Absolute configuration of lippifoliane and africanane derivatives

Autores
Cerda García Rojas, Carlos M.; Coronel, Angelina del Carmen; Perotti, Marina Elvira; Catalan, Cesar Atilio Nazareno; Joseph Nathan, Pedro
Año de publicación
2005
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The absolute configuration of naturally occurring lippifoliane derivatives isolated from the widely used plant Lippia integrifolia was assigned by analysis of the circular dichroism data in combination with density functional theory minimum energy molecular models of (1S,4A,6S,9S,10R)-lippifolian-1-ol-5-one (1), (4R,9S,10R)-lippifoli-1(6)-en-5-one (2), and (4S,9S,10R)-lippifoli-1(6)-en-4- ol-5-one (3) and application of the octant rule for saturated ketone 1 and the helicity rules for α,β-unsaturated ketones 2 and 3. The results were reinforced by the anomalous dispersion effect observed in the X-ray diffraction analysis of (4S,9S,10R)-4,10,11-tribromo-10,11-seco-lippifoli-1(6)-en-5-one (4) prepared from 2. The biogenetic relationships between lippifolianes 1-3 and africanane derivatives 7-9 and 13 isolated from the same species, together with chiroptical data for africananes isolated from the Hepaticae family, complete a stereochemical scenario in relation to the absolute configuration of africananes from L. integrifolia.
Fil: Cerda García Rojas, Carlos M.. Instituto Politécnico Nacional; México
Fil: Coronel, Angelina del Carmen. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Fil: Perotti, Marina Elvira. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Fil: Catalan, Cesar Atilio Nazareno. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Fil: Joseph Nathan, Pedro. Instituto Politécnico Nacional; México
Materia
Absolute configuration
Lippia integrifolia
Lippifoliane derivatives
Africanane derivatives
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:11336/100279
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/100279
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Absolute configuration of lippifoliane and africanane derivativesCerda García Rojas, Carlos M.Coronel, Angelina del CarmenPerotti, Marina ElviraCatalan, Cesar Atilio NazarenoJoseph Nathan, PedroAbsolute configurationLippia integrifoliaLippifoliane derivativesAfricanane derivativeshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The absolute configuration of naturally occurring lippifoliane derivatives isolated from the widely used plant Lippia integrifolia was assigned by analysis of the circular dichroism data in combination with density functional theory minimum energy molecular models of (1S,4A,6S,9S,10R)-lippifolian-1-ol-5-one (1), (4R,9S,10R)-lippifoli-1(6)-en-5-one (2), and (4S,9S,10R)-lippifoli-1(6)-en-4- ol-5-one (3) and application of the octant rule for saturated ketone 1 and the helicity rules for α,β-unsaturated ketones 2 and 3. The results were reinforced by the anomalous dispersion effect observed in the X-ray diffraction analysis of (4S,9S,10R)-4,10,11-tribromo-10,11-seco-lippifoli-1(6)-en-5-one (4) prepared from 2. The biogenetic relationships between lippifolianes 1-3 and africanane derivatives 7-9 and 13 isolated from the same species, together with chiroptical data for africananes isolated from the Hepaticae family, complete a stereochemical scenario in relation to the absolute configuration of africananes from L. integrifolia.Fil: Cerda García Rojas, Carlos M.. Instituto Politécnico Nacional; MéxicoFil: Coronel, Angelina del Carmen. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaFil: Perotti, Marina Elvira. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaFil: Catalan, Cesar Atilio Nazareno. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; ArgentinaFil: Joseph Nathan, Pedro. Instituto Politécnico Nacional; MéxicoAmerican Chemical Society2005-05info: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/11336/100279Cerda García Rojas, Carlos M.; Coronel, Angelina del Carmen; Perotti, Marina Elvira; Catalan, Cesar Atilio Nazareno; Joseph Nathan, Pedro; Absolute configuration of lippifoliane and africanane derivatives; American Chemical Society; Journal of Natural Products; 68; 5; 5-2005; 659-6650163-3864CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/np050004ninfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/np050004ninfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:08:44Zoai:ri.conicet.gov.ar:11336/100279instacron: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 15:08:45.232CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Absolute configuration of lippifoliane and africanane derivatives
title Absolute configuration of lippifoliane and africanane derivatives
spellingShingle Absolute configuration of lippifoliane and africanane derivatives
Cerda García Rojas, Carlos M.
