Manoyl oxide diterpenoids from Grindelia scorzonerifolia

Two new norditerpenoids, 4β-hydroxy-19-normanoyl oxide (1) and 4α-hydroxy-18-normanoyl oxide (2), the new 18-O-α-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 Arg...

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Detalles Bibliográficos
Autores: Ybarra, María Inés, Popich, Susana Beatriz, Borkosky, Susana Alicia, Asakawa, Yoshinori, Bardon, Alicia del Valle
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2005
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/100866
Acceso en línea:http://hdl.handle.net/11336/100866
Access Level:acceso abierto
Palabra clave:Grindelia scorzonerifolia
Manoyl oxide diterpenoids
Spodoptera frugiperda
https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
Descripción
Sumario:Two new norditerpenoids, 4β-hydroxy-19-normanoyl oxide (1) and 4α-hydroxy-18-normanoyl oxide (2), the new 18-O-α-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. © 2005 American Chemical Society and American Society of Pharmacognosy.