17R(18S)epoxyeicosatetraenoic acid, a cytochrome P-450 metabolite of 20:5n-3 in monkey seminal vesicles, is metabolized to novel prostaglandins

Biochem Biophys Res Commun. 1991 Aug 15;178(3):1444-50. doi: 10.1016/0006-291x(91)91055-h.

Abstract

Eicosapentaenoic acid (20:5n-3) is metabolized by cytochrome P-450w3 of monkey seminal vesicles to 17R(18S)epoxy-5,8,11,14-eicosatetraenoic acid (17R(18S)EpETE). PGH synthase is abundant in this tissue. Racemic 17(18)EpETE was therefore investigated as a substrate of PGH synthase. The main products were identified as two diastereoisomers of 17(18)epoxyprostaglandin E2, which were formed in a 4:5 ratio. The structures were confirmed by authentic material. The natural epoxide enantiomer can thus be metabolized to novel 17R(18S)epoxyprostaglandins.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Arachidonic Acids / metabolism*
  • Chromatography, High Pressure Liquid
  • Cytochrome P-450 Enzyme System / metabolism*
  • Eicosapentaenoic Acid / metabolism*
  • Haplorhini
  • Male
  • Mass Spectrometry
  • Microsomes / metabolism*
  • Prostaglandins / isolation & purification
  • Prostaglandins / metabolism*
  • Seminal Vesicles / metabolism*
  • Stereoisomerism

Substances

  • Arachidonic Acids
  • Prostaglandins
  • 17,18-epoxy-5,8,11,14-eicosatetraenoic acid
  • Cytochrome P-450 Enzyme System
  • Eicosapentaenoic Acid