Vera Nancy, Popich Susana, Luna Liliana, Cravero Raquel, González Sierra Manuel, Bardón Alicia
Departamento de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, 4000 Tucumán, Argentina.
Chem Biodivers. 2006 Jan;3(1):21-6. doi: 10.1002/cbdv.200690002.
The phagodepression activity of five coumarins (= 2H-1-benzopyran-2-ones), 6-hydroxy-7-isoprenyloxycoumarin (1), 6-methoxy-7-isoprenyloxycoumarin (2), 6,7-methylenedioxycoumarin (3), 5-methoxy-6,7-methylenedioxycoumarin (4), and 6-methoxy-7-(2-hydroxyethoxy)coumarin (5), from the Argentine native herb Pterocaulon polystachyum, was tested against Spodoptera frugiperda (Lepidoptera: Noctuidae) larvae. Two analogs, scopoletin (6) and 2-methoxy-2-methyl-3,4,5,6,7,8-hexahydro-3H-chromen-5-one (7), synthesized in our laboratory, were also evaluated for comparison. The compounds were added to an artificial diet at doses ranging from 50 to 200 microg per g of diet. Natural coumarins induced 100% of phagodepression when 200 microg were added per g of diet. Binary equimolar mixtures of the natural coumarins were phagodepressors against S. frugiperda surpassing the expected additive responses, indicating that these compounds can act synergistically against S. frugiperda larvae. Compounds 1 and 3 (non-methoxylated coumarins), and the equimolar mixture of both, displayed the strongest phagodepression. Additionally, 50 microg/g of 1 and 3 incorporated to the larval diet caused 80 and 50% of pupal mortality, respectively, while a 100 microg/g dose of compounds 2, 4, 6, and 7 produced 60, 50, 10, and 80% pupal mortality, respectively. Larval growing rate during the early larval instars was significantly reduced by treatments with the methylenedioxycoumarins 3 and 4. Coincidentally, the larval period duration was significantly increased by the latter compounds.
对从阿根廷本土草本植物多穗翼茎草中提取的5种香豆素(即2H-1-苯并吡喃-2-酮),6-羟基-7-异戊烯氧基香豆素(1)、6-甲氧基-7-异戊烯氧基香豆素(2)、6,7-亚甲二氧基香豆素(3)、5-甲氧基-6,7-亚甲二氧基香豆素(4)和6-甲氧基-7-(2-羟基乙氧基)香豆素(5),针对草地贪夜蛾(鳞翅目:夜蛾科)幼虫进行了摄食抑制活性测试。还对在我们实验室合成的两种类似物,东莨菪素(6)和2-甲氧基-2-甲基-3,4,5,6,7,8-六氢-3H-色烯-5-酮(7)进行了评估以作比较。将这些化合物以每克饲料50至200微克的剂量添加到人工饲料中。当每克饲料添加200微克天然香豆素时,会引起100%的摄食抑制。天然香豆素的二元等摩尔混合物对草地贪夜蛾是摄食抑制剂,其效果超过预期的相加反应,表明这些化合物对草地贪夜蛾幼虫可产生协同作用。化合物1和3(非甲氧基化香豆素)以及二者的等摩尔混合物表现出最强的摄食抑制作用。此外,每克幼虫饲料中添加50微克的1和3分别导致80%和50%的蛹死亡率,而每克饲料100微克剂量的化合物2、4、6和7分别产生60%、50%、10%和80%的蛹死亡率。用亚甲二氧基香豆素3和4处理显著降低了幼虫早期龄期的幼虫生长速率。巧合的是,后两种化合物显著延长了幼虫期的持续时间。