STEROIDSPrepared byDr. N.GOPINATHANASSISTANT PROFESSORDEPARTMENT OF PHARMACEUTICAL CHEMISTRYFACULTY OF PHARMACYSRI RAMACHANDRA UNIVERSITYCHENNAI-116TAMILNADU

Benzene

Naphthalene

Anthracene

Phenanthrene

Perhydro phenanthrene

cyclopentane

Cyclo penatano perhydro phenanthrene

Ring

A B

C D

Back bone of steroid

CH3

CH3

C 17 position

CH3

CYCLOPENTANO PERHYDRO PHENANTHRENE

Introduction

• Seventeen carbon atoms• Four fused rings • Three six member

cyclohexane rings A, B and C• one five-

member cyclopentane ring D

STEROLS

• Steroids with a hydroxyl group at position three and a skeleton derived from cholestane.

History of steroids

• Cholesterol• Chole - bile • sterol - solid • Greek term

History of steroids

• 1927 {Chemistry} Heinrich Otto Wieland and in 1928 (Chemistry) Adolf Otto Reinhold Windaus

• Constitution of sterols and their connection to vitamins.

History of steroids

• 1939 (Chemistry) Adolf Butenandt and Leopold Ruzicka – Isolation and structural studies of steroid sex hormones, and related studies on higher terpenes

History of steroids

• 1950 (Physiology or Medicine) Edward Calvin Kendall, Tadeus Reichstein, and Philip Hench – Structure and biological effects of adrenal hormone.

History of steroids

• 1965 (Chemistry) Robert Burns Woodward – In part, for the synthesis of cholesterol, cortisone, and lanosterol.

History of steroids

• 1969 (Chemistry) Derek Barton and Odd Hassel – Development of the concept of conformation in chemistry, emphasizing the steroid nucleus.

History of steroids

• 1975 (Chemistry) Vladimir Prelog – In part, for developing methods to determine the stereochemical course of cholesterol biosynthesis from mevalonic acid via squalene

Therapeutic agent

• Birth control

• Hormonal replacement therapy

• Anti-Inflammatory agent

• Cancer treatment

Use of steroids

• Mineralocorticoids effects on Na+, K+ and fluid balance

• Glucocorticoids effects on carbohydrate, protein and fat metabolism

• Androgens effect on muscle development, maturity and coordination.

Identification test

• Libermann Burchard test• Sample is treated with chloroform,

acetic anhydride and sulphuric acid is added along the sides the chloroform layer becomes green in color.

• Dehydrogenated with selenium at 360 degree celsius yield Diels hydrocarbon

Salkowski Reaction

To 2ml of the extract

Add 2ml of chloroform

2ml conc. Sulphuric acid

Shake well

Three different types of steroids

– Anabolic steroid-Most commonly abused

• Function: To increase muscle mass and strength

– Cortico steroid• Function: Artificial cortisone, medically injected to

reduces inflammation and injury.

– Androgenic steroid-Has an anabolic effects on bones, skeletal muscle and vocal chords.

• Function: Used to treat muscle and bone degeneration.

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 mostly possess a two carbon side chain

• 3.Cardiac Glycoside :- where R is a lactone ring . The glycosides also contains 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 a carboxylic acid moiety

5.Sapogenins :- where R contains an oxacyclic (etheral) ring system

Classification of Sterols

Based on their source

(a) Zoosterols:- such sterols those are obtained from of plants are obtained from the animal kingdom only.

(i) Cholesterol, .

(ii)coprostanol.etc

Phytosterols:-such sterols those are derived from the plant sources.

(c) Mycosterols :- such sterols those are obtained from either yeast or fungi.

Miscellaneous

• Zymosterol

• Episterol

• Iophenol

Classification

Estrogen

Estrogen

Adernocortical Steriods

Adernal cortex(Synthesizes two classes of steroids)

Androgen(19 carbon atoms)

Corticosteriods (21 carbon atoms)

Mineralocorticoids (Electrolyte balance regulating)

Glucocorticoids (Carbohydrate metabolism regulating)

Hydrocortisone(cortisol)

Aldosterone

Mevelonate pathway

Steroids from cholesterol

Thank you