Evidence for a 5(6)-epoxytetraene intermediate in the biosynthesis of lipoxins in human leukocytes. Conversion into lipoxin A by cytosolic epoxide hydrolase

FEBS Letters
T PuustinenB Samuelsson

Abstract

The existence of a 15(S)-hydroxy-5,6-oxido-7,9,13-trans-11-cis-eicosatetraenoic acid intermediate in the biosynthesis of lipoxins A and B has recently been proposed. In the present study, human leukocytes were exposed to 15-HETE and the divalent cation ionophore A23187 and alcohol trapping studies were performed. The products containing alkyltetraenes were isolated and characterized. HPLC analysis, UV spectroscopy and GC/MS of the products showed that 5,15-dihydroxy-14-O-alkyleicosatetraenoic acids were formed, indicating that 5(6)-epoxytetraenes (precursor of the trapping product) were formed in human leukocytes. To gain further evidence for the role of 5(6)-epoxytetraene intermediate in the biosynthesis of lipoxins, (15)-hydroxy-5,6-oxido-7,9,13-trans-11-cis-eicosatetraenoic acid was prepared by total chemical synthesis. When added to purified human liver cytosolic epoxide hydrolase, the epoxide was rapidly and quantitatively converted into LXA. The results provide further evidence for the role of a 5(6)epoxytetraene intermediate in the biosynthesis of lipoxins.

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Citations

May 22, 1988·Biochimica Et Biophysica Acta·R BrasseurC N Serhan
Aug 22, 1989·Biochimica Et Biophysica Acta·C F NgP Y Wong
Jul 30, 1991·Biochimica Et Biophysica Acta·A F Rowley
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Dec 15, 1988·Biochemical and Biophysical Research Communications·C EdeniusJ A Lindgren
Sep 2, 2005·Journal of Medicinal Chemistry·K C Nicolaou

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