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DFT Studies on the Antioxidant Activity of Naringenin and Its Derivatives: Effects of the Substituents at C3

The radical scavenging activity of a flavonoid is largely influenced by its structure. The effects of the substituents at C3 position on the antioxidant activity of naringenin were carried out using the density functional theory (DFT) method. The reaction enthalpies related with the three well-estab...

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Autores principales: Zheng, Yan-Zhen, Deng, Geng, Guo, Rui, Chen, Da-Fu, Fu, Zhong-Min
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6470621/
https://www.ncbi.nlm.nih.gov/pubmed/30909377
http://dx.doi.org/10.3390/ijms20061450
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author Zheng, Yan-Zhen
Deng, Geng
Guo, Rui
Chen, Da-Fu
Fu, Zhong-Min
author_facet Zheng, Yan-Zhen
Deng, Geng
Guo, Rui
Chen, Da-Fu
Fu, Zhong-Min
author_sort Zheng, Yan-Zhen
collection PubMed
description The radical scavenging activity of a flavonoid is largely influenced by its structure. The effects of the substituents at C3 position on the antioxidant activity of naringenin were carried out using the density functional theory (DFT) method. The reaction enthalpies related with the three well-established mechanisms were analyzed. Excellent correlations were found between the reaction enthalpies and Hammett sigma constants. Equations obtained from the linear regression can be helpful in the selection of suitable candidates for the synthesis of novel naringenin derivatives with enhanced antioxidant properties. In the gas and benzene phases, the antioxidant activity of naringenin was enhanced by the electron-donating substituents via weakening the bond dissociation enthalpy (BDE). In the water phase, it was strengthened by electron-withdrawing groups—via lowering the proton affinity (PA). The electronic effect of the substituent on the BDE of naringenin is mainly governed by the resonance effect, while that on the ionization potential (IP) and PA of naringenin is mainly controlled by the field/inductive effect.
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spelling pubmed-64706212019-04-26 DFT Studies on the Antioxidant Activity of Naringenin and Its Derivatives: Effects of the Substituents at C3 Zheng, Yan-Zhen Deng, Geng Guo, Rui Chen, Da-Fu Fu, Zhong-Min Int J Mol Sci Article The radical scavenging activity of a flavonoid is largely influenced by its structure. The effects of the substituents at C3 position on the antioxidant activity of naringenin were carried out using the density functional theory (DFT) method. The reaction enthalpies related with the three well-established mechanisms were analyzed. Excellent correlations were found between the reaction enthalpies and Hammett sigma constants. Equations obtained from the linear regression can be helpful in the selection of suitable candidates for the synthesis of novel naringenin derivatives with enhanced antioxidant properties. In the gas and benzene phases, the antioxidant activity of naringenin was enhanced by the electron-donating substituents via weakening the bond dissociation enthalpy (BDE). In the water phase, it was strengthened by electron-withdrawing groups—via lowering the proton affinity (PA). The electronic effect of the substituent on the BDE of naringenin is mainly governed by the resonance effect, while that on the ionization potential (IP) and PA of naringenin is mainly controlled by the field/inductive effect. MDPI 2019-03-22 /pmc/articles/PMC6470621/ /pubmed/30909377 http://dx.doi.org/10.3390/ijms20061450 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Zheng, Yan-Zhen
Deng, Geng
Guo, Rui
Chen, Da-Fu
Fu, Zhong-Min
DFT Studies on the Antioxidant Activity of Naringenin and Its Derivatives: Effects of the Substituents at C3
title DFT Studies on the Antioxidant Activity of Naringenin and Its Derivatives: Effects of the Substituents at C3
title_full DFT Studies on the Antioxidant Activity of Naringenin and Its Derivatives: Effects of the Substituents at C3
title_fullStr DFT Studies on the Antioxidant Activity of Naringenin and Its Derivatives: Effects of the Substituents at C3
title_full_unstemmed DFT Studies on the Antioxidant Activity of Naringenin and Its Derivatives: Effects of the Substituents at C3
title_short DFT Studies on the Antioxidant Activity of Naringenin and Its Derivatives: Effects of the Substituents at C3
title_sort dft studies on the antioxidant activity of naringenin and its derivatives: effects of the substituents at c3
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6470621/
https://www.ncbi.nlm.nih.gov/pubmed/30909377
http://dx.doi.org/10.3390/ijms20061450
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