Antimalarial activity of piperidine alkaloids from Senna spectabilis and semisynthetic derivatives
Autor(a) principal: | |
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Data de Publicação: | 2014 |
Outros Autores: | , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.5935/0103-5053.20140195 http://hdl.handle.net/11449/114545 |
Resumo: | In our continuing work looking for new anti-infective lead compounds from Brazilian biomes, the two known piperidine alkaloids ( - )-cassine and ( - )-spectaline were isolated from the flowers of Senna spectabilis (syn. Cassia spectabilis). Their structures were elucidated using a combination of spectroscopic and spectrometric data analysis. Further, these compounds were acetylated yielding the derivatives ( - )-3-O-acetylcassine and ( - )-3-O-acetylspectaline. All compounds were screened against P. falciparum-infected red blood cells (RBC) in culture, aiming to identify antimalarial prototypes. Among all compounds screened, the first two alkaloids (IC50 1.82 µM and IC50 2.76 µM) were more effective than the derivatives (IC50 24.47 µM and IC50 25.14 µM) in comparison to the standard compound chloroquine (IC50 0.30 µM). These data show that piperidine alkaloids constitute a class of natural products that feature a broad spectrum of biological activities, and are, therefore, important templates for drug design, including antimalarial. |
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Antimalarial activity of piperidine alkaloids from Senna spectabilis and semisynthetic derivativespiperidine alkaloidsSenna spectabilissemisynthetic derivativesantimalarial activityPlasmodium falciparumIn our continuing work looking for new anti-infective lead compounds from Brazilian biomes, the two known piperidine alkaloids ( - )-cassine and ( - )-spectaline were isolated from the flowers of Senna spectabilis (syn. Cassia spectabilis). Their structures were elucidated using a combination of spectroscopic and spectrometric data analysis. Further, these compounds were acetylated yielding the derivatives ( - )-3-O-acetylcassine and ( - )-3-O-acetylspectaline. All compounds were screened against P. falciparum-infected red blood cells (RBC) in culture, aiming to identify antimalarial prototypes. Among all compounds screened, the first two alkaloids (IC50 1.82 µM and IC50 2.76 µM) were more effective than the derivatives (IC50 24.47 µM and IC50 25.14 µM) in comparison to the standard compound chloroquine (IC50 0.30 µM). These data show that piperidine alkaloids constitute a class of natural products that feature a broad spectrum of biological activities, and are, therefore, important templates for drug design, including antimalarial.Dando continuidade as pesquisas de identificação de metabólitos secundários com propriedades anti-infecciosas potenciais a partir de espécies de plantas dos biomas brasileiros, dois alcaloides piperidínicos ( - )-cassina e ( - )-espectalina foram isolados das flores de Senna spectabilis (sin. Cassia spectabilis). As estruturas destes compostos foram elucidadas a partir de dados espectroscópicos e espectrométricos. Adicionalmente, esses alcaloides foram acetilados, resultando nos derivados ( - )-3-O-acetilcassina e ( - )-3-O-acetilespectalina. Todas as substâncias foram submetidas ao bioensaio empregando culturas de eritrócitos, infectadas com Plasmodium falciparum, um teste específico para avaliação antimalárica. Dentre as substâncias avaliadas, os dois primeiros alcaloides (IC50 1,82 µM e IC50 2,76 µM) foram mais potentes que os derivados (IC50 24,47 µM e IC50 25,14 µM) em comparação com a cloroquina (IC50 0,30 µM), utilizada como padrão. Estes dados mostram que os alcaloides piperidínicos constituem uma classe de produtos naturais que apresenta amplo espectro de atividades biológicas, sendo portanto, importantes modelos para o planejamento de fármacos, incluindo os antimaláricos.Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Universidade Federal de Uberlândia Instituto de QuímicaUniversidade Estadual Paulista Instituto de Química Departamento de Química OrgânicaUniversidade de São Paulo Instituto de Biociências Departamento de FisiologiaUniversidade Federal do Triângulo Mineiro Instituto de Ciências Exatas, Naturais e Educação Departamento de QuímicaUniversidade Estadual Paulista Instituto de Química Departamento de Química OrgânicaSociedade Brasileira de QuímicaUniversidade Federal de Uberlândia (UFU)Universidade Estadual Paulista (Unesp)Universidade de São Paulo (USP)Universidade Federal do Triângulo Mineiro (UFTM)Pivatto, MarcosBaccini, Luciene R. [UNESP]Sharma, AbhinayNakabashi, MynaDanuello, AmandaViegas Júnior, ClaudioGarcia, Celia R. S.Bolzani, Vanderlan da Silva [UNESP]2015-02-02T12:39:38Z2015-02-02T12:39:38Z2014-10-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article1900-1906application/pdfhttp://dx.doi.org/10.5935/0103-5053.20140195Journal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 25, n. 10, p. 1900-1906, 2014.0103-5053http://hdl.handle.net/11449/11454510.5935/0103-5053.20140195S0103-50532014001000015S0103-50532014001000015.pdf4484083685251673SciELOreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengJournal of the Brazilian Chemical Society1.4440,357info:eu-repo/semantics/openAccess2023-11-25T06:17:02Zoai:repositorio.unesp.br:11449/114545Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462023-11-25T06:17:02Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
