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.
E H Oliw  1
Affiliations
  • 1. Department of Pharmaceutical Pharmacology, Uppsala University Biomedical Centre, Sweden.
PMID: 1908237 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.

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