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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/100081
Ver los metadatos del registro completo
id |
CONICETDig_637d3ae93020c758a74122797d88372d |
---|---|
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 |
_version_ |
1846082826346168320 |
score |
13.22299 |