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A computational investigation on the antioxidant potential of myricetin 3,4′-di-O-α-L-rhamnopyranoside

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Abstract

In this work, we present a computational study on the antioxidant potential of myricetin 3,4\(^{\prime }\)-di-O-α-L-rhamnopyranoside (Compound M). A density functional theory (DFT) approach with the B3LYP and LC-ωPBE functionals and with both the 6-311G(d,p) and 6-311+G(d,p) basis sets was used. The focus of the investigation was on the structural and energetic parameters including both bond dissociation enthalpies (BDEs) and ionization potentials (IPs), which provide information on the potential antioxidant activity. The properties computed were compared with BDEs and IPs available in the literature for myricetin, a compound well known for presenting antioxidant activity (and the parent molecule of the compound of interest in the present work). Myricetin 3,4\(^{\prime }\)-di-O-α-L-rhamnopyranoside presented the lowest BDE to be 79.13 kcal/mol (as determined using B3LYP/6-311G(d,p) in water) while myricetin has a quite similar value (within 3.4 kcal/mol). IPs computed in the gas phase [B3LYP/6-311G(d,p)] are 157.18 and 161.4 kcal/mol for myricetin 3,4\(^{\prime }\)-di-O-α-L-rhamnopyranoside and myricetin, respectively. As the values of BDEs are considerably lower than the ones probed for IPs (in the gas phase or in any given solvent environment), the hydrogen atom transfer mechanism is preferred over the single electron transfer mechanism. The BDEs obtained suggest that myricetin 3,4\(^{\prime }\)-di-O-α-L-rhamnopyranoside can present antioxidant potential as good as the parent molecule myricetin (a well-known antioxidant). Therefore, experimental tests on the antioxidant activity of Compound M are encouraged.

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Acknowledgements

The Brazilian agency CNPq funded this work (Process number: 306266/2016-4). AB thanks the Natural Sciences and Engineering Research Council of Canada for funding (NSERC - Discovery Grant). This research was supported in part by PL-Grid Infrastructure.

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Authors and Affiliations

  1. Departamento de Química, Universidade Federal de Mato Grosso, Cuiabá, Mato Grosso, 78060-900, Brazil

    Rodrigo A. Mendes, Shawan K. C. Almeida, Iuri N. Soares, Renato G. Freitas & Gabriel L. C. de Souza

  2. Institute of Physics, Polish Academy of Sciences, aleja Lotników 32/46, 02 668, Warsaw, Poland

    Cristina A. Barboza

  3. Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada

    Alex Brown

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  1. Rodrigo A. Mendes
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  2. Shawan K. C. Almeida
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  3. Iuri N. Soares
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  7. Gabriel L. C. de Souza
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Correspondence to Gabriel L. C. de Souza.

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Supplementary Material

Cartesian coordinates for the optimized geometries determined using the B3LYP and LC-ω PBE functionals with the 6-311G(d,p) and the 6-311+G(d,p) basis set in the gas phase, water, methanol, ethanol, and n-hexane can be found in the Supplementary Material.

This paper belongs to Topical Collection XIX - Brazilian Symposium of Theoretical Chemistry (SBQT2017)

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Cartesian coordinates for the optimized geometries determined using the B3LYP and LC-ω PBE functionals with the 6-311G(d,p) and the 6-311+G(d,p) basis set in the gas phase, water, methanol, ethanol, and n-hexane can be found in the Supplementary Material.

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Mendes, R.A., Almeida, S.K.C., Soares, I.N. et al. A computational investigation on the antioxidant potential of myricetin 3,4′-di-O-α-L-rhamnopyranoside. J Mol Model 24, 133 (2018). https://doi.org/10.1007/s00894-018-3663-2

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