Absolute Configuration and Selective Trypanocidal Activity of Gaudichaudianic Acid Enantiomers

Autores
Batista, João M.; Batista, Andrea N. L.; Rinaldo, Daniel; Vilegas, Wagner; Ambrósio, Daniela L.; Cicarelli, Regina M. B.; Bolzani, Vanderlan S.; Kato, Massuo J.; Nafie, Laurence A.; López, Silvia Noelí; Furlan, Maysa
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Gaudichaudianic acid, a prenylated chromene isolated from Piper gaudichaudianum, has been described as a potent trypanocidal compound against the Y-strain of Trypanosoma cruzi. We herein describe its isolation as a racemic mixture followed by enantiomeric resolution using chiral HPLC and determination of the absolute configuration of the enantiomers as (þ)-S and ()-R by means of a combination of electronic and vibrational circular dichroism using density functional theory calculations. Investigation of the EtOAc extract of the roots, stems, and leaves from both adult specimens and seedlings of P.gaudichaudianum revealed that gaudichaudianic acid is biosynthesized as a racemic mixture from the seedling stage onward. Moreover, gaudichaudianic acid was found exclusively in the roots of seedlings, while it is present in all organs of the adult plant. Trypanocidal assays indicated that the (þ)-enantiomer was more active than its antipode. Interestingly, mixtures of enantiomers showed a synergistic effect, with the racemic mixture being the most active.
Fil: Batista, João M.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Batista, Andrea N. L.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Rinaldo, Daniel. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Vilegas, Wagner. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Ambrósio, Daniela L.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Cicarelli, Regina M. B.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Bolzani, Vanderlan S.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Kato, Massuo J.. Universidade de Sao Paulo; Brasil
Fil: Nafie, Laurence A.. Syracuse University; Estados Unidos
Fil: López, Silvia Noelí. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Furlan, Maysa. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Materia
GAUDICHAUDIANIC
ABSOLUTE CONFIGURATION
TRYPANOCIDAL
SYNERGISM
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:11336/268454
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/268454
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Absolute Configuration and Selective Trypanocidal Activity of Gaudichaudianic Acid EnantiomersBatista, João M.Batista, Andrea N. L.Rinaldo, DanielVilegas, WagnerAmbrósio, Daniela L.Cicarelli, Regina M. B.Bolzani, Vanderlan S.Kato, Massuo J.Nafie, Laurence A.López, Silvia NoelíFurlan, MaysaGAUDICHAUDIANICABSOLUTE CONFIGURATIONTRYPANOCIDALSYNERGISMhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Gaudichaudianic acid, a prenylated chromene isolated from Piper gaudichaudianum, has been described as a potent trypanocidal compound against the Y-strain of Trypanosoma cruzi. We herein describe its isolation as a racemic mixture followed by enantiomeric resolution using chiral HPLC and determination of the absolute configuration of the enantiomers as (þ)-S and ()-R by means of a combination of electronic and vibrational circular dichroism using density functional theory calculations. Investigation of the EtOAc extract of the roots, stems, and leaves from both adult specimens and seedlings of P.gaudichaudianum revealed that gaudichaudianic acid is biosynthesized as a racemic mixture from the seedling stage onward. Moreover, gaudichaudianic acid was found exclusively in the roots of seedlings, while it is present in all organs of the adult plant. Trypanocidal assays indicated that the (þ)-enantiomer was more active than its antipode. Interestingly, mixtures of enantiomers showed a synergistic effect, with the racemic mixture being the most active.Fil: Batista, João M.. Universidade Estadual Paulista Julio de Mesquita Filho; BrasilFil: Batista, Andrea N. L.. Universidade Estadual Paulista Julio de Mesquita Filho; BrasilFil: Rinaldo, Daniel. Universidade Estadual Paulista Julio de Mesquita Filho; BrasilFil: Vilegas, Wagner. Universidade Estadual Paulista Julio de Mesquita Filho; BrasilFil: Ambrósio, Daniela L.. Universidade Estadual Paulista Julio de Mesquita Filho; BrasilFil: Cicarelli, Regina M. B.. Universidade Estadual Paulista Julio de Mesquita Filho; BrasilFil: Bolzani, Vanderlan S.. Universidade Estadual Paulista Julio de Mesquita Filho; BrasilFil: Kato, Massuo J.. Universidade de Sao Paulo; BrasilFil: Nafie, Laurence A.. Syracuse University; Estados UnidosFil: López, Silvia Noelí. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; ArgentinaFil: Furlan, Maysa. Universidade Estadual Paulista Julio de Mesquita Filho; BrasilAmerican Chemical Society2011-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/268454Batista, João M.; Batista, Andrea N. L.; Rinaldo, Daniel; Vilegas, Wagner; Ambrósio, Daniela L.; et al.; Absolute Configuration and Selective Trypanocidal Activity of Gaudichaudianic Acid Enantiomers; American Chemical Society; Journal of Natural Products; 74; 5; 4-2011; 1154-11600163-3864CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://pubs.acs.org/doi/pdf/10.1021/np200085hinfo:eu-repo/semantics/altIdentifier/doi/10.1021/np200085hinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:01:20Zoai:ri.conicet.gov.ar:11336/268454instacron: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:34982025-09-03 10:01:20.334CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Absolute Configuration and Selective Trypanocidal Activity of Gaudichaudianic Acid Enantiomers
title Absolute Configuration and Selective Trypanocidal Activity of Gaudichaudianic Acid Enantiomers
spellingShingle Absolute Configuration and Selective Trypanocidal Activity of Gaudichaudianic Acid Enantiomers
Batista, João M.
