Lipids

Lipids

lipos : fat or lard

a heterogeneous class of naturally occurring
organic compounds classified together on the
basis of common solubility properties.
insoluble in water, but soluble in organic
solvents including diethyl ether,
dichloromethane, and acetone

Major Classes of Lipids

1. Saponifiable Lipids
- they can be hydrolyzed under alkaline
conditions to yield salts of fatty acids.
2. Nonsaponifiable Lipids
- they do not undergo hydrolysis reaction in
alkaline solution

Saponifiable Lipids

Glycerol esters

Non-glycerol esters

triaylglycerol

waxes

phosphoacylglycerol

sphingolipids

Non-saponifiable Lipids

steroids

eicosanoids

terpenes

pheromones

vitamins

Fatty acids

Building blocks of all saponifiable lipids

Monocarboxylic acids that contain long,
unbranched hydrocarbon chains generally 1226 carbon atoms in length

Classification of Fatty Acids

Saturated fatty acids

Monounsaturated fatty acids
Polyunsaturated fatty acids

Common
Name

IUPAC Name

Formula

lauric

n-dodecanoic

C11H23COOH

palmitic
stearic

n-hexadecanoic
n-octadecanoic

C15H31COOH
C17H35COOH

palmitoleic

cis-9-hexadecenoic

C15H29COOH

oleic

cis-9-octadecenoic

C17H33COOH

linoleic

cis,cis9,12octadecadienoic

C17H31COO
H

Fatty acids
Omega 3- polyunsaturated fatty acid
- endmost double bond three carbons
away from the methyl end
-linolenic acid, eicosapentaenoic acid, docosahexaenoic
acid

Omega 6-polyunsaturated fatty acid

- endmost double bond six carbons
from the methyl end
-linoleic acid, arachidonic acid

away

Essential Fatty acids

are fatty acids that are needed by the human

body and must be obtained from dietary
sources because they can not be synthesized
within the body from other substances.

Essential Fatty acids

Linoleic acid
-proper membrane
structure
-in infants: for growth

Linolenic acid

proper membrane structure

Triglyceride

Triglyceride: an ester of glycerol with three

fatty acids.

Fats and Oils

Fats
Solid at room
temperature
Animal sources

Oils
Liquid at room
temperature
Plant sources

Kinds of Triacylglycerol

Simple
Mixed

Complex Lipids

Phospholipids

contain an alcohol, two fatty acids, and a phosphate

ester.

Glycolipids

Complex lipids that contain a carbohydrate.

Glycerophospholipids

Glycerophospholipids are the second most

abundant group of naturally occurring lipids.

They are also called phosphoglycerides.

Found almost exclusively in plant and animal
membranes, which typically consist of 40% -50%
phosphoacylglycerols and 50% - 60% proteins.

Glycerophospholipids

WAXES

water-insoluble and hard to hydrolyze

often used to provide a protective
coating (leaves, skin, fur, hair, etc.)
ester of a fatty acid and a long-chain
alcohol
ex: bees wax

Sphingolipids

Long chain amino dialcohol sphingosine

Major constituents of cell membranes
Found in the coatings of nerve axons (myelin).

Glycolipids

Glycolipid: a complex lipid that contains a

carbohydrate.

The carbohydrate is either glucose or galactose.

The cerebrosides are ceramide mono- or
oligosaccharides.

Glycolipids
Cerebrosides
- the simplest of such carbohydrate
containing lipids (glucose or galactose)
- occur in the brain and myelin sheath
of nerves
Gangliosides
- contain more complex CHO units (7)
- substances occur in the gray matter of
the brain
- myelin sheath

Steroids

Steroids: a group of plant and animal lipids that

have this tetracyclic ring structure.

Steroids- Cholesterol

the most abundant steroid in the human

body, and also the most important.

It is a component in plasma membranes in

all animal cells.
It is the precursor of all steroid hormones
and bile acids.

Steroids- Cholesterol

associated with hardening of the arteries

appears to coat the arteries plaque
formation, resulting to increased blood pressure
from

narrowing of arteries
reduced ability of arteries to stretch
clot formation, which leads to

myocardial infarction
stroke

Steroids Sex Hormones

major groups

estrogens

female sex hormones

synthesized in the ovaries and adrenal cortex
responsible for female secondary sex characteristics at
onset of puberty and for regulation of menstrual cycle
stimulate development of mammary glands during
pregnancy
induce estrus (heat) in animals

Steroids Sex Hormones

androgens

male sex hormones

synthesized in the testes and adrenal cortex
promote development of secondary male characteristics
promote muscle growth

Steroids Sex Hormones

progestins

pregnancy hormones
synthesized in the ovaries and placenta
prepare lining of uterus for implantation of fertilized
ovum
suppress ovulation

Steroids Adrenocortical Hormones

produced by adrenal glands

types

mineralocorticoids

control balance of Na+ and K+ ions in cells

glucocorticoids

control glucose metabolism

counteract inflammation

Eicosanoids

from the Greek word eikos meaning twenty

unsaturated fatty acids
contains 20 carbons

The physiological effects of eicosanoids

1.

2.
3.
4.
5.

6.

The inflammatory response, a normal response to

tissue damage
The production of pain and fever
The regulation of blood pressure
The induction of blood clotting
The control of the reproduction functions, such as
induction of labor
The regulation of the sleep / wake cycle

Common Fatty Acids

Prostaglandins
1.

2.

3.

4.

Contains a cyclopentane ring and oxygen containing functional

groups
family of physiologically potent lipids present in minute amounts
in most body tissues
originally isolated from seminal fluid (named after the prostate
gland)
all are derived from arachidonic acid , OMEGA 6 , (20:4)

Prostaglandins
1.

biological effects

stimulation of smooth muscles

regulation of steroid production
inhibition of gastric secretion
inhibition of hormone-sensitive lipases
inhibition/stimulation of platelet aggregation
regulation of nerve transmission
sensitization to pain
mediation of inflammatory response

Prostaglandins & Blood Clotting

1.

thromboxane A2
1.
2.
3.

produced by platelets in blood

stimulates constriction of blood vessels
stimulates aggregation of platelets (blood clotting)

prostacyclin
.
.

produced by cells that line blood vessels

reverses effects of thromboxane A2

aspirin therapy 1/day following strokes; acts as

anticoagulant/anti-platelet aggregation

Prostaglandins & Inflammatory

Response
1.
2.
3.

protective mechanism when tissue is damaged

results in swelling, redness, fever and pain
promoted by prostaglandins
aspirin and ibuprofen
anti-inflammatories
block prostaglandin synthesis
cause reduction in this response

Prostaglandins & Smooth Muscle

Contractions
prostaglandins stimulate contractions in the
reproduction system uterine contractions
. dysmenorrhea
1.

painful menstruation
evidence shows that this may result from an excess
of prostaglandins
usually counteracted by Ibuprofen

Prostaglandins & the

Gastrointestinal Tract
1.

prostaglandins
1.

2.
3.

inhibit the secretion of hydrochloric acid in the

stomach
increase secretion of mucus layer
protects mucosa from acid invasion

aspirin inhibits prostaglandin production

.

extended use may cause stomach ulcers

Prostaglandins Other Effects

1.

in the kidneys
1.
2.

cause renal blood vessels to dilate

aid in excretion of water and electrolytes

in the respiratory tract

.

.
.

produced by white blood cells (WBCs) in the lungs

leukotrienes
cause constriction of bronchial tube asthma
other prostaglandins act as bronchodilators