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Why is quercetin a better antioxidant than taxifolin? Theoretical study of mechanisms involving activated forms

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Abstract

The stronger antioxidant capacity of the flavonoid quercetin (Q) compared with taxifolin (dihydroquercetin, T) has been the subject of previous experimental and theoretical studies. Theoretical work has focused on the analysis of hydrogen bond dissociation energies (BDE) of the OH phenolic groups, but consider mechanisms that only involve the transfer of one hydrogen atom. In the present work we consider other mechanisms involving a second hydrogen transfer in reactions with free radicals. The relative stability of the radicals formed after the first hydrogen transfer reaction is considered in discussing the antioxidant activity of Q and T. In terms of global and local theoretical reactivity descriptors, we propose that the radical arising from Q should be more persistent in the environment and with the capability to react with a second radical by hydrogen transfer, proton transfer and electron transfer mechanisms. These mechanisms could be responsible of the stronger antioxidant capacity of Q.

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Acknowledgments

This work was partially funded by the Millennium Scientific Initiative (Ministerio de Economía, Fomento y Turismo) (Grant P10-035-F), Fondo Nacional de Desarrollo Científico y Tecnológico (Grants: 11090431 and 11110241) and The Research Office of the University of Medellín, project 626. E.O. thanks to the Fondo de atracción a Postdoctorado, Universidad de Talca.

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Authors and Affiliations

  1. Departamento de Ciencias Químicas, Facultad de Ciencias Exactas, Universidad Andres Bello, Av. República 275, Santiago, Chile

    Edison Osorio & William Tiznado

  2. Centro de Bioinformática y Simulación Molecular, Universidad de Talca, 2 Norte 685, Casilla 721, Talca, Chile

    Edison Osorio

  3. Facultad de Química, Pontificia Universidad Católica de Chile, Vicuña Mackenna 4860, Casilla 306, Correo 22, Santiago, Chile

    Edwin G. Pérez

  4. Departamento de Química, Facultad de Ciencias, Universidad de Chile, Las Palmeras 3425, Casilla 653, Santiago, Chile

    Carlos Areche & Bruce K. Cassels

  5. Departamento de Biología, Facultad de Ciencias Biológicas, Universidad Andres Bello, Av. República 217, Santiago, Chile

    Lina María Ruiz

  6. Departamento de Ciencias Básicas, Universidad de Medellín, Carrera 87 N° 30-65, Medellín, Colombia

    Elizabeth Flórez

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  1. Edison Osorio
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  7. William Tiznado
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Correspondence to William Tiznado.

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Osorio, E., Pérez, E.G., Areche, C. et al. Why is quercetin a better antioxidant than taxifolin? Theoretical study of mechanisms involving activated forms. J Mol Model 19, 2165–2172 (2013). https://doi.org/10.1007/s00894-012-1732-5

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  • DOI: https://doi.org/10.1007/s00894-012-1732-5

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