An abietane diterpene from Salvia cuspidata and some new derivatives are active against Trypanosoma cruzi

Autores
Lozano, Esteban Sebastián; Spina Zapata, Renata María; Tonn, Carlos Eugenio; Sosa Escudero, Miguel Angel; Cifuente, Diego Alberto
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The Plant Kingdom is an excellent source for obtaining natural compounds with antiprotozoal activity. In the present work, we studied the effect of the diterpene 12-hydroxy-11,14-diketo-6,8,12-abietatrien-19,20-olide (HABTO) obtained from the aerial parts of Salvia cuspidata on Trypanosoma cruzi epimastigotes.This compound was found to inhibit parasite growth even at low concentrations (IC50 5 lg/mL) and with low toxicity on mammalian cells. In addition, this diterpene induced an intense vacuolization within the parasites. In order to obtain analogs with greater lipophilicity, chemical modifications on the enol moiety were carried out to obtain the acetyl (AABTO), the sylil (SABTO) and the allyl (ALLABTO) derivatives. We observed that the SABTO was the most effective one on the parasites, and the effect could be attributed to a greater lipophilicity of this compound. Taking into account these datawe conclude that the increase of lipophilicity by chemical modifications is an adequate strategy for improving the trypanocidal activity of this kind abietane diterpenes.
Fil: Lozano, Esteban Sebastián. Consejo Nacional de Investigaciones Cienti­ficas y Tecnicas. Centro Cientifico Tecnologico Mendoza. Instituto Histologia y Embriologia de Mendoza "Dr. M. Burgos"; Argentina
Fil: Spina Zapata, Renata María. Consejo Nacional de Investigaciones Cienti­ficas y Tecnicas. Centro Cientifico Tecnologico Mendoza. Instituto Histologia y Embriologia de Mendoza "Dr. M. Burgos"; Argentina
Fil: Tonn, Carlos Eugenio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Sosa Escudero, Miguel Angel. Consejo Nacional de Investigaciones Cienti­ficas y Tecnicas. Centro Cientifico Tecnologico Mendoza. Instituto Histologia y Embriologia de Mendoza "Dr. M. Burgos"; Argentina
Fil: Cifuente, Diego Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones en Tecnología Química; Argentina
Materia
Productos Naturales
Diterpenos
Tripanosoma Cruzi
Salvia Cuspidata
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/5820
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/5820
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling An abietane diterpene from Salvia cuspidata and some new derivatives are active against Trypanosoma cruziLozano, Esteban SebastiánSpina Zapata, Renata MaríaTonn, Carlos EugenioSosa Escudero, Miguel AngelCifuente, Diego AlbertoProductos NaturalesDiterpenosTripanosoma CruziSalvia Cuspidatahttps://purl.org/becyt/ford/1.6https://purl.org/becyt/ford/1The Plant Kingdom is an excellent source for obtaining natural compounds with antiprotozoal activity. In the present work, we studied the effect of the diterpene 12-hydroxy-11,14-diketo-6,8,12-abietatrien-19,20-olide (HABTO) obtained from the aerial parts of Salvia cuspidata on Trypanosoma cruzi epimastigotes.This compound was found to inhibit parasite growth even at low concentrations (IC50 5 lg/mL) and with low toxicity on mammalian cells. In addition, this diterpene induced an intense vacuolization within the parasites. In order to obtain analogs with greater lipophilicity, chemical modifications on the enol moiety were carried out to obtain the acetyl (AABTO), the sylil (SABTO) and the allyl (ALLABTO) derivatives. We observed that the SABTO was the most effective one on the parasites, and the effect could be attributed to a greater lipophilicity of this compound. Taking into account these datawe conclude that the increase of lipophilicity by chemical modifications is an adequate strategy for improving the trypanocidal activity of this kind abietane diterpenes.Fil: Lozano, Esteban Sebastián. Consejo Nacional de Investigaciones Cienti­ficas y Tecnicas. Centro Cientifico Tecnologico Mendoza. Instituto Histologia y Embriologia de Mendoza "Dr. M. Burgos"; ArgentinaFil: Spina Zapata, Renata María. Consejo Nacional de Investigaciones Cienti­ficas y Tecnicas. Centro Cientifico Tecnologico Mendoza. Instituto Histologia y Embriologia de Mendoza "Dr. M. Burgos"; ArgentinaFil: Tonn, Carlos Eugenio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones en Tecnología Química; ArgentinaFil: Sosa Escudero, Miguel Angel. Consejo Nacional de Investigaciones Cienti­ficas y Tecnicas. Centro Cientifico Tecnologico Mendoza. Instituto Histologia y Embriologia de Mendoza "Dr. M. Burgos"; ArgentinaFil: Cifuente, Diego Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones en Tecnología Química; ArgentinaElsevier2015-10info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/5820Lozano, Esteban Sebastián; Spina Zapata, Renata María; Tonn, Carlos Eugenio; Sosa Escudero, Miguel Angel; Cifuente, Diego Alberto; An abietane diterpene from Salvia cuspidata and some new derivatives are active against Trypanosoma cruzi; Elsevier; Bioorganic & Medicinal Chemistry Letters; 25; 23; 10-2015; 5481-54840960-894Xenginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0960894X15301906info:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmcl.2015.10.082info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:33:54Zoai:ri.conicet.gov.ar:11336/5820instacron: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 10:33:54.543CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv An abietane diterpene from Salvia cuspidata and some new derivatives are active against Trypanosoma cruzi
title An abietane diterpene from Salvia cuspidata and some new derivatives are active against Trypanosoma cruzi
