Antifungal diastereomeric furanones from Mutisia friesiana: structural determination and conformational analysis

Autores
Viturro, Carmen Ines; Maier, Marta Silvia; Stortz, Carlos Arturo; de la Fuente, Juana Rosa
Año de publicación
2001
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Two diastereomeric furanones, (4S,5S)-5-(4-methyl-3-pentenyl)-4-hydroxy-5-methyldihydrofuran-2-one 1 and (4S,5R)-5-(4-methyl-3-pentenyl)-4-hydroxy-5-methyldihydrofuran-2-one 2 were isolated for the first time from the shrub Mutisia friesiana. The relative stereochemistries of 1 and 2 were ascertained from NOESY NMR data and confirmed by a combination of molecular modeling (molecular mechanics and ab initio molecular orbital calculations) and NMR data. Comparison between experimentaland calculated 1H?1H vicinal coupling constants revealed that both furanones exist in an equilibrium of two stable conformers of the five-membered ring. Application of Mosher?s method suggests that both diastereomeric furanones have the same (S)-configuration at C-(4) and are epimers at C-(5). Furanones 1 and 2 showed antifungal activity against the pathogenic fungus Cladosporium cucumerinum.
Fil: Viturro, Carmen Ines. Universidad Nacional de Jujuy; Argentina
Fil: Maier, Marta Silvia. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Fil: Stortz, Carlos Arturo. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: de la Fuente, Juana Rosa. Universidad Nacional de Salta. Facultad de Ciencias Exactas; Argentina
Materia
Furanones
Mutisia fresiana
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:11336/138063
Acceder
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network_name_str CONICET Digital (CONICET)
spelling Antifungal diastereomeric furanones from Mutisia friesiana: structural determination and conformational analysisViturro, Carmen InesMaier, Marta SilviaStortz, Carlos Arturode la Fuente, Juana RosaFuranonesMutisia fresianahttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Two diastereomeric furanones, (4S,5S)-5-(4-methyl-3-pentenyl)-4-hydroxy-5-methyldihydrofuran-2-one 1 and (4S,5R)-5-(4-methyl-3-pentenyl)-4-hydroxy-5-methyldihydrofuran-2-one 2 were isolated for the first time from the shrub Mutisia friesiana. The relative stereochemistries of 1 and 2 were ascertained from NOESY NMR data and confirmed by a combination of molecular modeling (molecular mechanics and ab initio molecular orbital calculations) and NMR data. Comparison between experimentaland calculated 1H?1H vicinal coupling constants revealed that both furanones exist in an equilibrium of two stable conformers of the five-membered ring. Application of Mosher?s method suggests that both diastereomeric furanones have the same (S)-configuration at C-(4) and are epimers at C-(5). Furanones 1 and 2 showed antifungal activity against the pathogenic fungus Cladosporium cucumerinum.Fil: Viturro, Carmen Ines. Universidad Nacional de Jujuy; ArgentinaFil: Maier, Marta Silvia. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaFil: Stortz, Carlos Arturo. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: de la Fuente, Juana Rosa. Universidad Nacional de Salta. Facultad de Ciencias Exactas; ArgentinaPergamon-Elsevier Science Ltd2001-08info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/138063Viturro, Carmen Ines; Maier, Marta Silvia; Stortz, Carlos Arturo; de la Fuente, Juana Rosa; Antifungal diastereomeric furanones from Mutisia friesiana: structural determination and conformational analysis; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 12; 7; 8-2001; 991-9980957-4166CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/abs/pii/S095741660100163Xinfo:eu-repo/semantics/altIdentifier/doi/10.1016/S0957-4166(01)00163-Xinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:24:35Zoai:ri.conicet.gov.ar:11336/138063instacron: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 14:24:36.119CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Antifungal diastereomeric furanones from Mutisia friesiana: structural determination and conformational analysis
title Antifungal diastereomeric furanones from Mutisia friesiana: structural determination and conformational analysis
spellingShingle Antifungal diastereomeric furanones from Mutisia friesiana: structural determination and conformational analysis
Viturro, Carmen Ines
Furanones
Mutisia fresiana
