Hobartine: A tetracyclic indole alkaloid extracted from Aristotelia chilensis (maqui)

Autores
Paz Robles, Cristian; Badilla Vidal, Natalia; Suarez, Sebastian; Baggio, Ricardo Fortunato
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The natural compound hobartine {systematic name: (1R)-3-[(1S,5S)-(4,4,8-trimethylbicyclo[3.3.1]non-7-en-2-yl)methyl]-2,3-dihydro-1H-indole}, C20H26N2, (I), is an indole alkaloid isolated from Aristotelia chilensis as part of a study of secondary metabolites from Chilean flora. The colourless compound has a tetracyclic structure closely related to the strongly coloured polymorphic structures discussed in Paz et al. [Acta Cryst. (2013), C69, 1509-1512] and Watson et al. [Acta Cryst. (1989), C45, 1322-1324]. The main differences reside in the absence of a keto group in (I) compared with the previous structures, as well as an endo double bond in (I) contrasting with the exo double bond found in the previous structures. The supramolecular structure of (I) in strongly related to the twofold screw axis, around which isolated chains build up, internally linked by an N - H⋯N hydrogen bond which is the only significant intermolecular interaction present in the structure.
Fil: Paz Robles, Cristian. Universidad de La Frontera; Chile
Fil: Badilla Vidal, Natalia. Universidad de La Frontera; Chile
Fil: Suarez, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Inorgánica, Analítica y Química Física; Argentina
Fil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica; Argentina
Materia
Alkaloid
Aristotelia Chilensis
Chilean Flora Metabolites
Crystal Structure
Hobartine
Maqui
Natural Products
Tetracyclic Compound
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:11336/83706
Acceder
id CONICETDig_38057e4b2e35785414a129925bf3fd7a
oai_identifier_str oai:ri.conicet.gov.ar:11336/83706
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Hobartine: A tetracyclic indole alkaloid extracted from Aristotelia chilensis (maqui)Paz Robles, CristianBadilla Vidal, NataliaSuarez, SebastianBaggio, Ricardo FortunatoAlkaloidAristotelia ChilensisChilean Flora MetabolitesCrystal StructureHobartineMaquiNatural ProductsTetracyclic Compoundhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The natural compound hobartine {systematic name: (1R)-3-[(1S,5S)-(4,4,8-trimethylbicyclo[3.3.1]non-7-en-2-yl)methyl]-2,3-dihydro-1H-indole}, C20H26N2, (I), is an indole alkaloid isolated from Aristotelia chilensis as part of a study of secondary metabolites from Chilean flora. The colourless compound has a tetracyclic structure closely related to the strongly coloured polymorphic structures discussed in Paz et al. [Acta Cryst. (2013), C69, 1509-1512] and Watson et al. [Acta Cryst. (1989), C45, 1322-1324]. The main differences reside in the absence of a keto group in (I) compared with the previous structures, as well as an endo double bond in (I) contrasting with the exo double bond found in the previous structures. The supramolecular structure of (I) in strongly related to the twofold screw axis, around which isolated chains build up, internally linked by an N - H⋯N hydrogen bond which is the only significant intermolecular interaction present in the structure.Fil: Paz Robles, Cristian. Universidad de La Frontera; ChileFil: Badilla Vidal, Natalia. Universidad de La Frontera; ChileFil: Suarez, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Inorgánica, Analítica y Química Física; ArgentinaFil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica; ArgentinaInternational Union of Crystallography2014-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/83706Paz Robles, Cristian; Badilla Vidal, Natalia; Suarez, Sebastian; Baggio, Ricardo Fortunato; Hobartine: A tetracyclic indole alkaloid extracted from Aristotelia chilensis (maqui); International Union of Crystallography; Acta Crystallographica Section C: Structural Chemistry; 70; 11-2014; 1075-10780108-27012053-2296CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1107/S205322961402258Xinfo:eu-repo/semantics/altIdentifier/url/http://scripts.iucr.org/cgi-bin/paper?S205322961402258Xinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:54:15Zoai:ri.conicet.gov.ar:11336/83706instacron: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 09:54:15.52CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Hobartine: A tetracyclic indole alkaloid extracted from Aristotelia chilensis (maqui)
title Hobartine: A tetracyclic indole alkaloid extracted from Aristotelia chilensis (maqui)
spellingShingle Hobartine: A tetracyclic indole alkaloid extracted from Aristotelia chilensis (maqui)
Paz Robles, Cristian
Alkaloid
Aristotelia Chilensis
Chilean Flora Metabolites
Crystal Structure
Hobartine
Maqui
Natural Products
Tetracyclic Compound
title_short Hobartine: A tetracyclic indole alkaloid extracted from Aristotelia chilensis (maqui)
title_full Hobartine: A tetracyclic indole alkaloid extracted from Aristotelia chilensis (maqui)
