Structural Studies and Spectroscopic properties of Quinolizidine Alkaloids (+) and (-)-Lupinine in different media

Autores
Ruiz Hidalgo, José; Iramain, Maximiliano Alberto; Brandan, Silvia Antonia
Año de publicación
2019
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The quinolizidine alkaloids, as numerous species of lupine (Lupinus spp.), are toxic andhave biological effect on the nervous system. Hence, four (+) and (-)- molecular structuresof quinolizidine alkaloid lupinine, named C0, C1a, C1b and C1c have been theoreticallydetermined in gas phase and in aqueous solution by using hybrid B3LYP/6-31G*calculations. The studied properties have evidenced that the most stable C1c form presentthe higher populations in both media while the predicted infrared, Raman, 1H-NMR and 13C-NMR and ultra-visible spectra suggest that probably other forms in lower proportioncould be also present in water, chloroform and benzene solutions, as evidenced by the lowRMSD values observed in the 1H- and 13C-NMR chemical shifts. The C1c form presentsthe lower corrected solvation energy in water while the NBO and AIM studies suggest forthis form a high stability in both media. In addition, the predicted ECD spectra of all (+)and (-)-lupinine forms in methanol solution evidence clearly that the C1b forms is presentin the solution because its spectrum presents a negative Cotton effect as observed in the experimental one.
Fil: Ruiz Hidalgo, José. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
Materia
LUPININE
ALKALOID
STRUCTURAL
SPECTROSCOPIC
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:11336/119322
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Structural Studies and Spectroscopic properties of Quinolizidine Alkaloids (+) and (-)-Lupinine in different mediaRuiz Hidalgo, JoséIramain, Maximiliano AlbertoBrandan, Silvia AntoniaLUPININEALKALOIDSTRUCTURALSPECTROSCOPIChttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The quinolizidine alkaloids, as numerous species of lupine (Lupinus spp.), are toxic andhave biological effect on the nervous system. Hence, four (+) and (-)- molecular structuresof quinolizidine alkaloid lupinine, named C0, C1a, C1b and C1c have been theoreticallydetermined in gas phase and in aqueous solution by using hybrid B3LYP/6-31G*calculations. The studied properties have evidenced that the most stable C1c form presentthe higher populations in both media while the predicted infrared, Raman, 1H-NMR and 13C-NMR and ultra-visible spectra suggest that probably other forms in lower proportioncould be also present in water, chloroform and benzene solutions, as evidenced by the lowRMSD values observed in the 1H- and 13C-NMR chemical shifts. The C1c form presentsthe lower corrected solvation energy in water while the NBO and AIM studies suggest forthis form a high stability in both media. In addition, the predicted ECD spectra of all (+)and (-)-lupinine forms in methanol solution evidence clearly that the C1b forms is presentin the solution because its spectrum presents a negative Cotton effect as observed in the experimental one.Fil: Ruiz Hidalgo, José. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; ArgentinaFil: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; ArgentinaJMES2019-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/119322Ruiz Hidalgo, José; Iramain, Maximiliano Alberto; Brandan, Silvia Antonia; Structural Studies and Spectroscopic properties of Quinolizidine Alkaloids (+) and (-)-Lupinine in different media; JMES; Journal of Materials and Environmental Sciences; 10; 9; 9-2019; 818-8312028-2508CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.jmaterenvironsci.com/Document/vol10/vol10_N9/JMES-2019-10-9-84-Tracanna.pdfinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:33:33Zoai:ri.conicet.gov.ar:11336/119322instacron: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 10:33:33.747CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Structural Studies and Spectroscopic properties of Quinolizidine Alkaloids (+) and (-)-Lupinine in different media
title Structural Studies and Spectroscopic properties of Quinolizidine Alkaloids (+) and (-)-Lupinine in different media
spellingShingle Structural Studies and Spectroscopic properties of Quinolizidine Alkaloids (+) and (-)-Lupinine in different media
Ruiz Hidalgo, José
LUPININE
ALKALOID
STRUCTURAL
SPECTROSCOPIC
title_short Structural Studies and Spectroscopic properties of Quinolizidine Alkaloids (+) and (-)-Lupinine in different media
title_full Structural Studies and Spectroscopic properties of Quinolizidine Alkaloids (+) and (-)-Lupinine in different media
