Antioxidation Mechanism Studies of Caffeic Acid: Identification of Antioxidation Products of Methyl Caffeate from Lipid Oxidation

As a part of a research project on the elucidation of the chain-breaking antioxidation mechanism of natural phenols in food components, caffeic acid, a polyphenolic acid widely distributed in edible plants, was investigated. The identification and time course analysis of the antioxidation reaction p...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2008-07, Vol.56 (14), p.5947-5952
Main Authors: Masuda, Toshiya, Yamada, Kazuki, Akiyama, Jun, Someya, Tatsushi, Odaka, Yuka, Takeda, Yoshio, Tori, Motoo, Nakashima, Katsuyuki, Maekawa, Tomomi, Sone, Yoshiaki
Format: Article
Language:English
Subjects:
antioxidant activity
antioxidants
Antioxidants - analysis
Antioxidants - chemistry
Antioxidation mechanism
biochemical pathways
Biological and medical sciences
caffeic acid
Caffeic Acids - analysis
Caffeic Acids - chemistry
chemical constituents of plants
chemical structure
Diels−Alder reaction
esters
ethyl linoleate
Food Chemistry/Biochemistry
Food industries
Fundamental and applied biological sciences. Psychology
Kinetics
Lipid Peroxidation
lipids
Magnetic Resonance Spectroscopy
methyl caffeate
o-quinone
Oxidation-Reduction
oxygen
peroxidases
peroxidation
physicochemical properties
Plants, Edible - chemistry
quinones
Quinones - chemistry
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Summary:As a part of a research project on the elucidation of the chain-breaking antioxidation mechanism of natural phenols in food components, caffeic acid, a polyphenolic acid widely distributed in edible plants, was investigated. The identification and time course analysis of the antioxidation reaction products from methyl caffeate were carried out in the ethyl linoleate oxidation system. The antioxidation reaction produced a quinone derivative of methyl caffeate as an antioxidation product during the initial stage, which was identified by 13C NMR. The quinone, however, was not the final product, and a further reaction occurred to produce several new peroxides. The isolation and structure determination of the peroxides revealed that they had tricyclic structures, which consisted of ethyl linoleate, methyl caffeate, and molecular oxygen. On the basis of the formation pathway of these products, an antioxidation reaction mechanism of methyl caffeate, including the redox reaction of the caffeate and Diels−Alder reaction of the produced peroxides, was proposed.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf800781b