Naslov
Free radical scavenging potency of quercetin catecholic colonic metabolites: thermodynamics of 2H+/2e- processes

Autori
Amić, Ana ; Lučić, Bono ; Stepanić, Višnja ; Marković, Zoran ; Marković, Svetlana ; Dimitrić Marković, Jasmina ; Amić, Dragan

Izvornik
Food chemistry (0308-8146) 218 (2017); 144-151

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Quercetin ; Colonic metabolites ; Catecholic compounds ; Radical scavenging ; Double HAT ; Double SPLET

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA