A new tropane alkaloid and other metabolites from Erythroxylum macrocalyx (Erythroxylaceae) and their antiproliferative activities
| Autor(a) principal: | |
|---|---|
| Data de Publicação: | 2021 |
| 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/47867 |
Resumo: | Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) (462401/2014-6; 304445/2017-7) |
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Silva Júnior, Lauro J. C. daAlves, Léia A.Silva, Valdenizia R.Santos, Luciano S.Bezerra, Daniel PereiraSoares, Milena Botelho PereiraDoriguetto, Antonio C.Barbosa, Luiz C. A.Nascimento, Jeferson C. doMacedo, Guadalupe E. L.Queiroz, Raphael F.Paula, Vanderlúcia F. de2021-06-25T14:41:42Z2021-06-25T14:41:42Z2021SILVA JUNIOR, Lauro J. C. da et al. A new tropane alkaloid and other metabolites from Erythroxylum macrocalyx (Erythroxylaceae) and their antiproliferative activities. Phytochemistry Letters, v. 41, p. 168-174, Feb. 2021.1874-3900https://www.arca.fiocruz.br/handle/icict/4786710.1016/j.phytol.2020.11.019Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) (462401/2014-6; 304445/2017-7)Fundação de Amparo à Pesquisa o Estado da Bahia (FAPESB) (RED038/2014; APP 029/2011)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) – Finance Code 001Universidade Estadual do Sudoeste da Bahia. Departamento de Ciências e Tecnologia. Laboratório de Produtos Naturais. Jequié, BA, Brasil.Universidade Estadual do Sudoeste da Bahia. Departamento de Ciências e Tecnologia. Laboratório de Produtos Naturais. Jequié, BA, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.Fundação Oswaldo Cruz. Instituto Gonçalo Moniz. Salvador, BA, Brasil.Universidade Federal de Alfenas. Instituto de Química. Alfenas, MG, Brasil.Universidade Federal de Minas Gerais. Instituto de Ciências Exatas. Departamento de Química. Belo Horizonte, MG, Brasil.Universidade Estadual do Sudoeste da Bahia. Departamento de Ciências e Tecnologia. Laboratório de Produtos Naturais. Jequié, BA, Brasil.Universidade Estadual do Sudoeste da Bahia. Departamento de Ciências Biológicas. Jequié, BA, Brasil.Universidade Estadual do Sudoeste da Bahia. Departamento de Ciências Naturais. Vitória da Conquista, BA, Brasil.Universidade Estadual do Sudoeste da Bahia. Departamento de Ciências e Tecnologia. Laboratório de Produtos Naturais. Jequié, BA, Brasil.A new tropane alkaloid 7β-acetoxy-6β-benzoyloxy-3α-hydroxytropane (1) was isolated from the twigs of Erythroxylum macrocalyx Mart. (Erythroxylaceae), along with the known substances: 6β,7β-dibenzoyloxy-3α-hydroxytropane (2), 6β,7β-dihydroxy-3α-(phenylacetoxy)tropane (3), 3α-benzoyloxy-6β,7β-dihydroxytropane (4), 6βbenzoyloxy-3α-(4-hydroxy-3,5-dimetoxybenzoyloxy)tropane (5), ombuin-3-rutinoside-5-glucoside (6), lupeol (7), taraxerol (8) and lupenone (9). Compounds 1 and 2 were also isolated from the leaves. The structures were established by analyses of 1D- and 2D-NMR and MS data, as well as by comparison with literature data for known compounds. The structure of 2 was also supported by X-ray crystallography analyses. The compounds were evaluated in vitro for their antibacterial and antiproliferative activities. Compound 5 showed high antiproliferative activity on liver hepatocellular carcinoma cells (HepG2) with IC50 value of 3.66 μg mL− 1 (8.29 μmol L-1), but no cytotoxic effect (IC50 > 25 μg mL-1) on human lymphoblast cell line. This study reveals the potential use of 5 as prototype for the synthesis of new antiproliferative agents.engElsevierErythroxylaceaeFígadoAlcalóidesCélulasLinhagem celularErythroxylum macrocalyxErythroxylaceaeTropane alkaloids7β-acetoxy-6β-benzoyloxy-3α-hydroxytropaneAntiproliferativeA new tropane alkaloid and other metabolites from Erythroxylum macrocalyx (Erythroxylaceae) and their antiproliferative activitiesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da FIOCRUZ (ARCA)instname:Fundação Oswaldo Cruz (FIOCRUZ)instacron:FIOCRUZLICENSElicense.txtlicense.txttext/plain; charset=utf-83097https://www.arca.fiocruz.br/bitstream/icict/47867/1/license.txt36b51ef91c52b5338d9d29ba0cc807bcMD51ORIGINALSilva Junior, Lauro J. C A new tropane....pdfSilva Junior, Lauro J. C A new tropane....pdfapplication/pdf1596761https://www.arca.fiocruz.br/bitstream/icict/47867/2/Silva%20Junior%2c%20Lauro%20J.%20C%20A%20new%20tropane....pdf33ee71b2062a16b736682ebc03d25daaMD52TEXTSilva Junior, Lauro J. C A new tropane....pdf.txtSilva Junior, Lauro J. C A new tropane....pdf.txtExtracted texttext/plain52939https://www.arca.fiocruz.br/bitstream/icict/47867/3/Silva%20Junior%2c%20Lauro%20J.%20C%20A%20new%20tropane....pdf.txt33c9d60d91a6eb2f7025cb98ff17e6c4MD53icict/478672023-03-15 14:34:28.997oai:www.arca.fiocruz.br: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Repositório InstitucionalPUBhttps://www.arca.fiocruz.br/oai/requestrepositorio.arca@fiocruz.bropendoar:21352023-03-15T17:34:28Repositório Institucional da FIOCRUZ (ARCA) - Fundação Oswaldo Cruz (FIOCRUZ)false |
