Tucumanin, a β-hydroxy-γ-lactone bistetrahydrofuranic acetogenin from Annona cherimolia, is a potent inhibitor of mitochondrial complex I

Autores
Barrachina, Isabel; Neske, Adriana; Granell, Susana; Bermejo, Almudena; Chahboune, Nadia; El Aouad, Noureddine; Alvarez, Olga; Bardon, Alicia del Valle; Zafra Polo, M. Carmen
Año de publicación
2004
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
A new β-hydroxy-γ-methyl-γ-lactone bistetrahydrofuranic acetogenin, tucumanin, with the infrequent symmetrical threo/trans/threo/trans/ threo relative configuration at the tetrahydrofuran rings was isolated from Annona cherimolia (Annonaceae) seeds. The inhibitory potency on the mitochondrial complex I of acetogenins with this relative configuration (tucumanin and asimicin) was compared with that shown by the corresponding pairs with an asymmetrical threo/trans/threo/trans/erythro relative configuration (laherradurin/rolliniastatin-2, and itrabin/molvizarin). All these compounds act as selective inhibitors of mitochondrial complex 1 in the 0.18 - 1.55 nM range.
Fil: Barrachina, Isabel. Universidad de Valencia; España
Fil: Neske, Adriana. Universidad Nacional de Tucumán; Argentina
Fil: Granell, Susana. Universidad de Valencia; España
Fil: Bermejo, Almudena. Universidad de Valencia; España
Fil: Chahboune, Nadia. Universidad de Valencia; España
Fil: El Aouad, Noureddine. Universidad de Valencia; España
Fil: Alvarez, Olga. Universidad Nacional de Tucumán; Argentina
Fil: Bardon, Alicia del Valle. 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: Zafra Polo, M. Carmen. Universidad de Valencia; España
Materia
β-hydroxy-γ-methyl-γ-lactone
Annona cherimolia (Annonaceae)
inhibitory potency
mitochondrial complex I
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:11336/99323
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/99323
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Tucumanin, a β-hydroxy-γ-lactone bistetrahydrofuranic acetogenin from Annona cherimolia, is a potent inhibitor of mitochondrial complex IBarrachina, IsabelNeske, AdrianaGranell, SusanaBermejo, AlmudenaChahboune, NadiaEl Aouad, NoureddineAlvarez, OlgaBardon, Alicia del ValleZafra Polo, M. Carmenβ-hydroxy-γ-methyl-γ-lactoneAnnona cherimolia (Annonaceae)inhibitory potencymitochondrial complex Ihttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A new β-hydroxy-γ-methyl-γ-lactone bistetrahydrofuranic acetogenin, tucumanin, with the infrequent symmetrical threo/trans/threo/trans/ threo relative configuration at the tetrahydrofuran rings was isolated from Annona cherimolia (Annonaceae) seeds. The inhibitory potency on the mitochondrial complex I of acetogenins with this relative configuration (tucumanin and asimicin) was compared with that shown by the corresponding pairs with an asymmetrical threo/trans/threo/trans/erythro relative configuration (laherradurin/rolliniastatin-2, and itrabin/molvizarin). All these compounds act as selective inhibitors of mitochondrial complex 1 in the 0.18 - 1.55 nM range.Fil: Barrachina, Isabel. Universidad de Valencia; EspañaFil: Neske, Adriana. Universidad Nacional de Tucumán; ArgentinaFil: Granell, Susana. Universidad de Valencia; EspañaFil: Bermejo, Almudena. Universidad de Valencia; EspañaFil: Chahboune, Nadia. Universidad de Valencia; EspañaFil: El Aouad, Noureddine. Universidad de Valencia; EspañaFil: Alvarez, Olga. Universidad Nacional de Tucumán; ArgentinaFil: Bardon, Alicia del Valle. 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: Zafra Polo, M. Carmen. Universidad de Valencia; EspañaGeorg Thieme Verlag Kg2004-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/99323Barrachina, Isabel; Neske, Adriana; Granell, Susana; Bermejo, Almudena; Chahboune, Nadia; et al.; Tucumanin, a β-hydroxy-γ-lactone bistetrahydrofuranic acetogenin from Annona cherimolia, is a potent inhibitor of mitochondrial complex I; Georg Thieme Verlag Kg; Planta Medica; 70; 9; 9-2004; 866-8680032-0943CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1055/s-2004-827237info:eu-repo/semantics/altIdentifier/url/https://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-2004-827237info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:28:09Zoai:ri.conicet.gov.ar:11336/99323instacron: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 14:28:10.264CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Tucumanin, a β-hydroxy-γ-lactone bistetrahydrofuranic acetogenin from Annona cherimolia, is a potent inhibitor of mitochondrial complex I
title Tucumanin, a β-hydroxy-γ-lactone bistetrahydrofuranic acetogenin from Annona cherimolia, is a potent inhibitor of mitochondrial complex I
spellingShingle Tucumanin, a β-hydroxy-γ-lactone bistetrahydrofuranic acetogenin from Annona cherimolia, is a potent inhibitor of mitochondrial complex I
Barrachina, Isabel
β-hydroxy-γ-methyl-γ-lactone
Annona cherimolia (Annonaceae)