title_short Antifungal diastereomeric furanones from Mutisia friesiana: structural determination and conformational analysis
title_full Antifungal diastereomeric furanones from Mutisia friesiana: structural determination and conformational analysis
title_fullStr Antifungal diastereomeric furanones from Mutisia friesiana: structural determination and conformational analysis
title_full_unstemmed Antifungal diastereomeric furanones from Mutisia friesiana: structural determination and conformational analysis
title_sort Antifungal diastereomeric furanones from Mutisia friesiana: structural determination and conformational analysis
dc.creator.none.fl_str_mv Viturro, Carmen Ines
Maier, Marta Silvia
Stortz, Carlos Arturo
de la Fuente, Juana Rosa
author Viturro, Carmen Ines
author_facet Viturro, Carmen Ines
Maier, Marta Silvia
Stortz, Carlos Arturo
de la Fuente, Juana Rosa
author_role author
author2 Maier, Marta Silvia
Stortz, Carlos Arturo
de la Fuente, Juana Rosa
author2_role author
author
author
dc.subject.none.fl_str_mv Furanones
Mutisia fresiana
topic Furanones
Mutisia fresiana
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Two diastereomeric furanones, (4S,5S)-5-(4-methyl-3-pentenyl)-4-hydroxy-5-methyldihydrofuran-2-one 1 and (4S,5R)-5-(4-methyl-3-pentenyl)-4-hydroxy-5-methyldihydrofuran-2-one 2 were isolated for the first time from the shrub Mutisia friesiana. The relative stereochemistries of 1 and 2 were ascertained from NOESY NMR data and confirmed by a combination of molecular modeling (molecular mechanics and ab initio molecular orbital calculations) and NMR data. Comparison between experimentaland calculated 1H?1H vicinal coupling constants revealed that both furanones exist in an equilibrium of two stable conformers of the five-membered ring. Application of Mosher?s method suggests that both diastereomeric furanones have the same (S)-configuration at C-(4) and are epimers at C-(5). Furanones 1 and 2 showed antifungal activity against the pathogenic fungus Cladosporium cucumerinum.
Fil: Viturro, Carmen Ines. Universidad Nacional de Jujuy; Argentina
Fil: Maier, Marta Silvia. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Fil: Stortz, Carlos Arturo. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Orgánica; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: de la Fuente, Juana Rosa. Universidad Nacional de Salta. Facultad de Ciencias Exactas; Argentina
description Two diastereomeric furanones, (4S,5S)-5-(4-methyl-3-pentenyl)-4-hydroxy-5-methyldihydrofuran-2-one 1 and (4S,5R)-5-(4-methyl-3-pentenyl)-4-hydroxy-5-methyldihydrofuran-2-one 2 were isolated for the first time from the shrub Mutisia friesiana. The relative stereochemistries of 1 and 2 were ascertained from NOESY NMR data and confirmed by a combination of molecular modeling (molecular mechanics and ab initio molecular orbital calculations) and NMR data. Comparison between experimentaland calculated 1H?1H vicinal coupling constants revealed that both furanones exist in an equilibrium of two stable conformers of the five-membered ring. Application of Mosher?s method suggests that both diastereomeric furanones have the same (S)-configuration at C-(4) and are epimers at C-(5). Furanones 1 and 2 showed antifungal activity against the pathogenic fungus Cladosporium cucumerinum.
publishDate 2001
dc.date.none.fl_str_mv 2001-08
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/11336/138063
Viturro, Carmen Ines; Maier, Marta Silvia; Stortz, Carlos Arturo; de la Fuente, Juana Rosa; Antifungal diastereomeric furanones from Mutisia friesiana: structural determination and conformational analysis; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 12; 7; 8-2001; 991-998
0957-4166
CONICET Digital
CONICET
url http://hdl.handle.net/11336/138063
identifier_str_mv Viturro, Carmen Ines; Maier, Marta Silvia; Stortz, Carlos Arturo; de la Fuente, Juana Rosa; Antifungal diastereomeric furanones from Mutisia friesiana: structural determination and conformational analysis; Pergamon-Elsevier Science Ltd; Tetrahedron: Asymmetry; 12; 7; 8-2001; 991-998
0957-4166
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://www.sciencedirect.com/science/article/abs/pii/S095741660100163X
info:eu-repo/semantics/altIdentifier/doi/10.1016/S0957-4166(01)00163-X
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_ 1846082669825228800
score 13.22299

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