Huang Jiulin, Xu Ming, Li Shaochen, He Jiani, Xu Hui
Research Institute of Pesticidal Design & Synthesis, College of Sciences/Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China; School of Chemistry & Chemical Engineering, Ankang University, Ankang 725000, Shaanxi Province, China.
Research Institute of Pesticidal Design & Synthesis, College of Sciences/Plant Protection, Northwest A&F University, Yangling 712100, Shaanxi Province, China.
Bioorg Med Chem Lett. 2017 Feb 1;27(3):511-517. doi: 10.1016/j.bmcl.2016.12.026. Epub 2016 Dec 9.
Podophyllotoxin is a naturally occurring non-alkaloid toxin isolated from the roots and rhizomes of Podophyllum peltatum and P. hexandrum. In continuation of our program aimed at the discovery and development of natural product-based insecticides, two series of ester derivatives of 4'-demethoxyepipodophyllotoxin/2'-chloro-4'-demethoxyepipodophyllotoxin were prepared. The structures of the target compounds were well characterized by 1H NMR, IR, optical rotation and mp. The precise three-dimensional structural information of 8j was further determined by single-crystal X-ray diffraction. Their insecticidal activity was tested against Mythimna separata Walker. These compounds showed delayed insecticidal activity. Among all derivatives, some compounds showed more potent insecticidal activity than toosendanin against M. separata; especially compounds 8k and 9k exhibited the most potent activity with the final mortality rates of 71.4%. Their structure-activity relationships were discussed.
鬼臼毒素是一种天然存在的非生物碱毒素，从盾叶鬼臼和喜马拉雅鬼臼的根及根茎中分离得到。为了继续我们旨在发现和开发基于天然产物的杀虫剂的项目，制备了4'-去甲氧基表鬼臼毒素/2'-氯-4'-去甲氧基表鬼臼毒素的两个系列的酯衍生物。目标化合物的结构通过1H NMR、IR、旋光度和熔点进行了很好的表征。8j的精确三维结构信息通过单晶X射线衍射进一步确定。测试了它们对粘虫Mythimna separata Walker的杀虫活性。这些化合物表现出延迟的杀虫活性。在所有衍生物中，一些化合物对粘虫的杀虫活性比川楝素更强；特别是化合物8k和9k表现出最强的活性，最终死亡率为71.4%。讨论了它们的构效关系。
