Journal
FOOD CHEMISTRY
Volume 218, Issue -, Pages 144-151Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.foodchem.2016.09.018
Keywords
Quercetin; Colonic metabolites; Catecholic compounds; Radical scavenging; Double HAT; Double SPLET
Funding
- Ministry of Science, Education and Sports of the Republic of Croatia
- Ministry of Science of the Republic of Serbia [172015, 174028]
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Reaction energetics of the double (2H(+)/2e(-)), i.e., the first 1H(+)/1e(-) (catechol -> phenoxyl radical) and the second 1H(+)/1e(-) (phenoxyl radical -> quinone) free radical scavenging mechanisms of quercetin and its six colonic catecholic metabolites (caffeic acid, hydrocaffeic acid, homoprotocatechuic acid, protocatechuic acid, 4-methylcatechol, and catechol) were computationally studied using density functional theory, with the aim to estimate the antiradical potency of these molecules. We found that second hydrogen atom transfer (HAT) and second sequential proton loss electron transfer (SPLET) mechanisms are less energy demanding than the first ones indicating 2H(+)/2e(-) processes as inherent to catechol moiety. The Gibbs free energy change for reactions of inactivation of selected free radicals indicate that catecholic colonic metabolites constitute an efficient group of more potent scavengers than quercetin itself, able to deactivate various free radicals, under different biological conditions. They could be responsible for the health benefits associated with regular intake of flavonoid-rich diet. (C) 2016 Elsevier Ltd. All rights reserved.
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