Mechanism of biosynthesis of 11R-and 12R-hydroxyeicosatetraenoic acids by eggs of the sea urchin Strongylocentrotus purpuratus

FEBS Letters
D J Hawkins, A R Brash

Abstract

11(R)-Hydroxyeicosatetraenoic acid [11(R)-HETE] and 12(R)-HETE are biosynthesized by eggs of the sea urchin S. purpuratus. We report here the isolation of the 11(4)- and 12(R)-hydroperoxy-eicosanoids from incubations of the desalted 30-50%(NH4)2SO4 fraction of the egg homogenate; biosynthesis required the addition of calcium but not NADPH. Egg 11- and 12-HETE were formed from octadeuterated arachidonic acid without loss of geminal 2H from C11 or C12, thus revealing that 11- or 12-keto intermediates are not involved in the biosynthesis. The results support the conclusion that egg 11(R)- and 12(R)-HETE are synthesized by a lipoxygenase and not by an NADPH-dependent cytochrome P450 monooxygenase mechanism.

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Citations

Aug 30, 2000·Prostaglandins & Other Lipid Mediators·H Kuhn
Nov 16, 2002·Prostaglandins & Other Lipid Mediators·Claus Schneider, Alan R Brash
Jun 17, 1998·Proceedings of the National Academy of Sciences of the United States of America·W E BoeglinA R Brash
Dec 1, 1989·Prostaglandins, Leukotrienes, and Essential Fatty Acids·D J Fretland, S W Djuric
Dec 3, 2005·Archives of Biochemistry and Biophysics·Monika MortimerIvar Järving
Oct 1, 1994·Prostaglandins, Leukotrienes, and Essential Fatty Acids·L De Petrocellis, V Di Marzo
May 15, 2007·Comparative Biochemistry and Physiology. Part B, Biochemistry & Molecular Biology·Edward C PopeAndrew F Rowley

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