Ent-kaurane derivatives from the root cortex of yacon and other three Smallanthus species (Heliantheae, Asteraceae)

Autores
Coll Araoz, Maria Victoria; Mercado, Maria Ines; Grau, Alfredo; Catalan, Cesar Atilio Nazareno
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The metabolites produced by the secretory canals of the root cortex from four Smallanthus species belonging to the yacon group were identified as ent-kaurane-type diterpenes. The dichloromethane root cortex extracts of the four species were treated with diazomethane and analyzed comparatively by GC-MS using a simple and rapid procedure which is very sensitive and reproducible permitting detection of minor components. In all cases, ent-16-kauren-19-oic acid (kaurenoic acid) methyl ester was the main component, differences being observed only in the minor components. The minor components identified were grandiflorenic acid methyl ester, ent-16-kauren-19-al, 16α,17-epoxy-15α-angeloyloxy-kauran-19-oic acid methyl ester and several O-acyl derivatives at C-15 or C-18 of kaurenoic acid. One of the minor components, 18-isobutyroyloxy-ent-kaur-16-en-19-oic acid is a new kaurenoic acid derivative. Grandiflorenic acid and 15-α-angeloyloxy-16,17-α-epoxy- ent-16-kauren-19-oic acid were present only in Smallanthus sonchifolius and Smallanthus siegesbeckius which showed very similar GC traces. The different GC profile of RC diterpenes from Smallanthus connatus and Smallanthus macroscyphus supports the view that they are different taxa. Some chemotaxonomic aspects of the genus Smallanthus and the subtribe Milleriinae are briefly discussed.
Fil: Coll Araoz, Maria Victoria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina. Universidad Nacional de Tucumán. Facultad de Ciencias Naturales e Instituto Miguel Lillo. Instituto de Ecología Regional; Argentina
Fil: Mercado, Maria Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina. Universidad Nacional de Tucumán. Facultad de Ciencias Naturales e Instituto Miguel Lillo. Instituto de Ecología Regional; Argentina
Fil: Grau, Alfredo. Universidad Nacional de Tucumán. Facultad de Ciencias Naturales e Instituto Miguel Lillo. Instituto de Ecología Regional; Argentina
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
Materia
Kaurenoic Acid Derivatives
Root Cortex Secretory Canals
Smallanthus Connatus
Smallanthus Macroscyphus
Smallanthus Siegesbeckius
Smallanthus Sonchifolius
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:11336/52462
Acceder
id CONICETDig_bdaefe81b297ee3eb65d64cf5930f12b
oai_identifier_str oai:ri.conicet.gov.ar:11336/52462
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Ent-kaurane derivatives from the root cortex of yacon and other three Smallanthus species (Heliantheae, Asteraceae)Coll Araoz, Maria VictoriaMercado, Maria InesGrau, AlfredoCatalan, Cesar Atilio NazarenoKaurenoic Acid DerivativesRoot Cortex Secretory CanalsSmallanthus ConnatusSmallanthus MacroscyphusSmallanthus SiegesbeckiusSmallanthus Sonchifoliushttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The metabolites produced by the secretory canals of the root cortex from four Smallanthus species belonging to the yacon group were identified as ent-kaurane-type diterpenes. The dichloromethane root cortex extracts of the four species were treated with diazomethane and analyzed comparatively by GC-MS using a simple and rapid procedure which is very sensitive and reproducible permitting detection of minor components. In all cases, ent-16-kauren-19-oic acid (kaurenoic acid) methyl ester was the main component, differences being observed only in the minor components. The minor components identified were grandiflorenic acid methyl ester, ent-16-kauren-19-al, 16α,17-epoxy-15α-angeloyloxy-kauran-19-oic acid methyl ester and several O-acyl derivatives at C-15 or C-18 of kaurenoic acid. One of the minor components, 18-isobutyroyloxy-ent-kaur-16-en-19-oic acid is a new kaurenoic acid derivative. Grandiflorenic acid and 15-α-angeloyloxy-16,17-α-epoxy- ent-16-kauren-19-oic acid were present only in Smallanthus sonchifolius and Smallanthus siegesbeckius which showed very similar GC traces. The different GC profile of RC diterpenes from Smallanthus connatus and Smallanthus macroscyphus supports the view that they are different taxa. Some chemotaxonomic aspects of the genus Smallanthus and the subtribe Milleriinae are briefly discussed.Fil: Coll Araoz, Maria Victoria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina. Universidad Nacional de Tucumán. Facultad de Ciencias Naturales e Instituto Miguel Lillo. Instituto