Manoyl oxide diterpenoids from Grindelia scorzonerifolia.
Two new norditerpenoids, 4beta-hydroxy-19-normanoyl oxide (1) and 4alpha-hydroxy-18-normanoyl oxide (2), the new 18-O-alpha-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.
Ybarra
María Inés
MI
Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, Tucumán 4000, Argentina.
Popich
Susana
S
Borkosky
Susana A
SA
Asakawa
Yoshinori
Y
Bardón
Alicia
A
D000818:Animals; D001118:Argentina; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005247:Feeding Behavior / Q000187:drug effects; D036623:Grindelia / Q000737:chemistry*; D007306:Insecticides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D007814:Larva / Q000187:drug effects; D008968:Molecular Conformation; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry*; D018411:Spodoptera / Q000187:drug effects*
C500763:4alpha-hydroxy-18-normanoyl oxide; C500762:4beta-hydroxy-19-normanoyl oxide; D004224:Diterpenes; D007306:Insecticides; C475535:manoyl oxide