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J Biol Chem, Vol. 274, Issue 16, 10863-10868, April 16, 1999
From the Departments of Pharmacology and Medicine, Vanderbilt
University, Nashville, Tennessee 37232-6602
Cyclopentenone prostaglandins
A2 and J2 are reactive compounds that
possess unique biological activities. However, the extent to which they
are formed in vivo remains unclear. In this study, we
explored whether D2/E2-isoprostanes undergo
dehydration in vivo to form
A2/J2-isoprostanes. Oxidation of arachidonic
acid in vitro generated a series of compounds that were
confirmed to be A2/J2-isoprostanes by mass
spectrometric analyses. A2/J2-isoprostanes were
detected in vivo esterified to lipids in livers from normal rats at a level of 5.1 ± 2.3 ng/g, and levels increased
dramatically by a mean of 24-fold following administration of
CCl4. An A2-isoprostane, 15-A2t-isoprostane, was obtained and found to readily
undergo Michael addition with glutathione and to adduct covalently to protein. A2/J2-isoprostanes could not be
detected in the circulation, even following CCl4
administration, which we hypothesized might be explained by rapid
formation of adducts. This was supported by finding that essentially
all the radioactivity excreted into the urine following infusion of
radiolabeled 15-A2t-isoprostane into a human volunteer was
in the form of a polar conjugate(s). These data identify a new class of
reactive compounds that are produced in vivo as products of
the isoprostane pathway that can exert biological effects relevant to
the pathobiology of oxidant injury.
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