The metabolism of the epoxide of testosterone by human placental microsomes.
Although 19-hydroxy-4beta,5-oxido-5beta-androstane-3,17 dione (2a) is converted to estradiol-17beta by human placental microsomes, the incubation of 17beta-hydroxy-4beta,5-oxido-5beta-androstan-3-one (2b) under the same conditions produces only metabolites which are more polar than 17beta-estradiol. The metabolites have been isolated and identified as 3alpha-hydroxy-4beta,5-oxido-5beta-androstan-17-one (4a), 4beta,5-oxido-5beta-androstane-3beta, 17beta-diol (5a) and 4beta,5-oxido-5beta-androstane-3alpha,17beta-diol (6a). These results indicate that functionalization at C-19 is a prerequisite for the biological aromatization of such androgen epoxides.
D002855:Chromatography, Thin Layer; D004852:Epoxy Compounds / Q000378:metabolism; D004958:Estradiol / Q000096:biosynthesis; D004970:Estrone / Q000096:biosynthesis; D005260:Female; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008861:Microsomes / Q000378:metabolism*; D010920:Placenta / Q000378:metabolism*; D011247:Pregnancy; D013055:Spectrophotometry, Infrared; D013739:Testosterone / Q000031:analogs & derivatives* / Q000378:metabolism
D004852:Epoxy Compounds; D004970:Estrone; D013739:Testosterone; D004958:Estradiol