Antioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study

Abstract 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 funct...

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Autores principales:	Yan-Zhen Zheng, Geng Deng, Qin Liang, Da-Fu Chen, Rui Guo, Rong-Cai Lai
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2017
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/41a17a157b07454b9ce4f79dde65b00a
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spelling	oai:doaj.org-article:41a17a157b07454b9ce4f79dde65b00a2021-12-02T12:31:48ZAntioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study10.1038/s41598-017-08024-82045-2322https://doaj.org/article/41a17a157b07454b9ce4f79dde65b00a2017-08-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-08024-8https://doaj.org/toc/2045-2322Abstract 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.Yan-Zhen ZhengGeng DengQin LiangDa-Fu ChenRui GuoRong-Cai LaiNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-11 (2017)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Yan-Zhen Zheng Geng Deng Qin Liang Da-Fu Chen Rui Guo Rong-Cai Lai Antioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study
description	Abstract 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.
format	article
author	Yan-Zhen Zheng Geng Deng Qin Liang Da-Fu Chen Rui Guo Rong-Cai Lai
author_facet	Yan-Zhen Zheng Geng Deng Qin Liang Da-Fu Chen Rui Guo Rong-Cai Lai
author_sort	Yan-Zhen Zheng
title	Antioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study
title_short	Antioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study
title_full	Antioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study
title_fullStr	Antioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study
title_full_unstemmed	Antioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study
title_sort	antioxidant activity of quercetin and its glucosides from propolis: a theoretical study
publisher	Nature Portfolio
publishDate	2017
url	https://doaj.org/article/41a17a157b07454b9ce4f79dde65b00a
work_keys_str_mv	AT yanzhenzheng antioxidantactivityofquercetinanditsglucosidesfrompropolisatheoreticalstudy AT gengdeng antioxidantactivityofquercetinanditsglucosidesfrompropolisatheoreticalstudy AT qinliang antioxidantactivityofquercetinanditsglucosidesfrompropolisatheoreticalstudy AT dafuchen antioxidantactivityofquercetinanditsglucosidesfrompropolisatheoreticalstudy AT ruiguo antioxidantactivityofquercetinanditsglucosidesfrompropolisatheoreticalstudy AT rongcailai antioxidantactivityofquercetinanditsglucosidesfrompropolisatheoreticalstudy
_version_	1718394273347403776

Antioxidant Activity of Quercetin and Its Glucosides from Propolis: A Theoretical Study

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