Vibrational circular dichroism of africanane and lippifoliane sesquiterpenes from Lippia integrifolia

Autores
Cerda García Rojas, Carlos M.; Catalan, Cesar Atilio Nazareno; Muro, Ana Carolina; Joseph Nathan, Pedro
Año de publicación
2008
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The agreement between theoretical and experimental vibrational circular dichroism curves of (4R,9R,10R)-(+)-african-l(5)-ene-2,6-dione (1) and (4R,9S,10R)-lippifoli-l(6)-en-5-one (2), isolated from the widely used plant Lippia integrifolia, allowed the determination of the conformation and absolute configuration of 1 and confirmed both structural features for 2. Molecular modeling of 1 and 2 was carried out by means of a systematic and a Monte Carlo search protocol followed by geometry optimization employing density functional theory calculations with the B3LYP/6-31G(d), B3LYP/ DGDZVP, and/or B3PW91/DGDZVP2 functionals/basis sets. Validation of the minimum energy conformations for both tricyclic substances was achieved by comparison of the experimental and theoretical vicinal 1H-1H NMR coupling constants obtained by DFT-GIAO calculations.
Fil: Cerda García Rojas, Carlos M.. Instituto Politécnico Nacional. Centro de Estudios Avanzados; México
Fil: Catalan, Cesar Atilio Nazareno. 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
Fil: Muro, Ana Carolina. 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
Fil: Joseph Nathan, Pedro. Instituto Politécnico Nacional. Centro de Estudios Avanzados; México
Materia
Vibrational Circular Dichroism
Sesquiterpenes
Lippia Integrifolia
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:11336/54644
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Vibrational circular dichroism of africanane and lippifoliane sesquiterpenes from Lippia integrifoliaCerda García Rojas, Carlos M.Catalan, Cesar Atilio NazarenoMuro, Ana CarolinaJoseph Nathan, PedroVibrational Circular DichroismSesquiterpenesLippia Integrifoliahttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The agreement between theoretical and experimental vibrational circular dichroism curves of (4R,9R,10R)-(+)-african-l(5)-ene-2,6-dione (1) and (4R,9S,10R)-lippifoli-l(6)-en-5-one (2), isolated from the widely used plant Lippia integrifolia, allowed the determination of the conformation and absolute configuration of 1 and confirmed both structural features for 2. Molecular modeling of 1 and 2 was carried out by means of a systematic and a Monte Carlo search protocol followed by geometry optimization employing density functional theory calculations with the B3LYP/6-31G(d), B3LYP/ DGDZVP, and/or B3PW91/DGDZVP2 functionals/basis sets. Validation of the minimum energy conformations for both tricyclic substances was achieved by comparison of the experimental and theoretical vicinal 1H-1H NMR coupling constants obtained by DFT-GIAO calculations.Fil: Cerda García Rojas, Carlos M.. Instituto Politécnico Nacional. Centro de Estudios Avanzados; MéxicoFil: Catalan, Cesar Atilio Nazareno. 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; ArgentinaFil: Muro, Ana Carolina. 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; ArgentinaFil: Joseph Nathan, Pedro. Instituto Politécnico Nacional. Centro de Estudios Avanzados; MéxicoAmerican Chemical Society2008-06info: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/11336/54644Cerda García Rojas, Carlos M.; Catalan, Cesar Atilio Nazareno; Muro, Ana Carolina; Joseph Nathan, Pedro; Vibrational circular dichroism of africanane and lippifoliane sesquiterpenes from Lippia integrifolia; American Chemical Society; Journal of Natural Products; 71; 6; 6-2008; 967-9710163-3864CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/abs/10.1021/np8000927info:eu-repo/semantics/altIdentifier/doi/10.1021/np8000927info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:33:06Zoai:ri.conicet.gov.ar:11336/54644instacron: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 09:33:06.373CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Vibrational circular dichroism of africanane and lippifoliane sesquiterpenes from Lippia integrifolia
title Vibrational circular dichroism of africanane and lippifoliane sesquiterpenes from Lippia integrifolia
spellingShingle Vibrational circular dichroism of africanane and lippifoliane sesquiterpenes from Lippia integrifolia
Cerda García Rojas, Carlos M.
