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Quantitative structure-activity relationship study for prediction of antifungal properties of phenolic compounds

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Abstract

Antifungal compounds are of interest to reduce commodity spoilage and exposure to mycotoxins. In this study, a series of quantitative structure-activity relationship (QSAR) equations based on topological properties were developed to gain insight into the antifungal activities of phenolic compounds. The molecules were geometry optimized using B3LYP/6-311+G** density functional theory calculations. Analysis of the frontier orbital properties revealed that conjugated phenolic compounds possessed smaller band gap energies. Genetic function approximation (GFA) on populations of 100 one to two descriptor models over 10,000 generations identified several models for antifungal activity against Fusarium verticillioides, Fusarium oxysporum, Aspergillus flavus, Aspergillus fumigatus, Penicillium expansum, and Penicillium brevicompactum. Phenolic compounds with greater antifungal activity possessed a lower electrophilicity index. The correlation coefficients for the one and two descriptor models ranged from 0.627 to 0.790 and 0.762 to 0.939, respectively. Molecular descriptors associated with electrostatic and topological properties are important to describe the antifungal activities of the phenolic compounds studied.

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Acknowledgments

Mention of trade names or commercial products in this publication is solely for the purpose of providing specific information and does not imply recommendation or endorsement by the United States Department of Agriculture (USDA). USDA is an equal opportunity provider and employer and the provider. We are grateful for Prof. Paola Gramatica and Prof. Kanul Roy for the use of their software.

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Authors and Affiliations

  1. Mycotoxin Prevention and Applied Microbiology Research Unit, United States Department of Agriculture, Agricultural Research Service, National Center for Agricultural Utilization Research, 1815 N. University St., Peoria, IL, 61604, USA

    Michael Appell, Yi-Shu Tu & Lijuan C. Wang

  2. Insilico Taiwan Inc., 17F No. 3 Park St. Nangang Dist., Taipei, 11503, Taiwan

    Yi-Shu Tu

  3. Renewable Product Technology Research Unit, United States Department of Agriculture, Agricultural Research Service, National Center for Agricultural Utilization Research, 1815 N. University St., Peoria, IL, 61604, USA

    David L. Compton & Kervin O. Evans

Authors
  1. Michael Appell
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  2. Yi-Shu Tu
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  3. David L. Compton
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  4. Kervin O. Evans
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  5. Lijuan C. Wang
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Correspondence to Michael Appell.

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All authors certify and assert that no animals or humans were used to obtain results reported in this research.

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The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

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Appell, M., Tu, YS., Compton, D.L. et al. Quantitative structure-activity relationship study for prediction of antifungal properties of phenolic compounds. Struct Chem 31, 1621–1630 (2020). https://doi.org/10.1007/s11224-020-01549-1

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