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Antioxidant Effects of Resveratrol and its Analogues against the Free‐Radical‐Induced Peroxidation of Linoleic Acid in Micelles
Author(s) -
Fang JianGuo,
Lu Man,
Chen ZhiHua,
Zhu HuiHe,
Li Yan,
Yang Li,
Wu LongMin,
Liu ZhongLi
Publication year - 2002
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20020916)8:18<4191::aid-chem4191>3.0.co;2-s
Subject(s) - chemistry , antioxidant , lipid peroxidation , resveratrol , linoleic acid , tocopherol , hydroxyl radical , ammonium bromide , radical , micelle , organic chemistry , medicinal chemistry , vitamin e , biochemistry , fatty acid , pulmonary surfactant , aqueous solution
The antioxidant effect of resveratrol (3,4′,5‐trihydroxy‐ trans ‐stilbene) and its analogues, that is, 4‐hydroxy‐ trans ‐stilbene (4‐HS), 3,5‐dihydroxy‐ trans ‐stilbene (3,5‐DHS), 4,4′‐dihydroxy‐ trans ‐stilbene (4,4′‐DHS), 3,4‐dihydroxy‐ trans ‐stilbene (3,4‐DHS), 3,4,5‐trihydroxy‐ trans ‐stilbene (3,4,5‐THS) and 3,4,4′‐trihydroxy‐ trans ‐stilbene (3,4,4′‐THS), against the peroxidation of linoleic acid has been studied in sodium dodecyl sulfate (SDS) and cetyltrimethyl ammonium bromide (CTAB) micelles. The peroxidation was initiated thermally by a water‐soluble azo initiator 2,2′‐azobis(2‐methylpropionamidine) dihydrochloride (AAPH), and the reaction kinetics were studied by monitoring the formation of linoleic acid hydroperoxides. The synergistic antioxidant effect of these compounds with α ‐tocopherol (vitamin E) was also studied by following the decay kinetics of α ‐tocopherol and the reaction intermediate, the α ‐tocopheroxyl radical. Kinetic analysis of the antioxidant process demonstrates that these compounds are effective antioxidants in micelles used either alone or in combination with α ‐tocopherol. The antioxidative action involves trapping the propagating lipid peroxyl radical and reducing the α ‐tocopheroxyl radical to regenerate α ‐tocopherol. It was found that the antioxidant activity of resveratrol analogues depends significantly on the position of the hydroxyl groups, the oxidation potential of the molecule and the reaction medium. Molecules with ortho ‐dihydroxyl and/or para ‐hydroxyl functionalities possess high activity.