Department of Agricultural, Food and Nutritional Science, University of Alberta, Edmonton, Alberta, Canada.
Pest Manag Sci. 2010 Dec;66(12):1298-303. doi: 10.1002/ps.2013. Epub 2010 Aug 26.
Natural limonoids are one group of compounds being studied for their insecticidal properties. To discover new limonoids with better activities, analogs were prepared via acylation and hydrolysis, and bioassayed.
Analogs were identified using one- and two-dimensional (COSY, HMQC and HMBC) (1) H and (13) C NMR, IR and MS. 3-O-Isovalerylswietenolide (13) and 3-O-isobutyrylswietenolide (14) showed excellent antifeedant activity, with DC(50) values of 0.19 and 0.009 mg L(-1) respectively, compared with the natural limonoid swietenolide (80.6 mg L(-1) ) against fourth-instar Spodoptera frugiperda (JE Smith) larvae.
This work shows that limonoid analogs prepared through semi-synthesis can be used as lead compounds for the development of new insecticides.
天然柠檬苦素是一类具有杀虫特性的化合物,正在被研究。为了发现具有更好活性的新柠檬苦素,通过酰化和水解制备了类似物,并进行了生物测定。
使用一维和二维(COSY、HMQC 和 HMBC)(1)H 和(13)C NMR、IR 和 MS 对类似物进行了鉴定。3-O-异戊酰swietenolide(13)和 3-O-异丁酰swietenolide(14)表现出优异的拒食活性,与天然柠檬苦素 swietenolide(80.6 mg/L)相比,对第四龄 Spodoptera frugiperda(JE Smith)幼虫的 DC(50)值分别为 0.19 和 0.009 mg/L。
这项工作表明,通过半合成制备的柠檬苦素类似物可用作开发新型杀虫剂的先导化合物。