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Isolation of two novel E prostaglandins in human seminal fluid.

1986; Elsevier BV; Volume: 261; Issue: 6 Linguagem: Inglês

10.1016/s0021-9258(17)35840-4

1083-351X

Ernst H. Oliw, Howard Sprecher, Mats Hámberg,

Prostate Cancer Treatment and Research

cis-8,11,14,17-[1-'4C]Eicosatetraenoic acid was incubated with microsomes of ram seminal vesicles and 1 mM glutathione for 3 min at 3'7 "C.The main metabolite was identified as 17,1&dehydroprostaglandinEl by capillary column gas chromatography-mass spectrometry.Human seminal fluid was analyzed for the presence of 17,18-dehydroprostaglandin El and prostaglandin E,.Whereas prostaglandin Es could be demonstrated by capillary gas chromatography-mass spectrometry, 17,18-dehydroprostaglandin El could not be found under these conditions.However, human seminal fluid contained two compounds with a similar polarity on reversed phase high performance liquid chromatography as 17,18-dehydroprostaglandin E, and prostaglandinEs.The two compounds were identified as 18,19-dehydroprostaglandin E1 and 18,19dehydroprostaglandin Es by gas chromatography-mass spectrometry, by UV analysis after conversion to the corresponding prostaglandin B compounds, and by ozonolysis.The amount of each of the two prostaglandins in human seminal fluid seemed to be in the same order of magnitude as the amount of prostagIandin Es.A common feature of eicosanoic fatty acids, which are substrates of fatty acid cyclooxygenase, is three c&double bonds between carbons S-9,11-12, and 14-15.Prostaglandins of the 1, 2, and 3 series are thus derived from three classical substrates, dihomogammalinolenic acid (8,11,14-20:3), arachidonic acid (5,8,11,14-20~4) and eicosapentaenoic acid (5,8,11,14,17-20:5), respectively (1).These three eicosanoids can also be metabolized to prostaglandins in Go, and human seminal fluid contains high concentrations of PGE1', PGE2, and PGE, (2, 3).The biosynthesis of these prostaglandins is influenced by the incorporation and release of the precursor acids from the phospholipids and by the capacity of the cyclooxygenase enzyme to metabolize the different precursor