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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
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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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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)
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
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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
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
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Stigmasterol
Closely related to β-Sitosterol
First isolate from calabar beans, but also found in soybean oil
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Bile acids
In the liver of humans and animals
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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
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Continued…
Digitalis or foxglove
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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Digitalis Lanata
Source of cardiac glycoside : digoxin and
desacetyllanatoside
• (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
On hydrolisis digoxin
yields 1 molecule of White, crystalline
digoxigenin and 3 of powder
digitoxose
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Deslanoside is desacetyllanatoside
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