V.G.

VAZE COLLEGE OF
ARTS, SCIENCE AND
COMMERCE
MSC PART-2, INTERNALS
STEROIDS
Name: Pranav Arun Patil
Roll no: A007
 TABLE OF CONTENTS
Sr No. Topic name Page No
3-4
1 Introduction
5-6
2 General Structure
7-8
3 Classification

4 Occurrence, Biological Role, Structural

Features of the following
9-12
I. Steroidal Hormones
II. Steroidal Alkaloids 13
14-15
III. Sterols
IV. Bile Acid 16-17

18
5 References
 INTRODUCTION
 Lipids are substances soluble in organic solvents and insoluble in water.
 The extraction of plant and animal tissues with organic solvents such as ether, chloroform or
benzene yields lipids. The lipids so obtained are of two main categories.
 The first includes those that are converted into water-soluble matter on saponification (alkaline
hydrolysis).
 The second group includes those that do not get converted into water-soluble matter on
saponification.
 "Steroids' are compounds falling into the latter category.

 Steroids (Greek stereos solid) are compounds possessing a characteristic tetracyclic carbon skeleton, the
perhydrocyclopentano phenanthrene nucleus.
 They include a wide range of naturally occurring compounds like the sterols, the bile acids, the sex hormones, the
adrenocortical hormones, the cardiac glycosides, the sapogenins and some alkaloids.
 The sterols, the bile acids, the sex hormones and the adrenocortical hormones have a number of functions in human
physiology and are of immense biological importance.
 The most important compound in this class is cholesterol. It is the most abundant steroid present in humans (around
200 8. per average adult) and the most important one as well since all other steroids are derived from it.

Gonane Androstane
Estrane

Cholane
Pregnane
 GENERAL STRUCTURE
 All steroids are related to a characteristic molecular structure composed of 17 carbon atom arranged in four rings
conventionally denoted by the letters A, B, C, and D bonded to 28 hydrogen atoms.

 This parent structure , named gonane (also known as the steroid nucleus), may be modified in a practically unlimited
number of ways by removal, replacement, or addition of a few atoms at a time; hundreds of steroids have been isolated
from plants and animals, and thousands more have been prepared.

 The steroid nucleus is a three-dimensional structure, and atoms or groups are attached to it by spatially directed
bonds. Although many stereoisomers of this nucleus are possible, the saturated nuclear structures of most classes of
natural steroids are alike, except at the junction of rings A and B. For example, androstane, common to a number of
natural and synthetic steroids, exists in two forms , in which the A/B ring fusions are called cis and trans,
respectively.
 In the cis isomer, bonds to the methyl group, CH3, and to the
hydrogen atom, H, both project upward from the general plane defined
by the rest of the molecule, whereas in the trans isomer, the methyl
group projects up and the hydrogen projects down.

 Usually, however, steroid structures are represented as plane

projection diagrams such as 4 and 5, which correspond to 2
and 3, respectively.
 Each carbon atom of a steroid molecule is numbered, and the
number is reserved to a particular position in the
hypothetical parent skeletal structure (6) whether this
position is occupied by a carbon atom or not.
 Steroids vary from one another in the nature of attached
groups, the position of the groups, and the configuration of
the steroid nucleus (or gonane). Small modifications in the
molecular structures of steroids can produce remarkable
differences in their biological activities.
 CLASSIFICATION
 Classification of steroids are done based on their function, with prominent members and examples related to their
functions.

 They are mainly grouped into two classes :corticosteroids (includes glucocorticoids and mineralocorticoids), and sex steroids
(includes progesterone, androgens and estrogens).

 Corticosteroids :

 They are a class of steroid hormones produced in the adrenal cortex of the vertebrates, as well as synthetic analogues
of these hormones.
 There are two main classes of corticosteroids that are glucocorticoids and mineralocorticoids and they are involved in
the various processes of the body, consisting of the stress response, immune response, and regulation of inflammation,
carbohydrate metabolism, protein catabolism, blood electrolyte levels, and behaviour.

