Hao Qian, Yingkun Hu, Ziyu Wang, Yu Zhou, Xinru Tan, Xunmeng Feng, Keyin Yu, Wenjun Wu and Jiwen Zhang*,
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引用次数: 0
摘要
Celangulin V 是一种新型植物杀虫剂,具有显著的生物活性和独特的分子靶标,但其复杂的多元醇酯结构阻碍了其在农业领域的广泛应用。为了发现结构更简单、生物活性更强的天南星素 V 类似物,我们启动了一个旨在简化其结构和评估杀虫效果的研究项目。在这项研究中,我们通过基于结构的合理设计方法设计了一系列新型 1-四氢萘酮衍生物,并采用简便的方法合成了这些衍生物。测定了目标化合物对Mythimna separata (M.separata)、Plutella xylostella和Rhopalosiphum padi的生物活性。结果表明,大多数合成化合物的活性都优于苍术素 V。值得注意的是,化合物 6.16 的杀虫活性比苍术素 V 的胃毒性高出 102 倍。分子对接分析表明,化合物 6.16 与 V-ATPase H 亚基的结合口袋与 Celangulin V 相同。这项研究为植物杀虫剂的结构优化提供了新的见解。
In-Depth Structural Simplification of Celangulin V: Design, Synthesis, and Biological Activity
Celangulin V is a novel botanical insecticide with significant bioactivity and a unique molecular target, but its complex polyol ester structure hinders its broader application in agriculture. To discover new analogues of celangulin V with a simpler structure and enhanced biological activities, we initiated a research project aimed at simplifying its structure and assessing insecticidal efficacy. In this study, a series of novel 1-tetralone derivatives were designed via a structure-based rational design approach and synthesized by a facile method. The biological activities of the target compounds were determined against Mythimna separata (M. separata), Plutella xylostella, and Rhopalosiphum padi. The results revealed that most of the synthesized compounds exhibited superior activities compared to celangulin V. Remarkably, the insecticidal activity of compound 6.16 demonstrated 102-fold greater stomach toxicity than celangulin V against M. separata. In addition, certain compounds showed significant contact toxicity against M. separata, a finding not reported previously in the structural optimization studies of celangulin V. Molecular docking analysis illustrated that the binding pocket of compound 6.16 with the H subunit of V-ATPase was the same as celangulin V. This study presents novel insights into the structural optimization of botanical pesticides.
期刊介绍:
The Journal of Agricultural and Food Chemistry publishes high-quality, cutting edge original research representing complete studies and research advances dealing with the chemistry and biochemistry of agriculture and food. The Journal also encourages papers with chemistry and/or biochemistry as a major component combined with biological/sensory/nutritional/toxicological evaluation related to agriculture and/or food.