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The basic antioxidant structure for flavonoid derivatives

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Abstract

An antioxidant structure–activity study is carried out in this work with ten flavonoid compounds using quantum chemistry calculations with the functional of density theory method. According to the geometry obtained by using the B3LYP/6-31G(d) method, the HOMO, ionization potential, stabilization energies, and spin density distribution showed that the flavonol is the more antioxidant nucleus. The spin density contribution is determinant for the stability of the free radical. The number of resonance structures is related to the π-type electron system. 3-hydroxyflavone is the basic antioxidant structure for the simplified flavonoids studied here. The electron abstraction is more favored in the molecules where ether group and 3-hydroxyl are present, nonetheless 2,3-double bond and carbonyl moiety are facultative.

The basic antioxidant structure for flavonoid derivatives

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Acknowledgments

The authors would like to thank Conselho Nacional de Pesquisa (CNPq) and Pro-Reitoria de Pesquisa da Universidade Federal do Pará (PROPESP/UFPA) for the financial support.

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Authors and Affiliations

  1. Núcleo de Estudos e Seleção de Biomoléculas da Amazônia, Instituto de Ciências da Saúde, Universidade Federal do Pará, 66075-110, Belém, PA, Brazil

    Anna P. S. Mendes & Rosivaldo S. Borges

  2. Pós-Graduação em Química, Instituto de Ciências Exatas e Naturais, Universidade Federal do Pará, 66075-110, Belém, PA, Brazil

    Anna P. S. Mendes & Luiz G. M. de Macedo

  3. Instituto de Química de São Carlos, Universidade de São Paulo, CP 780, 13560-970, São Carlos, SP, Brazil

    Rosivaldo S. Borges & Albérico B. F. da Silva

  4. Pós-Graduação em Física, Instituto de Ciências Exatas e Naturais, Universidade Federal do Pará, 66075-110, Belém, PA, Brazil

    Antonio M. J. Chaves Neto

Authors
  1. Anna P. S. Mendes
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  2. Rosivaldo S. Borges
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  3. Antonio M. J. Chaves Neto
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  4. Luiz G. M. de Macedo
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  5. Albérico B. F. da Silva
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Correspondence to Rosivaldo S. Borges.

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Mendes, A.P.S., Borges, R.S., Neto, A.M.J.C. et al. The basic antioxidant structure for flavonoid derivatives. J Mol Model 18, 4073–4080 (2012). https://doi.org/10.1007/s00894-012-1397-0

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  • DOI: https://doi.org/10.1007/s00894-012-1397-0

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