Mevalonate 3 Flashcards
Typifies the fundamental structure of the steroids
Cholesterol
Steroidal surface-active agents with soap-like properties
Steroidal saponins
Steroidal agents which have the ability to cause foaming and hemolyze blood cells
Steroidal saponins
Monocotyledonous family sources of steroidal saponins
Dioscoreaceae
Agavaceae
Liliaceae
3 characteristic features of steroidal saponins
Spiroketal at C-22
Common configuration at C-22
Sugar residues on 3ß-hydroxyl
5 steroidal saponins
Diosgenin Yamogenin/hecogenin Solasodine/tomatidine Smilagenin/sarsasapogenin Tigogenin/neotigogenin
Used to strengthen a weakened heart and allow it to function more efficiently
Cardioactive glycosides
Treatment of dropsy, an accumulation of water in the body tissues
Cardioactive glycosides
Therapeutic action of cardioactive glycosides depends on _____& on _____
Structure of the aglycone
Type & number of sugar units attached
Plants where cardioactive glycosides are confined to
Angiosperms
Aglycone more common than bufadienolides
Cardenolides
2 types of aglycone
Cardenolides
Bufadienolides
Aglycone with 23-C compounds
Cardenolides
Example of cardenolide
Digitoxigenin
Source of digitoxigenin
Digitalis purpurea
Example of bufadienolides
Hellebrigenin
Aglycone with 24-C compounds
Bufadienolides
Source of hellebrigenin
Helleborus niger
4 characteristic features of cardioactive glycosides
Cis-fusion of A/B and C/D rings
14ß-hydroxyl
Unsaturated lactone at C-17ß
Sugar residues on 3ß-hydroxyl
Family sources of cardenolides
Apocynaceae (Strophantus)
Liliaceae (Convallaria)
Scrophulariaceae (Digitalis)
Asclepiaceae (Asclepias syriaca)
Family sources of bufadienolides
Liliaceae (Urginea)
Ranunculaceae (Helleborus)
7 Examples of cardenolides
Digitoxigenin Gitoxigenin Gitaloxigenin Digoxigenin Diginatigenin Strophantidin Ouabigenin
5 examples of bufadienolides
Scillarenin Scillirosidin Hellebrigenin Bufalin 19-norbufalin
Precursor of hellebrigenin via 5ß hydroxylation and C19 oxidation
Bufalin
Source of bufalin
Bufo spp.
Bufadienolide found in human eye;
Believed to regulate ATPase activity
19-norbufalin
Main sterols found in plants
Phytosterols
Modified triterpenoids containing the tetracyclic ring system of lanosterol but lacking the 3-methyl groups at C4 and C14
Steroids
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Contains additional unsaturation in the side chain, a trans-22 double bond
Stigmasterol
Has a ß-oriented 24-methyl, trans-22 double bond, and additional 7 unsaturation
Ergosterol
Predominant steroid found in fungi
Ergosterol
Contains 24-ethylidene substituent
Fucosterol
Source of fucosterol
Brown algae, Fucus spp. (Fam. Fucaceae)
Antibacterial agent active against gram (+) bacteria
Fusidic acid
Source of fusidic acid
Acremonium fusidioides
Substrates for alkylation in phytosterol biosynthesis
Cycloartenol (plants and algae)
Lanosterol (fungi)
Term used for several related steroids and their metabolites that are essential for the absorption and utilization of calcium
Vitamin D (Sunshine vitamin)
Sterol metabolite formed photochemically in animals from 7-dehydrocholesterol by the sun’s irradiation of the skin
Vitamin D3 (Cholecalciferol)
Immediate 5,7 diene precursor of cholesterol
7-dehydrocholesterol
7-dehydrocholesterol forms _______ via photochemical rxn
Precholecalciferol
Precholecalciferol is converted to ______ via thermal 1,7-hydrogen shift
Cholecalciferol
May be obtained from ergosterol;
Employed as a rodenticide
Vitamin D2 (Ergocalciferol)
Active form of vit. D
Calcitriol
Stimulates absorption of calcium and phosphate in the intestine and the mobilization of calcium in the bone
Calcitriol
Used for chronic vit. D deficiency
Calcitriol
Substance prepared by synthetic reduction of tachysterol;
Closely related to ergocalciferol and possesses useful vit. D activity
Dihydrotachysterol
Plant derived sterols necessary for insect growth
Ecdysones
Brassinosteroids
Very polar sterols
Ecdysones
Have moulting hormone activty allowing larval development and metamorphosis
Ecdysones
