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Creating molecular diversity from antioxidants in Brazilian propolis. Combination of TOPS-MODE QSAR and virtual structure generation

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Abstract

A QSAR model for antioxidative activity based on the Sub-Structural Molecular Design (TOPS-MODE) approach is developed for a series of compounds present in Brazilian propolis. This approach permitted the structural interpretation of the antioxidative activity of these compounds in terms of bond contributions. By these means we have identified the structural groups and regions that contribute to the antioxidative activity of the cinnamic acid and flavonoid derivatives present in the propolis. These results were then used to identify the positions and substituents to be used in a virtual compound generation experiment. Using this approach a total of 327 compounds were generated from which more than 70 are predicted to be more active than the most powerful antioxidants in the Brazilian propolis. From these 70 compounds less than 20 have been reported in the literature. Consequently, a high proportion of novel compounds with potential antioxidative activity has been identified by the current approach. This contributes to enhance the molecular diversity of the analogues of Brazilian propolis compounds with antioxidative properties.

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Authors and Affiliations

  1. Safety and Environmental Assurance Centre (SEAC), Unilever Colworth, Sharnbrook, Bedford, U.K.

    Ernesto Estrada & Grace Patlewicz

  2. RIAIDT, University of Santiago de Compostela, Santiago de Compostela, Spain (Author for correspondence, E-mail

    Ernesto Estrada

  3. Grupo de Síntese Orgânica, Universidade Bandeirante de São Paulo, Vila Guilherme, CEP, São Paulo, SP, Brasil

    Jose A. Quincoces

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  1. Ernesto Estrada
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  2. Jose A. Quincoces
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  3. Grace Patlewicz
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Correspondence to Ernesto Estrada.

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Estrada, E., Quincoces, J.A. & Patlewicz, G. Creating molecular diversity from antioxidants in Brazilian propolis. Combination of TOPS-MODE QSAR and virtual structure generation. Mol Divers 8, 21–33 (2004). https://doi.org/10.1023/B:MODI.0000006804.97390.40

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