperature. while
unsaturated F.As are liquids.
- Fatty acids form micelles
- Fatty acids are weakly acidic

Saturated Fatty Acids

un-branched hydro-carbon
(CH2) chains

monocarboxyl
ic
acids

* Exposure of the lipid rich food to oxygen for long time may spoil
and the lipid is said to
be Rancid. Rancidity results from the cleavage of double bond
in unsaturated F. A that
produce aldehyde and carboxylic acid with low M.wt bad smell

In the unsaturated F. A
the cis configuration
double bond forces a kink
(bend) in the hydrocarbon
chain
Unsaturated chains bend
and pack in a less ordered
way, with greater potential
for motion
F.A with one or more kinks cannot
pack together as tightly as fully
saturated F.A and their
interactions are weaker
So the unsaturated F.As take less
thermal energy to disorder these
poorly ordered arrays of
unsaturated F.As
they have
lower melting points

Triglyceride

Storage lipids: Fatty Acids and Triacylglycerols

Triacylglycerols: is a compound formed by esterification of three fatty

acids to glycerol. An acyl group is the group that remains after the
OH group is removed from a fatty acid. Thus, as the name implies,
triacylglycerols contain three fatty acid residues (acyl groups ) esterified
to glycerol. The older name Triglyceride is also used.
A simple Triacylglycerols: is formed from the reaction of glycerol with three
identical fatty acids. (This is rare in nature).
A mixed Triacylglycerols: is formed from the reaction of glycerol with three
non-identical fatty acids. Most naturally occurring triacylglycerols are
mixed ones. Fats and oils that are biologically important are complex mixtures
of mixed triaclglycerols. No single triacylglycerol structure adequately describes
a naturally occurring fat or oil

O
O
Acyl Group

OH

Esters are carboxylic acid

derivatives in which the OH group
of the carboxylic acid has been
replaced with an OR group
O
O
R-C-O-H

R-C-O-R

Glycerol

3 F.As

18

Triacylglycerol (Triglyceride)
3H2O
Acyl group

18

18
CH2OH-CHOH-CH2OH

A simple Triacylglycerol
has three identical fatty acid

A mixed
Triacylglycerol
has three fatty acids
(but more than one
kind )

A mixed Triacylglycerol has three fatty acids (but

more than one kind )

Acyl group

12

Most naturally occurring triacylglycerols

are mixed ones
No single triacylglycerol
structure adequately describes a

3 Acyl groups

Triacylglycerol

Fats and oils: are naturally occurring mixtures of triesters formed from the
reaction between three fatty acid molecules and a glycerol (an alcohol
with three hydroxyl groups).
Fats: are triacylglycerol mixtures that have a relatively high percentage of
saturated fatty acids. (Fats are solids).
Oils: are triacylglycerol mixtures that have a relatively high percentage of
unsaturated fatty acids. (Oils are liquids).
Blood cholesterol: all current dietary recommendations stress reducing
saturated fat intake. (Butter to margarine or partially hydrogenated
vegetable oils rather than animal fats). However, recent research suggest
that partially hydrogenated products as bad as saturated fats, or
even worse, in raising blood cholesterol levels. Why? During
hydrogenation some of the unsaturated double bonds that are naturally
present in the cis configuration, are isomerized to the trans configuration.
Avoid both

trans fatty acid

margarine) and

(partially hydrogenated vegetable oils like

saturated fats (animal fats like butter).

Omega 6: (poultry, eggs, avocado, nuts, cereals, whole grain bread, most
vegetable oils, linseed, pumpkin seeds)
Omega 3: (linseeds, oily Fish, salmon, Hazel nuts, eggs, meat)

Saturated Fatty Acids

un-branched hydro-carbon
(CH2) chains

monocarboxyl
ic
acids

Low level of HDL Cholesterol predispose to coronary and

peripheral arterial disease

LDL= Low Density Lipids

HDL= Heavy Density Lipids

cis configuration

trans configuration

Phosphoacylglycerols:

are triesters of glycerol in which

two OH groups are esterified with fatty acids and the third is
esterified with phosphoric acid, which in turn is esterified to an
alcohol.

Phosphoacylglycerols serve as major components of cell

membranes. The nature of the alcohol attached to the phosphoric
acid group determines the specific function of the
phosphoacylglycerol. The most abundant phosphoacylglycerols have
one of the amino alcohols: cholin, ethanolamine, or serine
attached to the phosphate group. Phosphoacylglycerols containing
these amino alcohols are respectively known as
phosphatidylcholines,
phophatidylethanolamines, and
phosphatidylserines.
There are two important things to notice about this model: (1) there is
a head part, the choline and phosphate, and (2) there are two
tails, the two fatty acid carbon chains. The head part is polar . The
two tails, the carbon chains, are nonpolar.
All Phosphoacylglycerols have similar structures (head and two
tails).
The polar head group of a phosphoacylglycerol is soluble in water.
The nonpolar tail chains are insoluble in water but soluble in
nonpolar substances.