Antimalarial activity of piperidine alkaloids from Senna spectabilis and semisynthetic derivatives |
title |
Antimalarial activity of piperidine alkaloids from Senna spectabilis and semisynthetic derivatives |
spellingShingle |
Antimalarial activity of piperidine alkaloids from Senna spectabilis and semisynthetic derivatives Pivatto, Marcos piperidine alkaloids Senna spectabilis semisynthetic derivatives antimalarial activity Plasmodium falciparum |
title_short |
Antimalarial activity of piperidine alkaloids from Senna spectabilis and semisynthetic derivatives |
title_full |
Antimalarial activity of piperidine alkaloids from Senna spectabilis and semisynthetic derivatives |
title_fullStr |
Antimalarial activity of piperidine alkaloids from Senna spectabilis and semisynthetic derivatives |
title_full_unstemmed |
Antimalarial activity of piperidine alkaloids from Senna spectabilis and semisynthetic derivatives |
title_sort |
Antimalarial activity of piperidine alkaloids from Senna spectabilis and semisynthetic derivatives |
author |
Pivatto, Marcos |
author_facet |
Pivatto, Marcos Baccini, Luciene R. [UNESP] Sharma, Abhinay Nakabashi, Myna Danuello, Amanda Viegas Júnior, Claudio Garcia, Celia R. S. Bolzani, Vanderlan da Silva [UNESP] |
author_role |
author |
author2 |
Baccini, Luciene R. [UNESP] Sharma, Abhinay Nakabashi, Myna Danuello, Amanda Viegas Júnior, Claudio Garcia, Celia R. S. Bolzani, Vanderlan da Silva [UNESP] |
author2_role |
author author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade Federal de Uberlândia (UFU) Universidade Estadual Paulista (Unesp) Universidade de São Paulo (USP) Universidade Federal do Triângulo Mineiro (UFTM) |
dc.contributor.author.fl_str_mv |
Pivatto, Marcos Baccini, Luciene R. [UNESP] Sharma, Abhinay Nakabashi, Myna Danuello, Amanda Viegas Júnior, Claudio Garcia, Celia R. S. Bolzani, Vanderlan da Silva [UNESP] |
dc.subject.por.fl_str_mv |
piperidine alkaloids Senna spectabilis semisynthetic derivatives antimalarial activity Plasmodium falciparum |
topic |
piperidine alkaloids Senna spectabilis semisynthetic derivatives antimalarial activity Plasmodium falciparum |
description |
In our continuing work looking for new anti-infective lead compounds from Brazilian biomes, the two known piperidine alkaloids ( - )-cassine and ( - )-spectaline were isolated from the flowers of Senna spectabilis (syn. Cassia spectabilis). Their structures were elucidated using a combination of spectroscopic and spectrometric data analysis. Further, these compounds were acetylated yielding the derivatives ( - )-3-O-acetylcassine and ( - )-3-O-acetylspectaline. All compounds were screened against P. falciparum-infected red blood cells (RBC) in culture, aiming to identify antimalarial prototypes. Among all compounds screened, the first two alkaloids (IC50 1.82 µM and IC50 2.76 µM) were more effective than the derivatives (IC50 24.47 µM and IC50 25.14 µM) in comparison to the standard compound chloroquine (IC50 0.30 µM). These data show that piperidine alkaloids constitute a class of natural products that feature a broad spectrum of biological activities, and are, therefore, important templates for drug design, including antimalarial. |
publishDate |
2014 |
dc.date.none.fl_str_mv |
2014-10-01 2015-02-02T12:39:38Z 2015-02-02T12:39:38Z |
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.uri.fl_str_mv |
http://dx.doi.org/10.5935/0103-5053.20140195 Journal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 25, n. 10, p. 1900-1906, 2014. 0103-5053 http://hdl.handle.net/11449/114545 10.5935/0103-5053.20140195 S0103-50532014001000015 S0103-50532014001000015.pdf 4484083685251673 |
url |
http://dx.doi.org/10.5935/0103-5053.20140195 http://hdl.handle.net/11449/114545 |
identifier_str_mv |
Journal of the Brazilian Chemical Society. Sociedade Brasileira de Química, v. 25, n. 10, p. 1900-1906, 2014. 0103-5053 10.5935/0103-5053.20140195 S0103-50532014001000015 S0103-50532014001000015.pdf 4484083685251673 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Journal of the Brazilian Chemical Society 1.444 0,357 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
1900-1906 application/pdf |
dc.publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
publisher.none.fl_str_mv |
Sociedade Brasileira de Química |
dc.source.none.fl_str_mv |
SciELO reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
|
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1797789814622257152 |