Effective Approach to Semi- Synthesis of Lupane and Ursane Brominated Derivatives and its Effects on Viability of Leishmania amazonensis
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2017 |
| Outros Autores: | , , , , |
| 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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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 |
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2019-05-28T14:37:40Z |
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2019-05-28T14:37:40Z |
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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. |
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https://www.arca.fiocruz.br/handle/icict/33251 |
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2378-9336 |
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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 |
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Annals of Medicinal Chemistry and Research |
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Annals of Medicinal Chemistry and Research |
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