Zhang Xin, Fan Hailing, Chen Quanjia, Pan Le, Jin Lu
College of Chemistry and Chemical Engineering, Xinjiang Agricultural University, 311 Nongda East Road, Urumqi 830052, China.
Engineering Research Centre of Cotton, Ministry of Education; College of Agriculture, Xinjiang Agricultural University, 311 Nongda East Road, Urumqi 830052, China.
J Agric Food Chem. 2025 Sep 10;73(36):22162-22172. doi: 10.1021/acs.jafc.5c01912. Epub 2025 Aug 27.
Naturally derived compounds often exhibit promising bioactivity. Coumarin is an important secondary metabolite widely found in various plants and fruits. In this work, a total of 30 novel Schiff base derivatives incorporating a coumarin moiety were synthesized and characterized using H NMR, C NMR, and HR-MS spectroscopies. The in vitro fungicidal activity of these compounds against four phytopathogenic fungi ( (), (), (), and ()) was systematically evaluated. Notably, compounds , , and demonstrated remarkable antifungal activity in vitro, achieving inhibition rates exceeding 90% against both and at a concentration of 100 μg/mL after 72 h of treatment. Compound , in particular, exhibited exceptionally low EC values against (1.62 μg/mL) and (2.50 μg/mL), dramatically outperforming the positive control (boscalid) (10.75 and 118.81 μg/mL, respectively) and highlighting the potential as a promising antifungal agent. The in vivo efficacy of compound against was also investigated, showing robust activity in suppressing fungal growth on the pear fruits. At 400 μg/mL, it achieved a curative efficacy of 94.3% after 7 days. SEM and TEM analyses of hyphae revealed that the antifungal agent disrupted cellular integrity, causing the leakage of intracellular contents and abnormal mitochondrial morphology. Moreover, compound exhibited high inhibitory activity of succinate dehydrogenase (SDH) with an IC value of 0.46 μg/mL, suggesting its role as an inhibitor of SDH. Molecular docking supported that compound had a strong affinity with SDH via hydrogen bonds, thereby exerting its inhibitory effect. These findings offer valuable insights and lay a foundation for the development of novel fungicides to combat plant diseases.
天然衍生化合物通常具有良好的生物活性。香豆素是一种重要的次生代谢产物，广泛存在于各种植物和水果中。在本研究中，共合成了30种含有香豆素部分的新型席夫碱衍生物，并通过氢核磁共振（¹H NMR）、碳核磁共振（¹³C NMR）和高分辨质谱（HR-MS）光谱进行了表征。系统评价了这些化合物对四种植物病原真菌（（此处原文真菌名称缺失）、（此处原文真菌名称缺失）、（此处原文真菌名称缺失）和（此处原文真菌名称缺失））的体外杀菌活性。值得注意的是，化合物（此处原文化合物编号缺失）、（此处原文化合物编号缺失）和（此处原文化合物编号缺失）在体外表现出显著的抗真菌活性，在100 μg/mL浓度下处理72小时后，对（此处原文真菌名称缺失）和（此处原文真菌名称缺失）的抑制率均超过90%。特别是化合物（此处原文化合物编号缺失）对（此处原文真菌名称缺失）（1.62 μg/mL）和（此处原文真菌名称缺失）（2.50 μg/mL）表现出极低的半数有效浓度（EC）值，显著优于阳性对照（啶酰菌胺）（分别为10.75和118.81 μg/mL），凸显了其作为一种有前景的抗真菌剂的潜力。还研究了化合物（此处原文化合物编号缺失）对（此处原文真菌名称缺失）的体内疗效，结果表明其在抑制梨果实上真菌生长方面具有强大活性。在400 μg/mL时，7天后其治疗效果达到94.3%。对菌丝的扫描电子显微镜（SEM）和透射电子显微镜（TEM）分析表明，该抗真菌剂破坏了细胞完整性，导致细胞内物质泄漏和线粒体形态异常。此外，化合物（此处原文化合物编号缺失）对琥珀酸脱氢酶（SDH）表现出高抑制活性，半数抑制浓度（IC）值为0.46 μg/mL，表明其作为SDH抑制剂的作用。分子对接表明化合物（此处原文化合物编号缺失）通过氢键与SDH具有很强的亲和力，从而发挥其抑制作用。这些发现提供了有价值的见解，并为开发新型杀菌剂以对抗植物病害奠定了基础。
