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Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda |
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| Authors: | Vera Nancy Misico Rosana Sierra Manuel González Asakawa Yoshinori Bardón Alicia |
| Affiliation: | aInstituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, 4000 Tucumán, Argentina bDepartamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria AR-1428, Argentina cInstituto de Química Orgánica y Síntesis (IQUIOS), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, 2000 Rosario, Argentina dFaculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan |
| Abstract: | Eudesmane-type sesquiterpenoids 3-(2,3-epoxy-2-methylbutyryloxy)-4-formoxy-11-hydroxy-6,7-dehydroeudesman-8-one (1) and 3-(2,3-epoxy-2-methylbutyryloxy)-4,7,11-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 3-(2,3-epoxy-2-methylbutyryloxy)-4-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 100 ppm. Our results, from feeding choice tests, indicated that most of the compounds deter larval feeding at the cited concentration. |
| Keywords: | Pluchea sagittalis Asteraceae Antifeedant activity Spodoptera frugiperda Eudesmanes Sesquiterpenoids |
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