 Glucocorticoids (also known as glucocorticosteroids) are a type of steroid hormone that belongs to the
corticosteroids family. Glucocorticoids are corticosteroids that bind to the glucocorticoid receptor, which can be
found in nearly every cell of a vertebrate species.
 Mineralocorticoids are a subclass of corticosteroids, which are steroid hormones themselves.
Mineralocorticoids are hormones that are produced in the adrenal cortex and maintain salt and water balance
in the body
 Sex Steroid Hormones:

 Sex hormones are steroid hormones that bind with vertebrate steroid
hormone receptors. They are also classified as sex steroids,
gonadocorticoids, and gonadal steroids.
 Androgens, estrogens, and progestogens are sex hormones.
 Slow genomic mechanisms, such as nuclear receptors, as well as fast
nongenomic mechanisms, such as membrane-associated receptors and
signalling cascades, mediate their effects.

 Progestogens, which can also be written as

progestogens or gestagens. They are the class of
steroid hormones that bind to and activate the
progesterone receptor (PR).

 Androgen is any natural or synthetic steroid hormone that

binds to receptors in vertebrates and regulates the production
and maintenance of male characteristics.

 Estrogen, also known as oestrogen, is a sex hormone that is

involved in the production and control of the female reproductive
system as well as secondary sex characteristics.
 OCCURRENCE, BIOLOGICAL ROLE, STRUCTURAL
FEATURES OF
 Steroidal Hormones:
 Steroidal hormones are nothing but steroids which acts as hormones. It includes corticosteroids and sex hormones.
Example of sex hormones are- progesterone, estrogen, and testosterone etc.

 Estrogen
Occurrence:
 It is a female sex hormone produced in ovary.
 It is obtained form urine of pregnant women.
Structural features:
 This hormone is regarded as derivative of saturated hydrocarbons.
 Ring A is aromatic in nature and therefore –OH group attached at C3
position is phenolic in nature.
 The ring D contains carbonyl group at C17 position. Ring B and C are trans
to each other.
 Oestrone when treated with hydroxyl amine yield oxime, which indicates
that it has ketonic group.
 Catalytic hydrogenation gives hydrocarbon.
Classification:

Estrone : it is the first estrogenic hormone.

Estradiol : It is another estrogenic hormone which contains –OH

group at c17 position

Biological importance:
 The uterine cycle is controlled of estrogen conjugation with progesterone.
 They are responsible for secondary sex character in female.
 They stimulate growth and development of female reproductive organs.
 After child birth estrogen is used to suppress lactation.

 Androgen

Occurrence :

 It is male sex hormone e.g. testosterone, 5-androsterone, 5-androsterone, etc.

 Testosterone is produced in the testis and metabolizes to androgen and dehydroepiandrosterone are excreted
through urine.
Structural Features :
 Androsterone when treated with hydroxylamine gives
oxime, this indicates the presence of keto group.
 X-ray analysis od androsterone indicates the presence of
steroidal nucleus and proves that –OH group and carbonyl
group are at opposite ends of the molecule.

Biological importance:

 Testosterone is the most important male sex hormone and

metabolizes to androsterone, which promotes muscle growth.
 It is responsible for deepening of voice.
 It promotes growth of body hairs and other male secondary cell
characteristics.
 Androgens are used in the treatment of enlarge prostrate.
  Progesterone
Occurrence:
 Progesterone is an endogenous steroid hormone that is commonly produced by the adrenal cortex as well as the gonads,
which consist of the ovaries and the testes.
 Progesterone is also secreted by the ovarian corpus luteum during the first ten weeks of pregnancy, followed by the placenta
in the later phase of pregnancy.
Structural features :
 It possess 6 chiral center.
 It reacts with two molecules of hydroxylamine to give two
molecules of oxime, this indicates the presence of two keto
groups.
 X-ray analysis indicates that the carbonyl group and acyl group are
opposite to each other.
 Catalytic hydrogenation need six hydrogen to convert two keto
groups into two –OH groups and reduces one double bond.
 This hormone is very sensitive to alkalis which indicates the
presence of ,-unsaturated keto groups.

