Abstract：
: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.
journal_name
Food Chemjournal_title
Food chemistryauthors
Amić A,Lučić B,Stepanić V,Marković Z,Marković S,Dimitrić Marković JM,Amić Ddoi
10.1016/j.foodchem.2016.09.018subject
Has Abstractpub_date
2017-03-01 00:00:00pages
144-151eissn
0308-8146issn
1873-7072pii
S0308-8146(16)31400-5journal_volume
218pub_type
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