17R(18S)epoxyeicosatetraenoic acid, a cytochrome P-450 metabolite of 20:5n-3 in monkey seminal vesicles, is metabolized to novel prostaglandins.
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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Department of Pharmaceutical Pharmacology, Uppsala University Biomedical Centre, Sweden.
D000818:Animals; D001095:Arachidonic Acids / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D003577:Cytochrome P-450 Enzyme System / Q000378:metabolism*; D015118:Eicosapentaenoic Acid / Q000378:metabolism*; D000882:Haplorhini; D008297:Male; D013058:Mass Spectrometry; D008861:Microsomes / Q000378:metabolism*; D011453:Prostaglandins / Q000302:isolation & purification / Q000378:metabolism*; D012669:Seminal Vesicles / Q000378:metabolism*; D013237:Stereoisomerism
D001095:Arachidonic Acids; D011453:Prostaglandins; C070378:17,18-epoxy-5,8,11,14-eicosatetraenoic acid; D003577:Cytochrome P-450 Enzyme System; D015118:Eicosapentaenoic Acid