Mechanism of antioxidant properties of quercetin and quercetin-DNA complex

• Published in: Journal of molecular modeling Vol. 26; no. 6; p. 133
• Main Authors: Song, Xiaoli, Wang, Yali, Gao, Liguo
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer Berlin Heidelberg 01.06.2020; Springer Nature B.V
• Subjects: Antioxidants; Antioxidants - pharmacology; Characterization and Evaluation of Materials; Chemistry; Chemistry and Materials Science; Computer Appl. in Life Sciences; Computer Applications in Chemistry; Deoxyribonucleic acid; DNA; DNA - chemistry; Enthalpy; Flavonoids; Free Radical Scavengers - pharmacology; Free radicals; Hydroxyl groups; Molecular docking; Molecular Docking Simulation; Molecular Medicine; Original Paper; Quercetin - chemistry; Quercetin - pharmacology; Scavenging; Theoretical and Computational Chemistry; Thiobarbituric acid; Radical scavenging activity; Fukui functions; BDE; Reactivity indices; DNA; Quercetin
• ISSN: 1610-2940; 0948-5023; 0948-5023
• DOI: 10.1007/s00894-020-04356-x

Quercetin is the most abundant flavonoid with potent antioxidant activities. In the current research, the antioxidant properties of quercetin and quercetin-DNA complex were investigated theoretically and experimentally. Free radical scavenging experiments with thiobarbituric acid–reactive substances (TBARS) and 1,1-diphenyl-2-trinitrophenylhydrazine (DPPH) indicate that quercetin can protect DNA from free radical damage, and the antioxidant activity of the quercetin-DNA complex is stronger than quercetin. Deoxyriboseadenine-quercetin-dimethylphosphinic acid (DA-Q-P) model was extracted from molecular docking. The contributions of hydroxyl groups in quercetin and DA-Q-P model molecules to the antioxidant activity were investigated by computation of bond dissociation enthalpy (BDE) parameter and Fukui function, at B3LYP/6-311++G(2d,2p) level of theory. The results outlined that the hydroxyl groups from the B ring (3′-OH and 4′-OH) have a lower BDE compared with the ones from the A and C rings (3-OH, 5-OH, and 7-OH) and hence define antioxidant activity. The computational result based on Fukui function shows that the B ring is an electrophilic region. The interaction of antioxidant with DNA discovered at the molecular level could provide the structural basis of the antioxidant property of active ingredients in the flavonoids. It is of great significance to study the interaction mechanism between the small drug molecules with DNA at the molecular level.