Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda

Autores
Vera, Nancy Roxana; Misico, Rosana Isabel; Gonzalez Sierra, Manuel; Asakawa, Yoshinori; Bardon, Alicia del Valle
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
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.
Fil: Vera, Nancy Roxana. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Fil: Misico, Rosana Isabel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Gonzalez Sierra, Manuel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Asakawa, Yoshinori. Tokushima Bunri University; Japón
Fil: Bardon, Alicia del Valle. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Materia
Antifeedant Activity
Asteraceae
Eudesmanes
Pluchea Sagittalis
Sesquiterpenoids
Spodoptera Frugiperda
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:11336/54467
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/54467
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperdaVera, Nancy RoxanaMisico, Rosana IsabelGonzalez Sierra, ManuelAsakawa, YoshinoriBardon, Alicia del ValleAntifeedant ActivityAsteraceaeEudesmanesPluchea SagittalisSesquiterpenoidsSpodoptera Frugiperdahttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Eudesmane-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.Fil: Vera, Nancy Roxana. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaFil: Misico, Rosana Isabel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; ArgentinaFil: Gonzalez Sierra, Manuel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; ArgentinaFil: Asakawa, Yoshinori. Tokushima Bunri University; JapónFil: Bardon, Alicia del Valle. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaPergamon-Elsevier Science Ltd2008-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/54467Vera, Nancy Roxana; Misico, Rosana Isabel; Gonzalez Sierra, Manuel; Asakawa, Yoshinori; Bardon, Alicia del Valle; Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda; Pergamon-Elsevier Science Ltd; Phytochemistry; 69; 8; 5-2008; 1689-16940031-9422CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.phytochem.2008.02.020info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S003194220800112Xinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:46:51Zoai:ri.conicet.gov.ar:11336/54467instacron: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:34982025-09-03 09:46:51.35CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda
title Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda
spellingShingle Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda
Vera, Nancy Roxana
Antifeedant Activity
Asteraceae
Eudesmanes
Pluchea Sagittalis
Sesquiterpenoids
Spodoptera Frugiperda
title_short Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda
title_full Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda
title_fullStr Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda
title_full_unstemmed Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda
title_sort Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda
dc.creator.none.fl_str_mv Vera, Nancy Roxana
Misico, Rosana Isabel
Gonzalez Sierra, Manuel
Asakawa, Yoshinori
Bardon, Alicia del Valle
author Vera, Nancy Roxana
author_facet Vera, Nancy Roxana
Misico, Rosana Isabel
Gonzalez Sierra, Manuel
Asakawa, Yoshinori
Bardon, Alicia del Valle
author_role author
author2 Misico, Rosana Isabel
Gonzalez Sierra, Manuel
Asakawa, Yoshinori
Bardon, Alicia del Valle
author2_role author
author
author
author
dc.subject.none.fl_str_mv Antifeedant Activity
Asteraceae
Eudesmanes
Pluchea Sagittalis
Sesquiterpenoids
Spodoptera Frugiperda
topic Antifeedant Activity
Asteraceae
Eudesmanes
Pluchea Sagittalis
Sesquiterpenoids
Spodoptera Frugiperda
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv 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.
Fil: Vera, Nancy Roxana. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Fil: Misico, Rosana Isabel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina
Fil: Gonzalez Sierra, Manuel. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Asakawa, Yoshinori. Tokushima Bunri University; Japón
Fil: Bardon, Alicia del Valle. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
description 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.
publishDate 2008
dc.date.none.fl_str_mv 2008-05
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/11336/54467
Vera, Nancy Roxana; Misico, Rosana Isabel; Gonzalez Sierra, Manuel; Asakawa, Yoshinori; Bardon, Alicia del Valle; Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda; Pergamon-Elsevier Science Ltd; Phytochemistry; 69; 8; 5-2008; 1689-1694
0031-9422
CONICET Digital
CONICET
url http://hdl.handle.net/11336/54467
identifier_str_mv Vera, Nancy Roxana; Misico, Rosana Isabel; Gonzalez Sierra, Manuel; Asakawa, Yoshinori; Bardon, Alicia del Valle; Eudesmanes from Pluchea sagittalis. Their antifeedant activity on Spodoptera frugiperda; Pergamon-Elsevier Science Ltd; Phytochemistry; 69; 8; 5-2008; 1689-1694
0031-9422
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.phytochem.2008.02.020
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S003194220800112X
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
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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 13.13397

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