Structure-antifeedant activity relationship of clerodane diterpenoids. Comparative study with withanolides and azadirachtin

Autores
Enriz, Ricardo Daniel; Baldoni, Hector Armando; Zamora, Miguel Angel; Jauregui, Esteban Adrian; Sosa, Marta Edit; Tonn, Carlos Eugenio; Luco, Juan Maria; Gordaliza, Marina
Año de publicación
2000
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A structure-antifeedant activity relationship (SAR) study of clerodane diterpenoids was carried out. Attention was focused on the feeding-deterrent activities exhibited toward Tenebrio molitor by clerodane diterpenoids and withanolides. Azadirachtin was chosen as a reference compound. SAR studies on the clerodane compounds indicate that the stereoelectronic factors are more important than the hydrophobic aspects as determinants of antifeedant activity. A furan ring in the side chain and a carbonyl α,β-unsaturated (or spiro-epoxide) group appear to be indispensable for the biological response. A conformational study indicate that the optimum interatomic distance between these moieties is a range between 9.5 and 10.5 A. In addition, a similar stereoelectronic response was found among withanolides and azadirachtin. On the basis of these results it is reasonable to imagine a closely related chemical mechanism for these compounds.
Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Baldoni, Hector Armando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Matemática Aplicada de San Luis "Prof. Ezio Marchi". Universidad Nacional de San Luis. Facultad de Ciencias Físico, Matemáticas y Naturales. Instituto de Matemática Aplicada de San Luis "Prof. Ezio Marchi"; Argentina
Fil: Zamora, Miguel Angel. Universidad Nacional de San Luis; Argentina
Fil: Jauregui, Esteban Adrian. Universidad Nacional de San Luis; Argentina
Fil: Sosa, Marta Edit. Universidad Nacional de San Luis; Argentina
Fil: Tonn, Carlos Eugenio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Luco, Juan Maria. Universidad Nacional de San Luis; Argentina
Fil: Gordaliza, Marina. Universidad de Salamanca; España
Materia
ANTIFEEDANT ACTIVITY
AZADIRACHTIN
CLERODANES
MINIMAL STRUCTURAL REQUIREMENTS
MOLECULAR MODELING
SAR
WITHANOLIDES
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:11336/134972
Acceder
id CONICETDig_08012a481ff62f85381d32f847e06203
oai_identifier_str oai:ri.conicet.gov.ar:11336/134972
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Structure-antifeedant activity relationship of clerodane diterpenoids. Comparative study with withanolides and azadirachtinEnriz, Ricardo DanielBaldoni, Hector ArmandoZamora, Miguel AngelJauregui, Esteban AdrianSosa, Marta EditTonn, Carlos EugenioLuco, Juan MariaGordaliza, MarinaANTIFEEDANT ACTIVITYAZADIRACHTINCLERODANESMINIMAL STRUCTURAL REQUIREMENTSMOLECULAR MODELINGSARWITHANOLIDEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A structure-antifeedant activity relationship (SAR) study of clerodane diterpenoids was carried out. Attention was focused on the feeding-deterrent activities exhibited toward Tenebrio molitor by clerodane diterpenoids and withanolides. Azadirachtin was chosen as a reference compound. SAR studies on the clerodane compounds indicate that the stereoelectronic factors are more important than the hydrophobic aspects as determinants of antifeedant activity. A furan ring in the side chain and a carbonyl α,β-unsaturated (or spiro-epoxide) group appear to be indispensable for the biological response. A conformational study indicate that the optimum interatomic distance between these moieties is a range between 9.5 and 10.5 A. In addition, a similar stereoelectronic response was found among withanolides and azadirachtin. On the basis of these results it is reasonable to imagine a closely related chemical mechanism for these compounds.Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; ArgentinaFil: Baldoni, Hector Armando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Matemática Aplicada de San Luis "Prof. Ezio Marchi". Universidad Nacional de San Luis. Facultad de Ciencias Físico, Matemáticas y Naturales. Instituto de Matemática Aplicada de San Luis "Prof. Ezio Marchi"; ArgentinaFil: Zamora, Miguel Angel. Universidad Nacional de San Luis; ArgentinaFil: Jauregui, Esteban Adrian. Universidad Nacional de San Luis; ArgentinaFil: Sosa, Marta Edit. Universidad Nacional de San Luis; ArgentinaFil: Tonn, Carlos Eugenio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: Luco, Juan Maria. Universidad Nacional de San Luis; ArgentinaFil: Gordaliza, Marina. Universidad de Salamanca; EspañaAmerican Chemical Society2000-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/134972Enriz, Ricardo Daniel; Baldoni, Hector Armando; Zamora, Miguel Angel; Jauregui, Esteban Adrian; Sosa, Marta Edit; et al.; Structure-antifeedant activity relationship of clerodane diterpenoids. Comparative study with withanolides and azadirachtin; American Chemical Society; Journal of Agricultural and Food Chemistry; 48; 4; 8-2000; 1384-13920021-85611520-5118CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jf990006binfo:eu-repo/semantics/altIdentifier/doi/10.1021/jf990006binfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:02:22Zoai:ri.conicet.gov.ar:11336/134972instacron: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:34982025-10-15 15:02:22.745CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Structure-antifeedant activity relationship of clerodane diterpenoids. Comparative study with withanolides and azadirachtin
title Structure-antifeedant activity relationship of clerodane diterpenoids. Comparative study with withanolides and azadirachtin
spellingShingle Structure-antifeedant activity relationship of clerodane diterpenoids. Comparative study with withanolides and azadirachtin
Enriz, Ricardo Daniel
ANTIFEEDANT ACTIVITY
AZADIRACHTIN
CLERODANES
MINIMAL STRUCTURAL REQUIREMENTS
MOLECULAR MODELING
SAR
WITHANOLIDES
title_short Structure-antifeedant activity relationship of clerodane diterpenoids. Comparative study with withanolides and azadirachtin
title_full Structure-antifeedant activity relationship of clerodane diterpenoids. Comparative study with withanolides and azadirachtin
title_fullStr Structure-antifeedant activity relationship of clerodane diterpenoids. Comparative study with withanolides and azadirachtin
title_full_unstemmed Structure-antifeedant activity relationship of clerodane diterpenoids. Comparative study with withanolides and azadirachtin
title_sort Structure-antifeedant activity relationship of clerodane diterpenoids. Comparative study with withanolides and azadirachtin
dc.creator.none.fl_str_mv Enriz, Ricardo Daniel
Baldoni, Hector Armando
Zamora, Miguel Angel
Jauregui, Esteban Adrian
Sosa, Marta Edit
Tonn, Carlos Eugenio
Luco, Juan Maria
Gordaliza, Marina
author Enriz, Ricardo Daniel
author_facet Enriz, Ricardo Daniel
Baldoni, Hector Armando
Zamora, Miguel Angel
Jauregui, Esteban Adrian
Sosa, Marta Edit
Tonn, Carlos Eugenio
Luco, Juan Maria
Gordaliza, Marina
author_role author
author2 Baldoni, Hector Armando
Zamora, Miguel Angel
Jauregui, Esteban Adrian
Sosa, Marta Edit
Tonn, Carlos Eugenio
Luco, Juan Maria
Gordaliza, Marina
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv ANTIFEEDANT ACTIVITY
AZADIRACHTIN
CLERODANES
MINIMAL STRUCTURAL REQUIREMENTS
MOLECULAR MODELING
SAR
WITHANOLIDES
topic ANTIFEEDANT ACTIVITY
AZADIRACHTIN
CLERODANES
MINIMAL STRUCTURAL REQUIREMENTS
MOLECULAR MODELING
SAR
WITHANOLIDES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A structure-antifeedant activity relationship (SAR) study of clerodane diterpenoids was carried out. Attention was focused on the feeding-deterrent activities exhibited toward Tenebrio molitor by clerodane diterpenoids and withanolides. Azadirachtin was chosen as a reference compound. SAR studies on the clerodane compounds indicate that the stereoelectronic factors are more important than the hydrophobic aspects as determinants of antifeedant activity. A furan ring in the side chain and a carbonyl α,β-unsaturated (or spiro-epoxide) group appear to be indispensable for the biological response. A conformational study indicate that the optimum interatomic distance between these moieties is a range between 9.5 and 10.5 A. In addition, a similar stereoelectronic response was found among withanolides and azadirachtin. On the basis of these results it is reasonable to imagine a closely related chemical mechanism for these compounds.