de Ecología Regional; ArgentinaFil: Mercado, Maria Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina. Universidad Nacional de Tucumán. Facultad de Ciencias Naturales e Instituto Miguel Lillo. Instituto de Ecología Regional; ArgentinaFil: Grau, Alfredo. Universidad Nacional de Tucumán. Facultad de Ciencias Naturales e Instituto Miguel Lillo. Instituto de Ecología Regional; ArgentinaFil: 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; ArgentinaPergamon-Elsevier Science Ltd2010-10info: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/11336/52462Coll Araoz, Maria Victoria; Mercado, Maria Ines; Grau, Alfredo; Catalan, Cesar Atilio Nazareno; Ent-kaurane derivatives from the root cortex of yacon and other three Smallanthus species (Heliantheae, Asteraceae); Pergamon-Elsevier Science Ltd; Biochemical Systematics And Ecology; 38; 5; 10-2010; 1042-10480305-1978CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.bse.2010.10.009info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0305197810002000info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:33:19Zoai:ri.conicet.gov.ar:11336/52462instacron: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:34982025-09-29 09:33:20.013CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Ent-kaurane derivatives from the root cortex of yacon and other three Smallanthus species (Heliantheae, Asteraceae)
title Ent-kaurane derivatives from the root cortex of yacon and other three Smallanthus species (Heliantheae, Asteraceae)
spellingShingle Ent-kaurane derivatives from the root cortex of yacon and other three Smallanthus species (Heliantheae, Asteraceae)
Coll Araoz, Maria Victoria
Kaurenoic Acid Derivatives
Root Cortex Secretory Canals
Smallanthus Connatus
Smallanthus Macroscyphus
Smallanthus Siegesbeckius
Smallanthus Sonchifolius
title_short Ent-kaurane derivatives from the root cortex of yacon and other three Smallanthus species (Heliantheae, Asteraceae)
title_full Ent-kaurane derivatives from the root cortex of yacon and other three Smallanthus species (Heliantheae, Asteraceae)
title_fullStr Ent-kaurane derivatives from the root cortex of yacon and other three Smallanthus species (Heliantheae, Asteraceae)
title_full_unstemmed Ent-kaurane derivatives from the root cortex of yacon and other three Smallanthus species (Heliantheae, Asteraceae)
title_sort Ent-kaurane derivatives from the root cortex of yacon and other three Smallanthus species (Heliantheae, Asteraceae)
dc.creator.none.fl_str_mv Coll Araoz, Maria Victoria
Mercado, Maria Ines
Grau, Alfredo
Catalan, Cesar Atilio Nazareno
author Coll Araoz, Maria Victoria
author_facet Coll Araoz, Maria Victoria
Mercado, Maria Ines
Grau, Alfredo
Catalan, Cesar Atilio Nazareno
author_role author
author2 Mercado, Maria Ines
Grau, Alfredo
Catalan, Cesar Atilio Nazareno
author2_role author
author
author
dc.subject.none.fl_str_mv Kaurenoic Acid Derivatives
Root Cortex Secretory Canals
Smallanthus Connatus
Smallanthus Macroscyphus
Smallanthus Siegesbeckius
Smallanthus Sonchifolius
topic Kaurenoic Acid Derivatives
Root Cortex Secretory Canals
Smallanthus Connatus
Smallanthus Macroscyphus
Smallanthus Siegesbeckius
Smallanthus Sonchifolius
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 metabolites produced by the secretory canals of the root cortex from four Smallanthus species belonging to the yacon group were identified as ent-kaurane-type diterpenes. The dichloromethane root cortex extracts of the four species were treated with diazomethane and analyzed comparatively by GC-MS using a simple and rapid procedure which is very sensitive and reproducible permitting detection of minor components. In all cases, ent-16-kauren-19-oic acid (kaurenoic acid) methyl ester was the main component, differences being observed only in the minor components. The minor components identified were grandiflorenic acid methyl ester, ent-16-kauren-19-al, 16α,17-epoxy-15α-angeloyloxy-kauran-19-oic acid methyl ester and several O-acyl derivatives at C-15 or C-18 of kaurenoic acid. One of the minor components, 18-isobutyroyloxy-ent-kaur-16-en-19-oic acid is a new kaurenoic acid derivative. Grandiflorenic acid and 15-α-angeloyloxy-16,17-α-epoxy- ent-16-kauren-19-oic acid were present only in Smallanthus sonchifolius and Smallanthus siegesbeckius which showed very similar GC traces. The different GC profile of RC diterpenes from Smallanthus connatus and Smallanthus macroscyphus supports the view that they are different taxa. Some chemotaxonomic aspects of the genus Smallanthus and the subtribe Milleriinae are briefly discussed.
