C-5-substituted antifeedant silphinene sesquiterpenes from Senecio palmensis

Matías Reina¹, Matthias Nold, Omar Santana

¹Instituto de Productos Naturales y Agrobiología, CSIC, Avenida Astrofísico F. Sánchez, 3, 38206 La Laguna, Tenerife, Spain.

|April 27, 2002

Abstract:

The new sesquiterpenes, 5alpha-senecioyloxysilphinen-3-one (5), 5alpha-tigloyloxysilphinen-3-one (7), and 3beta-hydroxy-5alpha-angeloyloxysilphinene (8), and the known compounds (6S)-2,10-bisaboladien-1-one (1), 6,7-epoxy-3(15)-caryophyllene (2), 6,7-epoxy-2,9-humuladiene (3), 5alpha-angeloyloxysilphinen-3-one (4), and 5alpha-acetoxysilphinen-3-one (6) were isolated from bioactive fractions of Senecio palmensis. The structures of these compounds were established by spectroscopic analysis and chemical evidence. The semisynthetic analogues silphinen-3,5-dione (9), 5alpha-hydroxysilphinen-3-one (10), 5beta-hydroxysilphinen-3-one (11), 5beta-acetoxysilphinen-3-one (12), and 5beta-isobutyryloxysilphinen-3-one (13) were generated to carry out a structure-activity study on the antifeedant action of these molecules against several divergent insect species.

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Abstract:

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