title_fullStr Hobartine: A tetracyclic indole alkaloid extracted from Aristotelia chilensis (maqui)
title_full_unstemmed Hobartine: A tetracyclic indole alkaloid extracted from Aristotelia chilensis (maqui)
title_sort Hobartine: A tetracyclic indole alkaloid extracted from Aristotelia chilensis (maqui)
dc.creator.none.fl_str_mv Paz Robles, Cristian
Badilla Vidal, Natalia
Suarez, Sebastian
Baggio, Ricardo Fortunato
author Paz Robles, Cristian
author_facet Paz Robles, Cristian
Badilla Vidal, Natalia
Suarez, Sebastian
Baggio, Ricardo Fortunato
author_role author
author2 Badilla Vidal, Natalia
Suarez, Sebastian
Baggio, Ricardo Fortunato
author2_role author
author
author
dc.subject.none.fl_str_mv Alkaloid
Aristotelia Chilensis
Chilean Flora Metabolites
Crystal Structure
Hobartine
Maqui
Natural Products
Tetracyclic Compound
topic Alkaloid
Aristotelia Chilensis
Chilean Flora Metabolites
Crystal Structure
Hobartine
Maqui
Natural Products
Tetracyclic Compound
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 natural compound hobartine {systematic name: (1R)-3-[(1S,5S)-(4,4,8-trimethylbicyclo[3.3.1]non-7-en-2-yl)methyl]-2,3-dihydro-1H-indole}, C20H26N2, (I), is an indole alkaloid isolated from Aristotelia chilensis as part of a study of secondary metabolites from Chilean flora. The colourless compound has a tetracyclic structure closely related to the strongly coloured polymorphic structures discussed in Paz et al. [Acta Cryst. (2013), C69, 1509-1512] and Watson et al. [Acta Cryst. (1989), C45, 1322-1324]. The main differences reside in the absence of a keto group in (I) compared with the previous structures, as well as an endo double bond in (I) contrasting with the exo double bond found in the previous structures. The supramolecular structure of (I) in strongly related to the twofold screw axis, around which isolated chains build up, internally linked by an N - H⋯N hydrogen bond which is the only significant intermolecular interaction present in the structure.
Fil: Paz Robles, Cristian. Universidad de La Frontera; Chile
Fil: Badilla Vidal, Natalia. Universidad de La Frontera; Chile
Fil: Suarez, Sebastian. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Química, Física de los Materiales, Medioambiente y Energía. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Química, Física de los Materiales, Medioambiente y Energía; Argentina. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Departamento de Química Inorgánica, Analítica y Química Física; Argentina
Fil: Baggio, Ricardo Fortunato. Comisión Nacional de Energía Atómica; Argentina
description The natural compound hobartine {systematic name: (1R)-3-[(1S,5S)-(4,4,8-trimethylbicyclo[3.3.1]non-7-en-2-yl)methyl]-2,3-dihydro-1H-indole}, C20H26N2, (I), is an indole alkaloid isolated from Aristotelia chilensis as part of a study of secondary metabolites from Chilean flora. The colourless compound has a tetracyclic structure closely related to the strongly coloured polymorphic structures discussed in Paz et al. [Acta Cryst. (2013), C69, 1509-1512] and Watson et al. [Acta Cryst. (1989), C45, 1322-1324]. The main differences reside in the absence of a keto group in (I) compared with the previous structures, as well as an endo double bond in (I) contrasting with the exo double bond found in the previous structures. The supramolecular structure of (I) in strongly related to the twofold screw axis, around which isolated chains build up, internally linked by an N - H⋯N hydrogen bond which is the only significant intermolecular interaction present in the structure.
publishDate 2014
dc.date.none.fl_str_mv 2014-11
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/11336/83706
Paz Robles, Cristian; Badilla Vidal, Natalia; Suarez, Sebastian; Baggio, Ricardo Fortunato; Hobartine: A tetracyclic indole alkaloid extracted from Aristotelia chilensis (maqui); International Union of Crystallography; Acta Crystallographica Section C: Structural Chemistry; 70; 11-2014; 1075-1078
0108-2701
2053-2296
CONICET Digital
CONICET
url http://hdl.handle.net/11336/83706
identifier_str_mv Paz Robles, Cristian; Badilla Vidal, Natalia; Suarez, Sebastian; Baggio, Ricardo Fortunato; Hobartine: A tetracyclic indole alkaloid extracted from Aristotelia chilensis (maqui); International Union of Crystallography; Acta Crystallographica Section C: Structural Chemistry; 70; 11-2014; 1075-1078
0108-2701
2053-2296
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1107/S205322961402258X
info:eu-repo/semantics/altIdentifier/url/http://scripts.iucr.org/cgi-bin/paper?S205322961402258X
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 International Union of Crystallography
publisher.none.fl_str_mv International Union of Crystallography
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_ 1844613649665097728
score 13.070432

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