Artículo

Lang, K.L.; Deagosto, E.; Zimmermann, L.A.; Machado, V.R.; Campos Bernardes, L.S.; Schenkel, E.P.; Duran, F.J.; Palermo, J.; Rossini, C. "Chemical modification produces species-specific changes in cucurbitacin antifeedant effect" (2013) Journal of Agricultural and Food Chemistry. 61(23):5534-5539
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Abstract:

Cucurbitacins are secondary metabolites that mediate insect plant interactions not only as allomones against generalists but also as kairomones for specialist herbivores. This study was undertaken to identify the potential of cucurbitacin derivatives as insect antifeedant agents. The antifeedant capacity against a Cucurbitaceae specialist [Epilachna paenulata (Coleoptera: Coccinellidae)] and a polyphagous insect [Pseudaletia adultera (Lepidoptera: Noctuidae)] was evaluated in preference tests in which the insects were given a choice between food plants either treated with the cucurbitacin derivatives or treated with the solvent. The activity was found not to be related to the basic cucurbitacin skeleton, as only 15 of the 28 tested cucurbitacin derivatives were active. Only one of the tested compounds was phagostimulant to the specialist insect (the hemissuccinate of 16-oxo-dihydrocucurbitacin B derivative), while all other active derivatives were deterrent against one of the insects (13 compounds) or both of them (3 compounds). Changes in ring A of the cucurbitacins, as well as in the side chain, modified the activity. As a general trend, when chemical modifications of the basic structure produced a change in activity, the response was opposite in both insects used as biodetectors, indicating that a selective variation in the activity may be achieved by chemical modifications of the cucurbitacin skeleton. © 2013 American Chemical Society.

Registro:

Documento: Artículo
Título:Chemical modification produces species-specific changes in cucurbitacin antifeedant effect
Autor:Lang, K.L.; Deagosto, E.; Zimmermann, L.A.; Machado, V.R.; Campos Bernardes, L.S.; Schenkel, E.P.; Duran, F.J.; Palermo, J.; Rossini, C.
Filiación:Laboratório de Química Farmaceîutica, Departamento de Cieîncias Farmaceîuticas, Universidade Federal de Santa Catarina, Santa Catarina-Brasil CEP, 88040-900 Florianopolis, SC, Brazil
Laboratorio de Ecología Química, Departamento de Química Orgánica, Universidad de la República, General Flores 2124, CP 11800 Montevideo, Uruguay
UMYMFOR-CONICET, Departamento de Química Orgánica, Universidad de Buenos Aires, 1428 Buenos Aires, Argentina
Palabras clave:anti-insect; antiherbivory; cucurbitacins; deterrent; semisynthesis; triterpenoid; anti-insect; antiherbivory; Cucurbitacins; deterrent; Semisynthesis; Triterpenoids; Musculoskeletal system; Chemical modification; cucurbitacin; plant extract; animal; article; beetle; chemical structure; chemistry; Cucurbitaceae; drug effect; feeding behavior; Lepidoptera; physiology; species difference; Animals; Beetles; Cucurbitaceae; Cucurbitacins; Feeding Behavior; Lepidoptera; Molecular Structure; Plant Extracts; Species Specificity; Coccinellidae; Coleoptera; Cucurbitaceae; Epilachna paenulata; Hexapoda; Lepidoptera; Mythimna; Noctuidae
Año:2013
Volumen:61
Número:23
Página de inicio:5534
Página de fin:5539
DOI: http://dx.doi.org/10.1021/jf4002457
Título revista:Journal of Agricultural and Food Chemistry
Título revista abreviado:J. Agric. Food Chem.
ISSN:00218561
CODEN:JAFCA
CAS:Cucurbitacins, 60137-06-6; Plant Extracts
Registro:https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_00218561_v61_n23_p5534_Lang

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Citas:

---------- APA ----------
Lang, K.L., Deagosto, E., Zimmermann, L.A., Machado, V.R., Campos Bernardes, L.S., Schenkel, E.P., Duran, F.J.,..., Rossini, C. (2013) . Chemical modification produces species-specific changes in cucurbitacin antifeedant effect. Journal of Agricultural and Food Chemistry, 61(23), 5534-5539.
http://dx.doi.org/10.1021/jf4002457
---------- CHICAGO ----------
Lang, K.L., Deagosto, E., Zimmermann, L.A., Machado, V.R., Campos Bernardes, L.S., Schenkel, E.P., et al. "Chemical modification produces species-specific changes in cucurbitacin antifeedant effect" . Journal of Agricultural and Food Chemistry 61, no. 23 (2013) : 5534-5539.
http://dx.doi.org/10.1021/jf4002457
---------- MLA ----------
Lang, K.L., Deagosto, E., Zimmermann, L.A., Machado, V.R., Campos Bernardes, L.S., Schenkel, E.P., et al. "Chemical modification produces species-specific changes in cucurbitacin antifeedant effect" . Journal of Agricultural and Food Chemistry, vol. 61, no. 23, 2013, pp. 5534-5539.
http://dx.doi.org/10.1021/jf4002457
---------- VANCOUVER ----------
Lang, K.L., Deagosto, E., Zimmermann, L.A., Machado, V.R., Campos Bernardes, L.S., Schenkel, E.P., et al. Chemical modification produces species-specific changes in cucurbitacin antifeedant effect. J. Agric. Food Chem. 2013;61(23):5534-5539.
http://dx.doi.org/10.1021/jf4002457