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.

中文翻译：

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预测酚类化合物抗真菌特性的定量构效关系研究

抗真菌化合物有助于减少商品腐败和霉菌毒素暴露。在这项研究中，开发了一系列基于拓扑特性的定量构效关系 (QSAR) 方程，以深入了解酚类化合物的抗真菌活性。使用 B3LYP/6-311+G** 密度泛函理论计算对分子进行几何优化。前沿轨道性质的分析表明，共轭酚类化合物具有较小的带隙能量。对超过 10,000 代的 100 个一到两个描述符模型的种群进行遗传函数近似 (GFA)，确定了几种抗真菌活性的模型，这些模型具有针对轮枝镰孢、尖孢镰刀菌、黄曲霉、烟曲霉、膨胀青霉和短柄青霉的抗真菌活性。具有较大抗真菌活性的酚类化合物具有较低的亲电指数。一个和两个描述符模型的相关系数范围分别为 0.627 到 0.790 和 0.762 到 0.939。与静电和拓扑特性相关的分子描述符对于描述所研究的酚类化合物的抗真菌活性很重要。