Positional specificity of gamma-ketol formation from linoleic acid hydroperoxides by a corn germ enzyme.

Lipids
H W GardnerD Weisleder

Abstract

We have shown unequivocally that the positional specificity of gamma-ketol formation by a corn germ enzyme was different from that observed previously by others with an alfalfa seedling enzyme. When the pure positional isomers of linoleic acid hydroperoxide served as substrates, the corn germ enzyme formed one of two gamma-ketols: 12-oxo-9-hydroxy-trans-10-octadeconoic acid from 13-hydroperoxys-10-octadecenoic acid from 13-hydroperoxy-cis-9,trans-11-octadecadienoic acid (99+% pure) and 10-oxo-13-hydroxy-trans-11-octadecenoic acid from 9-hydroperoxy-trans-10,cis-12-octadecadienoic acid (96% pure). Also isolated from these reactions was one of two alpha-ketols commonly found as a result of catalysis by linoleic acid hydroperoxide isomerase: 12-oxo-13-hydroxy-cis-9-octadecenoic acid from the 13-hydroperoxide and 10-oxo-9-hydroxy-cis-12-octadecenoic acid from the 9-hydroperoxide. Evidence is offered that gamma-ketol formation is catalyzed by linoleic acid hydroperoxide isomerase, the same enzyme responsible for alpha-ketol production.

References

Aug 1, 1975·Lipids·D D Christianson, H W Gardner
May 25, 1966·Biochemical and Biophysical Research Communications·D C Zimmerman
Sep 1, 1970·Plant Physiology·D C Zimmerman, B A Vick

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Citations

Oct 1, 1995·Journal of Lipid Mediators and Cell Signalling·A R Brash, W C Song
Nov 16, 2002·Prostaglandins & Other Lipid Mediators·Nathalie Tijet, Alan R Brash
Apr 21, 1999·Progress in Lipid Research·A Grechkin
Jul 15, 1991·European Journal of Biochemistry·A N GrechkinA V Ilyasov
Feb 26, 1979·Biochimica Et Biophysica Acta·S GrossmanB Sredni
Sep 30, 1977·Zeitschrift Für Lebensmittel-Untersuchung Und -Forschung·W Heimann, U Timm

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