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23-10-2011
Sterol
Structure of Cholesterol
Molecular formula: C27H45OH
• Molecular formula: C27H45OH
• Possesses cyclopentanoperhydrophenanthrene
nucleus
• Has an –OH group at C3
• Unsaturated double bond between C5 & C6
• Two –CH3 groups at C10 & C13
Properties of cholesterol
• White or faintly yellow crystalline solid
• Almost odourless
• Insoluble in water and soluble in ether, chloroform, hot alcohol,
ethyl acetate & vegetable oils
• Easily crystallizes from such solution in colourless, rhombic plates
with one or more characteristic notches in the corner
• Melting point: 147oC – 150oC
• It can take up two halogen atoms
Forms of cholesterol
• Free form & ester form
• Ester from is esterified with fatty acids at –OH group at
C3 position
• The various fatty acids, which form cholesterol esters are:
Linoleic acid 50%
Oleic acid 18%
Palmitic acid 11%
Arachidonic acid 5%
Other fatty acids 16%
Cont..
• In brain & nervous tissue, free form predominates whereas
in adrenal cortex its occurs mainly as esterified form
• Esterification of cholesterol
Lecithin + Cholesterol Lysolecithin + Cholesterol ester
LCAT
Sterols: Cholesterol
• Functions
– Component of cell membranes
– Precursor to other substances
• Sterol hormones
• Vitamin D
• Bile acids
• Synthesis
– Made mainly in the liver
• Food sources
– Found only in animal foods
Other sterols
• 7-Dehydrocholesterol
• Ergosterol
• Stigmasterol & Sitosterol
• coprosterol
Eicosanoids
Cycloxygenase Lipoxygenase
Prostanoids • Leukotrienes (LTs)
• Lipoxins (LXs)
Prostaglandins (PGs) Prostacyclins (PG-I) Thromboxanes (Tx)
Prostaglandins
• All naturally occurring PGs are 20C fatty acids containing
a cyclopentane ring
• Salient structural features:
- OH group at 15 position
- trans double bond at 13 position
• Synthesized aerobically from polyunsaturated fatty acid
arachidonic acid with the help of multienzyme complex.
Classification of prostaglandins
1. PG-E group: PGE1, PGE2 & PGE3
2. PG-F group: PGF1, PGF2 & PGF3
3. PG-A group: PG-A1, PG-A2, 19-OH PG-A1, 19-OH PG-A2
4. PG-B group: PG-B1, PG-B2, 19-OH PG-B1, 19-OH PG-B2
Besides above 14 PGs, PG-C & PG-D group have also been
recognised
Functions of prostaglandins
• Antihypertensive: lowers BP
• Inhibits platelets aggregation
• Inhibits gastric secretion
• Stimulates GI musculature (purgative action)
• Bronchodilation, used in treatment of bronchial asthma
• Increases uterine contration, can be used as abortifacient
• Renal action: increases RPF, ↑ in GFR, diuresis
• Stimulates renin secretion from JG cells
Cont..
• Metabolic effects:
Decreases lipolysis
Insulin like effect
TSH like effect
Steroidogenesis
THANK
YOU

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cholesterol.pptx

  • 4. • Molecular formula: C27H45OH • Possesses cyclopentanoperhydrophenanthrene nucleus • Has an –OH group at C3 • Unsaturated double bond between C5 & C6 • Two –CH3 groups at C10 & C13
  • 5. Properties of cholesterol • White or faintly yellow crystalline solid • Almost odourless • Insoluble in water and soluble in ether, chloroform, hot alcohol, ethyl acetate & vegetable oils • Easily crystallizes from such solution in colourless, rhombic plates with one or more characteristic notches in the corner • Melting point: 147oC – 150oC • It can take up two halogen atoms
  • 6. Forms of cholesterol • Free form & ester form • Ester from is esterified with fatty acids at –OH group at C3 position • The various fatty acids, which form cholesterol esters are: Linoleic acid 50% Oleic acid 18% Palmitic acid 11% Arachidonic acid 5% Other fatty acids 16%
  • 7. Cont.. • In brain & nervous tissue, free form predominates whereas in adrenal cortex its occurs mainly as esterified form • Esterification of cholesterol Lecithin + Cholesterol Lysolecithin + Cholesterol ester LCAT
  • 8. Sterols: Cholesterol • Functions – Component of cell membranes – Precursor to other substances • Sterol hormones • Vitamin D • Bile acids • Synthesis – Made mainly in the liver • Food sources – Found only in animal foods
  • 9. Other sterols • 7-Dehydrocholesterol • Ergosterol • Stigmasterol & Sitosterol • coprosterol
  • 10. Eicosanoids Cycloxygenase Lipoxygenase Prostanoids • Leukotrienes (LTs) • Lipoxins (LXs) Prostaglandins (PGs) Prostacyclins (PG-I) Thromboxanes (Tx)
  • 11. Prostaglandins • All naturally occurring PGs are 20C fatty acids containing a cyclopentane ring • Salient structural features: - OH group at 15 position - trans double bond at 13 position • Synthesized aerobically from polyunsaturated fatty acid arachidonic acid with the help of multienzyme complex.
  • 12. Classification of prostaglandins 1. PG-E group: PGE1, PGE2 & PGE3 2. PG-F group: PGF1, PGF2 & PGF3 3. PG-A group: PG-A1, PG-A2, 19-OH PG-A1, 19-OH PG-A2 4. PG-B group: PG-B1, PG-B2, 19-OH PG-B1, 19-OH PG-B2 Besides above 14 PGs, PG-C & PG-D group have also been recognised
  • 13. Functions of prostaglandins • Antihypertensive: lowers BP • Inhibits platelets aggregation • Inhibits gastric secretion • Stimulates GI musculature (purgative action) • Bronchodilation, used in treatment of bronchial asthma • Increases uterine contration, can be used as abortifacient • Renal action: increases RPF, ↑ in GFR, diuresis • Stimulates renin secretion from JG cells
  • 14. Cont.. • Metabolic effects: Decreases lipolysis Insulin like effect TSH like effect Steroidogenesis