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(Received for publication, April 23, 1997, and in revised form, June 12, 1997)
From the Inflammatory Diseases Unit, Roche Bioscience,
Palo Alto, California 94303
Because of its structural similarity to
polyunsaturated fatty acids, anandamide could serve as substrate for
enzymes such as lipoxygenases and cyclooxygenases, which metabolize
polyunsaturated fatty acids to potent bioactive metabolites. Here the
ability of recombinant human cyclooxygenase-1 (hCOX-1) and
cyclooxygenase-2 (hCOX-2) to metabolize anandamide was studied.
Baculovirus-expressed and -purified hCOX-2, but not hCOX-1, effectively
oxygenated anandamide. Reverse phase high pressure liquid
chromatography analysis of the products derived from
1-14C-labeled anandamide showed that the products
formed are similar to those formed with arachidonic acid as substrate.
The major prostanoid product derived from anandamide was determined by
mass spectrometry to be prostaglandin E2 ethanolamide.
Incubation of anandamide with lysates and the intact cell line
expressing COX-2 but not that of COX-1 produced prostaglandin
E2 ethanolamide. These results demonstrate the existence of
a COX-2-mediated pathway for anandamide metabolism, and the metabolites
formed represent a novel class of prostaglandins.
Volume 272, Number 34,
Issue of August 22, 1997
pp. 21181-21186
©1997 by The American Society for Biochemistry and Molecular Biology, Inc.
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