Cytotoxic Alkaloids from the Stem of Xylopia laevigata
Autor(a) principal: | |
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Data de Publicação: | 2016 |
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/16530 |
Resumo: | CAPES, CNPq, FAPESB, FAPITEC/SE, Fundação Araucária and Finep for financial support and fellowships as well as Dr. Ana Paula do N. Prata for botanical identification and the flow cytometry platform of FIOCRUZ-Bahia |
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Menezes, Leociley Rocha AlencarCosta, Cinara Oliveira D' SousaRodrigues, Ana Carolina Borges da CruzSanto, Felipe R do ENepel, AngelitaDutra, Lívia MacedoSilva, Felipe Moura Araujo daSoares, Milena Botelho PereiraBarison, AnderssonCosta, Emmanoel VilaçaBezerra, Daniel Pereira2016-12-13T17:41:00Z2016-12-13T17:41:00Z2016MENEZES, L. R. A. et al. Cytotoxic Alkaloids from the Stem of Xylopia laevigata. Molecules, v. 21, p. 890, 2016.1420-3049https://www.arca.fiocruz.br/handle/icict/1653010.3390/molecules21070890CAPES, CNPq, FAPESB, FAPITEC/SE, Fundação Araucária and Finep for financial support and fellowships as well as Dr. Ana Paula do N. Prata for botanical identification and the flow cytometry platform of FIOCRUZ-BahiaFederal University of Sergipe. Department of Chemistry. Aracaju, SE, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, BrasilFederal University of Paraná. NMR Center. Curitiba, PR, BrasilFederal University of Paraná. NMR Center. Curitiba, PR, BrasilFederal University of Amazonas. Department of Chemistry. Manaus, AM, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, Brasil / Hospital São Rafael. Center of Biotechnology and Cell Therapy. Salvador, BA, BrasilFederal University of Paraná. NMR Center. Curitiba, PR, BrasilFederal University of Amazonas. Department of Chemistry. Manaus, AM, BrasilFundação Oswaldo Cruz. Centro de Pesquisas Gonçalo Moniz. Salvador, BA, BrasilXylopia laevigata (Annonaceae), known locally as "meiú" or "pindaíba", is widely used in folk medicine in Northeastern Brazil. In the present work, we performed phytochemical analyses of the stem of X. laevigata, which led to the isolation of 19 alkaloids: (-)-roemerine, (+)-anonaine, lanuginosine, (+)-glaucine, (+)-xylopine, oxoglaucine, (+)-norglaucine, asimilobine, (-)-xylopinine, (+)-norpurpureine, (+)-N-methyllaurotetanine, (+)-norpredicentrine, (+)-discretine, (+)-calycinine, (+)-laurotetanine, (+)-reticuline, (-)-corytenchine, (+)-discretamine and (+)-flavinantine. The in vitro cytotoxic activity toward the tumor cell lines B16-F10 (mouse melanoma), HepG2 (human hepatocellular carcinoma), K562 (human chronic myelocytic leukemia) and HL-60 (human promyelocytic leukemia) and non-tumor peripheral blood mononuclear cells (PBMCs) was tested using the Alamar Blue assay. Lanuginosine, (+)-xylopine and (+)-norglaucine had the highest cytotoxic activity. Additionally, the pro-apoptotic effects of lanuginosine and (+)-xylopine were investigated in HepG2 cells using light and fluorescence microscopies and flow cytometry-based assays. Cell morphology consistent with apoptosis and a marked phosphatidylserine externalization were observed in lanuginosine- and (+)-xylopine-treated cells, suggesting induction of apoptotic cell death. In addition, (+)-xylopine treatment caused G₂/M cell cycle arrest in HepG2 cells. These data suggest that X. laevigata is a potential source for cytotoxic alkaloids.engMDPIXylopia laevigataAnnonaceaeAlcalóidesCitotoxicidadeApoptoseXylopia laevigataAnnonaceaeAlkaloidsCytotoxicityApoptosisCytotoxic Alkaloids from the Stem of Xylopia laevigatainfo: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-82991https://www.arca.fiocruz.br/bitstream/icict/16530/1/license.txt5a560609d32a3863062d77ff32785d58MD51ORIGINALMenezes LRA Cytotoxic alkaloids....pdfMenezes LRA Cytotoxic alkaloids....pdfapplication/pdf959962https://www.arca.fiocruz.br/bitstream/icict/16530/2/Menezes%20LRA%20Cytotoxic%20alkaloids....pdf13eba0c2de728f48fa918fbb6df10a04MD52TEXTMenezes LRA Cytotoxic alkaloids....pdf.txtMenezes LRA Cytotoxic alkaloids....pdf.txtExtracted 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14:34:06.378oai:www.arca.fiocruz.br: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ório 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dc.title.pt_BR.fl_str_mv |
