STRUCTURE AND PROPERTIES

OF
STEROIDS,CHOLESTEROL,BILE
SALTS AND STEROID
HARMONES
Structure Of Steroids
• Steroid, any of a class of natural or synthetic organic
compounds characterized by a molecular structure of 17
carbon atoms arranged in four rings. consisting of three fused
six-membered and one five-membered ring.
• These are compound which are widely distributed in animals
and plant. Steroids name derived from sterol. Steroids are
characterized by the presence of 1,2 cyclopentophenthrene.
• The steroid group includes all the sex hormones adrenals
cortical hormones, bile acids, and sterols of vertebrates, as
well as the molting hormones of insects and many other
physiologically active substances of animals and plants.
• Steroids vary from one another in the nature of attached
groups, the position of the groups, and the configuration of
the steroid nucleus (orgonane). Small modifications in the
molecular structures of steroids can produce remarkable
differences in their biological activities
Classification
Various authors used slightly different means of classifying the steroids. But here
the one selected here divides them into five categories depending on the type of
substituent group at C-17,i.e., group R
1.Sterols.- where R is an aliphatic side chain. They contain usually one or more
hydroxyl groups attached in alicyclic linkage
2.Sex Hormones:- where R bears a ketonic or hydroxyl group and mostlypossess
a two carbon side chain
3.Cardiac Glycoside - where R is a lactone ring. The glycosides alsocontains
sugars linked through oxygen in other parts of the molecule. Normally on
hydrolysis it yields this sugar together with cardiac aglycon.
4.Bile Acids where R is essentially a five-carbon side chain ending with
acarboxylic acid moiety5.Sapogenins where R contains an oxacyclic (etheral) ring
system.
5.Sapogenins -where R contains an oxacyclic (etheral) ring system
The sterol may be further sub divided into the following three categories,
namely:
a)Zoosterols:- such sterols those are obtained from of plants are obtained
from the animal kingdom only

b)Phytosterols: such sterols those are derived from the plant

sources.

c)Mycosterols: such sterols those are obtained from either yeast or

fungi
SEX HORMONES:
Sex hormones are usually classified under the following three
heads, namely:
PROPERTIES OF STEROIDS:
 We see that steroids in the body can act as hormones, and, therefore, their
presence can impact a number of things from your growth to your sexual
development. For example, steroid hormones are secreted by the testes and
ovaries. From the testes, we see testosterone, which is the male sex hormone
that guides male sexual development. From the ovaries, we see estrogen,
which is the female sex hormone that guides female sexual development.
 Steroid hormones are also produced by the adrenal cortex, which is the outer
portion of your adrenal gland that you can find sitting on top of your kidneys.
Cortisol is one important adrenal cortex steroid hormone, and it regulates
carbohydrate metabolism and has an anti-inflammatory effect on the body.
Aldosterone is another steroid hormone that comes from the adrenal cortex. It
helps maintain blood pressure and regulate the salt and water balance in your
body.
Cholesterol :
 Cholesterol is the most highly decorated small molecule in biology. Thirteen
Nobel Prizes have been awarded to scientists who devoted major parts of
their careers to cholesterol. Ever since it was isolated from gallstones in
1784, cholesterol has exerted an almost hypnotic fascination for scientists
from the most diverse areas of science and medicine.. Cholesterol is a Janus-
faced molecule. The very property that makes it useful in cell membranes,
namely its absolute insolubility in water, also makes it lethal
• Cholesterol is the most abundant steroid in animals
• Plants have very small amounts (but have related compounds).
• It's a major component of cell membranes, and affects the fluidity of the membrane due to its
bulky structure.
• Is a precursor for biosynthesis of many other steroids.
• Cholesterol is called a sterol because it contains an alcohol group.
• We can obtain cholesterol from our diet (animal products), but our liver can also synthesize all
the cholesterol that we need." The liver synthesizes more cholesterol when dietary intake is low.
• Excessive blood cholesterol is associated with atherosclerosis and formation of gallstones
PROPERTIES OF CHOLESTEROL:
1.Membrane:- Cholesterol accounts for roughly 30% of all animal cell
membranes. It is required for the construction and maintenance of membranes, as
well as the modulation of membrane fluidity over a wide range of physiological
temperatures.
2.Gates:- Cholesterol plays a role in intracellular transport, cell signalling, and
nerve conduction within the cell membrane.
3. Signalling:- Cholesterol plays a role in cell signaling by assisting in the
development of lipid rafts in the plasma membrane, which carry receptor proteins
together with high concentrations of second messenger molecules.
4. Chemical Precursor:- Cholesterol is a precursor molecule for many
biochemical processes within cells. It is the precursor molecule for the synthesis
of vitamin D and all steroid hormones, including the adrenal gland hormones
cortisol and aldosterone, as well as the sex hormones progesterone, estrogens,
and testosterone, and their equivalents, in the calcium metabolism.
 BILE SALTS
 Bile acids,Bile salts are bile acids compounded with a cation, usually sodium/ In
humans, the salts of taurocholic acid and glycocholic acid (derivatives of cholic acid)
represent approximately eighty percent of all bile salts.Bile acids, glycine and taurine
conjugates, and 7-alpha-dehydroxylated derivatives (deoxycholic acid and lithocholic
acid) are all found in human intestinal bile.
 An increase in bile flow is exhibited with an increased secretion of bile acids .
 The main function of bile acid is to facilitate the formation of micelles, which
promotes processing of dietary fat.
 Biles acids, are synthesized from cholesterol in the liver. They are cholic acid and
chenodeoxy cholic acid .
 Examples are Glycocholic acid and Taurocholic acid or Glycochenodeoxycholic acid
orTaurochenodeoxycholic acid .Since bile has alkaline pH and it has sodium and
potassium, the bile exists as corresponding salts. They are sodium glycocholate and
sodium taurocholate. These are called as bile salts.
Functions of bile salts:
 Lowering the surface tension: They have the capacity to lower the surface
tension, they aid in the emulsification of fats and tend to stabilize such
emulsions.
 Accelerate the action of pancreatic lipase: In the presence of bile salts, a
colipase binds to lipase and shifts the optimal pH of the enzyme from 9 to 6.
 Micelles formation: Bile salts form micelles with faty acids, mono and
diacyl glycerols and also triglycerides which are made water soluble and
helps absorption.
 Absorption of vitamins: they aid in the absorption of fat soluble
vitamins(A, D, E andK) and also carotene by forming complexes more
soluble in water ( hydrotropic action).
 Intestinal motility: They stimulate the intestinal motility.
REFERENCES
1.https://www.slideshare.net/vasanramkumar/steroids-ppt
2.https://www.slideshare.net/HARISHANKARSAHU/steroids- 52790313
3. Essentials of medical pharmacology, by K.D. THRIPATHI, 6th edition,
pg.no.231-307
4. Principle of medicinal chemistry, by WILLIUM O FOYE, 3rd edition,
pg.no.785-795
5. Organic chemistry of natural of natural product by GURDEEP R
CHATWAL, 2nd vol.pg.no. 4.60-4.97 84