Fil: Enriz, Ricardo Daniel. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis. Universidad Nacional de San Luis. Facultad de Ciencias Físico Matemáticas y Naturales. Instituto Multidisciplinario de Investigaciones Biológicas de San Luis; Argentina
Fil: Baldoni, Hector Armando. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Matemática Aplicada de San Luis "Prof. Ezio Marchi". Universidad Nacional de San Luis. Facultad de Ciencias Físico, Matemáticas y Naturales. Instituto de Matemática Aplicada de San Luis "Prof. Ezio Marchi"; Argentina
Fil: Zamora, Miguel Angel. Universidad Nacional de San Luis; Argentina
Fil: Jauregui, Esteban Adrian. Universidad Nacional de San Luis; Argentina
Fil: Sosa, Marta Edit. Universidad Nacional de San Luis; Argentina
Fil: Tonn, Carlos Eugenio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - San Luis. Instituto de Investigaciones en Tecnología Química. Universidad Nacional de San Luis. Facultad de Química, Bioquímica y Farmacia. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Luco, Juan Maria. Universidad Nacional de San Luis; Argentina
Fil: Gordaliza, Marina. Universidad de Salamanca; España
description A structure-antifeedant activity relationship (SAR) study of clerodane diterpenoids was carried out. Attention was focused on the feeding-deterrent activities exhibited toward Tenebrio molitor by clerodane diterpenoids and withanolides. Azadirachtin was chosen as a reference compound. SAR studies on the clerodane compounds indicate that the stereoelectronic factors are more important than the hydrophobic aspects as determinants of antifeedant activity. A furan ring in the side chain and a carbonyl α,β-unsaturated (or spiro-epoxide) group appear to be indispensable for the biological response. A conformational study indicate that the optimum interatomic distance between these moieties is a range between 9.5 and 10.5 A. In addition, a similar stereoelectronic response was found among withanolides and azadirachtin. On the basis of these results it is reasonable to imagine a closely related chemical mechanism for these compounds.
publishDate 2000
dc.date.none.fl_str_mv 2000-08
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/11336/134972
Enriz, Ricardo Daniel; Baldoni, Hector Armando; Zamora, Miguel Angel; Jauregui, Esteban Adrian; Sosa, Marta Edit; et al.; Structure-antifeedant activity relationship of clerodane diterpenoids. Comparative study with withanolides and azadirachtin; American Chemical Society; Journal of Agricultural and Food Chemistry; 48; 4; 8-2000; 1384-1392
0021-8561
1520-5118
CONICET Digital
CONICET
url http://hdl.handle.net/11336/134972
identifier_str_mv Enriz, Ricardo Daniel; Baldoni, Hector Armando; Zamora, Miguel Angel; Jauregui, Esteban Adrian; Sosa, Marta Edit; et al.; Structure-antifeedant activity relationship of clerodane diterpenoids. Comparative study with withanolides and azadirachtin; American Chemical Society; Journal of Agricultural and Food Chemistry; 48; 4; 8-2000; 1384-1392
0021-8561
1520-5118
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/jf990006b
info:eu-repo/semantics/altIdentifier/doi/10.1021/jf990006b
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
_version_ 1846083164954427392
score 13.22299

Publicaciones similares