Further monoterpene chromane esters from Peperomia obtusifolia: VCD determination of the absolute configuration of a new diastereomeric mixture

Autores
Batista Junior, João Marcos; Batista, Andrea N. L.; Kato, Massuo J.; Bolzani, Vanderlan S.; López, Silvia Noelí; Nafie, Laurence A.; Furlan, Maysa
Año de publicación
2012
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A reinvestigation of the monoterpene chromane ester enriched fraction from Peperomia obtusifolia using chiral chromatography led to the identification of a minor peak, which was elucidated by NMR and HRMS as fenchyl-3,4-dihydro-5- hydroxy-2,7-dimethyl-8-(3″-methyl-2″-butenyl)-2-(4′-methyl- 1′,3′-pentadienyl)-2H-1-benzopyran-6-carboxylate, the same structure assigned to two other fenchyl esters described previously, pointing out a stereoisomeric relationship among them. Further NMR analysis revealed that it was actually a mixture of two compounds, whose absolute configurations were determined by VCD measurements. Although, almost no vibrational transitions could be assigned to the chiral chromane, the experimental VCD spectrum was largely opposite to that obtained for the average experimental VCD [(2S,1‴R,2‴R,4‴S + 2R,1‴R,2‴R,4‴S)/2] for fenchol derivatives. These results allowed us to assign the putative compounds as a racemic mixture of the chiral chromane esterified with the monoterpene (1S,2S,4R)-fenchol, which had not been identified in our early work.
Fil: Batista Junior, João Marcos. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Batista, Andrea N. L.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Kato, Massuo J.. Universidade de Sao Paulo; Brasil
Fil: Bolzani, Vanderlan S.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: López, Silvia Noelí. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina
Fil: Nafie, Laurence A.. Syracuse University; Estados Unidos
Fil: Furlan, Maysa. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Materia
CHIRAL CHROMATOGRAPHY
NATURAL PRODUCTS
PIPERACEAE
VIBRATIONAL CIRCULAR DICHROISM
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:11336/193846
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/193846
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Further monoterpene chromane esters from Peperomia obtusifolia: VCD determination of the absolute configuration of a new diastereomeric mixtureBatista Junior, João MarcosBatista, Andrea N. L.Kato, Massuo J.Bolzani, Vanderlan S.López, Silvia NoelíNafie, Laurence A.Furlan, MaysaCHIRAL CHROMATOGRAPHYNATURAL PRODUCTSPIPERACEAEVIBRATIONAL CIRCULAR DICHROISMhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A reinvestigation of the monoterpene chromane ester enriched fraction from Peperomia obtusifolia using chiral chromatography led to the identification of a minor peak, which was elucidated by NMR and HRMS as fenchyl-3,4-dihydro-5- hydroxy-2,7-dimethyl-8-(3″-methyl-2″-butenyl)-2-(4′-methyl- 1′,3′-pentadienyl)-2H-1-benzopyran-6-carboxylate, the same structure assigned to two other fenchyl esters described previously, pointing out a stereoisomeric relationship among them. Further NMR analysis revealed that it was actually a mixture of two compounds, whose absolute configurations were determined by VCD measurements. Although, almost no vibrational transitions could be assigned to the chiral chromane, the experimental VCD spectrum was largely opposite to that obtained for the average experimental VCD [(2S,1‴R,2‴R,4‴S + 2R,1‴R,2‴R,4‴S)/2] for fenchol derivatives. These results allowed us to assign the putative compounds as a racemic mixture of the chiral chromane esterified with the monoterpene (1S,2S,4R)-fenchol, which had not been identified in our early work.Fil: Batista Junior, João Marcos. Universidade Estadual Paulista Julio de Mesquita Filho; BrasilFil: Batista, Andrea N. L.. Universidade Estadual Paulista Julio de Mesquita Filho; BrasilFil: Kato, Massuo J.. Universidade de Sao Paulo; BrasilFil: Bolzani, Vanderlan S.. Universidade Estadual Paulista Julio de Mesquita Filho; BrasilFil: López, Silvia Noelí. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; ArgentinaFil: Nafie, Laurence A.. Syracuse University; Estados UnidosFil: Furlan, Maysa. Universidade Estadual Paulista Julio de Mesquita Filho; BrasilPergamon-Elsevier Science Ltd2012-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/193846Batista Junior, João Marcos; Batista, Andrea N. L.; Kato, Massuo J.; Bolzani, Vanderlan S.; López, Silvia Noelí; et al.; Further monoterpene chromane esters from Peperomia obtusifolia: VCD determination of the absolute configuration of a new diastereomeric mixture; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 53; 45; 10-2012; 6051-60540040-4039CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2012.08.113info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0040403912015006info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T15:41:27Zoai:ri.conicet.gov.ar:11336/193846instacron: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 15:41:27.616CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Further monoterpene chromane esters from Peperomia obtusifolia: VCD determination of the absolute configuration of a new diastereomeric mixture
title Further monoterpene chromane esters from Peperomia obtusifolia: VCD determination of the absolute configuration of a new diastereomeric mixture
spellingShingle Further monoterpene chromane esters from Peperomia obtusifolia: VCD determination of the absolute configuration of a new diastereomeric mixture
Batista Junior, João Marcos
CHIRAL CHROMATOGRAPHY
NATURAL PRODUCTS
PIPERACEAE
VIBRATIONAL CIRCULAR DICHROISM
title_short Further monoterpene chromane esters from Peperomia obtusifolia: VCD determination of the absolute configuration of a new diastereomeric mixture
title_full Further monoterpene chromane esters from Peperomia obtusifolia: VCD determination of the absolute configuration of a new diastereomeric mixture
title_fullStr Further monoterpene chromane esters from Peperomia obtusifolia: VCD determination of the absolute configuration of a new diastereomeric mixture
title_full_unstemmed Further monoterpene chromane esters from Peperomia obtusifolia: VCD determination of the absolute configuration of a new diastereomeric mixture
title_sort Further monoterpene chromane esters from Peperomia obtusifolia: VCD determination of the absolute configuration of a new diastereomeric mixture
dc.creator.none.fl_str_mv Batista Junior, João Marcos
Batista, Andrea N. L.
