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NI LUH PUTU VIDYA

PARAMITA

STEROID

Intoduction
A steroid is an organic compound namely “lipid
terpenoid” with four rings arranged in a
specific configuration.
Steroid occur in plants, animals, and fungi

Examples include the dietary lipid cholesterol, the

sex hormones estradiol and testosterone and
the antiinflammatory drug dexamethasone.

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• Steroids have two principal

biological functions:
• certain steroids (such as
cholesterol) are important
components of cell
membranes which
alter membrane fluidity, and
many steroids are signaling
molecules which
activate steroid hormone
receptors.

Nomenclature
• A steroid is any compound that
contains a
cyclopentanoperhydrophenanthr
ene nucleus
• The chemical nomenclature of
steroids is based on this
fundamental carbocycle with
adjacent side-chain carbon
atoms
• Steroids are numbered and rings
are lettered as indicated in the
structural formula for cholesterol

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steroids widely distributed in animals and plants

Example : steroid which have biological activities

• includes the development and control of the reproductive

tract in humans (estradiol, progesterone, testosterone),
• the molting of insects (ecdysone),
• the induction of sexual reproduction in aquatic fungi
(antheridiol)

Some steroids contribute to therapeutic

applications, such as
• carditionics (digitoxin),
• vitamin D precursors (ergosterol),
• oral contraceptive agents (semisynthetic estrogens and
progestins),
• anti-inflammatory agents (corticosteroids), and
• anabolic agents (androgens)

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Sterols occur in animal and plant oils and fats

They are crystalline compound and contain an

alcoholic group

They occur free or as esters of the higher fatty acids,

and are isolated from the unsaponifiable portion of
oils and fats.
The steroids that are obtained from animal sources 
zoosterols

From plant sources  phytosterols

From yeast and fungi  mycosterols

Animal sterols :

• 1. Cholesterol
• 2. Cholestanol (5α-cholestanol-
3β-ol)
• 3. coprostanol (5β-cholestanol-
3β-ol ol)

Plant sterols :

• 1. β -sitosterol
• 2. stigmasterol

Fungi : ergosterol

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Steroid anabolik

Kortikosteroid (glukokortikoid,
mineralkortikoid)

PENGGOLONGAN Steroid sex

Fitosterol

Ergosterol

Continued…

• The structures of
steroids are based on
the 1, 2-
cyclopentenophenanthr
ene skeleton

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Biosintesis Terpenoid-steroid

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Skema
Biosintesis
Plant Sterol

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Colour Reactions of
Cholesterol

• The Salkowaski reaction

(1908):When concentrated
sulphuric acid is added to
cholesterol in chloroform, a red
colour is produced in the
chloroformlayer.
• The Liebermann- Burchard
reaction (1885, 1890): A
greenish colour is developed
when the solution of
cholesterol in chloroform is
treated with concentrated
sulphuric acid and acetic
anhydride.

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STEROL
The
compound BILE acids
which is
has
nucleus Cardiac glycoside
steroid
Steroid hormone

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Sterol
Cholesterol  human gallstone

β-Sitosterol—plants  wheat germ oil, corn oil, cotton

seed oil

Stigmasitosterol—closely related to β-Sitosterol soy

bean oil  precursor pregnance type steroid hormon

Ergosterol  fungi

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Cholesterol
The most widely occuring sterol is
cholesterol.
It was first isolated from human
gallstones
Found in all animal tissue. It is one
of the chief constituents of lanolin

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Ergosterol
Also known as provitamin D2,
because upon ultraviolet irradiation
Fungal genus Claviceps

Ergosterol forms esters, e.g., acetate

with acetic anhydride

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β-Sitosterol (22, 23-dihydrostigmasterol)

Most common sterol in plants

Widely distributed throughout the plant kingdom and may be obtained

from wheat germ oil, corn oil, cotton seed oil, and other seed oil
β-Sitotsterol lowers plasma concentration of Low Density Lipoprotein
(LDL), has no effect on Very Low Density Lipoprotein (VLDL)
The sterol is believed to lower plasm alevels of cholesterol by interfering
with its absorption.
Dose: 6 gm (withcoffee, tea or milk) taken 30 minutes before meals and at
bet time
The unwanted effectsinclude laxative nausea and vomiting

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Stigmasterol
Closely related to β-Sitosterol

First isolate from calabar beans, but also found in soybean oil

The double bond at the position 22 of stigmasterol allows it to be more

readily converted into the pregnance type steroid hormone than β-
Sitosterol
The extraction of stigmasterol from soybean oil is an important
commercial process

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Bile acids
In the liver of humans and animals

Collected in bile  bile acids

Primary bile acids  cholic acid and chenodesoxycholic acid

Secondary form  desoxycholic acid (from cholic acid), lithocholic

acid (from chenodesoxycholic acid)  produced in intestinal tract

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Cardiac glycoside
Some steroids present in nature are characterized by the highly spesific and powerful
action that they exert on cardiac muscle
These steroids occur as glycosides with sugar attached at the 3-position of the steroid
nucleus
Because of their action on heart muscle, they are named cardiac glycoside

2 types of steroids aglycone or genin ; cardenolides dan bufadienolids

Cardenolida (fam : Schropulariaceae , species Digitalis)

Bufadienolida (fam : Liliaceae , species Urginea)

Uses : congestive heart failure,

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Continued…
Digitalis or foxglove

All species digitalis (D. purpurea, D. lanata, D. grandiflora)

Constituent : digitoxin, gitoxin, gitalotoxin

The total concentration varies appreciably with the plant source and the conditions of
growth, also the manner of treatment of plant material

To ensure potency, the leaves must be rapidly and gently dried at 50 – 60 °C as soon as
the plants are harvested  because the leaf contains hydrolitic enzymes which if not
rapidly inactivates cleave the glycosides linkages, thereby giving to the less active genins

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obtained D. purpurea, D. lanata and other

digitalis species

On hydrolisis digitoxin yields 1 molecule of

Digitoxin digitoxigenin (aglycone) and 3 of
digitoxose (glycon)
(cardiotonic
glycoside ) White or pale buff, odorless,
microcrystalline powder

Insoluble in water, sligthly soluble in

alcohol,

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Digitalis Lanata
Source of cardiac glycoside : digoxin and
desacetyllanatoside

All glycoside are derivatives of 5 different aglycones 

• (1) digitoxigenin,
• (2) gitoxigenin
• (3) gitaloxigenin (aglycone of 1,2,3 are also found in D. purpurea)
• (4) Digoxigenin
• (5) diginatigenin ( aglycone of 4 and 5 only found in D. lanata

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Digoxin

most widely used of

Obtained from the
the cardiotonic
leaves of D. lanata
glycosides

On hydrolisis digoxin
yields 1 molecule of White, crystalline
digoxigenin and 3 of powder
digitoxose

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Deslanoside is desacetyllanatoside

In hydrolysis yields 1 molecule of

digoxigenin, 3 of digitoxose and 1 of
glucose
Deslanoside White, crystalline powder

Frequently used to attain rapid initial

loading by parenteral administration

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• Alkaloids based on the steroid

Steroidal nucleus are not very widely
distributed, being resricted to
alkaloids plants of the Holarrhena,
Solanum and Veratrum species

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