Absolute configuration
Lippia integrifolia
Lippifoliane derivatives
Africanane derivatives
title_short Absolute configuration of lippifoliane and africanane derivatives
title_full Absolute configuration of lippifoliane and africanane derivatives
title_fullStr Absolute configuration of lippifoliane and africanane derivatives
title_full_unstemmed Absolute configuration of lippifoliane and africanane derivatives
title_sort Absolute configuration of lippifoliane and africanane derivatives
dc.creator.none.fl_str_mv Cerda García Rojas, Carlos M.
Coronel, Angelina del Carmen
Perotti, Marina Elvira
Catalan, Cesar Atilio Nazareno
Joseph Nathan, Pedro
author Cerda García Rojas, Carlos M.
author_facet Cerda García Rojas, Carlos M.
Coronel, Angelina del Carmen
Perotti, Marina Elvira
Catalan, Cesar Atilio Nazareno
Joseph Nathan, Pedro
author_role author
author2 Coronel, Angelina del Carmen
Perotti, Marina Elvira
Catalan, Cesar Atilio Nazareno
Joseph Nathan, Pedro
author2_role author
author
author
author
dc.subject.none.fl_str_mv Absolute configuration
Lippia integrifolia
Lippifoliane derivatives
Africanane derivatives
topic Absolute configuration
Lippia integrifolia
Lippifoliane derivatives
Africanane derivatives
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 absolute configuration of naturally occurring lippifoliane derivatives isolated from the widely used plant Lippia integrifolia was assigned by analysis of the circular dichroism data in combination with density functional theory minimum energy molecular models of (1S,4A,6S,9S,10R)-lippifolian-1-ol-5-one (1), (4R,9S,10R)-lippifoli-1(6)-en-5-one (2), and (4S,9S,10R)-lippifoli-1(6)-en-4- ol-5-one (3) and application of the octant rule for saturated ketone 1 and the helicity rules for α,β-unsaturated ketones 2 and 3. The results were reinforced by the anomalous dispersion effect observed in the X-ray diffraction analysis of (4S,9S,10R)-4,10,11-tribromo-10,11-seco-lippifoli-1(6)-en-5-one (4) prepared from 2. The biogenetic relationships between lippifolianes 1-3 and africanane derivatives 7-9 and 13 isolated from the same species, together with chiroptical data for africananes isolated from the Hepaticae family, complete a stereochemical scenario in relation to the absolute configuration of africananes from L. integrifolia.
Fil: Cerda García Rojas, Carlos M.. Instituto Politécnico Nacional; México
Fil: Coronel, Angelina del Carmen. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Fil: Perotti, Marina Elvira. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Fil: Catalan, Cesar Atilio Nazareno. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química Orgánica; Argentina
Fil: Joseph Nathan, Pedro. Instituto Politécnico Nacional; México
description The absolute configuration of naturally occurring lippifoliane derivatives isolated from the widely used plant Lippia integrifolia was assigned by analysis of the circular dichroism data in combination with density functional theory minimum energy molecular models of (1S,4A,6S,9S,10R)-lippifolian-1-ol-5-one (1), (4R,9S,10R)-lippifoli-1(6)-en-5-one (2), and (4S,9S,10R)-lippifoli-1(6)-en-4- ol-5-one (3) and application of the octant rule for saturated ketone 1 and the helicity rules for α,β-unsaturated ketones 2 and 3. The results were reinforced by the anomalous dispersion effect observed in the X-ray diffraction analysis of (4S,9S,10R)-4,10,11-tribromo-10,11-seco-lippifoli-1(6)-en-5-one (4) prepared from 2. The biogenetic relationships between lippifolianes 1-3 and africanane derivatives 7-9 and 13 isolated from the same species, together with chiroptical data for africananes isolated from the Hepaticae family, complete a stereochemical scenario in relation to the absolute configuration of africananes from L. integrifolia.
publishDate 2005
dc.date.none.fl_str_mv 2005-05
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/11336/100279
Cerda García Rojas, Carlos M.; Coronel, Angelina del Carmen; Perotti, Marina Elvira; Catalan, Cesar Atilio Nazareno; Joseph Nathan, Pedro; Absolute configuration of lippifoliane and africanane derivatives; American Chemical Society; Journal of Natural Products; 68; 5; 5-2005; 659-665
0163-3864
CONICET Digital
CONICET
url http://hdl.handle.net/11336/100279
identifier_str_mv Cerda García Rojas, Carlos M.; Coronel, Angelina del Carmen; Perotti, Marina Elvira; Catalan, Cesar Atilio Nazareno; Joseph Nathan, Pedro; Absolute configuration of lippifoliane and africanane derivatives; American Chemical Society; Journal of Natural Products; 68; 5; 5-2005; 659-665
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/np050004n
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/np050004n
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 13.22299

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