title: Metabolism of 5 alpha-androstane-3 beta,17 beta-diol in bald and hairy areas of the scalp.
abstract: In androgen target tissues, testosterone undergoes extensive biotransformation to 5 alpha-dihydrotestosterone which in turn is metabolized into 5 alpha-androstane-3 alpha,17 beta-diol and 5 alpha-androstane-3 beta,17 beta-diol. From studies mainly in the prostate, it has been shown that 5 alpha-androstane-3 beta, 17 beta-diol can be further converted to 5 alpha-androstane-3 beta,6 alpha(beta)/7 alpha(beta),17 beta-triols. The present studies show that among the metabolites of 5 alpha-androstane-3 beta,17 beta-diol in scalp homogenates, three were isolated by thin-layer chromatography and identified against standard steroids: 5 alpha-dihydrotestosterone, epiandrosterone, and 5 alpha-androstanedione. Another peak was observed near the origin with a greater polarity than 5 alpha-androstane-3 beta,17 beta-diol. The chromatograms obtained by incubating 5 alpha-androstane-3 beta,17 beta-diol with scalp and prostate homogenates are similar, and it is known that the polar metabolites in the prostate are 5 alpha-androstane-3 beta,6 alpha(beta)/7 alpha(beta),17 beta-triols, suggesting that these steroids are formed in both tissues. In addition, the similarity of chromatograms and mass spectra, obtained when 3 beta-diol polar metabolite(s) and authentic 5 alpha-androstane-3 beta,7 beta,17 beta-triol were subjected to GC/MS, confirms this hypothesis. The dependence of the formation of polar metabolites on the substrate (5 alpha-androstane-3 beta, 17 beta-diol) concentration (50 nM-1.3 microM) was studied and resulted in saturation and linear Lineweaver plots from both bald and hairy areas of the scalp.(ABSTRACT TRUNCATED AT 250 WORDS)
authors.affiliation: Department of Pharmacology, School of Medicine, University of Extremadura, Badajoz, Spain.
authors.forename: M J
authors.initials: MJ
authors.lastname: Caballero
mesh_terms: D000505:Alopecia / Q000378:metabolism*; D015113:Androstane-3,17-diol / Q000378:metabolism*; D000738:Androsterone / Q000378:metabolism; D013196:Dihydrotestosterone / Q000378:metabolism; D005043:Etiocholanolone / Q000031:analogs & derivatives / Q000378:metabolism; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D007700:Kinetics; D008297:Male; D012535:Scalp / Q000378:metabolism*
chemical_list: D013196:Dihydrotestosterone; D015113:Androstane-3,17-diol; C006576:androstane-3,17-dione; D005043:Etiocholanolone; D000738:Androsterone