Cytotoxic Alkaloids from the Stem of Xylopia laevigata |
title |
Cytotoxic Alkaloids from the Stem of Xylopia laevigata |
spellingShingle |
Cytotoxic Alkaloids from the Stem of Xylopia laevigata Menezes, Leociley Rocha Alencar Xylopia laevigata Annonaceae Alcalóides Citotoxicidade Apoptose Xylopia laevigata Annonaceae Alkaloids Cytotoxicity Apoptosis |
title_short |
Cytotoxic Alkaloids from the Stem of Xylopia laevigata |
title_full |
Cytotoxic Alkaloids from the Stem of Xylopia laevigata |
title_fullStr |
Cytotoxic Alkaloids from the Stem of Xylopia laevigata |
title_full_unstemmed |
Cytotoxic Alkaloids from the Stem of Xylopia laevigata |
title_sort |
Cytotoxic Alkaloids from the Stem of Xylopia laevigata |
author |
Menezes, Leociley Rocha Alencar |
author_facet |
Menezes, Leociley Rocha Alencar Costa, Cinara Oliveira D' Sousa Rodrigues, Ana Carolina Borges da Cruz Santo, Felipe R do E Nepel, Angelita Dutra, Lívia Macedo Silva, Felipe Moura Araujo da Soares, Milena Botelho Pereira Barison, Andersson Costa, Emmanoel Vilaça Bezerra, Daniel Pereira |
author_role |
author |
author2 |
Costa, Cinara Oliveira D' Sousa Rodrigues, Ana Carolina Borges da Cruz Santo, Felipe R do E Nepel, Angelita Dutra, Lívia Macedo Silva, Felipe Moura Araujo da Soares, Milena Botelho Pereira Barison, Andersson Costa, Emmanoel Vilaça Bezerra, Daniel Pereira |
author2_role |
author author author author author author author author author author |
dc.contributor.author.fl_str_mv |
Menezes, Leociley Rocha Alencar Costa, Cinara Oliveira D' Sousa Rodrigues, Ana Carolina Borges da Cruz Santo, Felipe R do E Nepel, Angelita Dutra, Lívia Macedo Silva, Felipe Moura Araujo da Soares, Milena Botelho Pereira Barison, Andersson Costa, Emmanoel Vilaça Bezerra, Daniel Pereira |
dc.subject.other.pt_BR.fl_str_mv |
Xylopia laevigata Annonaceae Alcalóides Citotoxicidade Apoptose |
topic |
Xylopia laevigata Annonaceae Alcalóides Citotoxicidade Apoptose Xylopia laevigata Annonaceae Alkaloids Cytotoxicity Apoptosis |
dc.subject.en.pt_BR.fl_str_mv |
Xylopia laevigata Annonaceae Alkaloids Cytotoxicity Apoptosis |
description |
CAPES, CNPq, FAPESB, FAPITEC/SE, Fundação Araucária and Finep for financial support and fellowships as well as Dr. Ana Paula do N. Prata for botanical identification and the flow cytometry platform of FIOCRUZ-Bahia |
publishDate |
2016 |
dc.date.accessioned.fl_str_mv |
2016-12-13T17:41:00Z |
dc.date.available.fl_str_mv |
2016-12-13T17:41:00Z |
dc.date.issued.fl_str_mv |
2016 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
MENEZES, L. R. A. et al. Cytotoxic Alkaloids from the Stem of Xylopia laevigata. Molecules, v. 21, p. 890, 2016. |
dc.identifier.uri.fl_str_mv |
https://www.arca.fiocruz.br/handle/icict/16530 |
dc.identifier.issn.pt_BR.fl_str_mv |
1420-3049 |
dc.identifier.doi.none.fl_str_mv |
10.3390/molecules21070890 |
identifier_str_mv |
MENEZES, L. R. A. et al. Cytotoxic Alkaloids from the Stem of Xylopia laevigata. Molecules, v. 21, p. 890, 2016. 1420-3049 10.3390/molecules21070890 |
url |
https://www.arca.fiocruz.br/handle/icict/16530 |
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eng |
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eng |
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openAccess |
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MDPI |
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MDPI |
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