Phosphatidylcholines: known as lecithins . The

enzyme lecithinase in the intestine hydrolyzes most of
it when taken orally (egg yolk and soybeans). Within
the body, it is prevalent in the cell membranes. It is
made by the liver; thus are not essential nutrients.
In food industry: are used as emulsifiers to promote
mixing of otherwise immiscible materials (found in:
mayonnaise, ice cream, and custards).
phophatidylethanolamines, and
phosphatidylserines: Known as cephalins. Found in
heart and liver tissues and in high concentrations in
the brain. They are important in blood clotting.

PhosphoacylglycerolsPhosphatidylcholine
Stearic acid
(18:0)
Oleic acid
(18: 1)

cholin,
ethanolamine,
or
serine
attached to
the phosphate
group

Head
is polar
Hydrophilic

phosphatidylcholines
,
phophatidylethanola
mines,

Two tails
are
nonpolar
Hydropho
bic

Sphingolipids:

are major constituents of cell membranes of the

body. They have structures based on the long-chain amino dialcohol
sphingosine. (derived from the amino dialcohol sphingosine).
All lipids derived from sphingosine have
(1) a fatty acid connected to the NH2 group via an amide linkage, and
(2) a group attached to the OH group on the terminal carbon atom via
an ester linkage. Also have head and two tails.
For sphingolipids, the fatty acid is one of the tails, and the
long carbon chain of sphingosine itself is the other
tail.
The additional component is the head, and it is phosphoric acidcholine group for particular model shown:

1- Sphingomyelins:

sphingolipds in which the esterifying group is

phosphoric acid to which choline is attached.
Found in all cell membranes and are important structural
components of the myelin sheaths , the protective and insulating
coating that surrounds nerves.

O
Sphingolpid general structure

H2O
Released:

H from NH2 sphingosine

OH from
COOH

sphingosine

C
NH2
Amide

2 Tails

head

Sphingomyelins

phosphoric acidcholine group

head

fatty acid +
sphingosine
two tails

Cerebrosides and Gagliosides: some sphingosinebased membrane lipids have a small carbohydrate
as the head group.
2- Cerebrosides, the simplest of such
carbohydrates-containing lipids, usually have a
glucose or galactose as the carbohydrate unit. The
cerebrosides, occur primarily in the brain (7% of
dry mass) and in the myelin sheath of nerves.
3- Gangliosides: contain more complex
carbohydrate heads; up to seven
monosaccharide units (oligo- ssacharides) are
present. These substances occur in the gray matter
of the brain as well as in the myelin sheaths.

sphingosine

Stearic acid
(fatty acid)
18:0

Cerebroside Structure

Monosaccharide
Galactose

Tryglicerides
Cerebroside mono
Phosphatidylinositol
Sphingomyelin
Ganglioside oligo
Phosphatidylcholine
Phosphatidic acid
Phosphatidylethanolamin
Phosphatidylserine

Glycerophosphlipid
Phosphatidylcholine

Sphingolipid Glycolipid

choline
choline

2 Fatty acids

Fatty acids
Sphingomyelin

Fatty acid

Glycolipid

Steroids:
1- Cholesterol:
2- Bile salts:
3- Steroid Hormones:
1- sex hormones:
2- adrenocortical
hormones:

Steroids: are lipids with structures based on a

fused-ring system involving three sixmembered rings and one five-membered ring.
The fused-ring system of steroids, called a steroid
nucleus. Rings are labeled with letters A,B,C,D
and each carbon atom is labeled with a number.
Numerous steroids have been isolated from plants,
animals, and human beings. Location of double
bonds within the fused-ring system and the
nature and location of substituents distinguish
one steroid from another. Most steroids have an
oxygen functional group (
O or OH) at
carbon 3 and some kinds of chain at carbon 17.
Many also have a double bond from carbon 5 to
either carbon 4 or carbon 6.

2 Methyl
groups
C10 C13

Hydroxyl
group
at C3

2
Methyl
groups
in the
Alkyl
side
Alkyl
chain
side
chain

1- Cholesterol: is the most abundant steroid

in human body. The name has Ol ending
because it is an alcohol, with an OH group
on carbon 3 of the steroid nucleus. In addition,
cholesterol has methyl group bonded to
carbon atoms 10 and 13 and a small
branched hydrocarbon chain on carbon 17 .
Within the human body, cholesterol is found
in:
-cell membranes (up to 25% by mass),
-nerve tissue, and
-brain tissue (about 10% by dry mass)
-gallstone: main component of gallstone.

