The identification and characterization of a new C19O3 steroid metabolite in the rat ventral prostate: 5 alpha-androstane-3 beta, 6 alpha, 17 beta-triol.
This study represents the first report of the formation of 5 alpha-androstane-3 beta, 6 alpha, 17 beta-triol (6 alpha-triol) by prostatic tissue. The 6 alpha-triol has been identified by rigorous methods and a chemical synthesis of this triol has been accomplished. This 6 alpha-triol is the major metabolite of 5 alpha-androstane-3 beta, 17 beta-diol (3 beta-diol) in the rat ventral prostate. A minor metabolite of 3 beta-diol has been identified as 5 alpha-androstane-3 beta, 7 alpha, 17 beta-triol (7 alpha-triol). Using a variety of C19 androstane substrates, the 6 alpha- and 7 alpha-triols were always found as the major components of the total 3 beta-hydroxy-5 alpha-androstane metabolites produced by the ventral prostate. Following intraperitoneal injection of 3H-3 beta-diol, both 6 alpha- and 7 alpha-triol were formed in vivo by the ventral prostate and found in the blood. The 6 alpha- and 7 alpha-triols were found to possess no androgenic activity when tested by the ventral prostatic growth bioassay in the castrate rat.
D000728:Androgens; D015113:Androstane-3,17-diol / Q000378:metabolism / Q000031:analogs & derivatives; D000731:Androstanes / Q000096:biosynthesis / Q000378:metabolism* / Q000494:pharmacology; D000818:Animals; D001681:Biological Assay; D002369:Castration; D006914:Hydroxysteroids / Q000494:pharmacology; D008297:Male; D009928:Organ Specificity; D011467:Prostate / Q000378:metabolism*; D051381:Rats; D013250:Steroid Hydroxylases / Q000378:metabolism
D000728:Androgens; D000731:Androstanes; D006914:Hydroxysteroids; D015113:Androstane-3,17-diol; C020202:androstane-3,6,17-triol; D013250:Steroid Hydroxylases