| dc.title.en.fl_str_mv |
A new tropane alkaloid and other metabolites from Erythroxylum macrocalyx (Erythroxylaceae) and their antiproliferative activities |
| title |
A new tropane alkaloid and other metabolites from Erythroxylum macrocalyx (Erythroxylaceae) and their antiproliferative activities |
| spellingShingle |
A new tropane alkaloid and other metabolites from Erythroxylum macrocalyx (Erythroxylaceae) and their antiproliferative activities Silva Júnior, Lauro J. C. da Erythroxylaceae Fígado Alcalóides Células Linhagem celular Erythroxylum macrocalyx Erythroxylaceae Tropane alkaloids 7β-acetoxy-6β-benzoyloxy-3α-hydroxytropane Antiproliferative |
| title_short |
A new tropane alkaloid and other metabolites from Erythroxylum macrocalyx (Erythroxylaceae) and their antiproliferative activities |
| title_full |
A new tropane alkaloid and other metabolites from Erythroxylum macrocalyx (Erythroxylaceae) and their antiproliferative activities |
| title_fullStr |
A new tropane alkaloid and other metabolites from Erythroxylum macrocalyx (Erythroxylaceae) and their antiproliferative activities |
| title_full_unstemmed |
A new tropane alkaloid and other metabolites from Erythroxylum macrocalyx (Erythroxylaceae) and their antiproliferative activities |
| title_sort |
A new tropane alkaloid and other metabolites from Erythroxylum macrocalyx (Erythroxylaceae) and their antiproliferative activities |
| author |
Silva Júnior, Lauro J. C. da |
| author_facet |
Silva Júnior, Lauro J. C. da Alves, Léia A. Silva, Valdenizia R. Santos, Luciano S. Bezerra, Daniel Pereira Soares, Milena Botelho Pereira Doriguetto, Antonio C. Barbosa, Luiz C. A. Nascimento, Jeferson C. do Macedo, Guadalupe E. L. Queiroz, Raphael F. Paula, Vanderlúcia F. de |
| author_role |
author |
| author2 |
Alves, Léia A. Silva, Valdenizia R. Santos, Luciano S. Bezerra, Daniel Pereira Soares, Milena Botelho Pereira Doriguetto, Antonio C. Barbosa, Luiz C. A. Nascimento, Jeferson C. do Macedo, Guadalupe E. L. Queiroz, Raphael F. Paula, Vanderlúcia F. de |
| author2_role |
author author author author author author author author author author author |
| dc.contributor.author.fl_str_mv |
Silva Júnior, Lauro J. C. da Alves, Léia A. Silva, Valdenizia R. Santos, Luciano S. Bezerra, Daniel Pereira Soares, Milena Botelho Pereira Doriguetto, Antonio C. Barbosa, Luiz C. A. Nascimento, Jeferson C. do Macedo, Guadalupe E. L. Queiroz, Raphael F. Paula, Vanderlúcia F. de |
| dc.subject.other.pt_BR.fl_str_mv |
Erythroxylaceae Fígado Alcalóides Células Linhagem celular |
| topic |
Erythroxylaceae Fígado Alcalóides Células Linhagem celular Erythroxylum macrocalyx Erythroxylaceae Tropane alkaloids 7β-acetoxy-6β-benzoyloxy-3α-hydroxytropane Antiproliferative |
| dc.subject.en.en.fl_str_mv |
Erythroxylum macrocalyx Erythroxylaceae Tropane alkaloids 7β-acetoxy-6β-benzoyloxy-3α-hydroxytropane Antiproliferative |
| description |
Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) (462401/2014-6; 304445/2017-7) |
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2021 |
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2021-06-25T14:41:42Z |
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2021-06-25T14:41:42Z |
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2021 |
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info:eu-repo/semantics/publishedVersion |
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info:eu-repo/semantics/article |
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SILVA JUNIOR, Lauro J. C. da et al. A new tropane alkaloid and other metabolites from Erythroxylum macrocalyx (Erythroxylaceae) and their antiproliferative activities. Phytochemistry Letters, v. 41, p. 168-174, Feb. 2021. |
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https://www.arca.fiocruz.br/handle/icict/47867 |
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1874-3900 |
| dc.identifier.doi.pt_BR.fl_str_mv |
10.1016/j.phytol.2020.11.019 |
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SILVA JUNIOR, Lauro J. C. da et al. A new tropane alkaloid and other metabolites from Erythroxylum macrocalyx (Erythroxylaceae) and their antiproliferative activities. Phytochemistry Letters, v. 41, p. 168-174, Feb. 2021. 1874-3900 10.1016/j.phytol.2020.11.019 |
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Elsevier |
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Elsevier |
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