Manoyl oxide diterpenoids from Grindelia scorzonerifolia

Autores
Ybarra, María Inés; Popich, Susana Beatriz; Borkosky, Susana Alicia; Asakawa, Yoshinori; Bardon, Alicia del Valle
Año de publicación
2005
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Two new norditerpenoids, 4β-hydroxy-19-normanoyl oxide (1) and 4α-hydroxy-18-normanoyl oxide (2), the new 18-O-α-L- arabinopyranosylmanoyl oxide (3a), and the known diterpenoids jhanol (4) and 18-hydroxy-13-epi-manoyl oxide (5) were isolated, together with other common plant constituents from an Argentine collection of Grindelia scorzonerifolia. The structures of the new compounds were established by extensive 1D and 2D NMR techniques and chemical transformations. Structural features of compounds 2 and 4 were verified by X-ray crystallographic analyses. The insecticidal effect of compound 3a was evaluated against the polyphagous pest Spodoptera frugiperda. Pupal and adult malformations leading to death occurred when 3a was incorporated in a larval diet at a concentration of 100 ppm. © 2005 American Chemical Society and American Society of Pharmacognosy.
Fil: Ybarra, María Inés. Universidad Nacional de Tucumán; Argentina
Fil: Popich, Susana Beatriz. Universidad Nacional de Tucumán; Argentina
Fil: Borkosky, Susana Alicia. Universidad Nacional de Tucumán; Argentina
Fil: Asakawa, Yoshinori. Tokushima Bunri University;
Fil: Bardon, Alicia del Valle. Universidad Nacional de Tucumán; Argentina. Tokushima Bunri University; . Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
Materia
Grindelia scorzonerifolia
Manoyl oxide diterpenoids
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:11336/100866
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/100866
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Manoyl oxide diterpenoids from Grindelia scorzonerifoliaYbarra, María InésPopich, Susana BeatrizBorkosky, Susana AliciaAsakawa, YoshinoriBardon, Alicia del ValleGrindelia scorzonerifoliaManoyl oxide diterpenoidsSpodoptera frugiperdahttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Two new norditerpenoids, 4β-hydroxy-19-normanoyl oxide (1) and 4α-hydroxy-18-normanoyl oxide (2), the new 18-O-α-L- arabinopyranosylmanoyl oxide (3a), and the known diterpenoids jhanol (4) and 18-hydroxy-13-epi-manoyl oxide (5) were isolated, together with other common plant constituents from an Argentine collection of Grindelia scorzonerifolia. The structures of the new compounds were established by extensive 1D and 2D NMR techniques and chemical transformations. Structural features of compounds 2 and 4 were verified by X-ray crystallographic analyses. The insecticidal effect of compound 3a was evaluated against the polyphagous pest Spodoptera frugiperda. Pupal and adult malformations leading to death occurred when 3a was incorporated in a larval diet at a concentration of 100 ppm. © 2005 American Chemical Society and American Society of Pharmacognosy.Fil: Ybarra, María Inés. Universidad Nacional de Tucumán; ArgentinaFil: Popich, Susana Beatriz. Universidad Nacional de Tucumán; ArgentinaFil: Borkosky, Susana Alicia. Universidad Nacional de Tucumán; ArgentinaFil: Asakawa, Yoshinori. Tokushima Bunri University; Fil: Bardon, Alicia del Valle. Universidad Nacional de Tucumán; Argentina. Tokushima Bunri University; . Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; ArgentinaAmerican Chemical Society2005-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/100866Ybarra, María Inés; Popich, Susana Beatriz; Borkosky, Susana Alicia; Asakawa, Yoshinori; Bardon, Alicia del Valle; Manoyl oxide diterpenoids from Grindelia scorzonerifolia; American Chemical Society; Journal of Natural Products; 68; 4; 4-2005; 554-5580163-3864CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/np040174kinfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/np040174kinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:07:13Zoai:ri.conicet.gov.ar:11336/100866instacron: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 10:07:13.589CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Manoyl oxide diterpenoids from Grindelia scorzonerifolia
title Manoyl oxide diterpenoids from Grindelia scorzonerifolia
spellingShingle Manoyl oxide diterpenoids from Grindelia scorzonerifolia
Ybarra, María Inés
