The identification and characterization of the c19o3 steroid metabolites of 5α-androstane-3β, 17β-diol produced by the canine prostate: 5α-androstane-3β, 6α, 17β-triol and 5α-androstane-3β, 7α, 17β-triol

John T. Isaacs, Ian R. McDermott, Donald S. Coffey

Research output: Contribution to journalArticlepeer-review

Abstract

This study has identified the polar metabolites of 5α-androstane-3β, 17β-diol(3β-diol) produced by the canine prostate. The major metabolite is 5α-androstane-3β, 7α, 17β-triol (7α-triol) accounting for approximately 80% of the total polar metabolites of 3β-diol. The remaining 20% is accounted for exclusively by another triol, 5α-androstane-3β, 6α, 17β-triol(6α-triol). This study has also characterized two enzymatic hydroxylases responsible for respective triol formation: 5α-androstane-3β, 17β-diol 6α-hydroxylase (6α-hydroxylase) and 5α-androstane-3β, 17β-diol 7α-hydroxylase (7α-hydroxylase). Both of these irreversible hydroxylases are located in the particulate fraction of the prostate and can utilize either NADH or NADPH as cofactor. Several in vitro steroid inhibitors of these hydroxylases were identified including cholesterol, estradiol and diethylstilbestrol. Neither of the hydroxylases were found to be decreased by castration (3 months) when expressed as activity/DNA. Using a variety of C19 androstane substrates, 6α- and 7α-triol were found to be major components of the total 3β-hydroxy-5α-androstane metabolites produced by the canine prostate.

Original languageEnglish (US)
Pages (from-to)139-156
Number of pages18
JournalSteroids
Volume35
Issue number2
DOIs
StatePublished - Feb 1980

Keywords

  • 17β-hydroxy-5α-androstan-3-one
  • 3β-hydroxy-5-androsten-17-one
  • 3β-hydroxy-5α-androstan-17-one
  • 4-androstene-3, 17-dione
  • 5α-androstane-3, 17-dione
  • 5α-dihydrotestosterone (DHT)
  • Androstanedione
  • Androstenedione
  • Dehydroepiandrosterone (DHEA)
  • Epiandrosterone
  • estradiol
  • estradiol-17β

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Endocrinology
  • Pharmacology
  • Clinical Biochemistry
  • Organic Chemistry

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