 Human blood plasma contains

about 50 mg of free cholesterol per
100 ml. and about 170 mg of
cholesterol esterified with various
fatty acids. The OH group on
carbon 3 is considered the head of
the molecule, it is small polar head
with limited water solubility. steroid
nucleus is the nonpolar part.

Cholesterol is the starting material ( Precursor ) for the

synthesis of numerous steroid hormones, vitamin D, and
bile salts. it regulates the fluidity of the cell membrane. So it
is essential to life,
In human liver 1 gm is produced each day (bodys need).
High blood cholesterol, high blood pressure and smoking are the
major risk factors for cardiovascular disease (CVD).
High blood cholesterol ---atherosclerosis (plaque in the
arteries)---- hardening of the arteries that serve the heart----reduced blood flow to heart muscle -------and can lead to
heart attack.
Reduce eating animal products (meat, dairy products and
fats) eat more fruits and vegetables (contains no
cholesterol).

steroid nucleus
Nonpolar part

2 Methyl
groups
C10 C13

Hydroxyl
group
at C3
OH group= Polar head

2
Methyl
groups
in the
Alkyl
side
Alkyl
chain
side
chain

2- Bile salts: are emulsifying agents that make

dietary lipids soluble in the aqueous
environment of the digestive tract. During
digestion, bile salts are released into the
intestine from the gallbladder, emulsifying
(solubilizing) fats and oils.
The two principle bile salts are:
a. sodium glycocholate (contains glycine) and
b. sodium taurocholate (contains taurine as
modified amino acid).

3- Steroid Hormones:
Hormones: chemical messengers produced by ductless glands. They
serve as a means of communication between various tissues. Not all
hormones are steroids. Cholesterol is the starting material for the
production of all steroid hormones.
Classes : 1- sex hormones:
a. Estrogens: the female sex hormones: (in the ovaries).
Responsible for the development of:
-female secondary sex characteristics at the onset of puberty
and for --regulation of the menstrual cycle. They also
-stimulate the development of the mammary glands during
pregnancy
-induce estrus (heat) in animal.
b. Androgens: the male sex hormones: (testes). Promote the
development of secondary male characteristics. They also
promote muscle growth.
c. Progestins: the pregnancy hormones: (ovaries and placenta).
Prepare the lining of the uterus for implantation of the fertilized
ovum. They also suppress ovulation.
2- adrenocortical hormones:

The following gives the structure of primary hormone in each

of the 3 sex hormones

##

##

*
Synthetic progestin Interferes with gestation of a A synthetic tissue
fertilized
Prevents ovulation
build steroid
egg and terminates a

2- Adrenocortical hormones:
a. Mineralocorticoids: control the balance of Na+ and
K+ ions in cells.
(
(aldosterol)
b. Glucocorticoids: (in adrenal glands)
control glucose metabolism and
counteract inflammation. (cortisol
or hydrocortisol).
rheumatoid arthritis

ontrol the balance of control glucose

a+ and K+ ions in cellsmetabolism
and counteract
inflammation

Mineralocorticoids

Used to control
inflammatory
Diseases: rheumatoid
arthritis

Synthetic

Glucocorticoids

Cortisone

Prednisolone
Anti- inflammation

Linoleic (omega6) and linolenic acids (Omega3)

(18)are needed for the synthesis of other longer-chain
poly-unsaturated acids, including:
1- Arachidonic acid (20), the major precursor of
eicosanoids, (hormon like) help regulate blood presure,
clotting, and produce pain and fever.
Unsaturated F.A

Eicosanoids:

derivetives of polyunsaturated 20-carbon

fatty acids. Arachidonic acid, 20:4 fatty acid is the precursor
of most eicosanoids. Produced by many cells. The name is
derived from Greek word ekos, twenty. It is hormone like
effective at extremely low concentrations locally.
The physiological effects of eicosanoids:
1- The inflammatory response, (to tissue damage).
2- The production of pain and fever.
3- The regulation of blood pressure .
4- The induction of blood clotting.
5- The control of reproduction functions, such as induction of
labor.
6- The regulation of the sleep/wake cycle.

There are 3 principle types of eicosanoids:

1- Prostaglandins: raising body temp., inhibit gastric juice,
relaxing smooth muscle, intensify pain, enhance
inflammatory response.
Aspirin: inactivate enzyme needed for
prostaglandin synthesis.
2- Thromboxanes: (Produced by platelets)
-formation of blood clots and
-promotes platelets aggregation.
3- leukotrins: (in WBCS).
-Inflammatory and hyper sensitivity (allergy)
responses are associated with elevated leukotriens.

