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Computational study of the hydrogen peroxide scavenging mechanism of allyl methyl disulfide, an antioxidant compound from garlic

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Abstract

Although many sulfur containing garlic compounds present antioxidant activity, little is known about molecular mechanisms through which these compounds react with reactive oxygen species. In this work, the reactivity and the hydrogen peroxide scavenger reaction mechanisms (including thermodynamics and kinetics aspects) of allyl methyl disulfide in aqueous phase are studied employing density functional theory computational methods. Three reactive sites susceptible for electrophilic attack are found over sulfur atoms and the double bond allyl moiety. For each detected site, one redox reaction is proposed and analyzed. All reactions are thermodynamically feasible, whereas attack over the methyl bound sulfur atom is kinetically favored.

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Acknowledgements

The authors thank UNSL and CONICET for the financial support. JCGM and EGVH are members of the Scientific Research Career of CONICET. MGD is fellow of CONICET.

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Authors and Affiliations

  1. Área de Química Física, Facultad de Química, Bioquímica y Farmacia, Universidad Nacional de San Luis, Ejército de Los Andes 950, 5700, San Luis, Argentina

    Esteban G. Vega-Hissi, Matias F. Andrada & Juan C. Garro Martinez

  2. Instituto Multidisciplinario de Investigaciones Biológicas (IMIBIO) – CONICET, Ejército de Los Andes 950, 5700, San Luis, Argentina

    Esteban G. Vega-Hissi, Mario G. Díaz & Juan C. Garro Martinez

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  1. Esteban G. Vega-Hissi
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Vega-Hissi, E.G., Andrada, M.F., Díaz, M.G. et al. Computational study of the hydrogen peroxide scavenging mechanism of allyl methyl disulfide, an antioxidant compound from garlic. Mol Divers 23, 985–995 (2019). https://doi.org/10.1007/s11030-019-09927-6

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