Inhibition of 2,2'-azobis(2,4-dimethylvaleronitrile)-induced lipid peroxidation by sesaminols.
We found that sesaminols, a mixture of sesaminol and its stereoisomers, are potent inhibitors of the oxidation of low-density lipoprotein induced by 2,2'-azobis(2,4-dimethylvaleronitrile). Although sesaminols strongly inhibit lipid peroxidation related to their ability to scavenge free radicals, their antioxidant effects have not been investigated. To confirm the involvement of the phenolic moiety in the sesaminol structure in antioxidant activity, sesaminols were reacted with 2,2'-azobis(2,4-dimethylvaleronitrile). The reaction products were isolated by high-performance liquid chromatography and found to have a 1-cyano-1,3-dimethyl-butyl-peroxyl group in their structures. These chemical structures suggest that the sesaminols reacted with the alkylperoxyl radicals to form four major reaction products that are stereoisomers of each other, although the stereochemistry of each isomer has not yet been confirmed. Further instrumental analyses of the reaction products may increase our understanding of the antioxidant activity of sesaminols.
Kang
M H
MH
Laboratory of Food and Biodynamics, Nagoya University Graduate School of Bioagricultural Sciences, Japan.
Katsuzaki
H
H
Osawa
T
T
D000975:Antioxidants / Q000494:pharmacology*; D001391:Azo Compounds / Q000494:pharmacology*; D002851:Chromatography, High Pressure Liquid; D004149:Dioxoles / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D005609:Free Radicals; D005663:Furans / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology*; D006801:Humans; D007536:Isomerism; D015227:Lipid Peroxidation / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009570:Nitriles / Q000494:pharmacology*; D010084:Oxidation-Reduction; D013997:Time Factors
D000975:Antioxidants; D001391:Azo Compounds; D004149:Dioxoles; D005609:Free Radicals; D005663:Furans; D009570:Nitriles; C055792:2,2'-azobis(2,4-dimethylvaleronitrile); C066016:sesaminol