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Fisetin and Robinetin antiradical activity under solvent effect: density functional theory study

Journal of Molecular Modeling volume 28, Article number: 240 (2022) Cite this article

Abstract

The structural and antioxidant activity of two flavonols, namely, Fisetin and Robinetin, have been investigated employing the density functional theory (DFT) using B3LYP functional and 6–311++G (d, p) basis set. The calculations were performed in the gas phase and under the solvent effect of water, dimethylsulfoxide (DMSO), methanol, and benzene. The hydrogen-atom transfer (HAT), single electron transfer followed by proton transfer (SET-PT), and sequential proton loss electron transfer (SPLET) mechanisms were investigated to rationalize the radical scavenging capacities and to identify the favored antioxidant mechanism. Hence, the bond dissociation enthalpies (BDE) ionization potential (IP), IE, proton dissociation enthalpy (PDE), proton affinity (PA), and electron transfer enthalpy (ETE) related to each mechanism were reported and discussed in function of the solvent effect. For both flavonols, the results showed that 4′-OH hydroxyl is the preferred active site following the trend 4′-OH > 3′-OH > 3-OH > (5′-OH) > 7-OH. Besides, the HAT mechanism is energetically the most favored pathway. The energetically favored solvents follow the trends water > DMSO > benzene > methanol and benzene > DMSO > methanol > water, for Fisetin and Robinetin, respectively.

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Data availability

All data generated or analyzed during this study are included in this published article.

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Acknowledgements

The authors thank Dr. Ahmed Abousafat and Dr. Durre Khalil for their technical English assistance. The calculations were performed thanks to the HPC resources of “Unité de Calcul intensif” of the University Frères Mentouri Constantine 1.

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Authors and Affiliations

  1. Centre de Recherche en Sciences Pharmaceutiques (CRSP), 25000, Constantine, Algeria

    Rafik Menacer

  2. Centre de Recherche Scientifique et Technique en Analyses Physico-Chimiques (CRAPC), Tipaza, Algeria

    Rafik Menacer

  3. Université des frères Mentouri-Constantine 1, Département de chimie, Laboratoire d’Obtention des Substances Thérapeutiques (LOST), Campus Chaabet-Ersas, 25000, Constantine, Algeria

    Seifeddine Rekkab & Zahia Kabouche

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Contributions

All authors contributed to the study. The first draft of the manuscript was written by Rafik Menacer and all authors commented on previous versions of the manuscript. All authors read and approved the final manuscript. The credit author statement is as follows:

Rafik Menacer: writing—original draft, conceptualization, methodology, resources, data curation, software, investigation, formal analysis, visualization, validation, writing—review and editing. Rekkab Seifeddine: resources, data curation, software, investigation, visualization. Zahia Kabouche: supervision, validation, writing—review and editing.

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Correspondence to Rafik Menacer.

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Highlights

• The antioxidant activity of Fisetin and Robinetin compounds was theoretically rationalized under gas phase and solvent effect of water, dimethylsulfoxide (DMSO), methanol, and benzene at B3LYP/6-311++G(d, p) level of theory.

• The fundamental mechanisms related to the antioxidant activity: hydrogen-atom transfer (HAT), single electron transfer followed by proton transfer (SET-PT), and Sequential Proton Loss Electron Transfer (SPLET), were investigated. It was found that the HAT mechanism is thermodynamically the most favored pathway.

• The favorable active hydroxyls associated with the antioxidant activity follow the trend 4′-OH > 3′-OH > 3-OH > (5′-OH) > 7-OH.

• The energetically favored solvents follow the trends water > DMSO > benzene > methanol and benzene > DMSO > methanol > water for Fisetin and Robinetin, respectively.

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Menacer, R., Rekkab, S. & Kabouche, Z. Fisetin and Robinetin antiradical activity under solvent effect: density functional theory study. J Mol Model 28, 240 (2022). https://doi.org/10.1007/s00894-022-05223-7

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