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Free Radical Scavenging by Natural Polyphenols: Atom versus Electron Transfer

Di Meo, Florent, Lemaur, Vincent, Cornil, Jérôme, Lazzaroni, Roberto, Duroux, Jean-Luc, Olivier, Yoann, Trouillas, Patrick·2013·The Journal of Physical Chemistry A

DOI 10.1021/jp3116319

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Abstract

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.

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Authors: Di Meo, F., Lemaur, V., Cornil, J., Lazzaroni, R., Duroux, J.-L., Olivier, Y., & Trouillas, P.
Venue: The Journal of Physical Chemistry A
Publisher: American Chemical Society (ACS)
Published: 2013-03-05
Volume: 117
Issue: 10
Pages: 2082-2092
ISSN: 1089-5639 (ISSN-L)
1520-5215
DOI: 10.1021/jp3116319
OpenAlex: W2325469858
Cited by: 294
References: 63
FWCI: 10.09
Type: journal article
Language: en
Open access: closed

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Free Radical Scavenging by Natural Polyphenols: Atom versus Electron Transfer

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