Chemical modification produces species-specific changes in Cucurbitacin Antifeedant effect

Autores
Lang, Karen L.; Deagosto, Emilio; Zimmermann, Lara Almida; Machado, Vanessa Rocha; Bernardes, Lílian Sibelle Campos; Schenkel, Eloir P.; Duran, Fernando Javier; Palermo, Jorge Alejandro; Rossini, Carmen
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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.
Fil: Lang, Karen L.. Universidade Federal de Santa Catarina; Brasil
Fil: Deagosto, Emilio. Universidad de la República; Uruguay
Fil: Zimmermann, Lara Almida. Universidade Federal de Santa Catarina; Brasil
Fil: Machado, Vanessa Rocha. Universidade Federal de Santa Catarina; Brasil
Fil: Bernardes, Lílian Sibelle Campos. Universidade Federal de Santa Catarina; Brasil
Fil: Schenkel, Eloir P.. Universidade Federal de Santa Catarina; Brasil
Fil: Duran, Fernando Javier. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Fil: Palermo, Jorge Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Fil: Rossini, Carmen. Universidad de la República; Uruguay
Materia
Antiinsecto
Deterrente
Triterpenoide
Antihervivoro
Cucurbitacinas
Semisintesis
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/26994
Acceder
id CONICETDig_0c83af0a8adc412b72caabb4f9d4dddf
oai_identifier_str oai:ri.conicet.gov.ar:11336/26994
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Chemical modification produces species-specific changes in Cucurbitacin Antifeedant effectLang, Karen L.Deagosto, EmilioZimmermann, Lara AlmidaMachado, Vanessa RochaBernardes, Lílian Sibelle CamposSchenkel, Eloir P.Duran, Fernando JavierPalermo, Jorge AlejandroRossini, CarmenAntiinsectoDeterrenteTriterpenoideAntihervivoroCucurbitacinasSemisintesishttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Cucurbitacins 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.Fil: Lang, Karen L.. Universidade Federal de Santa Catarina; BrasilFil: Deagosto, Emilio. Universidad de la República; UruguayFil: Zimmermann, Lara Almida. Universidade Federal de Santa Catarina; BrasilFil: Machado, Vanessa Rocha. Universidade Federal de Santa Catarina; BrasilFil: Bernardes, Lílian Sibelle Campos. Universidade Federal de Santa Catarina; BrasilFil: Schenkel, Eloir P.. Universidade Federal de Santa Catarina; BrasilFil: Duran, Fernando Javier. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaFil: Palermo, Jorge Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaFil: Rossini, Carmen. Universidad de la República; UruguayAmerican Chemical Society2013-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/26994Lang, Karen L.; Deagosto, Emilio; Zimmermann, Lara Almida; Machado, Vanessa Rocha; Bernardes, Lílian Sibelle Campos; et al.; Chemical modification produces species-specific changes in Cucurbitacin Antifeedant effect; American Chemical Society; Journal Of Agricultural And Food Chemistry; 61; 23; 5-2013; 5534-55390021-8561CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/0.1021/jf4002457info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/jf4002457info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:29:48Zoai:ri.conicet.gov.ar:11336/26994instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:29:48.862CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Chemical modification produces species-specific changes in Cucurbitacin Antifeedant effect
title Chemical modification produces species-specific changes in Cucurbitacin Antifeedant effect
spellingShingle Chemical modification produces species-specific changes in Cucurbitacin Antifeedant effect
Lang, Karen L.
Antiinsecto
Deterrente
Triterpenoide
Antihervivoro
Cucurbitacinas
Semisintesis
title_short Chemical modification produces species-specific changes in Cucurbitacin Antifeedant effect
title_full Chemical modification produces species-specific changes in Cucurbitacin Antifeedant effect
title_fullStr Chemical modification produces species-specific changes in Cucurbitacin Antifeedant effect
title_full_unstemmed Chemical modification produces species-specific changes in Cucurbitacin Antifeedant effect
title_sort Chemical modification produces species-specific changes in Cucurbitacin Antifeedant effect
dc.creator.none.fl_str_mv Lang, Karen L.
Deagosto, Emilio
Zimmermann, Lara Almida
Machado, Vanessa Rocha
Bernardes, Lílian Sibelle Campos
Schenkel, Eloir P.
Duran, Fernando Javier
Palermo, Jorge Alejandro
Rossini, Carmen
author Lang, Karen L.
author_facet Lang, Karen L.
Deagosto, Emilio
Zimmermann, Lara Almida
Machado, Vanessa Rocha
Bernardes, Lílian Sibelle Campos
Schenkel, Eloir P.
Duran, Fernando Javier
Palermo, Jorge Alejandro
Rossini, Carmen
author_role author
author2 Deagosto, Emilio
Zimmermann, Lara Almida
Machado, Vanessa Rocha
Bernardes, Lílian Sibelle Campos
Schenkel, Eloir P.
Duran, Fernando Javier
Palermo, Jorge Alejandro
Rossini, Carmen
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Antiinsecto
Deterrente
Triterpenoide
Antihervivoro
Cucurbitacinas
Semisintesis
topic Antiinsecto
Deterrente
Triterpenoide
Antihervivoro
Cucurbitacinas
Semisintesis
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv 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.
Fil: Lang, Karen L.. Universidade Federal de Santa Catarina; Brasil
Fil: Deagosto, Emilio. Universidad de la República; Uruguay
Fil: Zimmermann, Lara Almida. Universidade Federal de Santa Catarina; Brasil
Fil: Machado, Vanessa Rocha. Universidade Federal de Santa Catarina; Brasil
Fil: Bernardes, Lílian Sibelle Campos. Universidade Federal de Santa Catarina; Brasil
Fil: Schenkel, Eloir P.. Universidade Federal de Santa Catarina; Brasil
Fil: Duran, Fernando Javier. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Fil: Palermo, Jorge Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Fil: Rossini, Carmen. Universidad de la República; Uruguay
description 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.
publishDate 2013
dc.date.none.fl_str_mv 2013-05
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/26994
Lang, Karen L.; Deagosto, Emilio; Zimmermann, Lara Almida; Machado, Vanessa Rocha; Bernardes, Lílian Sibelle Campos; et al.; Chemical modification produces species-specific changes in Cucurbitacin Antifeedant effect; American Chemical Society; Journal Of Agricultural And Food Chemistry; 61; 23; 5-2013; 5534-5539
0021-8561
CONICET Digital
CONICET
url http://hdl.handle.net/11336/26994
identifier_str_mv Lang, Karen L.; Deagosto, Emilio; Zimmermann, Lara Almida; Machado, Vanessa Rocha; Bernardes, Lílian Sibelle Campos; et al.; Chemical modification produces species-specific changes in Cucurbitacin Antifeedant effect; American Chemical Society; Journal Of Agricultural And Food Chemistry; 61; 23; 5-2013; 5534-5539
0021-8561
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/0.1021/jf4002457
info:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/abs/10.1021/jf4002457
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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