C-19-steroid 7 alpha-hydroxylation by rat testes. Isolation and identification of: 7 alpha, 17 beta-dihydroxy-5 alpha-androstan-3-one, 5 alpha-androstan-3 alpha, 7 alpha, 17 beta-triol and 5 alpha-androstane-3 beta, 7 alpha, 17 beta-triol.
From incubations of testosterone with rat testicular homogenates in the presence of a NADPH-generating system, the following 7 alpha-hydroxylated metabolites could be isolated and identified: 7 alpha, 17 beta-dihydroxy-4-androsten-3-one (7 alpha-hydroxy-testosterone), 7 alpha-17 beta-dihydroxy-5 alpha-androstan-3-one (7 alpha-hydroxy-Dht), 5 alpha-androstan-3 alpha, 7 alpha, 17 beta-triol (7 alpha-hydroxy-3 alpha-A'DIOL) and 5 alpha-androstane-3 beta, 7 alpha, 17 beta-triol (7 alpha-hydroxy-3 beta-A'DIOL). To our knowledge this is the first demonstration of the formation of 5 alpha-reduced-7 alpha-hydroxylated metabolites of testosterone in the male gonad. These 5 alpha-reduced-7 alpha-hydroxylated metabolites could also be isolated after incubations of 5 alpha-androstane-3 alpha, 17 beta-diol (3 alpha-A'DIOL) with testicular homogenates in the presence of A NADPH-generating system. Measured as the sum of 7 alpha-hydroxy-testosterone, 7 alpha-hydroxy-Dht. 7 alpha-hydroxy-3 alpha-A'DIOL and 7 alpha-hydroxy-3 beta-A'DIOL formed using testosterone as substrate, total 7 alpha-hydroxylase activity was six times higher in testes of mature rats than in testes from animals 23 days old. With 3 alpha-A'DIOL as substrate total 7 alpha-hydroxylase in the mature testis was about three times greater than in the sexually immature testis.
D015113:Androstane-3,17-diol / Q000031:analogs & derivatives / Q000378:metabolism*; D000732:Androstanols / Q000378:metabolism*; D000818:Animals; D001189:Aryl Hydrocarbon Hydroxylases; D006915:Hydroxytestosterones / Q000378:metabolism*; D007536:Isomerism; D008297:Male; D009249:NADP / Q000378:metabolism; D051381:Rats; D011919:Rats, Inbred Strains; D013250:Steroid Hydroxylases / Q000378:metabolism*; D013739:Testosterone / Q000031:analogs & derivatives*
D000732:Androstanols; D006915:Hydroxytestosterones; C034823:7-hydroxydihydrotestosterone; C015680:androstane-3,7,17-triol; D015113:Androstane-3,17-diol; D013739:Testosterone; D009249:NADP; D013250:Steroid Hydroxylases; D001189:Aryl Hydrocarbon Hydroxylases; C029009:steroid hormone 7-alpha-hydroxylase