黄酮的三维定量结构及其对次氯酸盐清除能力的活性关系,Journal of Agricultural and Food Chemistry

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黄酮的三维定量结构及其对次氯酸盐清除能力的活性关系
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2022-07-10 , DOI: 10.1021/acs.jafc.2c03860
Xin Yang ₁ , Tian Wang ₂ , Petar Žuvela ₂ , Mingtai Sun ₃ , Chunyuhang Xu ₁ , Hongling Zheng ₁ , Xiang Wang ₁ , Linzhi Jing ₄ , Ke Du ₁ , Suhua Wang ₃ , Ming Wah Wong ₂ , Dejian Huang _{1,

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Affiliation

黄酮类化合物是一类广泛存在于植物界的多酚类物质，被认为是理想的次氯酸盐清除剂。然而，据我们所知，很少有研究关注黄酮类化合物与次氯酸盐清除能力之间的构效关系。在这里，我们首次报告了三维定量结构和活性关系（3D-QSAR）结合比较分子场分析（CoMFA）和比较分子相似指数分析（CoMSIA）。建立并比较了四个来自 CoMFA 和 CoMSIA 的具有不同描述符组合的模型；包含空间和静电场的 CoMFA 模型显示出巨大的潜力 ( R ² = 0.989; Q ²= 0.818) 根据内部和外部验证标准的预测质量。此外，测定了平均局部电离能 (ALIE)、静电势 (ESP) 和轨道加权双描述符 (OWDD)，以确定黄酮类化合物清除次氯酸盐能力的关键结构部分。计算结果表明，次氯酸（HClO）作为亲电子试剂与具有最高负电荷密度的C6碳进行亲电加成，受黄酮上的官能团影响。DFT计算机理揭示了水对单氯化反应和二氯化反应的催化作用，其特点是低活化能垒，以及中性而不是高能碳正离子中间体的参与。

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Three-Dimensional Quantitative Structure and Activity Relationship of Flavones on Their Hypochlorite Scavenging Capacity

Flavonoids, a class of polyphenolic substances widely present in the plant realm, are considered as ideal hypochlorite scavengers. However, to our knowledge, little study has focused on the structure–activity relationship between flavonoids and hypochlorite scavenging capacity. Herein, we report for the first time the three-dimensional quantitative structure and activity relationship (3D-QSAR) combined with comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA). Four models derived from CoMFA and CoMSIA with different combinations of descriptors were built and compared; the CoMFA model, which included both steric and electrostatic fields, showed great potential (R² = 0.989; Q² = 0.818) in predictive quality according to both internal and external validation criteria. Additionally, the average local ionization energy (ALIE), electrostatic potential (ESP), and orbital weighted dual descriptor (OWDD) were determined to identify the key structural moiety for scavenging capacity of flavonoids against hypochlorite. The computational results indicated that hypochlorous acid (HClO) serves as an electrophile undergoing electrophilic addition to the C6 carbon, which has the highest negative charge density, which are influenced by the functional groups on the flavones. The DFT calculated mechanism revealed the catalytic role of water of mono- and di-chlorination reactions, characterized by low activation barriers, and the involvement of neutral, instead of high-energy carbocation, intermediates.

更新日期：2022-07-10

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