Faculdade de Engenharia Química, Universidade Federal do Pará, Campus Universitário do Guamá, 66075-900 Belém, PA, Brazil.
Chem Biodivers. 2009 Sep;6(9):1427-34. doi: 10.1002/cbdv.200800212.
The essential oils of the specimens of Piper aduncum that occur in deforested areas of Brazilian Amazon, North Brazil, are rich in dillapiole (35-90%), a derivative of phenylpropene, to which are attributed biological properties. On the other hand, the oils of the specimens with occurrence in the Atlantic Forest, and Northeastern and Southeastern Brazil, do not contain dillapiole, but only terpene compounds such as (E)-nerolidol and linalool. One specimen existing in the Amazon was hydrodistilled. The obtained oil was fractioned on a silica chromatographic column, resulting in fractions rich in dillapiole (95.0-98.9%) utilized for analyses by GC and GC/MS, structural characterization by NMR, confirmation of their biological properties, and to obtain the isomer isodillapiole. Dillapiole showed a fungicide action against the fungus Clinipellis perniciosa (witches' broom) by inhibition of its basidiospores, in concentrations ranging from 0.6 to 1.0 ppm. The larvicide and insecticide actions of dillapiole were tested against the larvae and the adult insects of Anopheles marajoara and Aedes aegypti (malaria and dengue mosquitoes), resulting in mortality of the larvae (48 h, 100%) at a concentration of 100 ppm, and mortality of the insects (30 min, 100%) at a concentration of 600 ppm. The isomeric isodillapiole showed no significant activity in the same biological tests.
产自巴西亚马逊地区、北巴西森林砍伐区的弯管胡椒标本的精油富含苯丙素衍生的丁香酚（35-90%），具有生物特性。另一方面，在大西洋森林以及巴西东北部和东南部发现的胡椒标本的精油不含丁香酚，只含有萜烯化合物，如（E）-橙花叔醇和芳樟醇。亚马逊地区的一个标本被水蒸气蒸馏。所得油在硅胶色谱柱上进行分离，得到富含丁香酚（95.0-98.9%）的馏分，用于 GC 和 GC/MS 分析、通过 NMR 进行结构表征、确认其生物特性，并获得其异构体异丁香酚。丁香酚在 0.6 至 1.0 ppm 的浓度范围内对病原菌菌Clinipellis perniciosa（扫帚菌）表现出杀菌作用，抑制其担孢子。丁香酚对幼虫和成年的 Anopheles marajoara 和 Aedes aegypti（疟疾和登革热蚊子）进行了杀幼虫和杀虫测试，结果表明在 100 ppm 的浓度下，幼虫的死亡率（48 h，100%），在 600 ppm 的浓度下，昆虫的死亡率（30 min，100%）。同系物异丁香酚在相同的生物测试中没有表现出显著的活性。
