Abstract
Human seminal fluid was recently found to contain 18,19-dehydroprostaglandins E 1 and E 2 (E. H. Oliw, H. Sprecher, and M. Hamberg, (1986) J. Biol. Chem. 261, 2675–2683). In the present study, the cis and trans isomers of 18,19-dehydroprostaglandins E 1 and E 2 were prepared by incubation of microsomes of ram vesicular glands and glutathione with the precursor fatty acids, 8( Z),11( Z),14( Z), 18( E Z )-eicosatetraenoic acids, and 5( Z),8( Z),11( Z),14( Z), 18( E Z )-eicosapentaenoic acids, and used as references to characterize the 18,19-dehydroprostaglandins of human seminal fluid. Based on separation by reversed-phase high-performance liquid chromatography, capillary gas chromatographymass spectrometry, and ozonolysis of the (−)-menthoxycarbonyl derivatives and on comparison with the authentic compounds, human seminal fluid was found to contain both the cis and trans isomers of 18,19-dehydroprostaglandins E 1 and E 2. Furthermore, human seminal fluid contained two related compounds, viz. 19,20-dehydroprostaglandins E 1 and E 2. The structures of these compounds were established by conversion into the corresponding prostaglandin B compounds, by mass spectrometric analysis and by chemical degradation by oxidative ozonolysis, which afforded, inter alia, 2( S)-hydroxyadipic acid.
Published Version
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