Steroids
description
Transcript of Steroids
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Steroids
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Steroids
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Steroid A/B and B/C Rings Resemble Decalin
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Methyl groups at C-10 and C-13 are “angular” methyl groups
Steroid B/ C, and C/D rings are trans fused
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Cholesterol
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Structure of Cholesterol
Cholesterol has the fundamental steroid skeleton modified as shown.
HO
CH3
H
H
H
CH3
CH3 CH3
CH3
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Biosynthesis of Cholesterol
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Cholesterol
HO
CH3
H
H
H
CH3
CH3 CH3
CH3
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Vitamin D
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Cholesterol
HO
CH3
H
H
H
CH3
CH3 CH3
CH3
Cholesterol is the precursor to vitamin D.Enzymes dehydrogenate cholesterol to introduce a second double bond in conjugation with the existing one. The product of this reaction is called 7-dehydrocholesterol.
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7-Dehydrocholesterol
HO
CH3
H H
CH3
CH3 CH3
CH3
Sunlight converts 7-dehydrocholesterol on the skin's surface to vitamin D3.
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Vitamin D3
HOH
CH3
CH3 CH3
CH3
Insufficient sunlight can lead to a deficiency of vitamin D3, interfering with Ca2+ transport and bone development. Rickets can result.
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Bile Acids
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Cholesterol
HO
CH3
H
H
H
CH3
CH3 CH3
CH3
Oxidation in the liver degrades the cholesterol side chain. Cholic acid is the most abundant of the bile acids.
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Cholic Acid
Salts of cholic acid amides (bile salts) act as emulsifying agents to aid digestion.
HO
CH3
H
H
H
CH3
CH3
HOH
HOO
OH
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Corticosteroids
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Cholesterol
HO
CH3
H
H
H
CH3
CH3 CH3
CH3
Enzymatic degradation of the side chain and oxidation of various positions on the steroid skeleton convert cholesterol to corticosteroids.
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Cortisone
Corticosteroids are involved in maintaining electrolyte levels, in the metabolism of carbohydrates, and in mediating the allergic response.
O
CH3
H
H
H
CH3OH
O
O
OH
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Sex Hormones
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Testosterone
Testosterone is the main male sex hormone.
OH
H
H
H3C
H3COH
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Estradiol
Estradiol is a female sex hormone involved in regulating the menstrual cycle and in reproduction.
HOH
H
H
H3COH
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Progesterone
Supresses ovulation during pregnancy.
OH
H
H
H3C
H3CO
FDA registers Enovid May 11, 1960 an estrogen and a progestin
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Elwood V. Jensen (1920-2012) Estrogen & Breast Cancer
Enzyme: ER-α
Using radiolabeled markers, Dr. Jensen discovered that estrogen (steroid based hormones) bind to a specific receptor protein, ER, in about 30% of breast cancer cells. In those cancers that are ER positive, inhibition of estrogen stops cell growth.
What type of enzyme inhibition could best stop the multiplication of breast cancer cells?
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Enzyme Inhibition: Estrogen & Breast Cancer
Enzyme: ER-α
Inhibiting a cancer cell’s division
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Estrogen Biosynthesis
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Enzyme Inhibition: Estrogen & Breast Cancer
Inhibiting a cancer cell’s division
Cytochrome p450
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Enzyme Inhibition
Exemestane Androstenedione
Aromatase: Cytochrome p450
Letrozole Anastrozole
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Synthetic Steroids
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Recognizing Lipids: Structural Differences
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Question
Which of the triglycerides below is optically active?
A) 1 and 3 B) 2 and 3 E) noneC) 3 only D) 1, 2, and 3
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Question
Misoprostol is classified as a
A) terpene. B) wax.C) steroid. D) prostaglandin.
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Question
The backbone of cephalosporin P is classified as a
A) prostaglandin. B) steroid.C) cholesterol. D) sesterpene.
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Question
Farnesol is classified as a
A) monoterpene.B) sesquiterpene.C) diterpene.D) triterpene.