Stereochemistry, total synthesis, and biological activity of 14,15-dihydroxy-5,8,10,12-eicosatetraenoic acid.
The stereochemistry of the major isomer of 14,15-dihydroxy-5,8,10,12-eicosatetraenoic acid formed from 15-hydroperoxyeicosatetraenoic acid in human leukocytes was determined. The structure (erythro-14(R),15(S]-14,15-dihydroxy-5,8-cis-10,12-trans-eicosatetraenoi c acid) was assigned based on sodium arsenite thin-layer chromatography, NMR spectroscopy, and comparison with material prepared by total synthesis. This compound was found to inhibit leukotriene B4-induced superoxide anion generation in human neutrophils (IC50 = 10(-8)-10(-7) M). Superoxide anion generation induced by either formylmethionyl-leucyl-phenylalanine or arachidonic acid was not affected.
D016718:Arachidonic Acid; D001095:Arachidonic Acids / Q000494:pharmacology; D001792:Blood Platelets / Q000502:physiology*; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D007202:Indicators and Reagents; D007975:Leukotriene B4 / Q000031:analogs & derivatives* / Q000097:blood / Q000138:chemical synthesis / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D009240:N-Formylmethionine Leucyl-Phenylalanine / Q000494:pharmacology; D009504:Neutrophils / Q000187:drug effects / Q000502:physiology*; D013481:Superoxides / Q000097:blood
D001095:Arachidonic Acids; D007202:Indicators and Reagents; D013481:Superoxides; D007975:Leukotriene B4; D016718:Arachidonic Acid; D009240:N-Formylmethionine Leucyl-Phenylalanine; C030723:14,15-leukotriene B4