Regiospecific and enantioselective metabolism of 8,9-epoxyeicosatrienoic acid by cyclooxygenase

  • Biochem Biophys Res Commun. 1992 Feb 28;183(1):138-43. doi: 10.1016/0006-291x(92)91619-2.
J Y Zhang  1 ,  C Prakash ,  K Yamashita ,  I A Blair
Affiliations
  • 1. Department of Pharmacology, Vanderbilt University, Nashville, TN 37232.
PMID: 1543485 DOI: 10.1016/0006-291x(92)91619-2
Abstract

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.

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