Isolation of 19,20-dehydroprostaglandins E1 and E2 in human seminal fluid and further studies on 18,19-dehydroprostaglandins E1 and E2.
Human seminal fluid was recently found to contain 18,19-dehydroprostaglandins E1 and E2 (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 E1 and E2 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 chromatography-mass 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 E1 and E2. Furthermore, human seminal fluid contained two related compounds, viz. 19,20-dehydroprostaglandins E1 and E2. 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)-hydroxy-adipic acid.
Oliw
E H
EH
Department of Pharmacology, Karolinska Institutet, Stockholm, Sweden.
Benthin
G
G
Hamberg
M
M
D055598:Chemical Phenomena; D002621:Chemistry; D002851:Chromatography, High Pressure Liquid; D015118:Eicosapentaenoic Acid / Q000378:metabolism; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D008297:Male; D013058:Mass Spectrometry; D008861:Microsomes / Q000378:metabolism; D011456:Prostaglandins B / Q000378:metabolism; D011458:Prostaglandins E / Q000032:analysis* / Q000096:biosynthesis; D012661:Semen / Q000032:analysis*; D012669:Seminal Vesicles / Q000378:metabolism; D013237:Stereoisomerism
D011456:Prostaglandins B; D011458:Prostaglandins E; D015118:Eicosapentaenoic Acid