PMID: 9536053Apr 29, 1998Paper

Soybean lipoxygenase-1 oxidizes 3Z-nonenal. A route to 4s-hydroperoxy-2e-nonenal and related products

Plant Physiology
H W Gardner, M J Grove

Abstract

In previous work with soybean (Glycine max), it was reported that the initial product of 3Z-nonenal (NON) oxidation is 4-hydroperoxy-2E-nonenal (4-HPNE). 4-HPNE can be converted to 4-hydroxy-2E-nonenal by a hydroperoxide-dependent peroxygenase. In the present work we have attempted to purify the 4-HPNE-producing oxygenase from soybean seed. Chromatography on various supports had shown that O2 uptake with NON substrate consistently coincided with lipoxygenase (LOX)-1 activity. Compared with oxidation of LOX's preferred substrate, linoleic acid, the activity with NON was about 400- to 1000-fold less. Rather than obtaining the expected 4-HPNE, 4-oxo-2E-nonenal was the principal product of NON oxidation, presumably arising from the enzyme-generated alkoxyl radical of 4-HPNE. In further work a precipitous drop in activity was noted upon dilution of LOX-1 concentration; however, activity could be enhanced by spiking the reaction with 13S-hydroperoxy-9Z, 11E-octadecadienoic acid. Under these conditions the principal product of NON oxidation shifted to the expected 4-HPNE. 4-HPNE was demonstrated to be 83% of the 4S-hydroperoxy-stereoisomer. Therefore, LOX-1 is also a 3Z-alkenal oxygenase, and it exerts the same stereospecificity of ox...Continue Reading

Citations

Aug 4, 2001·Lipids·H W Gardner, N Deighton
Nov 16, 2002·Prostaglandins & Other Lipid Mediators·Alexander N Grechkin
Apr 12, 2003·Progress in Lipid Research·Koji Uchida
Apr 21, 1999·Progress in Lipid Research·A Grechkin
Apr 28, 2001·Biochimica Et Biophysica Acta·P SpitellerG Spiteller
Dec 22, 1999·The Plant Journal : for Cell and Molecular Biology·N DeightonB Williamson
Apr 2, 1999·European Journal of Biochemistry·M KohlmannI Feussner
Feb 16, 2008·Critical Reviews in Food Science and Nutrition·María D Guillén, Encarnación Goicoechea
Jun 6, 2003·Bioscience, Biotechnology, and Biochemistry·Hisao KurodaMasachika Takashio
Oct 12, 2000·Biochemical and Biophysical Research Communications·M A NoordermeerJ F Vliegenthart
Jan 25, 2011·Bioorganic Chemistry·Lucas E ChohanyCharles H Clapp

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