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J. Biol. Chem., Vol. 259, Issue 22, 14048-14053, 11, 1984
NK Hopkins, TD Oglesby, GL Bundy and RR Gorman
Incubation of cultured human umbilical vein endothelial cells with [1-
14C]arachidonic acid, followed by reverse-phase high-pressure liquid
chromatography analysis, results in the appearance of two principal
radioactive products besides 6-keto-prostaglandin F1 alpha. The first peak
is 12-L-hydroxy-5,8,10-heptadecatrienoic acid, a hydrolysis product of the
prostaglandin endoperoxide. The second peak was esterified, converted to
the trimethylsilyl ether derivative, and analyzed by gas
chromatography-mass spectrometry and shown to be the lipoxygenase product
15(S)-hydroxy-5,8,11,13-eicosatetraenoic acid (15- HETE). Incubation of the
15-HETE precursor 15(S)-hydroperoxy-5,8,11,13- eicosatetraenoic acid
(15-HPETE) with endothelial cells results in the formation of four distinct
UV absorbing peaks. UV and gas chromatography-mass spectrometry analysis
showed these peaks to be 8,15(S)-dihydroxy-5,8,11,13-eicosatetraenoic acids
(8,15-diHETE) differing only in their hydroxyl configuration and cis trans
double- bond geometry. Formation of 8,15-diHETE molecules suggests the
prior formation of the unstable epoxide molecule
14(S),15(S)-trans-oxido-5,8- Z-14,15-leukotriene A4 or an attack at C-10 of
15-HPETE by an enzyme with mechanistic features in common with a
12-lipoxygenase. The observation that endothelial cells can synthesize both
15-HETE and 8,15- diHETE molecules suggests that this cell type contains
both a 15- lipoxygenase and a system that can synthesize 14,15-leukotriene
A4.
Biosynthesis and metabolism of 15-hydroperoxy-5,8,11,13- eicosatetraenoic acid by human umbilical vein endothelial cells
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