Cui Yucheng, Duan Wengui, Lin Guishan, Bi Youqiong, Meng Luqiong, Deng Huan, Li Baoyu, Li Hao
School of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, P. R. China.
Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, Nanning 530004, P. R. China.
J Agric Food Chem. 2025 Jun 25;73(25):15533-15542. doi: 10.1021/acs.jafc.5c01265. Epub 2025 Jun 10.
In an attempt to discover natural-product-derived novel green herbicides, 26 novel 3-carene-based acylhydrazone compounds were designed and synthesized. Their chemical structures were characterized by FTIR, NMR, HRMS, NOESY, and single-crystal X-ray diffraction. The herbicidal activity of the target compounds was evaluated, and the target compound exhibited good herbicidal activity against the dicotyledonous plant and the monocotyledonous plant L. The EC values of its herbicidal activity against the two tested plants were better than or similar to those of the positive control diuron. The structure-activity relationship of compounds and was investigated by DFT theoretical calculation. The action mechanism of herbicidal activity was explored through various methods including the inhibitory activity of laccase, fluorescence quenching of laccase, chelating property of compound to Cu, molecular docking, and molecular dynamic simulation. Furthermore, the cytotoxicity of compound against normal human kidney cells (HEK293T cells) was also preliminarily evaluated. All of these results showed that compound may exert its good herbicidal activity by inhibiting laccase. Therefore, it deserves further investigation as a promising novel low-toxicity green herbicidal lead compound.
为了发现源自天然产物的新型绿色除草剂，设计并合成了26种新型的基于3-蒈烯的酰腙化合物。通过傅里叶变换红外光谱（FTIR）、核磁共振（NMR）、高分辨质谱（HRMS）、核Overhauser效应光谱（NOESY）和单晶X射线衍射对其化学结构进行了表征。对目标化合物的除草活性进行了评估，目标化合物对双子叶植物和单子叶植物L表现出良好的除草活性。其对两种受试植物的除草活性的半数有效浓度（EC）值优于或类似于阳性对照敌草隆。通过密度泛函理论（DFT）计算研究了化合物的构效关系。通过包括漆酶抑制活性、漆酶荧光猝灭、化合物与铜的螯合性能、分子对接和分子动力学模拟等多种方法探索了除草活性的作用机制。此外，还初步评估了化合物对正常人肾细胞（HEK293T细胞）的细胞毒性。所有这些结果表明，化合物可能通过抑制漆酶发挥其良好的除草活性。因此，作为一种有前景的新型低毒绿色除草先导化合物，它值得进一步研究。
