Ybarra María Inés, Popich Susana, Borkosky Susana A, Asakawa Yoshinori, Bardón Alicia
Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, Tucumán 4000, Argentina.
J Nat Prod. 2005 Apr;68(4):554-8. doi: 10.1021/np040174k.
Two new norditerpenoids, 4beta-hydroxy-19-normanoyl oxide (1) and 4alpha-hydroxy-18-normanoyl oxide (2), the new 18-O-alpha-l-arabinopyranosylmanoyl oxide (3a), and the known diterpenoids jhanol (4) and 18-hydroxy-13-epi-manoyl oxide (5) were isolated, together with other common plant constituents from an Argentine collection of Grindelia scorzonerifolia. The structures of the new compounds were established by extensive 1D and 2D NMR techniques and chemical transformations. Structural features of compounds 2 and 4 were verified by X-ray crystallographic analyses. The insecticidal effect of compound 3a was evaluated against the polyphagous pest Spodoptera frugiperda. Pupal and adult malformations leading to death occurred when 3a was incorporated in a larval diet at a concentration of 100 ppm.
从阿根廷采集的苦苣菜属植物中分离出两种新的降二萜类化合物，4β-羟基-19-降阿魏酰氧化物（1）和4α-羟基-18-降阿魏酰氧化物（2），新的18-O-α-L-阿拉伯吡喃糖基阿魏酰氧化物（3a），以及已知的二萜类化合物苦苣菜醇（4）和18-羟基-13-表阿魏酰氧化物（5），还有其他常见的植物成分。通过广泛的一维和二维核磁共振技术以及化学转化确定了新化合物的结构。化合物2和4的结构特征通过X射线晶体学分析得到验证。评估了化合物3a对多食性害虫草地贪夜蛾的杀虫效果。当3a以100 ppm的浓度添加到幼虫饲料中时，会导致蛹和成虫畸形并死亡。
