C-15-functionalized eudesmanolides from Mikania campanulata

Autores
Krautmann, Marta Irene; Contreras Marañon de Riscala, Elmira; Burgueño Tapia, Eleuterio; Mora Pérez, Yolanda; Catalan, Cesar Atilio Nazareno; Joseph-Nathan, Pedro
Año de publicación
2007
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The aerial parts of Mikania campanulata Gardner afforded the nine new eudesmanolides (1S,4S,5S,6S,7S,10R)-1-hydroxy-15-acetoxyeudesm-11(13)-en-6,12- olide (1), (1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12- olide (2), (1R,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12- olide (3), (1R,4S,5S,6S,7S,10R)-1-hydroxy-4,15-diacetoxyeudesm-11(13)-en-6,12- olide (4), (1S,4R,5S,6S,7S,10R)-1,15-diacetoxy-4-hydroxyeudesm-11(13)-en-6,12- olide (5), (1S,5S,6S,7S,10R)-1-hydroxy-15-acetoxyeudesma-4(15),11(13)-dien-6,12- olide (6), (1S,5S,6S,7S,10R)-1,15-dihydroxyeudesma-3,11(13)-dien-6,12-olide (7a), (1S,2R,5S,6S,7S,10R)-1,2,15-trihydroxyeudesma-3,11 (13)-dien-6,12-olide (8a), and (1R,6S,7S,10R)-1,15-dihydroxyeudesma-4,11(13)-dien-6,12-olide (9a), among which the last three were characterized as their corresponding peracetates (7b-9b). The structures of 1-6 and 7b-9b were elucidated using 1D and 2D NMR measurements, while that of major constituent 1 was confirmed by single-crystal X-ray diffraction analysis, and its absolute configuration evidenced from vibrational circular dichroism measurements, which were compared to results obtained from density functional theory calculations. The chemistry of the large genus Mikania is briefly analyzed. © 2007 American Chemical Society and American Society of Pharmacognosy.
Fil: Krautmann, Marta Irene. Universidad Nacional de Tucumán; Argentina
Fil: Contreras Marañon de Riscala, Elmira. Universidad Nacional de Tucumán; Argentina
Fil: Burgueño Tapia, Eleuterio. Instituto Politécnico Nacional; México
Fil: Mora Pérez, Yolanda. CENTRO DE INVESTIGACIÓN Y DE ESTUDIOS AVANZADOS ; INSTITUTO POLITÉCNICO NACIONAL; . Instituto Politécnico Nacional; México
Fil: Catalan, Cesar Atilio Nazareno. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina. Universidad Nacional de Tucumán; Argentina
Fil: Joseph-Nathan, Pedro. Instituto Politécnico Nacional; México
Materia
MIKANIA
LACTONE
EUDESMANOLIDE
EUPATORIAE
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:11336/100081
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/100081
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling C-15-functionalized eudesmanolides from Mikania campanulataKrautmann, Marta IreneContreras Marañon de Riscala, ElmiraBurgueño Tapia, EleuterioMora Pérez, YolandaCatalan, Cesar Atilio NazarenoJoseph-Nathan, PedroMIKANIALACTONEEUDESMANOLIDEEUPATORIAEhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The aerial parts of Mikania campanulata Gardner afforded the nine new eudesmanolides (1S,4S,5S,6S,7S,10R)-1-hydroxy-15-acetoxyeudesm-11(13)-en-6,12- olide (1), (1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12- olide (2), (1R,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12- olide (3), (1R,4S,5S,6S,7S,10R)-1-hydroxy-4,15-diacetoxyeudesm-11(13)-en-6,12- olide (4), (1S,4R,5S,6S,7S,10R)-1,15-diacetoxy-4-hydroxyeudesm-11(13)-en-6,12- olide (5), (1S,5S,6S,7S,10R)-1-hydroxy-15-acetoxyeudesma-4(15),11(13)-dien-6,12- olide (6), (1S,5S,6S,7S,10R)-1,15-dihydroxyeudesma-3,11(13)-dien-6,12-olide (7a), (1S,2R,5S,6S,7S,10R)-1,2,15-trihydroxyeudesma-3,11 (13)-dien-6,12-olide (8a), and (1R,6S,7S,10R)-1,15-dihydroxyeudesma-4,11(13)-dien-6,12-olide (9a), among which the last three were characterized as their corresponding peracetates (7b-9b). The structures of 1-6 and 7b-9b were elucidated using 1D and 2D NMR measurements, while that of major constituent 1 was confirmed by single-crystal X-ray diffraction analysis, and its absolute configuration evidenced from vibrational circular dichroism measurements, which were compared to results obtained from density functional theory calculations. The chemistry of the large genus Mikania is briefly analyzed. © 2007 American Chemical Society and American Society of Pharmacognosy.Fil: Krautmann, Marta Irene. Universidad Nacional de Tucumán; ArgentinaFil: Contreras Marañon de Riscala, Elmira. Universidad Nacional de Tucumán; ArgentinaFil: Burgueño Tapia, Eleuterio. Instituto Politécnico Nacional; MéxicoFil: Mora Pérez, Yolanda. CENTRO DE INVESTIGACIÓN Y DE ESTUDIOS AVANZADOS ; INSTITUTO POLITÉCNICO NACIONAL; . Instituto Politécnico Nacional; MéxicoFil: Catalan, Cesar Atilio Nazareno. