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Natural Alkaloid Waltherione F-Derived Hydrazide Compounds Evaluated in an Agricultural Fungicidal Field
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2023-08-03 , DOI: 10.1021/acs.jafc.3c03937 Zhanfang Chen 1 , Hongbin Fang 1 , Jing Chang 1 , Tiancheng Zhang 1 , Yanhong Cui 2 , Lingxiao Zhang 1 , Junkang Sui 1 , Qingping Ma 1 , Peisen Su 1 , Juyuan Wang 1 , Jing Ru 3 , Yucheng Gu 4 , Hengjia Zhang 1 , Xuewen Hua 1
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2023-08-03 , DOI: 10.1021/acs.jafc.3c03937 Zhanfang Chen 1 , Hongbin Fang 1 , Jing Chang 1 , Tiancheng Zhang 1 , Yanhong Cui 2 , Lingxiao Zhang 1 , Junkang Sui 1 , Qingping Ma 1 , Peisen Su 1 , Juyuan Wang 1 , Jing Ru 3 , Yucheng Gu 4 , Hengjia Zhang 1 , Xuewen Hua 1
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In this project, quinoline and quinolone-containing hydrazide compounds were designed and synthesized by introducing a bioactive hydrazide group into the skeleton of waltherione F. The fungicidal activity revealed that some hydrazide compounds exhibited excellent and broad-spectrum fungicidal activity; especially, compounds E8, E12, and E16 showed more than 90% or even 100% inhibition rates against most pathogens at 50 μg·mL–1. The fungicidal mechanism indicated that compound E8 may affect the normal function of the plasma membrane, further generating changes in the morphology and subcellular structure of mycelia. Simultaneously, Fusarium graminearum may resist the E8-treated stress through the metabolic pathways related to l-glutamate, l-glutamine, and glutathione. Finally, the effect of compound E8 on wheat seedling’s growth and the toxicity to zebrafish were accomplished. These results will provide important guidance to discover novel fungicidal lead compounds and explore new targets, which are effective ways to alleviate the increasingly severe drug resistance.
中文翻译：
天然生物碱 Waltherione F 衍生酰肼化合物在农业杀菌领域的评价
本项目通过在waltherione F骨架中引入具有生物活性的酰肼基团，设计合成了喹啉及含喹诺酮的酰肼类化合物。杀菌活性表明，部分酰肼类化合物表现出优异的广谱杀菌活性；尤其是化合物E8、E12和E16在50 μg·mL –1浓度下对大多数病原体显示出90%以上甚至100%的抑制率。杀菌机制表明，化合物E8可能影响质膜的正常功能，进一步产生菌丝体形态和亚细胞结构的变化。同时，禾谷镰刀菌可能通过与L-谷氨酸、L-谷氨酰胺和谷胱甘肽相关的代谢途径抵抗E8处理的应激。最后研究了化合物E8对小麦幼苗生长的影响以及对斑马鱼的毒性。这些结果将为发现新型杀菌先导化合物和探索新靶点提供重要指导，是缓解日益严重的耐药性的有效途径。
更新日期：2023-08-03
中文翻译：
天然生物碱 Waltherione F 衍生酰肼化合物在农业杀菌领域的评价
本项目通过在waltherione F骨架中引入具有生物活性的酰肼基团，设计合成了喹啉及含喹诺酮的酰肼类化合物。杀菌活性表明，部分酰肼类化合物表现出优异的广谱杀菌活性；尤其是化合物E8、E12和E16在50 μg·mL –1浓度下对大多数病原体显示出90%以上甚至100%的抑制率。杀菌机制表明，化合物E8可能影响质膜的正常功能，进一步产生菌丝体形态和亚细胞结构的变化。同时，禾谷镰刀菌可能通过与L-谷氨酸、L-谷氨酰胺和谷胱甘肽相关的代谢途径抵抗E8处理的应激。最后研究了化合物E8对小麦幼苗生长的影响以及对斑马鱼的毒性。这些结果将为发现新型杀菌先导化合物和探索新靶点提供重要指导，是缓解日益严重的耐药性的有效途径。
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