College of Agriculture, Shanxi Agricultural University, Taigu, 030801, Shanxi Province, PR China; Key Laboratory of Integrated Pest Management on Crops in Northwestern Loess Plateau of Ministry of Agriculture, Northwest A&F University, Yangling 712100, Shaanxi Province, PR China.
College of Agriculture, Shanxi Agricultural University, Taigu, 030801, Shanxi Province, PR China.
Bioorg Chem. 2020 Apr;97:103696. doi: 10.1016/j.bioorg.2020.103696. Epub 2020 Feb 24.
Xanthatin, a natural sesquiterpene lactone, occurs as one of the major constituents of Xanthium plants (Compositae) and exhibits many important biological properties. To discover natural products-based pesticides, forty-nine Michael-type thiol/amino adducts of xanthatin were synthesized and characterized, while their pesticidal activities were investigated. Among them, compounds 2c, 2h, 2i, and 2t exhibited more potent antifungal activity against Botrytis cinerea (IC = 0.96, 0.38, 6.33, and 7.21 µg/mL, respectively) than xanthatin and the two commercial fungicides. Compounds 2t and 2u displayed broad-spectrum and excellent antifungal effects against all tested phytopathogenic fungi, while their IC values ranged from 7.21 to 75.88 µg/mL. Compounds 2a, 2f, 2l, 2m, 2v, 7c, 7e, 7h, 7i, and 7j showed moderate larvicidal activity against Plutella xylostella Linnaeus. Furthermore, compounds 2b, 7g, and 7h demonstrated significant ovicidal activity against P. xylostella with the LC values of 14.04, 10.00, and 11.95 mg/L, respectively. These findings suggest that thiol/amino appended in the C-13 position of xanthatin may improve antifungal and ovicidal activities for the derivatives. It was also noticed that the exocyclic double bond of xanthatin is crucial for its larvicidal activity. This work also provides some important hints for further design, synthesis, and structural modification of the xanthanolides sesquiterpene lactones toward development of the new environmentally friendly pesticides for sustainable agricultural production.
Xanthatin 是一种天然倍半萜内酯，作为菊科（Compositae）植物的主要成分之一存在，具有许多重要的生物学特性。为了发现基于天然产物的杀虫剂，合成并表征了 xanthatin 的 49 种迈克尔型硫醇/氨基加合物，并研究了它们的杀虫活性。其中，化合物 2c、2h、2i 和 2t 对灰葡萄孢（Botrytis cinerea）的抗真菌活性比 xanthatin 和两种商业杀菌剂更强（IC = 0.96、0.38、6.33 和 7.21μg/mL）。化合物 2t 和 2u 对所有测试的植物病原菌真菌表现出广谱和优异的抗真菌作用，而其 IC 值范围为 7.21 至 75.88μg/mL。化合物 2a、2f、2l、2m、2v、7c、7e、7h、7i 和 7j 对小菜蛾（Plutella xylostella Linnaeus）具有中等的杀虫活性。此外，化合物 2b、7g 和 7h 对小菜蛾表现出显著的杀卵活性，LC 值分别为 14.04、10.00 和 11.95mg/L。这些发现表明，在 xanthatin 的 C-13 位引入巯基/氨基可能会提高衍生物的抗真菌和杀卵活性。还注意到 xanthatin 的环外双键对于其杀虫活性至关重要。这项工作还为 xanthanolide 倍半萜内酯的进一步设计、合成和结构修饰提供了一些重要线索，以开发用于可持续农业生产的新型环保杀虫剂。