Vibrational Circular Dichroism
Sesquiterpenes
Lippia Integrifolia
title_short Vibrational circular dichroism of africanane and lippifoliane sesquiterpenes from Lippia integrifolia
title_full Vibrational circular dichroism of africanane and lippifoliane sesquiterpenes from Lippia integrifolia
title_fullStr Vibrational circular dichroism of africanane and lippifoliane sesquiterpenes from Lippia integrifolia
title_full_unstemmed Vibrational circular dichroism of africanane and lippifoliane sesquiterpenes from Lippia integrifolia
title_sort Vibrational circular dichroism of africanane and lippifoliane sesquiterpenes from Lippia integrifolia
dc.creator.none.fl_str_mv Cerda García Rojas, Carlos M.
Catalan, Cesar Atilio Nazareno
Muro, Ana Carolina
Joseph Nathan, Pedro
author Cerda García Rojas, Carlos M.
author_facet Cerda García Rojas, Carlos M.
Catalan, Cesar Atilio Nazareno
Muro, Ana Carolina
Joseph Nathan, Pedro
author_role author
author2 Catalan, Cesar Atilio Nazareno
Muro, Ana Carolina
Joseph Nathan, Pedro
author2_role author
author
author
dc.subject.none.fl_str_mv Vibrational Circular Dichroism
Sesquiterpenes
Lippia Integrifolia
topic Vibrational Circular Dichroism
Sesquiterpenes
Lippia Integrifolia
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The agreement between theoretical and experimental vibrational circular dichroism curves of (4R,9R,10R)-(+)-african-l(5)-ene-2,6-dione (1) and (4R,9S,10R)-lippifoli-l(6)-en-5-one (2), isolated from the widely used plant Lippia integrifolia, allowed the determination of the conformation and absolute configuration of 1 and confirmed both structural features for 2. Molecular modeling of 1 and 2 was carried out by means of a systematic and a Monte Carlo search protocol followed by geometry optimization employing density functional theory calculations with the B3LYP/6-31G(d), B3LYP/ DGDZVP, and/or B3PW91/DGDZVP2 functionals/basis sets. Validation of the minimum energy conformations for both tricyclic substances was achieved by comparison of the experimental and theoretical vicinal 1H-1H NMR coupling constants obtained by DFT-GIAO calculations.
Fil: Cerda García Rojas, Carlos M.. Instituto Politécnico Nacional. Centro de Estudios Avanzados; México
Fil: Catalan, Cesar Atilio Nazareno. 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
Fil: Muro, Ana Carolina. 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
Fil: Joseph Nathan, Pedro. Instituto Politécnico Nacional. Centro de Estudios Avanzados; México
description The agreement between theoretical and experimental vibrational circular dichroism curves of (4R,9R,10R)-(+)-african-l(5)-ene-2,6-dione (1) and (4R,9S,10R)-lippifoli-l(6)-en-5-one (2), isolated from the widely used plant Lippia integrifolia, allowed the determination of the conformation and absolute configuration of 1 and confirmed both structural features for 2. Molecular modeling of 1 and 2 was carried out by means of a systematic and a Monte Carlo search protocol followed by geometry optimization employing density functional theory calculations with the B3LYP/6-31G(d), B3LYP/ DGDZVP, and/or B3PW91/DGDZVP2 functionals/basis sets. Validation of the minimum energy conformations for both tricyclic substances was achieved by comparison of the experimental and theoretical vicinal 1H-1H NMR coupling constants obtained by DFT-GIAO calculations.
publishDate 2008
dc.date.none.fl_str_mv 2008-06
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/11336/54644
Cerda García Rojas, Carlos M.; Catalan, Cesar Atilio Nazareno; Muro, Ana Carolina; Joseph Nathan, Pedro; Vibrational circular dichroism of africanane and lippifoliane sesquiterpenes from Lippia integrifolia; American Chemical Society; Journal of Natural Products; 71; 6; 6-2008; 967-971
0163-3864
CONICET Digital
CONICET
url http://hdl.handle.net/11336/54644
identifier_str_mv Cerda García Rojas, Carlos M.; Catalan, Cesar Atilio Nazareno; Muro, Ana Carolina; Joseph Nathan, Pedro; Vibrational circular dichroism of africanane and lippifoliane sesquiterpenes from Lippia integrifolia; American Chemical Society; Journal of Natural Products; 71; 6; 6-2008; 967-971
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/url/https://pubs.acs.org/doi/abs/10.1021/np8000927
info:eu-repo/semantics/altIdentifier/doi/10.1021/np8000927
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 13.070432

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