Method to produce 9(S)-hydroperoxides of linoleic and linolenic acids by maize lipoxygenase. 2001

H W Gardner, and M J Grove
Mycotoxin Research, NCAUR, ARS, USDA, Peoria, Illinois 61604, USA. gardnehw@mail.ncaur.usda.gov

Seed from maize (corn) Zea mays provides a ready source of 9-lipoxygenase that oxidizes linoleic acid and linolenic acid into 9(S)-hydroperoxy-10(E),12(Z)-octadecadienoic acid and 9(S)-hydroperoxy-10(E),12(Z),15(Z)-octadecatrienoic acid, respectively. Corn seed has a very active hydroperoxide-decomposing enzyme, allene oxide synthase (AOS), which must be removed prior to oxidizing the fatty acid. A simple pH 4.5 treatment followed by centrifugation removes most of the AOS activity. Subsequent purification by ammonium sulfate fractional precipitation results in negligible improvement in 9-hydroperoxide formation. This facile alternative method of preparing 9-hydroperoxides has advantages over other commonly used plant lipoxygenases.

UI MeSH Term Description Entries
D008054 Lipid Peroxides Peroxides produced in the presence of a free radical by the oxidation of unsaturated fatty acids in the cell in the presence of molecular oxygen. The formation of lipid peroxides results in the destruction of the original lipid leading to the loss of integrity of the membranes. They therefore cause a variety of toxic effects in vivo and their formation is considered a pathological process in biological systems. Their formation can be inhibited by antioxidants, such as vitamin E, structural separation or low oxygen tension. Fatty Acid Hydroperoxide,Lipid Peroxide,Lipoperoxide,Fatty Acid Hydroperoxides,Lipid Hydroperoxide,Lipoperoxides,Acid Hydroperoxide, Fatty,Acid Hydroperoxides, Fatty,Hydroperoxide, Fatty Acid,Hydroperoxide, Lipid,Hydroperoxides, Fatty Acid,Peroxide, Lipid,Peroxides, Lipid
D008084 Lipoxygenase An enzyme of the oxidoreductase class primarily found in PLANTS. It catalyzes reactions between linoleate and other fatty acids and oxygen to form hydroperoxy-fatty acid derivatives. Lipoxidase,Linoleate-Oxygen Oxidoreductase,Lipoxygenase-1,Lipoxygenase-2,Linoleate Oxygen Oxidoreductase,Lipoxygenase 1,Lipoxygenase 2,Oxidoreductase, Linoleate-Oxygen
D002851 Chromatography, High Pressure Liquid Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed. Chromatography, High Performance Liquid,Chromatography, High Speed Liquid,Chromatography, Liquid, High Pressure,HPLC,High Performance Liquid Chromatography,High-Performance Liquid Chromatography,UPLC,Ultra Performance Liquid Chromatography,Chromatography, High-Performance Liquid,High-Performance Liquid Chromatographies,Liquid Chromatography, High-Performance
D003313 Zea mays A plant species of the family POACEAE. It is a tall grass grown for its EDIBLE GRAIN, corn, used as food and animal FODDER. Corn,Indian Corn,Maize,Teosinte,Zea,Corn, Indian
D006863 Hydrogen-Ion Concentration The normality of a solution with respect to HYDROGEN ions; H+. It is related to acidity measurements in most cases by pH pH,Concentration, Hydrogen-Ion,Concentrations, Hydrogen-Ion,Hydrogen Ion Concentration,Hydrogen-Ion Concentrations
D012639 Seeds The encapsulated embryos of flowering plants. They are used as is or for animal feed because of the high content of concentrated nutrients like starches, proteins, and fats. Rapeseed, cottonseed, and sunflower seed are also produced for the oils (fats) they yield. Diaspores,Elaiosomes,Embryos, Plant,Plant Embryos,Plant Zygotes,Zygotes, Plant,Diaspore,Elaiosome,Embryo, Plant,Plant Embryo,Plant Zygote,Seed,Zygote, Plant
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D017962 alpha-Linolenic Acid A fatty acid that is found in plants and involved in the formation of prostaglandins. Linolenic Acid,Linolenate,alpha-Linolenic Acid, (E,E,E)-Isomer,alpha-Linolenic Acid, (E,E,Z)-Isomer,alpha-Linolenic Acid, (E,Z,E)-Isomer,alpha-Linolenic Acid, (E,Z,Z)-Isomer,alpha-Linolenic Acid, (Z,E,E)-Isomer,alpha-Linolenic Acid, (Z,E,Z)-Isomer,alpha-Linolenic Acid, (Z,Z,E)-Isomer,alpha-Linolenic Acid, Ammonium Salt,alpha-Linolenic Acid, Calcium Salt,alpha-Linolenic Acid, Lithium Salt,alpha-Linolenic Acid, Magnesium Salt,alpha-Linolenic Acid, Potassium Salt,alpha-Linolenic Acid, Sodium Salt,alpha-Linolenic Acid, Tin(2+) Salt,alpha-Linolenic Acid, Zinc Salt,alpha Linolenic Acid,alpha Linolenic Acid, Ammonium Salt,alpha Linolenic Acid, Calcium Salt,alpha Linolenic Acid, Lithium Salt,alpha Linolenic Acid, Magnesium Salt,alpha Linolenic Acid, Potassium Salt,alpha Linolenic Acid, Sodium Salt,alpha Linolenic Acid, Zinc Salt
D019787 Linoleic Acid A doubly unsaturated fatty acid, occurring widely in plant glycosides. It is an essential fatty acid in mammalian nutrition and is used in the biosynthesis of prostaglandins and cell membranes. (From Stedman, 26th ed) 9,12-Octadecadienoic Acid,Linoleate,9-trans,12-trans-Octadecadienoic Acid,Linoelaidic Acid,Linoelaidic Acid, (E,Z)-Isomer,Linoleic Acid, (E,E)-Isomer,Linoleic Acid, (Z,E)-Isomer,Linoleic Acid, (Z,Z)-Isomer,Linoleic Acid, (Z,Z)-Isomer, 14C-Labeled,Linoleic Acid, Ammonium Salt, (Z,Z)-Isomer,Linoleic Acid, Calcium Salt, (Z,Z)-Isomer,Linoleic Acid, Potassium Salt, (Z,Z)-Isomer,Linoleic Acid, Sodium Salt, (E,E)-Isomer,Linoleic Acid, Sodium Salt, (Z,Z)-Isomer,Linolelaidic Acid,cis,cis-9,12-Octadecadienoic Acid,trans,trans-9,12-Octadecadienoic Acid,9 trans,12 trans Octadecadienoic Acid,9,12 Octadecadienoic Acid,Acid, 9,12-Octadecadienoic

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