Chelation of the Optimal Antifungal Pogostone Analogue with Copper(II) to Explore the Dual Antifungal and Antibacterial Agent

文献类型： 外文期刊

第一作者： Wang, Delong

作者： Wang, Delong;Yuan, Chunxia;Li, Yunpeng;Bai, Shuhong;Fang, Yali;Zhang, Zhijia;Feng, Juntao;Wang, Yong

作者机构：

关键词： pogostoneanalogue; alkyl side chain; antifungaland antibacterial activities; control efficacy; mode of action

期刊名称：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY （ 影响因子：6.1； 五年影响因子：6.3 ）

ISSN： 0021-8561

年卷期： 2024 年 72 卷 8 期

页码：

收录情况： SCI

摘要： In an ongoing effort to explore more potent antifungal pogostone (Po) analogues, we maintained the previously identified 3-acetyl-4-hydroxy-2-pyrone core motif while synthesizing a series of Po analogues with variations in the alkyl side chain. The in vitro bioassay results revealed that compound 21 was the most potent antifungal analogue with an EC50 value of 1.1 mu g/mL against Sclerotinia sclerotiorum (Lib.) de Bary. Meanwhile, its Cu(II) complex 34 manifested significantly enhanced antibacterial activity against Xanthomonas campestris pv campestris (Xcc) with a minimum inhibitory concentration (MIC) value of 300 mu g/mL compared with 21 (MIC = 700 mu g/mL). Complex 34 exhibited a striking preventive effect against S. sclerotiorum and Xcc in rape leaves, with control efficacies of 98.8% (50 mu g/mL) and 80.7% (1000 mu g/mL), respectively. The 3D-QSAR models generated using Topomer comparative molecular field analysis indicated that a shorter alkyl chain (carbon atom number <8), terminal rings, or electron-deficient groups on the alkyl side chain are beneficial for antifungal potency. Further, bioassay results revealed that the component of 21 in complex 34 dominated the antifungal activity, but the introduction of Cu(II) significantly enhanced its antibacterial activity. The toxicological observations demonstrated that 21 could induce abnormal mitochondrial morphology, loss of mitochondrial membrane potential, and reactive oxygen species (ROS) accumulation in S. sclerotiorum. The enzyme assay results showed that 21 is a moderate promiscuous inhibitor of mitochondrial complexes II and III. Besides, the introduction of Cu(II) to 34 could promote the disruption of the cell membrane and intracellular proteins and the ROS level in Xcc compared with 21. In summary, these results highlight the potential of 34 as a dual antifungal and antibacterial biocide for controlling rape diseases or as a promising candidate for further optimization.

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