A DFT Analysis on Antioxidant and Antiradical Activities from Anthraquinones Isolated from the Cameroonian Flora
The present work is devoted to the exploration antioxidant and antiradical activity of twenty anthraquinones isolated from the Cameroonian flora at B3LYP/6-311++G(d,p) level of theory using the B3LYP/6-31 + G(d,p) geometrical data as geometry optimization starting points. The single electron transfe...
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| Format: | Article |
| Language: | English |
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Wiley
2019-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2019/7684941 |
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| author | Judith Caroline Ngo Nyobe Laurent Gael Eyia Andiga Désiré Bikele Mama Baruch Ateba Amana Joseph Zobo Mfomo Toze Flavien Aristide Alfred Jean Claude Ndom |
| author_facet | Judith Caroline Ngo Nyobe Laurent Gael Eyia Andiga Désiré Bikele Mama Baruch Ateba Amana Joseph Zobo Mfomo Toze Flavien Aristide Alfred Jean Claude Ndom |
| author_sort | Judith Caroline Ngo Nyobe |
| collection | DOAJ |
| description | The present work is devoted to the exploration antioxidant and antiradical activity of twenty anthraquinones isolated from the Cameroonian flora at B3LYP/6-311++G(d,p) level of theory using the B3LYP/6-31 + G(d,p) geometrical data as geometry optimization starting points. The single electron transfer mechanism has been adopted to examine both biological activities. The classification of the antiradical profile to integrate the electrodonating power (ω−), electroaccepting power (ω+), donor index (Rd) and acceptor index (Ra) has been performed using the donor-acceptor map (DAM). The antioxidant and radical powers of compounds analyzed have been compared to that of two classical vitamins (vitamin C and gallic acid). The stability of each anthraquinone derivative of the molecular library has been developed according to thermodynamic and kinetic concepts. The global reactivity descriptors (GRDs; electrophilicity index (ω), electronegativity (χ), global softness (S), and global hardness (η)) have been used to analyze the reactivity. The topological analysis of optimized structures indicates that the strength of the hydrogen bonds formed is situated between 44.205 and 52.001 kJ/mol. Our B3LYP results reveal that 3-methoxy-1-vismiaquinone (in a configuration without hydrogen bond) exhibits the best antioxidant capacity in gas phase. A comparison between antioxidant performance of molecules examined and that of classical vitamins (gallic acid, caffeic acid, ferulic acid, and ascorbic acid (vitamin C)) displayed the fact that the single electron transfer (SET) mechanism is more prominent for compounds of the molecular library analyzed. In the same vein, the antiradical behaviors of anthraquinone derivatives have shown to be higher than that of gallic acid and vitamin C in gas phase and water. The 5,8-dihydroxy-2-methylantraquinone structure in a configuration bearing one hydrogen bond has been found to be the best antiradical of the series in aqueous solution. |
| format | Article |
| id | doaj-art-fa8c9fc6defb4ef4b760d72afd543ffc |
| institution | Kabale University |
| issn | 2090-9063 2090-9071 |
| language | English |
| publishDate | 2019-01-01 |
| publisher | Wiley |
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| series | Journal of Chemistry |
| spelling | doaj-art-fa8c9fc6defb4ef4b760d72afd543ffc2025-02-03T01:12:35ZengWileyJournal of Chemistry2090-90632090-90712019-01-01201910.1155/2019/76849417684941A DFT Analysis on Antioxidant and Antiradical Activities from Anthraquinones Isolated from the Cameroonian FloraJudith Caroline Ngo Nyobe0Laurent Gael Eyia Andiga1Désiré Bikele Mama2Baruch Ateba Amana3Joseph Zobo Mfomo4Toze Flavien Aristide Alfred5Jean Claude Ndom6Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157, Douala, CameroonDepartment of Inorganic Chemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, CameroonDepartment of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157, Douala, CameroonDepartment of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157, Douala, CameroonDepartment of Forestry and Wood Engeneering, Advances Teachers Training College for Technical Education, University of Douala, P.O. Box 24157, Douala, CameroonDepartment of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157, Douala, CameroonDepartment of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157, Douala, CameroonThe present work is devoted to the exploration antioxidant and antiradical activity of twenty anthraquinones isolated from the Cameroonian flora at B3LYP/6-311++G(d,p) level of theory using the B3LYP/6-31 + G(d,p) geometrical data as geometry optimization starting points. The single electron transfer mechanism has been adopted to examine both biological activities. The classification of the antiradical profile to integrate the electrodonating power (ω−), electroaccepting power (ω+), donor index (Rd) and acceptor index (Ra) has been performed using the donor-acceptor map (DAM). The antioxidant and radical powers of compounds analyzed have been compared to that of two classical vitamins (vitamin C and gallic acid). The stability of each anthraquinone derivative of the molecular library has been developed according to thermodynamic and kinetic concepts. The global reactivity descriptors (GRDs; electrophilicity index (ω), electronegativity (χ), global softness (S), and global hardness (η)) have been used to analyze the reactivity. The topological analysis of optimized structures indicates that the strength of the hydrogen bonds formed is situated between 44.205 and 52.001 kJ/mol. Our B3LYP results reveal that 3-methoxy-1-vismiaquinone (in a configuration without hydrogen bond) exhibits the best antioxidant capacity in gas phase. A comparison between antioxidant performance of molecules examined and that of classical vitamins (gallic acid, caffeic acid, ferulic acid, and ascorbic acid (vitamin C)) displayed the fact that the single electron transfer (SET) mechanism is more prominent for compounds of the molecular library analyzed. In the same vein, the antiradical behaviors of anthraquinone derivatives have shown to be higher than that of gallic acid and vitamin C in gas phase and water. The 5,8-dihydroxy-2-methylantraquinone structure in a configuration bearing one hydrogen bond has been found to be the best antiradical of the series in aqueous solution.http://dx.doi.org/10.1155/2019/7684941 |
| spellingShingle | Judith Caroline Ngo Nyobe Laurent Gael Eyia Andiga Désiré Bikele Mama Baruch Ateba Amana Joseph Zobo Mfomo Toze Flavien Aristide Alfred Jean Claude Ndom A DFT Analysis on Antioxidant and Antiradical Activities from Anthraquinones Isolated from the Cameroonian Flora Journal of Chemistry |
| title | A DFT Analysis on Antioxidant and Antiradical Activities from Anthraquinones Isolated from the Cameroonian Flora |
| title_full | A DFT Analysis on Antioxidant and Antiradical Activities from Anthraquinones Isolated from the Cameroonian Flora |
| title_fullStr | A DFT Analysis on Antioxidant and Antiradical Activities from Anthraquinones Isolated from the Cameroonian Flora |
| title_full_unstemmed | A DFT Analysis on Antioxidant and Antiradical Activities from Anthraquinones Isolated from the Cameroonian Flora |
| title_short | A DFT Analysis on Antioxidant and Antiradical Activities from Anthraquinones Isolated from the Cameroonian Flora |
| title_sort | dft analysis on antioxidant and antiradical activities from anthraquinones isolated from the cameroonian flora |
| url | http://dx.doi.org/10.1155/2019/7684941 |
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