Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda
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 par...
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2008
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| LEADER | 11053caa a22012977a 4500 | ||
|---|---|---|---|
| 001 | PAPER-5939 | ||
| 003 | AR-BaUEN | ||
| 005 | 20230518203537.0 | ||
| 008 | 190411s2008 xx ||||fo|||| 00| 0 eng|d | ||
| 024 | 7 | |2 scopus |a 2-s2.0-42749092079 | |
| 024 | 7 | |2 cas |a 3alpha-(2,3-epoxy-2-methylbutyryloxy)-4alpha-formoxy-11-hydroxy-6,7-dehydroeudesman-8-one; eudesmane, 473-11-0; Plant Preparations; Sesquiterpenes; Sesquiterpenes, Eudesmane | |
| 040 | |a Scopus |b spa |c AR-BaUEN |d AR-BaUEN | ||
| 030 | |a PYTCA | ||
| 100 | 1 | |a Vera, N. | |
| 245 | 1 | 0 | |a Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda |
| 260 | |c 2008 | ||
| 270 | 1 | 0 | |m Bardón, A.; Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, 4000 Tucumán, Argentina; email: alisan@unt.edu.ar |
| 506 | |2 openaire |e Política editorial | ||
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| 504 | |a Blaney, W.M., Simmonds, M.S.J., Ley, S.V., Anderson, J.C., Toogood, P.L., Antifeedant effects of azadirachtin and structurally related compounds on lepidopterous larvae (1990) Entomologia Experimentalis et Applicata, 55, pp. 149-160 | ||
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| 504 | |a Perez-García, F., Marín, E., Parella, T., Adzet, T., Cañigueral, S., Activity of taraxasteryl acetate on inflammation and heat shock protein synthesis (2005) Phytomedicine, 12, pp. 278-284 | ||
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| 504 | |a Soraru, S.B., Bandoni, A.L., (1979) Plantas de la Medicina Popular Argentina, , Ed. Albatros, Buenos Aires | ||
| 504 | |a Srivastava, R.P., Proksch, P., Wray, V., Toxicity and antifeedant activity of a sesquiterpene lactone from Encelia against Spodoptera littoralis (1990) Phytochemistry, 29, pp. 3445-3448 | ||
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| 504 | |a note | ||
| 520 | 3 | |a 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. |l eng | |
| 536 | |a Detalles de la financiación: Consejo Nacional de Investigaciones Científicas y Técnicas | ||
| 536 | |a Detalles de la financiación: Agencia Nacional de Promoción Científica y Tecnológica | ||
| 536 | |a Detalles de la financiación: Universidad Nacional de Tucumán | ||
| 536 | |a Detalles de la financiación: Authors thank Ms. Y. Okamoto (TBU, Japan) for recording mass sprectra, Dr. M. Tanaka (TBU) for 600 MHz NMR, and Mr. S. Takaoka (TBU) for X-ray crystallographic analysis. Work in Argentina was supported by grants from Agencia Nacional de Promoción Científica y Tecnológica (ANPCyT), Consejo Nacional de Investigaciones Científicas y Técnicas de Argentina (CONICET) and Consejo de Investigaciones de la Universidad Nacional de Tucumán (CIUNT). Appendix A | ||
| 593 | |a Instituto de Química Orgánica, Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán, Ayacucho 471, 4000 Tucumán, Argentina | ||
| 593 | |a Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Pabellón 2, Ciudad Universitaria AR-, 1428, Argentina | ||
| 593 | |a Instituto de Química Orgánica y Síntesis (IQUIOS), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario, Suipacha 531, 2000 Rosario, Argentina | ||
| 593 | |a Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima, 770-8514, Japan | ||
| 690 | 1 | 0 | |a ANTIFEEDANT ACTIVITY |
| 690 | 1 | 0 | |a ASTERACEAE |
| 690 | 1 | 0 | |a EUDESMANES |
| 690 | 1 | 0 | |a PLUCHEA SAGITTALIS |
| 690 | 1 | 0 | |a SESQUITERPENOIDS |
| 690 | 1 | 0 | |a SPODOPTERA FRUGIPERDA |
| 690 | 1 | 0 | |a 3ALPHA (2,3 EPOXY 2 METHYLBUTYRYLOXY) 4ALPHA FORMOXY 11 HYDROXY 6,7 DEHYDROEUDESMAN 8 ONE |
| 690 | 1 | 0 | |a 3ALPHA-(2,3-EPOXY-2-METHYLBUTYRYLOXY)-4ALPHA-FORMOXY-11-HYDROXY-6,7-DEHYDROEUDESMAN-8-ONE |
| 690 | 1 | 0 | |a EUDESMANE |
| 690 | 1 | 0 | |a PLANT MEDICINAL PRODUCT |
| 690 | 1 | 0 | |a SESQUITERPENE |
| 690 | 1 | 0 | |a ANIMAL |
| 690 | 1 | 0 | |a ARMYWORM |
| 690 | 1 | 0 | |a ARTICLE |
| 690 | 1 | 0 | |a ASTERACEAE |
| 690 | 1 | 0 | |a CHEMICAL STRUCTURE |
| 690 | 1 | 0 | |a CHEMISTRY |
| 690 | 1 | 0 | |a DRUG EFFECT |
| 690 | 1 | 0 | |a FEEDING BEHAVIOR |
| 690 | 1 | 0 | |a LARVA |
| 690 | 1 | 0 | |a PLANT |
| 690 | 1 | 0 | |a SYNTHESIS |
| 690 | 1 | 0 | |a X RAY CRYSTALLOGRAPHY |
| 690 | 1 | 0 | |a ANIMALS |
| 690 | 1 | 0 | |a ASTERACEAE |
| 690 | 1 | 0 | |a CRYSTALLOGRAPHY, X-RAY |
| 690 | 1 | 0 | |a FEEDING BEHAVIOR |
| 690 | 1 | 0 | |a LARVA |
| 690 | 1 | 0 | |a MOLECULAR STRUCTURE |
| 690 | 1 | 0 | |a PLANT COMPONENTS, AERIAL |
| 690 | 1 | 0 | |a PLANT PREPARATIONS |
| 690 | 1 | 0 | |a SESQUITERPENES |
| 690 | 1 | 0 | |a SESQUITERPENES, EUDESMANE |
| 690 | 1 | 0 | |a SPODOPTERA |
| 690 | 1 | 0 | |a ASTERACEAE |
| 690 | 1 | 0 | |a CABRERA |
| 690 | 1 | 0 | |a HEXAPODA |
| 690 | 1 | 0 | |a LEPIDOPTERA |
| 690 | 1 | 0 | |a PLUCHEA SAGITTALIS |
| 690 | 1 | 0 | |a SPODOPTERA FRUGIPERDA |
| 700 | 1 | |a Misico, R. | |
| 700 | 1 | |a Sierra, M.G. | |
| 700 | 1 | |a Asakawa, Y. | |
| 700 | 1 | |a Bardón, A. | |
| 773 | 0 | |d 2008 |g v. 69 |h pp. 1689-1694 |k n. 8 |p Phytochemistry |x 00319422 |w (AR-BaUEN)CENRE-88 |t Phytochemistry | |
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