Lipids Part Iii Steroids

……………………………
Messenger STEROID HORMONES

Lipids
Hormone that is a cholesterol derivative
2 Major Classes of Steroid Hormones
1. Sex Hormones
3 Major Groups of Sex Hormones
A. Estrogens → Female Sex Hormones

B. Androgens → Male Sex Hormones
C. Progestins → Pregnancy Hormones
……………………………
……………………………
Messenger
Lipids
STEROID HORMONES
Hormon Biochemical substance, produced by a

ductless gland, that has a messenger
e function.
It serves as a means of communication

between various tissues.
Note: Some hormones, not all, are lipids.

Estrogens
→Synthesized in the ovaries and Adrenal Cortex

→Functions:
 Responsible for the development of female secondary
sex characteristics at the onset of puberty
 For regulation of the menstrual cycle

 Stimulate the development of mammary glands during
pregnancy and induce estrus (heat) in animals
Estrogens
→Estradiol
o Primary Estrogen
o Synthesized from the corresponding male
hormone (testosterone) by aromatization of the A
ring
Estrogens
→Estradiol
o Regulates the cyclic changes occuring in the
uterus and ovaries known as the menstrual cycle
o Menstrual Cycle
As the cycle begins, the level of estradiol in the

body rises, which in turn causes the lining of
the uterus to thicken.
Estrogens
→Estradiol
o Menstrual Cycle
As the cycle begins, the level of estradiol in the
body rises, which in turn causes the lining of
the uterus to thicken.
 Luteinizing hormone (LH) triggers ovulation
and when the ovum is fertilized, increased
progesterone levels will inhibit any further
ovulation.
Estrogens
→Estradiol
o Menstrual Cycle
 Both estradiol and progesterone promote
further preparation of the uterine lining to
receive the fertilized ovum.
 If no fertilization takes place, progesterone
production stops altogether, and estradiol
production decreases. This halt decreases the
thickening of the uterine lining, which is sloughed
off with accompanying bleeding during
menstruation.
Estrogens
→Estradiol
o Menstrual Cycle
 Progesterone is essential for the implantation
of the fertilized ovum because blocking its
action leads to termination of pregnancy.
 A drug, now widely used in France and China,

called mifepristone or RU486 acts as a
competitor to progesterone.
Estrogens
→Estradiol
o Menstrual Cycle
 Levels of sex hormones in
the bloodstream during
the phases of one
menstrual cycle in which
pregnancy does not occur.
Estrogens
→Estradiol
o Menstrual Cycle
Estrogens
→Estradiol
o Menstrual Cycle
Androgen
→Synthesized in testes and adrenal cortex

→Functions:
 Responsible for the development of male secondary
sex characteristics
 Promote muscle growth
→Testosterone
o Primary Androgen
Androgen
→Testosterone
o Promotes the normal growth of male
genital organs
o Synthesized in the testes from
cholesterol
Progestins
→Synthesized in the ovaries and the

placenta and prepare the lining of the
uterus for implantation of the fertilized
ovum.
……………………………
Lipids
Hormone that is a cholesterol derivative
2 Major Classes of Steroid Hormones
2. Adrenocorticoid Hormones
2 Types of Adrenocorticoid Hormones
A. Mineralocorticoids → Control the balance of Na+ and K+

ions in cells and body fluids
B. Glucocorticoids → Control Glucose metabolism and

counteract inflammation
……………………………
Lipids
 Product of Adrenal glands
A. Mineralocorticoids
o Aldosterone- major mineralocorticoids

-Increased secretion of enhances the reabsorption
of Na+ and Cl- ions in the kidney tubules and
- Controls tissue swelling). because it affects Na+
increases the loss of K +
concentration which controls water retention in the

tissues
……………………………
Lipids
 Product of Adrenal glands
B. Glucocorticoid
o Cortisol- major glucocorticoids
 It increases the glucose and glycogen

concentrations in the body by synthesizing fatty
acids from fat storage cells and amino acids from
body proteins in the liver.
……………………………
Messenger Eicosanoids
Lipids
 It is an oxygenated C20 fatty acid derivative that
functions as a messenger lipid.
 The metabolic precursor for most eicosanoids is
arachidonic acid, the 20:4 fatty acid
 They are hormonlike molecules rather than true

hormones because they are not transported in the
bloodstream to their site of action. They exert their
effects in tissues where they are synthesized.
……………………………
Lipids
1. Prostaglandins
o Messenger lipid that is a C20 fatty acid derivative

that contains a cyclopentane ring an oxygen-
containing functional groups.
o Name came from the discovery that prostaglandins

can be found in prostate gland.
……………………………
Lipids
1. Prostaglandins
o Twenty carbon fatty acids are converted into a

prostaglandin structure when the eight and twelfth carbon
atoms of the fatty acid become connected to form a five-
membered ring.
o The enzyme catalyzing this reaction is called cyclooxygenase

