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Antioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study
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Antioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study
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Journal Article
Antioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study
2017
Overview
Among the multiple components of propolis, flavonoids contribute greatly to the antioxidant activities of propolis. Flavonoids mainly exist in the form of sugar-conjugated derivatives. Quercetin glycosides represent the predominant flavonoid fraction in propolis. In this work, density functional theory (DFT) calculations were applied to analyze the antioxidative properties of quercetin and its glucosides in the gas and in the liquid phase (ethanol, water). Three main antioxidant mechanisms, hydrogen atom transfer (HAT), single electron transfer followed by proton transfer (SET-PT) and sequential proton loss electron transfer (SPLET) were used to analyze the antioxidative capacity of the investigated compounds. Solvent effects dominantly affect SET-PT and SPLET. Thus, the thermodynamically preferred mechanism can be altered. HAT and SPLET are the thermodynamically dominant mechanisms in gas and solvent phases, respectively. Therefore, in the gas phase, the sequence of the antioxidative capacity is similar with the bond dissociation enthalpy values: quercetin > quercetin-5-
O
-glucoside > quercetin-7-
O
-glucoside > quercetin-3-
O
-glucoside > quercetin-3′-
O
-glucoside > quercetin-4′-
O
-glucoside. While, in the solvent phases, the sequence is similar with the proton affinity values: quercetin-4′-
O
-glucoside > quercetin-5-
O
-glucoside > quercetin > quercetin-3-
O
-glucoside > quercetin-7-
O
-glucoside > quercetin-3′-
O
-glucoside. OH groups in B-ring and C-ring contribute mainly to the antioxidative activities of quercetin and glucosides compared with A-ring.
Publisher
Nature Publishing Group UK,Nature Publishing Group,Nature Portfolio
Subject
