The Flow of the Redox Energy in Quercetin during Its Antioxidant Activity in Water
Most studies on the antioxidant activity of flavonoids like Quercetin (Q) do not consider that it comprises a series of sequential reactions. Therefore, the present study examines how the redox energy flows through the molecule during Q’s antioxidant activity, by combining experimental data with qua...
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MDPI AG
2020-08-01
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| Series: | International Journal of Molecular Sciences |
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| Online Access: | https://www.mdpi.com/1422-0067/21/17/6015 |
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| author | Zhengwen Li Mohamed Moalin Ming Zhang Lily Vervoort Erik Hursel Alex Mommers Guido R. M. M. Haenen |
| author_facet | Zhengwen Li Mohamed Moalin Ming Zhang Lily Vervoort Erik Hursel Alex Mommers Guido R. M. M. Haenen |
| author_sort | Zhengwen Li |
| collection | DOAJ |
| description | Most studies on the antioxidant activity of flavonoids like Quercetin (Q) do not consider that it comprises a series of sequential reactions. Therefore, the present study examines how the redox energy flows through the molecule during Q’s antioxidant activity, by combining experimental data with quantum calculations. It appears that several main pathways are possible. Pivotal are subsequently: deprotonation of the 7-OH group; intramolecular hydrogen transfer from the 3-OH group to the 4-Oxygen atom; electron transfer leading to two conformers of the Q radical; deprotonation of the OH groups in the B-ring, leading to three different deprotonated Q radicals; and finally electron transfer of each deprotonated Q radical to form the corresponding quercetin quinones. The quinone in which the carbonyl groups are the most separated has the lowest energy content, and is the most abundant quinone. The pathways are also intertwined. The calculations show that Q can pick up redox energy at various sites of the molecule which explains Q’s ability to scavenge all sorts of reactive oxidizing species. In the described pathways, Q picked up, e.g., two hydroxyl radicals, which can be processed and softened by forming quercetin quinone. |
| first_indexed | 2024-03-10T17:03:34Z |
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| id | doaj.art-0dd113c3d5994a8f81f90222ed76ab5a |
| institution | Directory Open Access Journal |
| issn | 1661-6596 1422-0067 |
| language | English |
| last_indexed | 2024-03-10T17:03:34Z |
| publishDate | 2020-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | International Journal of Molecular Sciences |
| spelling | doaj.art-0dd113c3d5994a8f81f90222ed76ab5a2023-11-20T10:52:24ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672020-08-012117601510.3390/ijms21176015The Flow of the Redox Energy in Quercetin during Its Antioxidant Activity in WaterZhengwen Li0Mohamed Moalin1Ming Zhang2Lily Vervoort3Erik Hursel4Alex Mommers5Guido R. M. M. Haenen6Department of Pharmacology and Toxicology, Faculty of Health, Medicine and Life Sciences, Maastricht University, P.O. Box 616, 6200 MD Maastricht, The NetherlandsDepartment of Pharmacology and Toxicology, Faculty of Health, Medicine and Life Sciences, Maastricht University, P.O. Box 616, 6200 MD Maastricht, The NetherlandsDepartment of Pharmacology and Toxicology, Faculty of Health, Medicine and Life Sciences, Maastricht University, P.O. Box 616, 6200 MD Maastricht, The NetherlandsDepartment of Pharmacology and Toxicology, Faculty of Health, Medicine and Life Sciences, Maastricht University, P.O. Box 616, 6200 MD Maastricht, The NetherlandsDepartment of Pharmacology and Toxicology, Faculty of Health, Medicine and Life Sciences, Maastricht University, P.O. Box 616, 6200 MD Maastricht, The NetherlandsDepartment of Pharmacology and Toxicology, Faculty of Health, Medicine and Life Sciences, Maastricht University, P.O. Box 616, 6200 MD Maastricht, The NetherlandsDepartment of Pharmacology and Toxicology, Faculty of Health, Medicine and Life Sciences, Maastricht University, P.O. Box 616, 6200 MD Maastricht, The NetherlandsMost studies on the antioxidant activity of flavonoids like Quercetin (Q) do not consider that it comprises a series of sequential reactions. Therefore, the present study examines how the redox energy flows through the molecule during Q’s antioxidant activity, by combining experimental data with quantum calculations. It appears that several main pathways are possible. Pivotal are subsequently: deprotonation of the 7-OH group; intramolecular hydrogen transfer from the 3-OH group to the 4-Oxygen atom; electron transfer leading to two conformers of the Q radical; deprotonation of the OH groups in the B-ring, leading to three different deprotonated Q radicals; and finally electron transfer of each deprotonated Q radical to form the corresponding quercetin quinones. The quinone in which the carbonyl groups are the most separated has the lowest energy content, and is the most abundant quinone. The pathways are also intertwined. The calculations show that Q can pick up redox energy at various sites of the molecule which explains Q’s ability to scavenge all sorts of reactive oxidizing species. In the described pathways, Q picked up, e.g., two hydroxyl radicals, which can be processed and softened by forming quercetin quinone.https://www.mdpi.com/1422-0067/21/17/6015flavonoidquercetinredox modulationantioxidantmolecular mechanismelectron transfer |
| spellingShingle | Zhengwen Li Mohamed Moalin Ming Zhang Lily Vervoort Erik Hursel Alex Mommers Guido R. M. M. Haenen The Flow of the Redox Energy in Quercetin during Its Antioxidant Activity in Water International Journal of Molecular Sciences flavonoid quercetin redox modulation antioxidant molecular mechanism electron transfer |
| title | The Flow of the Redox Energy in Quercetin during Its Antioxidant Activity in Water |
| title_full | The Flow of the Redox Energy in Quercetin during Its Antioxidant Activity in Water |
| title_fullStr | The Flow of the Redox Energy in Quercetin during Its Antioxidant Activity in Water |
| title_full_unstemmed | The Flow of the Redox Energy in Quercetin during Its Antioxidant Activity in Water |
| title_short | The Flow of the Redox Energy in Quercetin during Its Antioxidant Activity in Water |
| title_sort | flow of the redox energy in quercetin during its antioxidant activity in water |
| topic | flavonoid quercetin redox modulation antioxidant molecular mechanism electron transfer |
| url | https://www.mdpi.com/1422-0067/21/17/6015 |
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