Iván J Montenegro1,2, Soledad Del Corral3, Georgina N Diaz Napal3, María C Carpinella3, Marco Mellado4, Alejandro M Madrid5, Joan Villena2, Sara M Palacios1, Mauricio A Cuellar6,7. 1. Escuela de Obstetricia y Puericultura, Facultad de Medicina, Campus de la Salud, Universidad de Valparaíso, Viña del Mar, Chile. 2. Centro de Investigaciones Biomédicas (CIB), Escuela de Medicina, Universidad de Valparaíso, Viña del Mar, Chile. 3. INSTITUTO DE INVESTIGACIONES EN RECURSOS NATURALES Y SUSTENTABILIDAD-Consejo Nacional de Investigaciones Científicas y Técnicas (IRNASUS-CONICET)-Universidad Católica de Córdoba, Córdoba, Argentina. 4. Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Valparaíso, Chile. 5. Departamento de Química, Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Valparaíso, Chile. 6. Facultad de Farmacia, Universidad de Valparaíso, Valparaíso, Chile. 7. Centro de Investigación Farmacopea Chilena (CIFAR), Universidad de Valparaíso, Valparaíso, Chile.
Abstract
BACKGROUND: The antifeedant activity of 18 sesquiterpenoids of the drimane family (polygodial, drimenol and derivatives) was investigated. RESULTS: Polygodial, drimanic and nordrimanic derivatives were found to exert antifeedant effects against two insect species, Spodoptera frugiperda and Epilachna paenulata, which are pests of agronomic interest, indicating that they have potential as biopesticide agents. Among the 18 compounds tested, the epoxynordrimane compound (11) and isonordrimenone (4) showed the highest activity [50% effective concentration (EC50 ) = 23.28 and 25.63 nmol cm-2 , respectively, against S. frugiperda, and 50.50 and 59.00 nmol/cm2 , respectively, against E. paenulata]. CONCLUSION: The results suggest that drimanic compounds have potential as new agents against S. frugiperda and E. paenulata. A quantitative structure-activity relationship (QSAR) analysis of the whole series, supported by electronic studies, suggested that drimanic compounds have structural features necessary for increasing antifeedant activity, namely a C-9 carbonyl group and an epoxide at C-8 and C-9.
BACKGROUND: The antifeedant activity of 18 sesquiterpenoids of the drimane family (polygodial, drimenol and derivatives) was investigated. RESULTS: Polygodial, drimanic and nordrimanic derivatives were found to exert antifeedant effects against two insect species, Spodoptera frugiperda and Epilachna paenulata, which are pests of agronomic interest, indicating that they have potential as biopesticide agents. Among the 18 compounds tested, the epoxynordrimane compound (11) and isonordrimenone (4) showed the highest activity [50% effective concentration (EC50 ) = 23.28 and 25.63 nmol cm-2 , respectively, against S. frugiperda, and 50.50 and 59.00 nmol/cm2 , respectively, against E. paenulata]. CONCLUSION: The results suggest that drimanic compounds have potential as new agents against S. frugiperda and E. paenulata. A quantitative structure-activity relationship (QSAR) analysis of the whole series, supported by electronic studies, suggested that drimanic compounds have structural features necessary for increasing antifeedant activity, namely a C-9 carbonyl group and an epoxide at C-8 and C-9.
Authors: Iván Montenegro; Alejandro Madrid; Mauricio Cuellar; Michael Seeger; Juan Felipe Alfaro; Ximena Besoain; Juan Pablo Martínez; Ingrid Ramirez; Yusser Olguín; Miryam Valenzuela Journal: Molecules Date: 2018-08-16 Impact factor: 4.411
Authors: Purity N Kipanga; Liesbeth Demuyser; Johannes Vrijdag; Elja Eskes; Petra D'hooge; Josphat Matasyoh; Geert Callewaert; Joris Winderickx; Patrick Van Dijck; Walter Luyten Journal: Int J Mol Sci Date: 2021-05-28 Impact factor: 5.923