On the structures of hydroxylated metabolites of estradiol 17-sulfate by rat liver microsomes

Steroids. 2002 Oct;67(11):907-15. doi: 10.1016/s0039-128x(02)00057-0.

Abstract

The metabolism of estradiol 17-sulfate (ES) by hepatic microsomes of female rats produced four new metabolites in addition to 2- and 4-hydroxyestradiol 17-sulfates (2- and 4-OH-ES), which were detected on an HPLC chromatogram. By comparison with synthetic specimens, three of these compounds were identified as 6alpha-, 6beta-, and 7beta-hydroxyestradiol 17-sulfates. To elucidate the structure of the remaining metabolite, a large-scale incubation of ES was carried out, followed by isolation using preparative HPLC to give the single material, which was assigned as 15beta-hydroxyestradiol 17-sulfate by instrumental analyses. On the other hand, when ES was incubated with the microsomes of male rats, 2-OH-ES was produced accompanied by two minor products: 4-OH-ES and a metabolite of unknown structure. The results show clearly that the metabolism of ES by rat hepatic microsomes is remarkably different between the sexes.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Chromatography, High Pressure Liquid
  • Estradiol / analogs & derivatives*
  • Estradiol / chemistry*
  • Estradiol / metabolism*
  • Female
  • Hydroxylation
  • Magnetic Resonance Spectroscopy
  • Male
  • Microsomes, Liver / metabolism*
  • Molecular Structure
  • Rats
  • Rats, Wistar
  • Sex Characteristics

Substances

  • estradiol 17-sulfate
  • Estradiol