Specific structural requirement for activity of ecdysones
14alpha-hydroxyl
7-6-keto function
5ß-configuration
Recently discovered plant hormones which have strong growth-promoting activities
Brassinosteroids
Chemical oxidation of ketones yielding an ester
Baeyer-Villiger oxidation
C-24 steroidal acids which occur in salt form in bile, secreted into the gut to emulsify and encourage digestion
Bile acids
Acts as detergents by virtue of their relatively nonpolar steroid nucleus and the polar side chain which contains a carboxylic acid
Bile acids
The carboxylic acid group is typically bound via an AMIDE linkage to _____ or ______
Glycine
Taurine
4 characteristic features of bile acids
C24 cholane skeleton
Cis-fusion of A/B rings
5C-carboxylic acid side chain
3alpha- and 7alpha-hydroxyls
3 examples of bile acids
Chenodeoxycholic acid
Ursodeoxycholic acid
Dehydrocholic acid
Used to dissolve cholesterol gallstones as an alternative to surgery
Ursodeoxycholic acid
May be used after surgery to improve biliary drainage
Dehydrocholic acid
2 cholesterol-lowering drugs;
Binds bile acids and prevent their reabsorption
Cholestyramine and Colestipol
Steroid hormones produced in adrenal cortex which contain pregnane C21 skeleton
Adrenocortical hormones/
Corticosteroids
Two main activity groups of corticosteroids
Glucocorticoids
Mineralocorticoids
Concerned with the synthesis of carbohydrates from proteins and deposition of glycogen in the liver;
Play an impt role in inflammatory processes
Glucocorticoids
2 examples of glucocorticoids
Hydrocortisone/cortisol
Corticosterone
5 Characteristic feature of glucocorticoids
C21 pregnane skeleton 17ß-COCH2OH side shain 11ß-hydroxyl 4-3-keto (usually) 17alpha-hydroxyl (usually)
Concerned with the control of electrolyte balance;
Active compu ds promoting retention of Na and Cl and the excretion of K
Mineralocorticoids
2 examples of mineralocorticoids
Aldosterone Desoxycorticosterone (cortexone)
3 characteristic features of mineralocorticoids
C21 pregnane skeleton
17ß-COCH2OH side chain
4-3-keto (usually)
Also known as progestins or gestogens
Progestogens
Female sex hormones concerned with preparing the uterus for pregnancy
Progestogens
Example of progestogens
Progesterone
Only naturally occurring progestational steroid
Progesterone
Secreted by corpus luteum following release of an ovum
Progesterone
Intermediate in corticosteroid biosynthesis
Progesterone
Progesterone is derived from cholesterol via______ in the formation of cardioactive glycoside
Pregnenolone
2 characteristic features of progesterone
C21 pregnane skeleton
4-3-keto
Female sex hormones produced in ovaries and placenta during pregnancy;
Reesponsible for female sex characteristics
Oestrogens/Estrogens
Controls menstrual cycle with progesterone
Oestrogens/Estrogens
Occurs in free form and as glucoronides at position 3
Estrogens
3 characteristic features of estrogens
C18 estrane skeleton
Aromatic A ring
No side chain
3 examples of estrogens
Estradiol
Oestrone
Oestriol
Catalyzes estrogen synthesis
Aromatase
Main target of aromatase inhibitors which are used in treatment of breast cancer
Aromatase
Male sex hormones secreted by testes;
Responsible for dev’t and maintenance of male sex characteristics
Androgens
Have a secondary physiological effect, an anabolic activity which stimulates growth of bone and muscle, and promotes storage of proteins
Androgens
4 Characteristic features of androgens
C19 androstane skeleton
No side chain
4-3-keto
17ß-hydroxyl
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid
24-methyl analogue of cholesterol
Campesterol
24-ethyl analogue of cholesterol
Sitosterol
Source of campesterol, sitosterol and stigmasterol
Soya beans, Glycine max (Fam. Fabaceae)
Characterized by an extra one-carbon substituents on side chain, attached to C24
Phytosterols
Found predominantly in free alcohol form, but also as esters with long chain fatty acids, as glycosides and as fatty acylated glycoside
Phytosterols
6 Examples of phytosterols
Campesterol Sitosterol Stigmasterol Ergosterol Fucosterol Fusidic acid