GAUDICHAUDIANIC
ABSOLUTE CONFIGURATION
TRYPANOCIDAL
SYNERGISM
title_short Absolute Configuration and Selective Trypanocidal Activity of Gaudichaudianic Acid Enantiomers
title_full Absolute Configuration and Selective Trypanocidal Activity of Gaudichaudianic Acid Enantiomers
title_fullStr Absolute Configuration and Selective Trypanocidal Activity of Gaudichaudianic Acid Enantiomers
title_full_unstemmed Absolute Configuration and Selective Trypanocidal Activity of Gaudichaudianic Acid Enantiomers
title_sort Absolute Configuration and Selective Trypanocidal Activity of Gaudichaudianic Acid Enantiomers
dc.creator.none.fl_str_mv Batista, João M.
Batista, Andrea N. L.
Rinaldo, Daniel
Vilegas, Wagner
Ambrósio, Daniela L.
Cicarelli, Regina M. B.
Bolzani, Vanderlan S.
Kato, Massuo J.
Nafie, Laurence A.
López, Silvia Noelí
Furlan, Maysa
author Batista, João M.
author_facet Batista, João M.
Batista, Andrea N. L.
Rinaldo, Daniel
Vilegas, Wagner
Ambrósio, Daniela L.
Cicarelli, Regina M. B.
Bolzani, Vanderlan S.
Kato, Massuo J.
Nafie, Laurence A.
López, Silvia Noelí
Furlan, Maysa
author_role author
author2 Batista, Andrea N. L.
Rinaldo, Daniel
Vilegas, Wagner
Ambrósio, Daniela L.
Cicarelli, Regina M. B.
Bolzani, Vanderlan S.
Kato, Massuo J.
Nafie, Laurence A.
López, Silvia Noelí
Furlan, Maysa
author2_role author
author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv GAUDICHAUDIANIC
ABSOLUTE CONFIGURATION
TRYPANOCIDAL
SYNERGISM
topic GAUDICHAUDIANIC
ABSOLUTE CONFIGURATION
TRYPANOCIDAL
SYNERGISM
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Gaudichaudianic acid, a prenylated chromene isolated from Piper gaudichaudianum, has been described as a potent trypanocidal compound against the Y-strain of Trypanosoma cruzi. We herein describe its isolation as a racemic mixture followed by enantiomeric resolution using chiral HPLC and determination of the absolute configuration of the enantiomers as (þ)-S and ()-R by means of a combination of electronic and vibrational circular dichroism using density functional theory calculations. Investigation of the EtOAc extract of the roots, stems, and leaves from both adult specimens and seedlings of P.gaudichaudianum revealed that gaudichaudianic acid is biosynthesized as a racemic mixture from the seedling stage onward. Moreover, gaudichaudianic acid was found exclusively in the roots of seedlings, while it is present in all organs of the adult plant. Trypanocidal assays indicated that the (þ)-enantiomer was more active than its antipode. Interestingly, mixtures of enantiomers showed a synergistic effect, with the racemic mixture being the most active.
Fil: Batista, João M.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Batista, Andrea N. L.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Rinaldo, Daniel. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Vilegas, Wagner. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Ambrósio, Daniela L.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Cicarelli, Regina M. B.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Bolzani, Vanderlan S.. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
Fil: Kato, Massuo J.. Universidade de Sao Paulo; Brasil
Fil: Nafie, Laurence A.. Syracuse University; Estados Unidos
Fil: López, Silvia Noelí. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Furlan, Maysa. Universidade Estadual Paulista Julio de Mesquita Filho; Brasil
description Gaudichaudianic acid, a prenylated chromene isolated from Piper gaudichaudianum, has been described as a potent trypanocidal compound against the Y-strain of Trypanosoma cruzi. We herein describe its isolation as a racemic mixture followed by enantiomeric resolution using chiral HPLC and determination of the absolute configuration of the enantiomers as (þ)-S and ()-R by means of a combination of electronic and vibrational circular dichroism using density functional theory calculations. Investigation of the EtOAc extract of the roots, stems, and leaves from both adult specimens and seedlings of P.gaudichaudianum revealed that gaudichaudianic acid is biosynthesized as a racemic mixture from the seedling stage onward. Moreover, gaudichaudianic acid was found exclusively in the roots of seedlings, while it is present in all organs of the adult plant. Trypanocidal assays indicated that the (þ)-enantiomer was more active than its antipode. Interestingly, mixtures of enantiomers showed a synergistic effect, with the racemic mixture being the most active.
publishDate 2011
dc.date.none.fl_str_mv 2011-04
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/11336/268454
Batista, João M.; Batista, Andrea N. L.; Rinaldo, Daniel; Vilegas, Wagner; Ambrósio, Daniela L.; et al.; Absolute Configuration and Selective Trypanocidal Activity of Gaudichaudianic Acid Enantiomers; American Chemical Society; Journal of Natural Products; 74; 5; 4-2011; 1154-1160
0163-3864
CONICET Digital
CONICET
url http://hdl.handle.net/11336/268454
identifier_str_mv Batista, João M.; Batista, Andrea N. L.; Rinaldo, Daniel; Vilegas, Wagner; Ambrósio, Daniela L.; et al.; Absolute Configuration and Selective Trypanocidal Activity of Gaudichaudianic Acid Enantiomers; American Chemical Society; Journal of Natural Products; 74; 5; 4-2011; 1154-1160
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/http://pubs.acs.org/doi/pdf/10.1021/np200085h
info:eu-repo/semantics/altIdentifier/doi/10.1021/np200085h
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
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score 13.13397

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