ABSTRACT
2,3-Dihydro-2-(4'-hydroxyphenyl)-3-methyl-5(E)-propenylbenzofuran (conocarpan) (1), 2-(4'-hydroxy-3'-methoxyphenyl)-3-methyl-5(E)- propenylbenzofuran (eupomatenoid-5) (2), and 2-(4'- hydroxyphenyl)-3-methyl-5(E)-propenylbenzofuran (eupomatenoid-6) (3), three known neolignans found for the first time in a species of the Piperaceae, were isolated from Piper decurrens via insecticidal bioassay-guided fractionation, along with a small quantity of a new related compound, 2,3-dihydro-5-formyl-2-(4'-hydroxyphenyl)-3-methylbenzofuran (decurrenal) (4), and 3,7,11,15-tetramethyl-2(E)-hexadecen-1-ol (trans-phytol).
Subject(s)
Insecticides/isolation & purification , Insecticides/toxicity , Lignans/isolation & purification , Lignans/toxicity , Plants/chemistry , Animals , Culicidae , Larva , Mass Spectrometry , Plant Extracts/chemistry , Plant Extracts/toxicityABSTRACT
Insecticidal and growth-reducing properties of extracts of 14 species of American neotropical Piperaceae were investigated by inclusion in diets of a polyphagous lepidopteran, the European corn borer,Ostrinia nubilalis. Nutritional indices suggested most extracts acted by postdigestive toxicity.Piper aduncum, P. tuberculatum, andP. decurrens were among the most active species and were subjected to bioassay-guided isolation of the active components. Dillapiol was isolated from the active fraction ofP. aduncum, piperlonguminine was isolated fromP. tuberculatum, and a novel neolignan fromP. decurrens. The results support other studies on Asian and AfricanPiper species, which suggest that lignans and isobutyl amides are the active defence compounds in this family.