Grindelia scorzonerifolia
Manoyl oxide diterpenoids
Spodoptera frugiperda
title_short Manoyl oxide diterpenoids from Grindelia scorzonerifolia
title_full Manoyl oxide diterpenoids from Grindelia scorzonerifolia
title_fullStr Manoyl oxide diterpenoids from Grindelia scorzonerifolia
title_full_unstemmed Manoyl oxide diterpenoids from Grindelia scorzonerifolia
title_sort Manoyl oxide diterpenoids from Grindelia scorzonerifolia
dc.creator.none.fl_str_mv Ybarra, María Inés
Popich, Susana Beatriz
Borkosky, Susana Alicia
Asakawa, Yoshinori
Bardon, Alicia del Valle
author Ybarra, María Inés
author_facet Ybarra, María Inés
Popich, Susana Beatriz
Borkosky, Susana Alicia
Asakawa, Yoshinori
Bardon, Alicia del Valle
author_role author
author2 Popich, Susana Beatriz
Borkosky, Susana Alicia
Asakawa, Yoshinori
Bardon, Alicia del Valle
author2_role author
author
author
author
dc.subject.none.fl_str_mv Grindelia scorzonerifolia
Manoyl oxide diterpenoids
Spodoptera frugiperda
topic Grindelia scorzonerifolia
Manoyl oxide diterpenoids
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 Two new norditerpenoids, 4β-hydroxy-19-normanoyl oxide (1) and 4α-hydroxy-18-normanoyl oxide (2), the new 18-O-α-L- arabinopyranosylmanoyl oxide (3a), and the known diterpenoids jhanol (4) and 18-hydroxy-13-epi-manoyl oxide (5) were isolated, together with other common plant constituents from an Argentine collection of Grindelia scorzonerifolia. The structures of the new compounds were established by extensive 1D and 2D NMR techniques and chemical transformations. Structural features of compounds 2 and 4 were verified by X-ray crystallographic analyses. The insecticidal effect of compound 3a was evaluated against the polyphagous pest Spodoptera frugiperda. Pupal and adult malformations leading to death occurred when 3a was incorporated in a larval diet at a concentration of 100 ppm. © 2005 American Chemical Society and American Society of Pharmacognosy.
Fil: Ybarra, María Inés. Universidad Nacional de Tucumán; Argentina
Fil: Popich, Susana Beatriz. Universidad Nacional de Tucumán; Argentina
Fil: Borkosky, Susana Alicia. Universidad Nacional de Tucumán; Argentina
Fil: Asakawa, Yoshinori. Tokushima Bunri University;
Fil: Bardon, Alicia del Valle. Universidad Nacional de Tucumán; Argentina. Tokushima Bunri University; . Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina
description Two new norditerpenoids, 4β-hydroxy-19-normanoyl oxide (1) and 4α-hydroxy-18-normanoyl oxide (2), the new 18-O-α-L- arabinopyranosylmanoyl oxide (3a), and the known diterpenoids jhanol (4) and 18-hydroxy-13-epi-manoyl oxide (5) were isolated, together with other common plant constituents from an Argentine collection of Grindelia scorzonerifolia. The structures of the new compounds were established by extensive 1D and 2D NMR techniques and chemical transformations. Structural features of compounds 2 and 4 were verified by X-ray crystallographic analyses. The insecticidal effect of compound 3a was evaluated against the polyphagous pest Spodoptera frugiperda. Pupal and adult malformations leading to death occurred when 3a was incorporated in a larval diet at a concentration of 100 ppm. © 2005 American Chemical Society and American Society of Pharmacognosy.
publishDate 2005
dc.date.none.fl_str_mv 2005-04
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/11336/100866
Ybarra, María Inés; Popich, Susana Beatriz; Borkosky, Susana Alicia; Asakawa, Yoshinori; Bardon, Alicia del Valle; Manoyl oxide diterpenoids from Grindelia scorzonerifolia; American Chemical Society; Journal of Natural Products; 68; 4; 4-2005; 554-558
0163-3864
CONICET Digital
CONICET
url http://hdl.handle.net/11336/100866
identifier_str_mv Ybarra, María Inés; Popich, Susana Beatriz; Borkosky, Susana Alicia; Asakawa, Yoshinori; Bardon, Alicia del Valle; Manoyl oxide diterpenoids from Grindelia scorzonerifolia; American Chemical Society; Journal of Natural Products; 68; 4; 4-2005; 554-558
0163-3864
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1021/np040174k
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/np040174k
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
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 13.13397

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