On the metabolism of epoxyeicosatrienoic acids by ram seminal vesicles: isolation of 5(6)epoxy-prostaglandin F1 alpha.
cis-5(6)Epoxy- and cis-14(15)epoxyeicosatrienoic acid are formed from arachidonic acid by monooxygenases. 5(6)Epoxyeicosatrienoic acid is metabolized by fatty acid cyclooxygenase of ram seminal vesicles and the major products were recently identified as 5(6)epoxy-PGE1 and two stereoisomers of 5-hydroxy-PGI1. The two isomers were likely formed from an unstable intermediate, 5(6)epoxy-PGF1 alpha. The isolation of 5(6)epoxy-PGF1 alpha is described here and 14(15)epoxyeicosatrienoic acid is shown to inhibit fatty acid cyclooxygenase of ram seminal vesicles, albeit less potently than eicosatetraynoic acid (IC50 0.18 and 0.05 mM, respectively).
D015126:8,11,14-Eicosatrienoic Acid / Q000031:analogs & derivatives / Q000378:metabolism*; D000527:Alprostadil / Q000031:analogs & derivatives*; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D005231:Fatty Acids, Unsaturated / Q000378:metabolism*; D066298:In Vitro Techniques; D007536:Isomerism; D008297:Male; D013058:Mass Spectrometry; D008861:Microsomes / Q000378:metabolism; D011458:Prostaglandins E / Q000096:biosynthesis*; D011460:Prostaglandins F / Q000096:biosynthesis*; D012669:Seminal Vesicles / Q000378:metabolism*; D012756:Sheep; D013237:Stereoisomerism
D005231:Fatty Acids, Unsaturated; D011458:Prostaglandins E; D011460:Prostaglandins F; C040776:5,6-epoxy-8,11,14-eicosatrienoic acid; C044367:5(6)-epoxyprostaglandin E1 alpha; C044368:5(6)-epoxyprostaglandin F1 alpha; D000527:Alprostadil; D015126:8,11,14-Eicosatrienoic Acid