Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda

Phytochemistry
Nancy VeraAlicia Bardón

Abstract

Eudesmane-type sesquiterpenoids 3alpha-(2,3-epoxy-2-methylbutyryloxy)-4alpha-formoxy-11-hydroxy-6,7-dehydroeudesman-8-one (1) and 3alpha-(2,3-epoxy-2-methylbutyryloxy)-4alpha,7alpha,11-trihydroxyeudesman-8-one (2), together with 10 known structurally related eudesmanes were isolated from the CHCl3 extract of aerial parts of Pluchea sagittalis (Lamarck) Cabrera. Their structures were deduced by extensive application of 1 and 2D NMR spectroscopic techniques and high and low resolution CIMS. X-ray crystallographic analysis of the known compound 3alpha-(2,3-epoxy-2-methylbutyryloxy)-4alpha-formoxycuauthemone (9) is reported here for the first time, and confirms the structural features for the series of the reported eudesmanes. All eudesmanes were tested for their antifeedant activity by incorporating them to an artificial diet of larvae of the polyphagous insect Spodoptera frugiperda at a concentration of 100ppm. Our results, from feeding choice tests, indicated that most of the compounds deter larval feeding at the cited concentration.

References

May 19, 2005·Phytomedicine : International Journal of Phytotherapy and Phytopharmacology·F Pérez-GarcíaS Cañigueral
Feb 13, 2007·Phytomedicine : International Journal of Phytotherapy and Phytopharmacology·A GomesA K Chakravarty

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Citations

Aug 21, 2013·Phytochemistry·Guo-Cai WangYao-Lan Li
Aug 21, 2009·Natural Product Reports·Braulio M Fraga
Nov 19, 2013·Chemistry & Biodiversity·Hidayat HussainIftikhar Ali
Mar 12, 2011·Journal of Ethnopharmacology·Sonia Maria FigueredoAdair Roberto Soares Santos
Nov 1, 2017·Natural Product Research·Ana C CarvalhoThiago A M Veiga

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