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(Received for publication, April 24, 1995) From the The free radical oxidation of arachidonic acid esterified to
glycerophospholipids is known to generate complex metabolites, termed
isoprostanes, that share structural features of prostaglandins derived
from prostaglandin H
Volume 270,
Number 29,
Issue of July 21, pp. 17273-17278, 1995
©1995 by The American Society for Biochemistry and Molecular Biology, Inc.
synthase. Furthermore, certain
isoprostanes have been found to exert biological activity through
endogenous receptors on cell surfaces. Using mass spectrometry and
ancillary techniques, the free radical oxidation of
1-hexadecanoyl-2-arachidonoyl-glycerophosphocholine was studied in the
search for products of arachidonic acid isomeric to the leukotrienes
that are derived from 5-lipoxygenase-catalyzed metabolism of
arachidonic acid. Several conjugated triene metabolites were
chromatographically separated from known 5-lipoxygenase products and
structures characterized as 5,12-dihydroxy-6,8,10,14-eicosatetraenoic
acid esterified to the glycerophosphocholine backbone. We have termed
these products as B
-isoleukotrienes. Following
saponification some, but not all, B-isoleukotrienes were
found to exert biological activity in elevating intracellular calcium
in Indo-1-loaded human polymorphonuclear leukocytes. This activity
could be blocked by a leukotriene B receptor antagonist. An
EC of approximately 30 nM was determined for one
unique B
-isoleukotriene with a relative retention index of
2.54. We have shown that free radical processes can lead to the
formation of biologically active isoleukotrienes in
glycerophosphocholine liposomes, and we propose that
B-isoleukotrienes may also be formed in membrane
glycerophospholipids as a result of lipid peroxidation during tissue
injury. Such B-isoleukotrienes could then mediate events of
tissue damage through activation of leukotriene B receptors
on target cells.
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