(COX, for short).
o The product, known as PGG2, is the common precursor of other
prostaglandins, including PGE and PGF.
……………………………
Lipids
1. Prostaglandins
o The COX enzyme comes in 2 Forms

 COX-1
- Catalyzes the normal physiological production of
prostaglandins, which are always present in the body.
- For example, PGE2 and PGF2a stimulated uterine
contractions and induce labor
- PGE2 lowers blood pressure by relaxing the muscles
around blood vessels. In aerosol form, this prostaglandin
is used to treat asthma. It opens up the bronchial tubes by
relaxing the surrounding muscles
……………………………
Lipids
1. Prostaglandins

 COX-1
- PGE1 is used as a decongestant; it opens up nasal
passages by constricting blood vessels
 COX-2
- Responsible for the production of prostaglandins in
inflammation.
……………………………
Lipids
1. Prostaglandins
 COX-2
- When a tissue is injured or damaged, special
inflammatory cells invade the injured tissue and
interact with resident cells
……………………………
Lipids
1. Prostaglandins
……………………………
Lipids
2. Thromboxanes
o It is a C20 fatty avid derivative that contains a
cyclic ether ring and oxygen-containing functional
groups.
o The cyclic structure involves a bond between
carbons 8 and 12.
o It promotes the formation of blood clots
o These substances are derived from PGH2, but their ring
is a cyclic acetal.
……………………………
Lipids
2. Thromboxanes
o It promotes the formation of blood clots

 When a blood vessel is ruptured, the first line of
defense is the platelets circulating in the blood,
which form an incipient clot
 Thromboxane A2 causes other platelets to clump,

thereby increasing the size of the blood clot.
……………………………
Lipids
2. Thromboxanes
o Aspirin and similar anti-inflammatory agents

inhibit the COX enzyme. PGH2 and thromboxane
synthesis is inhibited, and blood clotting is
impaired.
 This effect has prompted many physicians to

recommend a daily dose of 81 mg aspirin for people at
risk for heart attack or stroke.
……………………………
Lipids
2. Thromboxanes
o Aspirin and similar anti-inflammatory agents

inhibit the COX enzyme. PGH2 and thromboxane
synthesis is inhibited, and blood clotting is
impaired.
 It also the reason why physicians forbid patients to
use aspirin and other anti-inflammatory agents for
a week before a planned surgery—aspirin and
other NSAIDs may cause excessive bleeding.
……………………………
Lipids
2. Thromboxanes
o A variety of NSAIDs inhibit COX enzymes. Ibuprofen

and indomethacin, both powerful painkillers, can block
the inhibitory effect of aspirin and thus eliminate its
anticlotting benefits. Therefore, the use of these NSAIDs
together with aspirin is not recommended. Other
painkillers, such as acetaminophen and diclofenac, do not
interfere with aspirin’s anticlotting ability and therefore
can be taken together.
……………………………
Lipids
2. Leukotrienes
o A group of substances derived from arachidonic
acid that act to mediate hormonal responses
o They are found in leukocytes (White Blood Cells)
o Associated with various inflammatory and

hypersensitivity responses.
……………………………
Lipids
2. Leukotrienes
o Leukotrienes activate the immune system after infection, injury, or
contact with allergens. Although their role in inflammatory processes is
beneficial to help fight diseases, higher levels of these chemicals can
contribute to conditions like asthma, arthritis and allergic reactions.
o They produce long-lasting muscle contractions, especially in the lungs,

and can cause asthma-like attacks.
o Cause inflammation and fever, so the inhibition of their production in the

body is a major pharmacological concern.
……………………………
Emulsification Lipids
Substance that can disperse
Emulsifier and stabilize water-insoluble
substances as colloidal particles
in an aqueous solution
Bile Acids
o It is a cholesterol derivative that functions as a lipid-
emulsifying agent in the aqueous environment of the
digestive tract.
……………………………
Bile Acids
o Oxidation products of Cholesterol
o Cholesterol is oxidized to the trihydroxy

derivative, and the end of the aliphatic
chain is oxidized to the carboxylic acid
which in turn forms an amide bond with an
amino acid, either glycine or taurine
……………………………
Bile Acids
Structure
o They are tri- or drihydroxy cholesterol derivatives
o The carbon 17 side chain of cholesterol has been

