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Computational Analysis on Antioxidant Activity of Four Characteristic Structural Units from Persimmon Tannin

Antioxidants are molecules that can prevent the harmful effects of oxygen, help capture and neutralize free radicals, and thus eliminate the damage of free radicals to the human body. Persimmon tannin (PT) has excellent antioxidant activity, which is closely related to its molecular structure. We re...

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Detalles Bibliográficos
Autores principales: Wang, Zhongmin, Liu, Zhigao, Wu, Chenxi, Liu, Songlin, Wang, Dianhui, Hu, Chaohao, Chen, Tao, Ran, Zhaojin, Gan, Weijiang, Li, Guiyin
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9821802/
https://www.ncbi.nlm.nih.gov/pubmed/36614657
http://dx.doi.org/10.3390/ma16010320
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author Wang, Zhongmin
Liu, Zhigao
Wu, Chenxi
Liu, Songlin
Wang, Dianhui
Hu, Chaohao
Chen, Tao
Ran, Zhaojin
Gan, Weijiang
Li, Guiyin
author_facet Wang, Zhongmin
Liu, Zhigao
Wu, Chenxi
Liu, Songlin
Wang, Dianhui
Hu, Chaohao
Chen, Tao
Ran, Zhaojin
Gan, Weijiang
Li, Guiyin
author_sort Wang, Zhongmin
collection PubMed
description Antioxidants are molecules that can prevent the harmful effects of oxygen, help capture and neutralize free radicals, and thus eliminate the damage of free radicals to the human body. Persimmon tannin (PT) has excellent antioxidant activity, which is closely related to its molecular structure. We report here a comparative study of four characteristic structural units from PT (epicatechin gallate (ECG), epigallocatechin gallate (EGCG), A−type linked ECG dimer (A−ECG dimer), A−type linked EGCG dimer (A−EGCG dimer)) to explore the structure–activity relationship by using the density functional theory. Based on the antioxidation mechanism of hydrogen atom transfer, the most favorable active site for each molecule exerts antioxidant activity is determined. The structural parameters, molecular electrostatic potential, and frontier molecular orbital indicate that the key active sites are located on the phenolic hydroxyl group of the B ring for ECG and EGCG monomers, and the key active sites of the two dimers are located on the phenolic hydroxyl groups of the A and D’ rings. The natural bond orbital and bond dissociation energy of the phenolic hydroxyl hydrogen atom show that the C(11)−OH in the ECG monomer and the C(12)−OH in the EGCG monomer are the most preferential sites, respectively. The most active site of the two A−linked dimers is likely located on the D’ ring C(20′) phenolic hydroxyl group. Based on computational analysis of quantum chemical parameters, the A−ECG dimer is a more potent antioxidant than the A−EGCG dimer, ECG, and EGCG. This computational analysis provides the structure–activity relationship of the four characteristic units which will contribute to the development of the application of PT antioxidants in the future.
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spelling pubmed-98218022023-01-07 Computational Analysis on Antioxidant Activity of Four Characteristic Structural Units from Persimmon Tannin Wang, Zhongmin Liu, Zhigao Wu, Chenxi Liu, Songlin Wang, Dianhui Hu, Chaohao Chen, Tao Ran, Zhaojin Gan, Weijiang Li, Guiyin Materials (Basel) Communication Antioxidants are molecules that can prevent the harmful effects of oxygen, help capture and neutralize free radicals, and thus eliminate the damage of free radicals to the human body. Persimmon tannin (PT) has excellent antioxidant activity, which is closely related to its molecular structure. We report here a comparative study of four characteristic structural units from PT (epicatechin gallate (ECG), epigallocatechin gallate (EGCG), A−type linked ECG dimer (A−ECG dimer), A−type linked EGCG dimer (A−EGCG dimer)) to explore the structure–activity relationship by using the density functional theory. Based on the antioxidation mechanism of hydrogen atom transfer, the most favorable active site for each molecule exerts antioxidant activity is determined. The structural parameters, molecular electrostatic potential, and frontier molecular orbital indicate that the key active sites are located on the phenolic hydroxyl group of the B ring for ECG and EGCG monomers, and the key active sites of the two dimers are located on the phenolic hydroxyl groups of the A and D’ rings. The natural bond orbital and bond dissociation energy of the phenolic hydroxyl hydrogen atom show that the C(11)−OH in the ECG monomer and the C(12)−OH in the EGCG monomer are the most preferential sites, respectively. The most active site of the two A−linked dimers is likely located on the D’ ring C(20′) phenolic hydroxyl group. Based on computational analysis of quantum chemical parameters, the A−ECG dimer is a more potent antioxidant than the A−EGCG dimer, ECG, and EGCG. This computational analysis provides the structure–activity relationship of the four characteristic units which will contribute to the development of the application of PT antioxidants in the future. MDPI 2022-12-29 /pmc/articles/PMC9821802/ /pubmed/36614657 http://dx.doi.org/10.3390/ma16010320 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/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 (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Communication
Wang, Zhongmin
Liu, Zhigao
Wu, Chenxi
Liu, Songlin
Wang, Dianhui
Hu, Chaohao
Chen, Tao
Ran, Zhaojin
Gan, Weijiang
Li, Guiyin
Computational Analysis on Antioxidant Activity of Four Characteristic Structural Units from Persimmon Tannin
title Computational Analysis on Antioxidant Activity of Four Characteristic Structural Units from Persimmon Tannin
title_full Computational Analysis on Antioxidant Activity of Four Characteristic Structural Units from Persimmon Tannin
title_fullStr Computational Analysis on Antioxidant Activity of Four Characteristic Structural Units from Persimmon Tannin
title_full_unstemmed Computational Analysis on Antioxidant Activity of Four Characteristic Structural Units from Persimmon Tannin
title_short Computational Analysis on Antioxidant Activity of Four Characteristic Structural Units from Persimmon Tannin
title_sort computational analysis on antioxidant activity of four characteristic structural units from persimmon tannin
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9821802/
https://www.ncbi.nlm.nih.gov/pubmed/36614657
http://dx.doi.org/10.3390/ma16010320
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