title_fullStr Structural Studies and Spectroscopic properties of Quinolizidine Alkaloids (+) and (-)-Lupinine in different media
title_full_unstemmed Structural Studies and Spectroscopic properties of Quinolizidine Alkaloids (+) and (-)-Lupinine in different media
title_sort Structural Studies and Spectroscopic properties of Quinolizidine Alkaloids (+) and (-)-Lupinine in different media
dc.creator.none.fl_str_mv Ruiz Hidalgo, José
Iramain, Maximiliano Alberto
Brandan, Silvia Antonia
author Ruiz Hidalgo, José
author_facet Ruiz Hidalgo, José
Iramain, Maximiliano Alberto
Brandan, Silvia Antonia
author_role author
author2 Iramain, Maximiliano Alberto
Brandan, Silvia Antonia
author2_role author
author
dc.subject.none.fl_str_mv LUPININE
ALKALOID
STRUCTURAL
SPECTROSCOPIC
topic LUPININE
ALKALOID
STRUCTURAL
SPECTROSCOPIC
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 quinolizidine alkaloids, as numerous species of lupine (Lupinus spp.), are toxic andhave biological effect on the nervous system. Hence, four (+) and (-)- molecular structuresof quinolizidine alkaloid lupinine, named C0, C1a, C1b and C1c have been theoreticallydetermined in gas phase and in aqueous solution by using hybrid B3LYP/6-31G*calculations. The studied properties have evidenced that the most stable C1c form presentthe higher populations in both media while the predicted infrared, Raman, 1H-NMR and 13C-NMR and ultra-visible spectra suggest that probably other forms in lower proportioncould be also present in water, chloroform and benzene solutions, as evidenced by the lowRMSD values observed in the 1H- and 13C-NMR chemical shifts. The C1c form presentsthe lower corrected solvation energy in water while the NBO and AIM studies suggest forthis form a high stability in both media. In addition, the predicted ECD spectra of all (+)and (-)-lupinine forms in methanol solution evidence clearly that the C1b forms is presentin the solution because its spectrum presents a negative Cotton effect as observed in the experimental one.
Fil: Ruiz Hidalgo, José. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Iramain, Maximiliano Alberto. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina
Fil: Brandan, Silvia Antonia. Universidad Nacional de Tucuman. Facultad de Bioquimica, Quimica y Farmacia. Instituto de Quimica Inorganica. Cátedra de Química General.; Argentina
description The quinolizidine alkaloids, as numerous species of lupine (Lupinus spp.), are toxic andhave biological effect on the nervous system. Hence, four (+) and (-)- molecular structuresof quinolizidine alkaloid lupinine, named C0, C1a, C1b and C1c have been theoreticallydetermined in gas phase and in aqueous solution by using hybrid B3LYP/6-31G*calculations. The studied properties have evidenced that the most stable C1c form presentthe higher populations in both media while the predicted infrared, Raman, 1H-NMR and 13C-NMR and ultra-visible spectra suggest that probably other forms in lower proportioncould be also present in water, chloroform and benzene solutions, as evidenced by the lowRMSD values observed in the 1H- and 13C-NMR chemical shifts. The C1c form presentsthe lower corrected solvation energy in water while the NBO and AIM studies suggest forthis form a high stability in both media. In addition, the predicted ECD spectra of all (+)and (-)-lupinine forms in methanol solution evidence clearly that the C1b forms is presentin the solution because its spectrum presents a negative Cotton effect as observed in the experimental one.
publishDate 2019
dc.date.none.fl_str_mv 2019-09
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/11336/119322
Ruiz Hidalgo, José; Iramain, Maximiliano Alberto; Brandan, Silvia Antonia; Structural Studies and Spectroscopic properties of Quinolizidine Alkaloids (+) and (-)-Lupinine in different media; JMES; Journal of Materials and Environmental Sciences; 10; 9; 9-2019; 818-831
2028-2508
CONICET Digital
CONICET
url http://hdl.handle.net/11336/119322
identifier_str_mv Ruiz Hidalgo, José; Iramain, Maximiliano Alberto; Brandan, Silvia Antonia; Structural Studies and Spectroscopic properties of Quinolizidine Alkaloids (+) and (-)-Lupinine in different media; JMES; Journal of Materials and Environmental Sciences; 10; 9; 9-2019; 818-831
2028-2508
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.jmaterenvironsci.com/Document/vol10/vol10_N9/JMES-2019-10-9-84-Tracanna.pdf
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 JMES
publisher.none.fl_str_mv JMES
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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