Naslov
A DFT Study on the Kinetics of HOO•, CH3OO•, and O2•− Scavenging by Quercetin and Flavonoid Catecholic Metabolites

Autori
Amić, Ana ; Mastiľák Cagardová, Denisa

Izvornik
Antioxidants (2076-3921) 12 (2023), 6; 10.3390/antiox12061154, 17

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

Ključne riječi
density functional theory (DFT) ; kinetics ; quercetin ; catecholic metabolites ; alphitonin ; 5-(3, 4-dihydroxyphenyl)-γ-valerolactone ; peroxyl radicals ; superoxide ; radical scavenging mechanisms

Sažetak
Reaction kinetics have been theoretically examined to ascertain the potency of quercetin (Q) and flavonoid catecholic metabolites 1–5 in the inactivation of HOO•, CH3OO•, and O2•− under physiological conditions. In lipidic media, the k TST/Eck overall rate constants for the proton- coupled electron transfer (PCET) mechanism indicate the catecholic moiety of Q and 1–5 as the most important in HOO• and CH3OO• scavenging. 5- (3, 4-Dihydroxyphenyl)-γ-valerolactone (1) and alphitonin (5) are the most potent scavengers of HOO• and CH3OO•, respectively. The k Mf overall rate constants, representing actual behavior in aqueous media, reveal Q as more potent in the inactivation of HOO• and CH3OO• via single electron transfer (SET). SET from 3-O− phenoxide anion of Q, a structural motif absent in 1–5, represents the most contributing reaction path to overall activity. All studied polyphenolics have a potency of O2•− inactivation via a concerted two- proton–coupled electron transfer (2PCET) mechanism. The obtained results indicate that metabolites with notable radical scavenging potency, and more bioavailability than ingested flavonoids, may contribute to human health- promoting effects ascribed to parent molecules.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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