inhibitory potency
mitochondrial complex I
title_short Tucumanin, a β-hydroxy-γ-lactone bistetrahydrofuranic acetogenin from Annona cherimolia, is a potent inhibitor of mitochondrial complex I
title_full Tucumanin, a β-hydroxy-γ-lactone bistetrahydrofuranic acetogenin from Annona cherimolia, is a potent inhibitor of mitochondrial complex I
title_fullStr Tucumanin, a β-hydroxy-γ-lactone bistetrahydrofuranic acetogenin from Annona cherimolia, is a potent inhibitor of mitochondrial complex I
title_full_unstemmed Tucumanin, a β-hydroxy-γ-lactone bistetrahydrofuranic acetogenin from Annona cherimolia, is a potent inhibitor of mitochondrial complex I
title_sort Tucumanin, a β-hydroxy-γ-lactone bistetrahydrofuranic acetogenin from Annona cherimolia, is a potent inhibitor of mitochondrial complex I
dc.creator.none.fl_str_mv Barrachina, Isabel
Neske, Adriana
Granell, Susana
Bermejo, Almudena
Chahboune, Nadia
El Aouad, Noureddine
Alvarez, Olga
Bardon, Alicia del Valle
Zafra Polo, M. Carmen
author Barrachina, Isabel
author_facet Barrachina, Isabel
Neske, Adriana
Granell, Susana
Bermejo, Almudena
Chahboune, Nadia
El Aouad, Noureddine
Alvarez, Olga
Bardon, Alicia del Valle
Zafra Polo, M. Carmen
author_role author
author2 Neske, Adriana
Granell, Susana
Bermejo, Almudena
Chahboune, Nadia
El Aouad, Noureddine
Alvarez, Olga
Bardon, Alicia del Valle
Zafra Polo, M. Carmen
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv β-hydroxy-γ-methyl-γ-lactone
Annona cherimolia (Annonaceae)
inhibitory potency
mitochondrial complex I
topic β-hydroxy-γ-methyl-γ-lactone
Annona cherimolia (Annonaceae)
inhibitory potency
mitochondrial complex I
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv A new β-hydroxy-γ-methyl-γ-lactone bistetrahydrofuranic acetogenin, tucumanin, with the infrequent symmetrical threo/trans/threo/trans/ threo relative configuration at the tetrahydrofuran rings was isolated from Annona cherimolia (Annonaceae) seeds. The inhibitory potency on the mitochondrial complex I of acetogenins with this relative configuration (tucumanin and asimicin) was compared with that shown by the corresponding pairs with an asymmetrical threo/trans/threo/trans/erythro relative configuration (laherradurin/rolliniastatin-2, and itrabin/molvizarin). All these compounds act as selective inhibitors of mitochondrial complex 1 in the 0.18 - 1.55 nM range.
Fil: Barrachina, Isabel. Universidad de Valencia; España
Fil: Neske, Adriana. Universidad Nacional de Tucumán; Argentina
Fil: Granell, Susana. Universidad de Valencia; España
Fil: Bermejo, Almudena. Universidad de Valencia; España
Fil: Chahboune, Nadia. Universidad de Valencia; España
Fil: El Aouad, Noureddine. Universidad de Valencia; España
Fil: Alvarez, Olga. Universidad Nacional de Tucumán; Argentina
Fil: Bardon, Alicia del Valle. 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: Zafra Polo, M. Carmen. Universidad de Valencia; España
description A new β-hydroxy-γ-methyl-γ-lactone bistetrahydrofuranic acetogenin, tucumanin, with the infrequent symmetrical threo/trans/threo/trans/ threo relative configuration at the tetrahydrofuran rings was isolated from Annona cherimolia (Annonaceae) seeds. The inhibitory potency on the mitochondrial complex I of acetogenins with this relative configuration (tucumanin and asimicin) was compared with that shown by the corresponding pairs with an asymmetrical threo/trans/threo/trans/erythro relative configuration (laherradurin/rolliniastatin-2, and itrabin/molvizarin). All these compounds act as selective inhibitors of mitochondrial complex 1 in the 0.18 - 1.55 nM range.
publishDate 2004
dc.date.none.fl_str_mv 2004-09
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/11336/99323
Barrachina, Isabel; Neske, Adriana; Granell, Susana; Bermejo, Almudena; Chahboune, Nadia; et al.; Tucumanin, a β-hydroxy-γ-lactone bistetrahydrofuranic acetogenin from Annona cherimolia, is a potent inhibitor of mitochondrial complex I; Georg Thieme Verlag Kg; Planta Medica; 70; 9; 9-2004; 866-868
0032-0943
CONICET Digital
CONICET
url http://hdl.handle.net/11336/99323
identifier_str_mv Barrachina, Isabel; Neske, Adriana; Granell, Susana; Bermejo, Almudena; Chahboune, Nadia; et al.; Tucumanin, a β-hydroxy-γ-lactone bistetrahydrofuranic acetogenin from Annona cherimolia, is a potent inhibitor of mitochondrial complex I; Georg Thieme Verlag Kg; Planta Medica; 70; 9; 9-2004; 866-868
0032-0943
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1055/s-2004-827237
info:eu-repo/semantics/altIdentifier/url/https://www.thieme-connect.de/products/ejournals/abstract/10.1055/s-2004-827237
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 Georg Thieme Verlag Kg
publisher.none.fl_str_mv Georg Thieme Verlag Kg
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_ 1846082743748788224
score 13.22299

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