Arachidonic acid, 20:4

fatty acid
is the precursor of most
eicosanoids

Plasma membranes
1- Plasma membranes: all cells are surrounded by plasma membrane that confines their
contents. 80% of the mass of a plasma membrane is lipid material.
It is a lipid bilayer made up of various phospholipids (phosphoacylglycerols and
sphingolipids). The nonpolar tails of the lipids are in the middle and the polar heads are
on the outside surface. Most lipid molecules in it contain at least one unsaturated fatty
acid. This makes kinks in their carbon chains, prevent tight packing of fatty acid chains.
(becomes liquid like) allowing numerous types of biochemicals to pass into and out of a
cell.

a. Cholesterol regulate membrane fluidity, fits between the fatty acid chains restricting
movements of F.A and making the membrane more rigid. While cholesterol adds firmness and
integrity to the plasma membrane and prevents it from becoming overly fluid, it also helps
maintain its fluidity.
At the high concentrations it is found in our cell's plasma membranes (close to 50 percent,
molecule for molecule) cholesterol helps separate the phospholipids so that the fatty acid
chains can't come together and cyrstallize.
Therefore, cholesterol helps prevent extremes-- whether too fluid, or too firm-- in the
consistency of the cell membrane

b. Proteins are also components of lipid bilayers, moving substances such as nutrients and
electrolytes across the membrane, and also act as receptors that bind hormones and
neurotransmitters.

kinks in their carbon chains, prevent tightpacking of fattyacidchains.

(becomes liquid like)

Proteins
Protei
ns

Proteins

lipid bilayer
Proteins

Cholesterol

Cholesterol: restrict
movements of F.A and making
the membrane more rigid

moving substances
such as
nutrients and
electrolytes
across the membrane

Kink

Kink

Kink

Vitamins

3 active forms in the body

1- retinol
2- retinal
3- retinoic acid
4- plant beta-carotene
converted in liver to vit A

Functions of vitamin A
1- Visual cycle: Rhodopsin (visual
pigment of the rod cells of the retina)
consists of:
(11-cis retinal + protein opsin).
When Rhodopsin exposed to light, a
series of photochemical isomerization
occurs, which results in the release of all
trans retinal and opsin.
This causes nerve impulse transmitted
by optic nerve to the brain.
Regeneration of Rhodopsin: Trans retinal,
after being released from Rhodopsin, is
isomerized to 11-cis retinal, which
spontaneously combines with opsin to
form Rhodopsin, thus completing the
cycle.
2- Growth: Animals deprived of vitamin
A, lose their apetite , their bone growth is
slow, their nervous system growth is
affected leading to CNS damage.
3- Reproduction: Retinol and retinal
are essential for reproduction, thus,
animals given vitamin A only as retinoic

In Retina
All trans retinol
All trans retinal
11-cis retinal

opsin

Rhodopsin

Exposed
to light

opsin

All trans retinal

VitaminA and vision

-11-cis retinal is a
component of
the visual pigment,
rhodopsin.

ulates: Ca+ Phosphorous metabolism

Ergocalciferol (vit
D2) &
Cholecalciferol (vit
D3)

Rickets:
Abnormal bone
formation,
resulting in skeletal
deformities,
Active form of (Vit D3)
muscle pain,
1,25-dihydroxycholecalciferol
enlarged liver and
Promote Ca & phosphorous
spleen
Absorption in the intestine
Cholecalciferol (vit D3)

7-dehydrocholestrol

Cholecalciferol (vit D3)

Active form of (Vit 3)

5-dihydroxycholecalciferol (Vit D3)

oxidant: protects other compounds from oxidation by being oxidized its

. Also protects vitamin A from

oxidation

The most
important location
Of vit E is the lung

pha-tocopherol is the most biologically active of other forms of Vitamin

Other forms are: beta, gamma, delta,

Newborn have sterile intestine

gets it from the milk only

Prothrombin

Thrombin

Vitamin K forms:
1- in plants: phylloquinone
Vit K1
2- in bacteria:
menaquinone Vit K2
3- for therapy: synthetic:
menadione

Fibrinogen

Fibrin

Source: is diet and intestinal

bacteria.
Antibiotic treatment may
lead to hypoprothrombinemia
in malnourished persons

Phospholipids

Storage lipids

Membrane lipids

Sphingolipids

Triglyceride

Storage lipids

Membrane lipids
Phospholipids

Glycolipids
Sphingolipids