Isolation and Identification of "Diazepam-Like" Compounds From Bovine Urine

Attempts to isolate the putative endogenous ligand for the benzodiazepine receptor from bovine urine resulted in the identification of three isoflavans: equol (1), 3',7-dihydroxyisoflavan (2), and 4'-hydroxy-7-methoxyisoflavan (9), as "diazepam-like" compounds. 3-Chloro-9H-carbaz...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1983-11, Vol.46 (6), p.852-861
Main Authors: Luk, Kin-Chun, Stern, Lorraine, Weigele, Manfred, O'Brien, Robert A, Spirt, Nena
Format: Article
Language:English
Subjects:
Animals
Binding, Competitive
Biological and medical sciences
Cattle
Chemical Phenomena
Chemistry
Diazepam - urine
Medical sciences
Neuropharmacology
Pharmacology. Drug treatments
Psycholeptics: tranquillizer, neuroleptic
Psychology. Psychoanalysis. Psychiatry
Psychopharmacology
Receptors, Cell Surface - metabolism
Receptors, GABA-A
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Summary:Attempts to isolate the putative endogenous ligand for the benzodiazepine receptor from bovine urine resulted in the identification of three isoflavans: equol (1), 3',7-dihydroxyisoflavan (2), and 4'-hydroxy-7-methoxyisoflavan (9), as "diazepam-like" compounds. 3-Chloro-9H-carbazole (17) was found to enhance the binding of diazepam in the benzodiazepine receptor binding assay. Pinosylvine monomethyl ether (18), indigo (20), and indirubin (21) were isolated as inactive compounds.
ISSN:0163-3864
1520-6025
DOI:10.1021/np50030a005