Effective Approach to Semi- Synthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensis

Detalhes bibliográficos
Autor(a) principal: Cargnin, Simone Tasca
Data de Publicação: 2017
Outros Autores: Staudt, Andressa Finkler, Santos, Ana Paula de Azevedo dos, Gosmann, Grace, Teles, Carolina Bioni Garcia, Gnoatto, Simone Baggio
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da FIOCRUZ (ARCA)
Texto Completo: https://www.arca.fiocruz.br/handle/icict/33251
Resumo: Universidade Federal do Rio Grande do Sul. Laboratório de Fitoquímica e Síntese Orgânica. Porto Alegre, RS, Brasil.
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spelling Cargnin, Simone TascaStaudt, Andressa FinklerSantos, Ana Paula de Azevedo dosGosmann, GraceTeles, Carolina Bioni GarciaGnoatto, Simone Baggio2019-05-28T14:37:40Z2019-05-28T14:37:40Z2017CARGNIN, Simone Tasca et al. Effective Approach to Semi-Synthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensis. Annals of Medicinal Chemistry and Research, p. 1-5, 2017.2378-9336https://www.arca.fiocruz.br/handle/icict/332512378-9336engAnnals of Medicinal Chemistry and ResearchEffective Approach to Semi- Synthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensisinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleUniversidade Federal do Rio Grande do Sul. Laboratório de Fitoquímica e Síntese Orgânica. Porto Alegre, RS, Brasil.Universidade Federal do Rio Grande do Sul. Laboratório de Fitoquímica e Síntese Orgânica. Porto Alegre, RS, Brasil.Fundação Oswaldo Cruz. Fiocruz Rondônia. Laboratório da Plataforma de Bioensaios de Malária e Leishmaniose. Porto Velho, RO, Brasil.Universidade Federal do Rio Grande do Sul. Laboratório de Fitoquímica e Síntese Orgânica. Porto Alegre, RS, Brasil.Fundação Oswaldo Cruz. Fiocruz Rondônia. Laboratório da Plataforma de Bioensaios de Malária e Leishmaniose. Porto Velho, RO, Brasil.Universidade Federal do Rio Grande do Sul. Laboratório de Fitoquímica e Síntese Orgânica. Porto Alegre, RS, Brasil.Pentacyclic triterpenes, especially ursolic and betulinic acid, are extracted eco-friendly from natural sources and are biologically active compounds. Semisynthesis tools have been employed in order to improve their biological activities. The bromination reaction could influence in the conformational structure of triterpenes skeleton and consequently, in their biological activity. In this work, we aim to survey and discuss an effective approach for semi-synthesis reactions to obtain betulinic acid (BA) and ursolic acid (UA) brominated derivatives and to evaluate their effects on viability of promastigote forms of Leishmania amazonensis. The bromination reaction protocol using N-bromosuccinimide (NBS) reagent was adapted for both triterpenes, aiming to obtain UA C12-Br and BA C30-Br modifications. The evaluation of leishmanicidal potential was performed using promastigotes forms of Leishmania (Leishmania) amazonensis and the viability was measured by MTT assay. According to spectroscopic data, the semi-synthesis of brominated triterpene derivatives using the methodology proposed was successfully accomplished. Bromination of the triterpene structures resulted in an increased antileishmanial activity comparing with the natural precursors, UA and BA. This report brings forth the discussion about the UA bromolactonization and BA C30-Br derivative semi-synthesis and characterization, and reports for the first time the activity of these derivatives on the viability of L. amazonensis, causative agent of leishmaniasis, a neglected tropical disease.TriterpenesUrsolic acidBetulinic acidBromination reactionLeishmania amazonensisinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txtlicense.txttext/plain; charset=utf-82991https://www.arca.fiocruz.br/bitstream/icict/33251/1/license.txt5a560609d32a3863062d77ff32785d58MD51ORIGINALEffective Approach to SemiSynthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensis.pdfEffective Approach to SemiSynthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensis.pdfapplication/pdf1352497https://www.arca.fiocruz.br/bitstream/icict/33251/2/Effective%20Approach%20to%20SemiSynthesis%20of%20Lupane%20and%20Ursane%20Brominated%20Derivatives%20and%20its%20Effects%20on%20Viability%20of%20Leishmania%20amazonensis.pdf2a7d2ab349a8c332ca7c3171bfd34768MD52TEXTEffective Approach to SemiSynthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensis.pdf.txtEffective Approach to SemiSynthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensis.pdf.txtExtracted texttext/plain22239https://www.arca.fiocruz.br/bitstream/icict/33251/3/Effective%20Approach%20to%20SemiSynthesis%20of%20Lupane%20and%20Ursane%20Brominated%20Derivatives%20and%20its%20Effects%20on%20Viability%20of%20Leishmania%20amazonensis.pdf.txt821e8ad7c545180fadb8741096d7f96bMD53icict/332512019-06-01 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dc.title.pt_BR.fl_str_mv Effective Approach to Semi- Synthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensis
title Effective Approach to Semi- Synthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensis
spellingShingle Effective Approach to Semi- Synthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensis
Cargnin, Simone Tasca
Triterpenes
Ursolic acid
Betulinic acid
Bromination reaction
Leishmania amazonensis
title_short Effective Approach to Semi- Synthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensis
title_full Effective Approach to Semi- Synthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensis
title_fullStr Effective Approach to Semi- Synthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensis
title_full_unstemmed Effective Approach to Semi- Synthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensis
title_sort Effective Approach to Semi- Synthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensis
author Cargnin, Simone Tasca
author_facet Cargnin, Simone Tasca
Staudt, Andressa Finkler
Santos, Ana Paula de Azevedo dos
Gosmann, Grace
Teles, Carolina Bioni Garcia
Gnoatto, Simone Baggio
author_role author
author2 Staudt, Andressa Finkler
Santos, Ana Paula de Azevedo dos
Gosmann, Grace
Teles, Carolina Bioni Garcia
Gnoatto, Simone Baggio
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Cargnin, Simone Tasca
Staudt, Andressa Finkler
Santos, Ana Paula de Azevedo dos
Gosmann, Grace
Teles, Carolina Bioni Garcia
Gnoatto, Simone Baggio
dc.subject.en.pt_BR.fl_str_mv Triterpenes
Ursolic acid
Betulinic acid
Bromination reaction
Leishmania amazonensis
topic Triterpenes
Ursolic acid
Betulinic acid
Bromination reaction
Leishmania amazonensis
description Universidade Federal do Rio Grande do Sul. Laboratório de Fitoquímica e Síntese Orgânica. Porto Alegre, RS, Brasil.
publishDate 2017
dc.date.issued.fl_str_mv 2017
dc.date.accessioned.fl_str_mv 2019-05-28T14:37:40Z
dc.date.available.fl_str_mv 2019-05-28T14:37:40Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
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status_str publishedVersion
dc.identifier.citation.fl_str_mv CARGNIN, Simone Tasca et al. Effective Approach to Semi-Synthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensis. Annals of Medicinal Chemistry and Research, p. 1-5, 2017.
dc.identifier.uri.fl_str_mv https://www.arca.fiocruz.br/handle/icict/33251
dc.identifier.issn.pt_BR.fl_str_mv 2378-9336
dc.identifier.eissn.none.fl_str_mv 2378-9336
identifier_str_mv CARGNIN, Simone Tasca et al. Effective Approach to Semi-Synthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensis. Annals of Medicinal Chemistry and Research, p. 1-5, 2017.
2378-9336
url https://www.arca.fiocruz.br/handle/icict/33251
dc.language.iso.fl_str_mv eng
language eng
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Annals of Medicinal Chemistry and Research
publisher.none.fl_str_mv Annals of Medicinal Chemistry and Research
dc.source.none.fl_str_mv reponame:Repositório Institucional da FIOCRUZ (ARCA)
instname:Fundação Oswaldo Cruz (FIOCRUZ)
instacron:FIOCRUZ
instname_str Fundação Oswaldo Cruz (FIOCRUZ)
instacron_str FIOCRUZ
institution FIOCRUZ
reponame_str Repositório Institucional da FIOCRUZ (ARCA)
collection Repositório Institucional da FIOCRUZ (ARCA)
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