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Reaction Dynamics of Flavonoids and Carotenoids as Antioxidants
Department of Chemistry, Renmin University of China, Zhongguancun Street, No. 59, Haidian District, Beijing, 100872, China
Food Chemistry, Department of Food Science, University of Copenhagen, Rolighedsvej 30, DK-1958 Frederiksberg C, Denmark
* Authors to whom correspondence should be addressed.
Received: 4 January 2012; in revised form: 30 January 2012 / Accepted: 3 February 2012 / Published: 21 February 2012
(This article belongs to the Special Issue Carotenoids
Abstract: Flavonoids and carotenoids with rich structural diversity are ubiquitously present in the plant kingdom. Flavonoids, and especially their glycosides, are more hydrophilic than most carotenoids. The interaction of flavonoids with carotenoids occurs accordingly at water/lipid interfaces and has been found important for the functions of flavonoids as antioxidants in the water phase and especially for the function of carotenoids as antioxidants in the lipid phase. Based on real-time kinetic methods for the fast reactions between (iso)flavonoids and radicals of carotenoids, antioxidant synergism during protection of unsaturated lipids has been found to depend on: (i) the appropriate distribution of (iso)flavonoids at water/lipid interface, (ii) the difference between the oxidation potentials of (iso)flavonoid and carotenoid and, (iii) the presence of electron-withdrawing groups in the carotenoid for facile electron transfer. For some (unfavorable) combinations of (iso)flavonoids and carotenoids, antioxidant synergism is replaced by antagonism, despite large potential differences. For contact with the lipid phase, the lipid/water partition coefficient is of importance as a macroscopic property for the flavonoids, while intramolecular rotation towards coplanarity upon oxidation by the carotenoid radical cation has been identified by quantum mechanical calculations to be an important microscopic property. For carotenoids, anchoring in water/lipid interface by hydrophilic groups allow the carotenoids to serve as molecular wiring across membranes for electron transport.
Keywords: flavonoids; carotenoids; antioxidant synergism; antioxidant antagonism; free radical kinetics
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MDPI and ACS Style
Han, R.-M.; Zhang, J.-P.; Skibsted, L.H. Reaction Dynamics of Flavonoids and Carotenoids as Antioxidants. Molecules 2012, 17, 2140-2160.
Han R-M, Zhang J-P, Skibsted LH. Reaction Dynamics of Flavonoids and Carotenoids as Antioxidants. Molecules. 2012; 17(2):2140-2160.
Han, Rui-Min; Zhang, Jian-Ping; Skibsted, Leif H. 2012. "Reaction Dynamics of Flavonoids and Carotenoids as Antioxidants." Molecules 17, no. 2: 2140-2160.