Dihydrocucurbitacin B: Semisynthesis of new glicoside derivatives
- Autores
- Machado, Vanessa R.; Lang, Karen L.; Duran, Fernando Javier; Cabrera, Gabriela Myriam; Palermo, Jorge Alejandro; Schenkel, Eloir P.; Bernardes, Lílian S. C.
- Año de publicación
- 2015
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- In the last ten years, the interest in natural and semi-synthetic cucurbitacin derivatives has increased, primarily due their cytotoxic and anti-tumoral activities. However, the isolation of glycosylated cucurbitacins has been difficult due the presence of β-glucosidase enzyme. With the aim of obtaining new glycosylated derivatives, the glycosylation of dihydrocucurbitacin B under Köenigs-Knorr and imidate reaction conditions was studied. Novel glycoside derivatives 16-(1,2-orthoacetate-3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-dihydrocucurbitacin B (2), 2-O-β-D-2,3,4,6-tetra-O-acetyl-galactopyranosyl dihydrocucurbitacin B (3) and 2-O-β-D-galactopyranosyl dihydrocucurbitacin B (4) were synthesized for the first time in 17% (2 and 3) and 48% (4) yields. 2015, Sociedade Brasileira de Quimica. All rights reserved.
Fil: Machado, Vanessa R.. Universidade Federal Da Santa Catarina; Brasil
Fil: Lang, Karen L.. Universidade Federal de Juiz de Fora;
Fil: Duran, Fernando Javier. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanalisis y Metodos Fisicos En Química Organica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanalisis y Metodos Fisicos En Química Organica; Argentina
Fil: Cabrera, Gabriela Myriam. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanalisis y Metodos Fisicos En Química Organica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanalisis y Metodos Fisicos En Química Organica; Argentina
Fil: Palermo, Jorge Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanalisis y Metodos Fisicos En Química Organica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanalisis y Metodos Fisicos En Química Organica; Argentina
Fil: Schenkel, Eloir P.. Universidade Federal Da Santa Catarina; Brasil
Fil: Bernardes, Lílian S. C.. Universidade Federal Da Santa Catarina; Brasil - Materia
-
Glycosylated Cucurbitacins
Molecular Modification
O-Glycosylation Reaction
Wilbrandia Ebracteata - 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:11336/16066
Ver los metadatos del registro completo
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Dihydrocucurbitacin B: Semisynthesis of new glicoside derivativesMachado, Vanessa R.Lang, Karen L.Duran, Fernando JavierCabrera, Gabriela MyriamPalermo, Jorge AlejandroSchenkel, Eloir P.Bernardes, Lílian S. C.Glycosylated CucurbitacinsMolecular ModificationO-Glycosylation ReactionWilbrandia Ebracteatahttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In the last ten years, the interest in natural and semi-synthetic cucurbitacin derivatives has increased, primarily due their cytotoxic and anti-tumoral activities. However, the isolation of glycosylated cucurbitacins has been difficult due the presence of β-glucosidase enzyme. With the aim of obtaining new glycosylated derivatives, the glycosylation of dihydrocucurbitacin B under Köenigs-Knorr and imidate reaction conditions was studied. Novel glycoside derivatives 16-(1,2-orthoacetate-3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-dihydrocucurbitacin B (2), 2-O-β-D-2,3,4,6-tetra-O-acetyl-galactopyranosyl dihydrocucurbitacin B (3) and 2-O-β-D-galactopyranosyl dihydrocucurbitacin B (4) were synthesized for the first time in 17% (2 and 3) and 48% (4) yields. 2015, Sociedade Brasileira de Quimica. All rights reserved.Fil: Machado, Vanessa R.. Universidade Federal Da Santa Catarina; BrasilFil: Lang, Karen L.. Universidade Federal de Juiz de Fora;Fil: Duran, Fernando Javier. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanalisis y Metodos Fisicos En Química Organica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanalisis y Metodos Fisicos En Química Organica; ArgentinaFil: Cabrera, Gabriela Myriam. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanalisis y Metodos Fisicos En Química Organica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanalisis y Metodos Fisicos En Química Organica; ArgentinaFil: Palermo, Jorge Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanalisis y Metodos Fisicos En Química Organica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanalisis y Metodos Fisicos En Química Organica; ArgentinaFil: Schenkel, Eloir P.. Universidade Federal Da Santa Catarina; BrasilFil: Bernardes, Lílian S. C.. Universidade Federal Da Santa Catarina; BrasilSociedade Brasileira de Química2015-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/16066Machado, Vanessa R.; Lang, Karen L.; Duran, Fernando Javier; Cabrera, Gabriela Myriam; Palermo, Jorge Alejandro; et al.; Dihydrocucurbitacin B: Semisynthesis of new glicoside derivatives; Sociedade Brasileira de Química; Química Nova; 38; 1; 1-2015; 37-410100-40421678-7064enginfo:eu-repo/semantics/altIdentifier/doi/10.5935/0100-4042.20140291info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:42:58Zoai:ri.conicet.gov.ar:11336/16066instacron: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 09:42:58.862CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Dihydrocucurbitacin B: Semisynthesis of new glicoside derivatives |
title |
Dihydrocucurbitacin B: Semisynthesis of new glicoside derivatives |
spellingShingle |
Dihydrocucurbitacin B: Semisynthesis of new glicoside derivatives Machado, Vanessa R. Glycosylated Cucurbitacins Molecular Modification O-Glycosylation Reaction Wilbrandia Ebracteata |
