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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2019
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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. |
format | Online Article Text |
id | pubmed-6470621 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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