Xia Qing, Dong Jianyang, Li Ling, Wang Qiang, Liu Yuxiu, Wang Qingmin
State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University , Tianjin 300071, People's Republic of China.
Collaborative Innovation Center of Chemical Science and Engineering (Tianjin) , Tianjin 300071, People's Republic of China.
J Agric Food Chem. 2018 Feb 14;66(6):1341-1348. doi: 10.1021/acs.jafc.7b05861. Epub 2018 Jan 31.
A series of novel genipin glycoside derivatives incorporating 11 glycosidic moieties at either the 1 or 10 position of genipin were designed and synthesized. These compounds exhibited moderate to excellent inhibitory activities against tobacco mosaic virus. Especially, the in vitro and in vivo activities of compounds 6e, 7c, 7d, 7f, 7h, and 7i were comparable to that of ribavirin. In particular, compound 7c, the mannosyl derivative of genipin at the 10 position, showed the best activity. The series of genipin glycosyl derivatives also displayed fungicidal activities against 14 kinds of phytopathogenic fungi, especially for Rhizoctonia cerealis and Sclerotinia sclerotiorum. Moreover, compound 6h exhibited good insecticidal activity against diamondback moth; compounds 7b, 7c, and 7g exhibited moderate insecticidal activity against three kinds of Lepidoptera pests (oriental armyworm, cotton bollworm, and corn borer); and compound 7e showed excellent larvacidal activities against mosquito.
设计并合成了一系列在京尼平的1位或10位引入11个糖苷部分的新型京尼平糖苷衍生物。这些化合物对烟草花叶病毒表现出中等至优异的抑制活性。特别是，化合物6e、7c、7d、7f、7h和7i的体外和体内活性与利巴韦林相当。尤其是10位的京尼平甘露糖基衍生物化合物7c表现出最佳活性。该系列京尼平糖基衍生物对14种植物病原真菌也具有杀菌活性，特别是对禾谷丝核菌和核盘菌。此外，化合物6h对小菜蛾表现出良好的杀虫活性；化合物7b、7c和7g对三种鳞翅目害虫（东方粘虫、棉铃虫和玉米螟）表现出中等杀虫活性；化合物7e对蚊子表现出优异的杀幼虫活性。