spellingShingle An abietane diterpene from Salvia cuspidata and some new derivatives are active against Trypanosoma cruzi
Lozano, Esteban Sebastián
Productos Naturales
Diterpenos
Tripanosoma Cruzi
Salvia Cuspidata
title_short An abietane diterpene from Salvia cuspidata and some new derivatives are active against Trypanosoma cruzi
title_full An abietane diterpene from Salvia cuspidata and some new derivatives are active against Trypanosoma cruzi
title_fullStr An abietane diterpene from Salvia cuspidata and some new derivatives are active against Trypanosoma cruzi
title_full_unstemmed An abietane diterpene from Salvia cuspidata and some new derivatives are active against Trypanosoma cruzi
title_sort An abietane diterpene from Salvia cuspidata and some new derivatives are active against Trypanosoma cruzi
dc.creator.none.fl_str_mv Lozano, Esteban Sebastián
Spina Zapata, Renata María
Tonn, Carlos Eugenio
Sosa Escudero, Miguel Angel
Cifuente, Diego Alberto
author Lozano, Esteban Sebastián
author_facet Lozano, Esteban Sebastián
Spina Zapata, Renata María
Tonn, Carlos Eugenio
Sosa Escudero, Miguel Angel
Cifuente, Diego Alberto
author_role author
author2 Spina Zapata, Renata María
Tonn, Carlos Eugenio
Sosa Escudero, Miguel Angel
Cifuente, Diego Alberto
author2_role author
author
author
author
dc.subject.none.fl_str_mv Productos Naturales
Diterpenos
Tripanosoma Cruzi
Salvia Cuspidata
topic Productos Naturales
Diterpenos
Tripanosoma Cruzi
Salvia Cuspidata
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.6
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The Plant Kingdom is an excellent source for obtaining natural compounds with antiprotozoal activity. In the present work, we studied the effect of the diterpene 12-hydroxy-11,14-diketo-6,8,12-abietatrien-19,20-olide (HABTO) obtained from the aerial parts of Salvia cuspidata on Trypanosoma cruzi epimastigotes.This compound was found to inhibit parasite growth even at low concentrations (IC50 5 lg/mL) and with low toxicity on mammalian cells. In addition, this diterpene induced an intense vacuolization within the parasites. In order to obtain analogs with greater lipophilicity, chemical modifications on the enol moiety were carried out to obtain the acetyl (AABTO), the sylil (SABTO) and the allyl (ALLABTO) derivatives. We observed that the SABTO was the most effective one on the parasites, and the effect could be attributed to a greater lipophilicity of this compound. Taking into account these datawe conclude that the increase of lipophilicity by chemical modifications is an adequate strategy for improving the trypanocidal activity of this kind abietane diterpenes.
Fil: Lozano, Esteban Sebastián. Consejo Nacional de Investigaciones Cienti­ficas y Tecnicas. Centro Cientifico Tecnologico Mendoza. Instituto Histologia y Embriologia de Mendoza "Dr. M. Burgos"; Argentina
Fil: Spina Zapata, Renata María. Consejo Nacional de Investigaciones Cienti­ficas y Tecnicas. Centro Cientifico Tecnologico Mendoza. Instituto Histologia y Embriologia de Mendoza "Dr. M. Burgos"; Argentina
Fil: Tonn, Carlos Eugenio. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones en Tecnología Química; Argentina
Fil: Sosa Escudero, Miguel Angel. Consejo Nacional de Investigaciones Cienti­ficas y Tecnicas. Centro Cientifico Tecnologico Mendoza. Instituto Histologia y Embriologia de Mendoza "Dr. M. Burgos"; Argentina
Fil: Cifuente, Diego Alberto. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico San Luis. Instituto de Investigaciones en Tecnología Química; Argentina
description The Plant Kingdom is an excellent source for obtaining natural compounds with antiprotozoal activity. In the present work, we studied the effect of the diterpene 12-hydroxy-11,14-diketo-6,8,12-abietatrien-19,20-olide (HABTO) obtained from the aerial parts of Salvia cuspidata on Trypanosoma cruzi epimastigotes.This compound was found to inhibit parasite growth even at low concentrations (IC50 5 lg/mL) and with low toxicity on mammalian cells. In addition, this diterpene induced an intense vacuolization within the parasites. In order to obtain analogs with greater lipophilicity, chemical modifications on the enol moiety were carried out to obtain the acetyl (AABTO), the sylil (SABTO) and the allyl (ALLABTO) derivatives. We observed that the SABTO was the most effective one on the parasites, and the effect could be attributed to a greater lipophilicity of this compound. Taking into account these datawe conclude that the increase of lipophilicity by chemical modifications is an adequate strategy for improving the trypanocidal activity of this kind abietane diterpenes.
publishDate 2015
dc.date.none.fl_str_mv 2015-10
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/11336/5820
Lozano, Esteban Sebastián; Spina Zapata, Renata María; Tonn, Carlos Eugenio; Sosa Escudero, Miguel Angel; Cifuente, Diego Alberto; An abietane diterpene from Salvia cuspidata and some new derivatives are active against Trypanosoma cruzi; Elsevier; Bioorganic & Medicinal Chemistry Letters; 25; 23; 10-2015; 5481-5484
0960-894X
url http://hdl.handle.net/11336/5820
identifier_str_mv Lozano, Esteban Sebastián; Spina Zapata, Renata María; Tonn, Carlos Eugenio; Sosa Escudero, Miguel Angel; Cifuente, Diego Alberto; An abietane diterpene from Salvia cuspidata and some new derivatives are active against Trypanosoma cruzi; Elsevier; Bioorganic & Medicinal Chemistry Letters; 25; 23; 10-2015; 5481-5484
0960-894X
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S0960894X15301906
info:eu-repo/semantics/altIdentifier/doi/
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmcl.2015.10.082
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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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