Fil: Coll Araoz, Maria Victoria. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina. Universidad Nacional de Tucumán. Facultad de Ciencias Naturales e Instituto Miguel Lillo. Instituto de Ecología Regional; Argentina
Fil: Mercado, Maria Ines. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Tucumán; Argentina. Universidad Nacional de Tucumán. Facultad de Ciencias Naturales e Instituto Miguel Lillo. Instituto de Ecología Regional; Argentina
Fil: Grau, Alfredo. Universidad Nacional de Tucumán. Facultad de Ciencias Naturales e Instituto Miguel Lillo. Instituto de Ecología Regional; Argentina
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
description The metabolites produced by the secretory canals of the root cortex from four Smallanthus species belonging to the yacon group were identified as ent-kaurane-type diterpenes. The dichloromethane root cortex extracts of the four species were treated with diazomethane and analyzed comparatively by GC-MS using a simple and rapid procedure which is very sensitive and reproducible permitting detection of minor components. In all cases, ent-16-kauren-19-oic acid (kaurenoic acid) methyl ester was the main component, differences being observed only in the minor components. The minor components identified were grandiflorenic acid methyl ester, ent-16-kauren-19-al, 16α,17-epoxy-15α-angeloyloxy-kauran-19-oic acid methyl ester and several O-acyl derivatives at C-15 or C-18 of kaurenoic acid. One of the minor components, 18-isobutyroyloxy-ent-kaur-16-en-19-oic acid is a new kaurenoic acid derivative. Grandiflorenic acid and 15-α-angeloyloxy-16,17-α-epoxy- ent-16-kauren-19-oic acid were present only in Smallanthus sonchifolius and Smallanthus siegesbeckius which showed very similar GC traces. The different GC profile of RC diterpenes from Smallanthus connatus and Smallanthus macroscyphus supports the view that they are different taxa. Some chemotaxonomic aspects of the genus Smallanthus and the subtribe Milleriinae are briefly discussed.
publishDate 2010
dc.date.none.fl_str_mv 2010-10
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/11336/52462
Coll Araoz, Maria Victoria; Mercado, Maria Ines; Grau, Alfredo; Catalan, Cesar Atilio Nazareno; Ent-kaurane derivatives from the root cortex of yacon and other three Smallanthus species (Heliantheae, Asteraceae); Pergamon-Elsevier Science Ltd; Biochemical Systematics And Ecology; 38; 5; 10-2010; 1042-1048
0305-1978
CONICET Digital
CONICET
url http://hdl.handle.net/11336/52462
identifier_str_mv Coll Araoz, Maria Victoria; Mercado, Maria Ines; Grau, Alfredo; Catalan, Cesar Atilio Nazareno; Ent-kaurane derivatives from the root cortex of yacon and other three Smallanthus species (Heliantheae, Asteraceae); Pergamon-Elsevier Science Ltd; Biochemical Systematics And Ecology; 38; 5; 10-2010; 1042-1048
0305-1978
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.bse.2010.10.009
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0305197810002000
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 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
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score 13.070432

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