title_short |
Dihydrocucurbitacin B: Semisynthesis of new glicoside derivatives |
title_full |
Dihydrocucurbitacin B: Semisynthesis of new glicoside derivatives |
title_fullStr |
Dihydrocucurbitacin B: Semisynthesis of new glicoside derivatives |
title_full_unstemmed |
Dihydrocucurbitacin B: Semisynthesis of new glicoside derivatives |
title_sort |
Dihydrocucurbitacin B: Semisynthesis of new glicoside derivatives |
dc.creator.none.fl_str_mv |
Machado, Vanessa R. Lang, Karen L. Duran, Fernando Javier Cabrera, Gabriela Myriam Palermo, Jorge Alejandro Schenkel, Eloir P. Bernardes, Lílian S. C. |
author |
Machado, Vanessa R. |
author_facet |
Machado, Vanessa R. Lang, Karen L. Duran, Fernando Javier Cabrera, Gabriela Myriam Palermo, Jorge Alejandro Schenkel, Eloir P. Bernardes, Lílian S. C. |
author_role |
author |
author2 |
Lang, Karen L. Duran, Fernando Javier Cabrera, Gabriela Myriam Palermo, Jorge Alejandro Schenkel, Eloir P. Bernardes, Lílian S. C. |
author2_role |
author author author author author author |
dc.subject.none.fl_str_mv |
Glycosylated Cucurbitacins Molecular Modification O-Glycosylation Reaction Wilbrandia Ebracteata |
topic |
Glycosylated Cucurbitacins Molecular Modification O-Glycosylation Reaction Wilbrandia Ebracteata |
purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
dc.description.none.fl_txt_mv |
In the last ten years, the interest in natural and semi-synthetic cucurbitacin derivatives has increased, primarily due their cytotoxic and anti-tumoral activities. However, the isolation of glycosylated cucurbitacins has been difficult due the presence of β-glucosidase enzyme. With the aim of obtaining new glycosylated derivatives, the glycosylation of dihydrocucurbitacin B under Köenigs-Knorr and imidate reaction conditions was studied. Novel glycoside derivatives 16-(1,2-orthoacetate-3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-dihydrocucurbitacin B (2), 2-O-β-D-2,3,4,6-tetra-O-acetyl-galactopyranosyl dihydrocucurbitacin B (3) and 2-O-β-D-galactopyranosyl dihydrocucurbitacin B (4) were synthesized for the first time in 17% (2 and 3) and 48% (4) yields. 2015, Sociedade Brasileira de Quimica. All rights reserved. Fil: Machado, Vanessa R.. Universidade Federal Da Santa Catarina; Brasil Fil: Lang, Karen L.. Universidade Federal de Juiz de Fora; Fil: Duran, Fernando Javier. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanalisis y Metodos Fisicos En Química Organica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanalisis y Metodos Fisicos En Química Organica; Argentina Fil: Cabrera, Gabriela Myriam. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanalisis y Metodos Fisicos En Química Organica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanalisis y Metodos Fisicos En Química Organica; Argentina Fil: Palermo, Jorge Alejandro. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanalisis y Metodos Fisicos En Química Organica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanalisis y Metodos Fisicos En Química Organica; Argentina Fil: Schenkel, Eloir P.. Universidade Federal Da Santa Catarina; Brasil Fil: Bernardes, Lílian S. C.. Universidade Federal Da Santa Catarina; Brasil |
description |
In the last ten years, the interest in natural and semi-synthetic cucurbitacin derivatives has increased, primarily due their cytotoxic and anti-tumoral activities. However, the isolation of glycosylated cucurbitacins has been difficult due the presence of β-glucosidase enzyme. With the aim of obtaining new glycosylated derivatives, the glycosylation of dihydrocucurbitacin B under Köenigs-Knorr and imidate reaction conditions was studied. Novel glycoside derivatives 16-(1,2-orthoacetate-3,4,6-tri-O-acetyl-α-D-glucopyranosyl)-dihydrocucurbitacin B (2), 2-O-β-D-2,3,4,6-tetra-O-acetyl-galactopyranosyl dihydrocucurbitacin B (3) and 2-O-β-D-galactopyranosyl dihydrocucurbitacin B (4) were synthesized for the first time in 17% (2 and 3) and 48% (4) yields. 2015, Sociedade Brasileira de Quimica. All rights reserved. |
publishDate |
2015 |
dc.date.none.fl_str_mv |
2015-01 |
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/11336/16066 Machado, Vanessa R.; Lang, Karen L.; Duran, Fernando Javier; Cabrera, Gabriela Myriam; Palermo, Jorge Alejandro; et al.; Dihydrocucurbitacin B: Semisynthesis of new glicoside derivatives; Sociedade Brasileira de Química; Química Nova; 38; 1; 1-2015; 37-41 0100-4042 1678-7064 |
url |
http://hdl.handle.net/11336/16066 |
identifier_str_mv |
Machado, Vanessa R.; Lang, Karen L.; Duran, Fernando Javier; Cabrera, Gabriela Myriam; Palermo, Jorge Alejandro; et al.; Dihydrocucurbitacin B: Semisynthesis of new glicoside derivatives; Sociedade Brasileira de Química; Química Nova; 38; 1; 1-2015; 37-41 0100-4042 1678-7064 |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/doi/10.5935/0100-4042.20140291 |
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 |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas |
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CONICET Digital (CONICET) |
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CONICET Digital (CONICET) |
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Consejo Nacional de Investigaciones Científicas y Técnicas |
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CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas |
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dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar |
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13.070432 |