Kato, Massuo J.
Bolzani, Vanderlan S.
López, Silvia Noelí
Nafie, Laurence A.
Furlan, Maysa
author Batista Junior, João Marcos
author_facet Batista Junior, João Marcos
Batista, Andrea N. L.
Kato, Massuo J.
Bolzani, Vanderlan S.
López, Silvia Noelí
Nafie, Laurence A.
Furlan, Maysa
author_role author
author2 Batista, Andrea N. L.
Kato, Massuo J.
Bolzani, Vanderlan S.
López, Silvia Noelí
Nafie, Laurence A.
Furlan, Maysa
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv CHIRAL CHROMATOGRAPHY
NATURAL PRODUCTS
PIPERACEAE
VIBRATIONAL CIRCULAR DICHROISM
topic CHIRAL CHROMATOGRAPHY
NATURAL PRODUCTS
PIPERACEAE
VIBRATIONAL CIRCULAR DICHROISM
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 reinvestigation of the monoterpene chromane ester enriched fraction from Peperomia obtusifolia using chiral chromatography led to the identification of a minor peak, which was elucidated by NMR and HRMS as fenchyl-3,4-dihydro-5- hydroxy-2,7-dimethyl-8-(3″-methyl-2″-butenyl)-2-(4′-methyl- 1′,3′-pentadienyl)-2H-1-benzopyran-6-carboxylate, the same structure assigned to two other fenchyl esters described previously, pointing out a stereoisomeric relationship among them. Further NMR analysis revealed that it was actually a mixture of two compounds, whose absolute configurations were determined by VCD measurements. Although, almost no vibrational transitions could be assigned to the chiral chromane, the experimental VCD spectrum was largely opposite to that obtained for the average experimental VCD [(2S,1‴R,2‴R,4‴S + 2R,1‴R,2‴R,4‴S)/2] for fenchol derivatives. These results allowed us to assign the putative compounds as a racemic mixture of the chiral chromane esterified with the monoterpene (1S,2S,4R)-fenchol, which had not been identified in our early work.
Fil: Batista Junior, João Marcos. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Batista, Andrea N. L.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Kato, Massuo J.. Universidade de Sao Paulo; Brasil
Fil: Bolzani, Vanderlan S.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: López, Silvia Noelí. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina
Fil: Nafie, Laurence A.. Syracuse University; Estados Unidos
Fil: Furlan, Maysa. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
description A reinvestigation of the monoterpene chromane ester enriched fraction from Peperomia obtusifolia using chiral chromatography led to the identification of a minor peak, which was elucidated by NMR and HRMS as fenchyl-3,4-dihydro-5- hydroxy-2,7-dimethyl-8-(3″-methyl-2″-butenyl)-2-(4′-methyl- 1′,3′-pentadienyl)-2H-1-benzopyran-6-carboxylate, the same structure assigned to two other fenchyl esters described previously, pointing out a stereoisomeric relationship among them. Further NMR analysis revealed that it was actually a mixture of two compounds, whose absolute configurations were determined by VCD measurements. Although, almost no vibrational transitions could be assigned to the chiral chromane, the experimental VCD spectrum was largely opposite to that obtained for the average experimental VCD [(2S,1‴R,2‴R,4‴S + 2R,1‴R,2‴R,4‴S)/2] for fenchol derivatives. These results allowed us to assign the putative compounds as a racemic mixture of the chiral chromane esterified with the monoterpene (1S,2S,4R)-fenchol, which had not been identified in our early work.
publishDate 2012
dc.date.none.fl_str_mv 2012-10
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/11336/193846
Batista Junior, João Marcos; Batista, Andrea N. L.; Kato, Massuo J.; Bolzani, Vanderlan S.; López, Silvia Noelí; et al.; Further monoterpene chromane esters from Peperomia obtusifolia: VCD determination of the absolute configuration of a new diastereomeric mixture; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 53; 45; 10-2012; 6051-6054
0040-4039
CONICET Digital
CONICET
url http://hdl.handle.net/11336/193846
identifier_str_mv Batista Junior, João Marcos; Batista, Andrea N. L.; Kato, Massuo J.; Bolzani, Vanderlan S.; López, Silvia Noelí; et al.; Further monoterpene chromane esters from Peperomia obtusifolia: VCD determination of the absolute configuration of a new diastereomeric mixture; Pergamon-Elsevier Science Ltd; Tetrahedron Letters; 53; 45; 10-2012; 6051-6054
0040-4039
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.tetlet.2012.08.113
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0040403912015006
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 Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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_ 1846083525591171072
score 13.22299

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