oxidized to a carboxylic acid.
o The oxidized acid side chain is bonded to an amino

acid (either glycine or taurine) through amide linkage.
……………………………
Bile Acids
……………………………
Bile Acids
o Bile Acids always carry an amino acid (either glycine

or taurine) attached to the side chain carboxyl group
via an amide linkage.
Bile
It is a fluid containing emulsifying agents that is
secreted by the liver, stored in the gallbladder, and
released into the small intestine during digestion.
……………………………
Bile Acids
Bile
• It is a medium through which bile acids are supplied
to the small intestine.
• It also contains bile pigments (breakdown products
of hemoglobin), cholesterol itself, and electrolytes
such as bicarbonate ion.
……………………………
Bile Acids
Function
s
o Powerful Detergent
 One end of the molecule is strongly hydrophilic because
of the negative charge, and the rest of the molecule is
largely hydrophobic which disperse dietary lipids in the
small intestine into fine emulsions, thereby facilitating
digestion.
 The dispersion of dietary lipids by bile salts is

similar to the action of soap on dirt.
……………………………
Bile Acids
Function
s
o Removal of excess cholesterol in 2 ways
 They are themselves breakdown products of
cholesterol (so cholesterol is eliminated via bile
salts)
 They solubilize deposited cholesterol in the

form of bile salt-cholesterol particles
……………………………
Protective-Coating Lipids: Biological
Waxes
Lipid that is a monoester of a
Biological long fatty acid and a long-chain
Wax alcohol
The fatty acids found in

biological waxes generally are
saturated and contain from 14-
36 carbon atoms.
……………………………
Waxes
Function
o Both humans and animals possess skin glands that secrete
biological waxes to protect hair and skin and to keep it pliable
and lubricated. With animal fur, waxes impart water
repellency to the fur. Birds, particularly aquatic birds, rely on
waxes secreted from preen glands to keep their feathers
water repellent. Such wax coatings also help minimize loss of
body heat when the bird is in cold water. Many plants,
particularly those that grow in arid regions, have leaves that
are coated with a thin layer of biological waxes, which serve to
prevent excessive evaporation of water and to protect against
parasite attack
……………………………
Waxes
Function
o Pharmaceutical use
o Cosmetics
o Polishing industries
 Carnauba wax- particularly hard wax whose uses involve high-gloss
finishes: automobile wax, boat wax, floor wax, and shoe wax.
 Lanolin (a mixture of waxes obtained from sheep wool)- used as a base
for skin creams and ointments intended to enhance water retention of
water (which softens the skin)

Lipids Part Iii Steroids

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Lipids Part Iii Steroids

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……………………………

Messenger STEROID HORMONES

2 Major Classes of Steroid Hormones

A. Estrogens → Female Sex Hormones

Hormon Biochemical substance, produced by a

It serves as a means of communication

Note: Some hormones, not all, are lipids.

→Synthesized in the ovaries and Adrenal Cortex

 For regulation of the menstrual cycle

As the cycle begins, the level of estradiol in the

 A drug, now widely used in France and China,

→Synthesized in testes and adrenal cortex

→Synthesized in the ovaries and the

2 Major Classes of Steroid Hormones

A. Mineralocorticoids → Control the balance of Na+ and K+

B. Glucocorticoids → Control Glucose metabolism and

o Aldosterone- major mineralocorticoids

concentration which controls water retention in the

o Cortisol- major glucocorticoids

 It increases the glucose and glycogen

 They are hormonlike molecules rather than true

o Messenger lipid that is a C20 fatty acid derivative

o Name came from the discovery that prostaglandins

o Twenty carbon fatty acids are converted into a

o The enzyme catalyzing this reaction is called cyclooxygenase

o The COX enzyme comes in 2 Forms

o The COX enzyme comes in 2 Forms

o It promotes the formation of blood clots

 Thromboxane A2 causes other platelets to clump,

o Aspirin and similar anti-inflammatory agents

 This effect has prompted many physicians to

o Aspirin and similar anti-inflammatory agents

o A variety of NSAIDs inhibit COX enzymes. Ibuprofen

o They are found in leukocytes (White Blood Cells)

o Associated with various inflammatory and

o They produce long-lasting muscle contractions, especially in the lungs,

o Cause inflammation and fever, so the inhibition of their production in the

o Cholesterol is oxidized to the trihydroxy

o The carbon 17 side chain of cholesterol has been

o The oxidized acid side chain is bonded to an amino

o Bile Acids always carry an amino acid (either glycine

 The dispersion of dietary lipids by bile salts is

 They solubilize deposited cholesterol in the

The fatty acids found in

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