Regiospecific and enantioselective metabolism of 8,9-epoxyeicosatrienoic acid by cyclooxygenase.
8(S),9(R)-epoxyeicosatrienoic acid, a major product of the renal cortex, was found to be a substrate for cyclooxygenase from human platelets and ram seminal vesicles. 11(R)-hydroxy-8(S),9(R)-epoxyeicosatrienoic acid was the sole metabolic product. The 8(R),9(S)-enantiomer formed both C-11 and C-15 hydroxylated metabolites. These novel findings suggest that the cyclooxygenase-dependent renal vasoconstrictor activity of 8(S),9(R)-epoxyeicosatrienoic acid may be due to the 11(R)-hydroxy metabolite.
Zhang
J Y
JY
Department of Pharmacology, Vanderbilt University, Nashville, TN 37232.
Prakash
C
C
Yamashita
K
K
Blair
I A
IA
D015126:8,11,14-Eicosatrienoic Acid / Q000031:analogs & derivatives* / Q000378:metabolism; D000818:Animals; D001792:Blood Platelets / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D006801:Humans; D007536:Isomerism; D008297:Male; D011451:Prostaglandin-Endoperoxide Synthases / Q000302:isolation & purification / Q000378:metabolism*; D012669:Seminal Vesicles / Q000378:metabolism*; D012756:Sheep / Q000378:metabolism
C050715:8,9-epoxyeicosatrienoic acid; D011451:Prostaglandin-Endoperoxide Synthases; D015126:8,11,14-Eicosatrienoic Acid