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    Free Radical Scavenging by Natural Polyphenols: Atom versus Electron Transfer
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    † Laboratoire de Chimie des Substances Naturelles EA-1069, Faculté de Pharmacie, Université de Limoges, 2 rue du Docteur Marcland, Limoges CEDEX, France
    ‡ Service de Chimie des Matériaux Nouveaux, Université de Mons - UMONS, Place du Parc 20, 7000 Mons, Belgium
    § Regional Center of Advanced Technologies and Materials, Department of Physical Chemistry, Faculty of Science, Palacký University, 17. listopadu 1192/12, 77146 Olomouc, Czech Republic
    *Tel: +33 (0) 555 435 927. Fax: +33 (0) 555 435 845. E-mail: [email protected]
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    The Journal of Physical Chemistry A

    Cite this: J. Phys. Chem. A 2013, 117, 10, 2082–2092
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    https://doi.org/10.1021/jp3116319
    Published February 18, 2013
    Copyright © 2013 American Chemical Society
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    Abstract

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    Polyphenols (synthetically modified or directly provided by human diet) scavenge free radicals by H-atom transfer and may thus decrease noxious effects due to oxidative stress. Free radical scavenging by polyphenols has been widely theoretically studied from the thermodynamic point of view whereas the kinetic point of view has been much less addressed. The present study describes kinetic-based structure–activity relationship for quercetin. This compound is very characteristic of the wide flavonoid subclass of polyphenols. H-atom transfer is a mechanism based on either atom or electron transfer. This is analyzed here by quantum chemical calculations, which support the knowledge acquired from experimental studies. The competition between the different processes is discussed in terms of the nature of the prereaction complexes, the pH, the formation of activated-deprotonated forms, and the atom- and electron-transfer efficiency. The role of the catechol moiety and the 3-OH group of quercetin as scavengers of different types of free radicals (CH3OO•, CH3O•, •OH, and •CH2OH) is rationalized. Identifying the exact mechanism and accurately evaluating kinetics is of fundamental importance to understand antioxidant behavior in physiological environments.

    Copyright © 2013 American Chemical Society

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    Thermodynamics of HAT between quercetin and the CH3OO• radical. Discussion on kinetic solvent effects (KSE). Energy difference between the highest occupied molecular orbitals of neutral and deprotonated quercetin and various radicals. This material is available free of charge via the Internet at http://pubs.acs.org.

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    Cite this: J. Phys. Chem. A 2013, 117, 10, 2082–2092
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