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina. Universidad Nacional de Tucumán; ArgentinaFil: Joseph-Nathan, Pedro. Instituto Politécnico Nacional; MéxicoAmerican Chemical Society2007-07info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/100081Krautmann, Marta Irene; Contreras Marañon de Riscala, Elmira; Burgueño Tapia, Eleuterio; Mora Pérez, Yolanda; Catalan, Cesar Atilio Nazareno; et al.; C-15-functionalized eudesmanolides from Mikania campanulata; American Chemical Society; Journal of Natural Products; 70; 7; 7-2007; 1173-11790163-3864CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1021/np070154tinfo:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/pdf/10.1021/np070154tinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:36:10Zoai:ri.conicet.gov.ar:11336/100081instacron: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 14:36:10.723CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv C-15-functionalized eudesmanolides from Mikania campanulata
title C-15-functionalized eudesmanolides from Mikania campanulata
spellingShingle C-15-functionalized eudesmanolides from Mikania campanulata
Krautmann, Marta Irene
MIKANIA
LACTONE
EUDESMANOLIDE
EUPATORIAE
title_short C-15-functionalized eudesmanolides from Mikania campanulata
title_full C-15-functionalized eudesmanolides from Mikania campanulata
title_fullStr C-15-functionalized eudesmanolides from Mikania campanulata
title_full_unstemmed C-15-functionalized eudesmanolides from Mikania campanulata
title_sort C-15-functionalized eudesmanolides from Mikania campanulata
dc.creator.none.fl_str_mv Krautmann, Marta Irene
Contreras Marañon de Riscala, Elmira
Burgueño Tapia, Eleuterio
Mora Pérez, Yolanda
Catalan, Cesar Atilio Nazareno
Joseph-Nathan, Pedro
author Krautmann, Marta Irene
author_facet Krautmann, Marta Irene
Contreras Marañon de Riscala, Elmira
Burgueño Tapia, Eleuterio
Mora Pérez, Yolanda
Catalan, Cesar Atilio Nazareno
Joseph-Nathan, Pedro
author_role author
author2 Contreras Marañon de Riscala, Elmira
Burgueño Tapia, Eleuterio
Mora Pérez, Yolanda
Catalan, Cesar Atilio Nazareno
Joseph-Nathan, Pedro
author2_role author
author
author
author
author
dc.subject.none.fl_str_mv MIKANIA
LACTONE
EUDESMANOLIDE
EUPATORIAE
topic MIKANIA
LACTONE
EUDESMANOLIDE
EUPATORIAE
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 aerial parts of Mikania campanulata Gardner afforded the nine new eudesmanolides (1S,4S,5S,6S,7S,10R)-1-hydroxy-15-acetoxyeudesm-11(13)-en-6,12- olide (1), (1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12- olide (2), (1R,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12- olide (3), (1R,4S,5S,6S,7S,10R)-1-hydroxy-4,15-diacetoxyeudesm-11(13)-en-6,12- olide (4), (1S,4R,5S,6S,7S,10R)-1,15-diacetoxy-4-hydroxyeudesm-11(13)-en-6,12- olide (5), (1S,5S,6S,7S,10R)-1-hydroxy-15-acetoxyeudesma-4(15),11(13)-dien-6,12- olide (6), (1S,5S,6S,7S,10R)-1,15-dihydroxyeudesma-3,11(13)-dien-6,12-olide (7a), (1S,2R,5S,6S,7S,10R)-1,2,15-trihydroxyeudesma-3,11 (13)-dien-6,12-olide (8a), and (1R,6S,7S,10R)-1,15-dihydroxyeudesma-4,11(13)-dien-6,12-olide (9a), among which the last three were characterized as their corresponding peracetates (7b-9b). The structures of 1-6 and 7b-9b were elucidated using 1D and 2D NMR measurements, while that of major constituent 1 was confirmed by single-crystal X-ray diffraction analysis, and its absolute configuration evidenced from vibrational circular dichroism measurements, which were compared to results obtained from density functional theory calculations. The chemistry of the large genus Mikania is briefly analyzed. © 2007 American Chemical Society and American Society of Pharmacognosy.