Biological importance:
 Progesterone plays an important role in your menstrual cycle and pregnancy. Progesterone creates a healthy
uterine lining to support a fertilized egg, embryo and fetus.
 Steroidal Alkaloids:
Occurrence:
 Steroidal alkaloids are nitrogenous derivatives of natural steroids.
 They are an important class of alkaloids and conventional secondary metabolites that occur in plants including
Solanaceae, Liliaceae, Apocynaceae, Buxaceae, amphibians and marine organisms.

Structural Features:

 Steroidal alkaloids are nitrogenous derivatives of natural

steroids.
 Steroidal alkaloids have organic ring backbones which
feature nitrogen-based functional groups.
 More specifically, they are distinguished by their tetracyclic
cyclopentanophenanthrene backbone that marks their close
relationship with sterols

Biological importance :
Steroidal alkaloids cover a wide range of bio-activities:
• Anti-microbial
• Anti-inflammatory
• Anti-estrogenic
 Sterols:
Occurrence:
 These are steroidal alcohols.
 They are present in animals and plants mainly in the form of oil and fats.
 They occur as free alcohol or as ester of higher fatty acids.

Classification:
 Zoosterol: These are obtained from animals e.g.
cholesterol.

 Phytosterol : They are obtained from plants either in free

state or as glycosides in many plants. E.g. Soyabean.

 Mycosterol: They are obtained from fungi or yeast. E.g.

Ergosterol.
 Structure Features:

 The –OH group at C3 is considered cis with respect to methyl

group –CH3 at C10.
 X-ray analysis reveals that the fusion of the ring B and C are trans
to each other.
 Hydrogen atom at C9 is trans to –CH3 group atC10.
 The –CH3 group at C10 and C13 are cis to each other.
 There are seven chiral centers at C5, C8, C9, C10, C13, C14,
C17.

Biological importance:
 Sterols are isoprenoid-derived lipids with essential roles in
cell structure, function, and physiology.
 As important components of biological membranes, sterols
interact with phospholipids and proteins within the
membrane, thereby regulating membrane fluidity,
permeability, and membrane protein functions.
  Bile Acids:
Occurrence:

 Bile acids are steroid acids found predominantly in the bile of mammals and other vertebrates. Diverse bile
acids are synthesized in the liver.
 Bile acids are conjugated with taurine or glycine residues to give anions called bile salts.
 Primary bile acids are those synthesized by the liver.
 Secondary bile acids result from bacterial actions in the colon.

Structural Features:
 All bile acids consist of two connecting
units, a rigid steroid nucleus and a short
aliphatic side chain
 The steroid nucleus of bile acids has the
saturated tetracyclic hydrocarbon
perhydrocyclopentanophenanthrene,
containing three six-member rings (A, B
and C) and a five member ring (D).
 In addition, there are angular methyl groups at positions C-
18 and C-19. In higher vertebrates, the bile acid nucleus is
curved (beaked) because the A and the B rings are in a cis-
fused configuration. Some bile acids in lower vertebrates,
known as allo-bile acids, are flat because of an A/B trans-
fusion (5a-stereochemistry).
 The side chain structure determines the class of the
compound (bile acids or bile alcohols).
 There are two major classes of bile acids depending on the
length of the side chain: C27 and C24 bile acids. In higher
vertebrates, C24 bile acids

Biological importance :
 The main function of bile acid is to facilitate digestion of fats
in the intestine.
 Bile acid is associated with fatty acids, cholesterol, fats that
are water insoluble and makes them soluble by forming
complexes. So that this substances are absorbed in blood.
 They are powerful emulsifying agents.
 REFERENCES

 Natural products chemistry and applications, Sujata V. Bhat, B.A,Nagasampagi and S. Meenakshi, Narosa Publishing
House, 2011.

 Natural Products: Chemistry and Biological Significance Interscience, J. Mann, R.S.Davidson, J.B.Hobbs, D.V.
Banthrope and J. B. Harborne, Longman, Essex, 1994.

 Organic Chemistry Natural Products Volume-II, O. P. Agarwal, Krishna Prakashan, 2011.

 Organic Chemistry, Vol 2, I.L. Finar, ELBS, 6th edition, Pearson

Thank you