Identification of 5,6-trans-epoxyeicosatrienoic acid in the phospholipids of red blood cells

doi:10.1074/jbc.M403962200

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Papers In Press, published online ahead of print June 22, 2004
J. Biol. Chem, 10.1074/jbc.M403962200
Submitted on April 9, 2004
Revised on June 18, 2004
Accepted on June 22, 2004

Identification of 5,6-trans-epoxyeicosatrienoic acid in the phospholipids of red blood cells

Houli Jiang, John C. McGiff, John Quilley, David Sacerdoti, L. Manmohan Reddy, John R. Falck, Fan Zhang, Kenneth M. Lerea, and Patrick Y-K Wong

Pharmacology, New York Medical College, Valhalla, NY 10595

Corresponding Author: houli_jiang{at}nymc.edu

A novel eicosanoid, 5,6-trans-epoxy-8Z,11Z,14Z-eicosatrienoic acid (5,6-trans-EET) was identified in rat red blood cells. Characterization of 5,6-trans-EET in the sn-2 position of the phospholipids was accomplished by hydrolysis with phospholipase A2 followed by gas chromatography/mass spectrometry as well as electrospray ionization tandem mass spectrometry (ESI-MS/MS) analyses. Presence of other trans-EETs was also demonstrated. The ability of both 5,6-trans-EET and its product 5,6-erythro-DHET to relax preconstricted renal interlobar arteries was significantly greater than that of 5,6-cis-EET. In contrast, 5,6-cis-EET and 5,6-trans-EET were equipotent in their capacity to inhibit collagen induced rat platelet aggregation, whereas 5,6-erythro-DHET was without effect. We propose that the red blood cells serve as a reservoir for epoxides which on release may act in a vasoregulatory capacity.

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