Fil: Krautmann, Marta Irene. Universidad Nacional de Tucumán; Argentina
Fil: Contreras Marañon de Riscala, Elmira. Universidad Nacional de Tucumán; Argentina
Fil: Burgueño Tapia, Eleuterio. Instituto Politécnico Nacional; México
Fil: Mora Pérez, Yolanda. CENTRO DE INVESTIGACIÓN Y DE ESTUDIOS AVANZADOS ; INSTITUTO POLITÉCNICO NACIONAL; . Instituto Politécnico Nacional; México
Fil: Catalan, Cesar Atilio Nazareno. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán. Instituto de Química del Noroeste. Universidad Nacional de Tucumán. Facultad de Bioquímica, Química y Farmacia. Instituto de Química del Noroeste; Argentina. Universidad Nacional de Tucumán; Argentina
Fil: Joseph-Nathan, Pedro. Instituto Politécnico Nacional; México
description The aerial parts of Mikania campanulata Gardner afforded the nine new eudesmanolides (1S,4S,5S,6S,7S,10R)-1-hydroxy-15-acetoxyeudesm-11(13)-en-6,12- olide (1), (1S,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12- olide (2), (1R,4S,5S,6S,7S,10R)-1,4-dihydroxy-15-acetoxyeudesm-11(13)-en-6,12- olide (3), (1R,4S,5S,6S,7S,10R)-1-hydroxy-4,15-diacetoxyeudesm-11(13)-en-6,12- olide (4), (1S,4R,5S,6S,7S,10R)-1,15-diacetoxy-4-hydroxyeudesm-11(13)-en-6,12- olide (5), (1S,5S,6S,7S,10R)-1-hydroxy-15-acetoxyeudesma-4(15),11(13)-dien-6,12- olide (6), (1S,5S,6S,7S,10R)-1,15-dihydroxyeudesma-3,11(13)-dien-6,12-olide (7a), (1S,2R,5S,6S,7S,10R)-1,2,15-trihydroxyeudesma-3,11 (13)-dien-6,12-olide (8a), and (1R,6S,7S,10R)-1,15-dihydroxyeudesma-4,11(13)-dien-6,12-olide (9a), among which the last three were characterized as their corresponding peracetates (7b-9b). The structures of 1-6 and 7b-9b were elucidated using 1D and 2D NMR measurements, while that of major constituent 1 was confirmed by single-crystal X-ray diffraction analysis, and its absolute configuration evidenced from vibrational circular dichroism measurements, which were compared to results obtained from density functional theory calculations. The chemistry of the large genus Mikania is briefly analyzed. © 2007 American Chemical Society and American Society of Pharmacognosy.
publishDate 2007
dc.date.none.fl_str_mv 2007-07
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/11336/100081
Krautmann, Marta Irene; Contreras Marañon de Riscala, Elmira; Burgueño Tapia, Eleuterio; Mora Pérez, Yolanda; Catalan, Cesar Atilio Nazareno; et al.; C-15-functionalized eudesmanolides from Mikania campanulata; American Chemical Society; Journal of Natural Products; 70; 7; 7-2007; 1173-1179
0163-3864
CONICET Digital
CONICET
url http://hdl.handle.net/11336/100081
identifier_str_mv Krautmann, Marta Irene; Contreras Marañon de Riscala, Elmira; Burgueño Tapia, Eleuterio; Mora Pérez, Yolanda; Catalan, Cesar Atilio Nazareno; et al.; C-15-functionalized eudesmanolides from Mikania campanulata; American Chemical Society; Journal of Natural Products; 70; 7; 7-2007; 1173-1179
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/np070154t
info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/pdf/10.1021/np070154t
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
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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