Abstract
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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Arachidonic Acid
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Arachidonic Acids / pharmacology
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Blood Platelets / physiology*
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Chromatography, High Pressure Liquid
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Chromatography, Thin Layer
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Gas Chromatography-Mass Spectrometry
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Humans
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Indicators and Reagents
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Leukotriene B4 / analogs & derivatives*
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Leukotriene B4 / blood
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Leukotriene B4 / chemical synthesis
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Leukotriene B4 / pharmacology
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Magnetic Resonance Spectroscopy
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N-Formylmethionine Leucyl-Phenylalanine / pharmacology
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Neutrophils / drug effects
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Neutrophils / physiology*
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Superoxides / blood
Substances
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Arachidonic Acids
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Indicators and Reagents
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Superoxides
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Leukotriene B4
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Arachidonic Acid
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N-Formylmethionine Leucyl-Phenylalanine
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14,15-leukotriene B4