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Abstract:

Eudesmane-type sesquiterpenoids 3α-(2,3-epoxy-2-methylbutyryloxy)-4α-formoxy-11-hydroxy-6,7-dehydroeudesman-8-one (1) and 3α-(2,3-epoxy-2-methylbutyryloxy)-4α,7α,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 3α-(2,3-epoxy-2-methylbutyryloxy)-4α-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. © 2008 Elsevier Ltd. All rights reserved.

Registro:

Documento: Artículo
Título:Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda
Autor:Vera, N.; Misico, R.; Sierra, M.G.; Asakawa, Y.; Bardón, A.
Filiación:Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, 4000 Tucumán, Argentina
Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria AR-, 1428, Argentina
Instituto de Química Orgánica y Síntesis (IQUIOS), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, 2000 Rosario, Argentina
Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima, 770-8514, Japan
Palabras clave:Antifeedant activity; Asteraceae; Eudesmanes; Pluchea sagittalis; Sesquiterpenoids; Spodoptera frugiperda; 3alpha (2,3 epoxy 2 methylbutyryloxy) 4alpha formoxy 11 hydroxy 6,7 dehydroeudesman 8 one; 3alpha-(2,3-epoxy-2-methylbutyryloxy)-4alpha-formoxy-11-hydroxy-6,7-dehydroeudesman-8-one; eudesmane; plant medicinal product; sesquiterpene; animal; armyworm; article; Asteraceae; chemical structure; chemistry; drug effect; feeding behavior; larva; plant; synthesis; X ray crystallography; Animals; Asteraceae; Crystallography, X-Ray; Feeding Behavior; Larva; Molecular Structure; Plant Components, Aerial; Plant Preparations; Sesquiterpenes; Sesquiterpenes, Eudesmane; Spodoptera; Asteraceae; Cabrera; Hexapoda; Lepidoptera; Pluchea sagittalis; Spodoptera frugiperda
Año:2008
Volumen:69
Número:8
Página de inicio:1689
Página de fin:1694
DOI: http://dx.doi.org/10.1016/j.phytochem.2008.02.020
Título revista:Phytochemistry
Título revista abreviado:Phytochemistry
ISSN:00319422
CODEN:PYTCA
CAS:3alpha-(2,3-epoxy-2-methylbutyryloxy)-4alpha-formoxy-11-hydroxy-6,7-dehydroeudesman-8-one; eudesmane, 473-11-0; Plant Preparations; Sesquiterpenes; Sesquiterpenes, Eudesmane
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00319422_v69_n8_p1689_Vera

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  • note

Citas:

---------- APA ----------
Vera, N., Misico, R., Sierra, M.G., Asakawa, Y. & Bardón, A. (2008) . Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda. Phytochemistry, 69(8), 1689-1694.
http://dx.doi.org/10.1016/j.phytochem.2008.02.020
---------- CHICAGO ----------
Vera, N., Misico, R., Sierra, M.G., Asakawa, Y., Bardón, A. "Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda" . Phytochemistry 69, no. 8 (2008) : 1689-1694.
http://dx.doi.org/10.1016/j.phytochem.2008.02.020
---------- MLA ----------
Vera, N., Misico, R., Sierra, M.G., Asakawa, Y., Bardón, A. "Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda" . Phytochemistry, vol. 69, no. 8, 2008, pp. 1689-1694.
http://dx.doi.org/10.1016/j.phytochem.2008.02.020
---------- VANCOUVER ----------
Vera, N., Misico, R., Sierra, M.G., Asakawa, Y., Bardón, A. Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda. Phytochemistry. 2008;69(8):1689-1694.
http://dx.doi.org/10.1016/j.phytochem.2008.02.020