Isolamento, caracterização química e avaliação do potencial anti-leishmania das flores de Arrabidaea brachypoda (DC) Bureau
Autor(a) principal: | |
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Data de Publicação: | 2023 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFMA |
Texto Completo: | https://tedebc.ufma.br/jspui/handle/tede/tede/4509 |
Resumo: | Leishmaniasis is characterized as a protozoal infection transmitted through the blood meal of a sandfly. The drugs used in the treatment have a series of side effects, high cost, high toxicity and difficulty in administration. Natural products then appear as an alternative to conventional treatment. Among them, there is Arrabidaea brachypoda, which is a shrub native to the cerrado and commonly used by the Brazilian population for the treatment of various diseases. Previous studies performed on hydroethanolic extract showed that the roots of the plant are rich in dimeric flavonoids, which act as possible therapeutic agents. The objective of this work was to study the antileishmanial activity of the extract and fractions of the flowers of Arrabidaea brachypoda, as well as the isolation and chemical characterization of active compounds. The extract was obtained by the percolation method with ethanol/water (7:3) and partitioned with dichloromethane (DCM) and ethyl acetate (AcOEt). To investigate the chemical diversity of the extract and fractions of Arrabidaea brachypoda, the GNPS (Global Natural Products Molecular Networking) platform was used, making it possible to record 19 compounds from the classes of flavones, flavonols, flavanones, isoflavones, simple coumarin and cinnamic acid and their derivatives through the analysis of correspondences with the spectral libraries. The in vitro assay against promastigotes of Leishmania amazonensis indicated high activity for the dichloromethane fraction (IC50 = 21.50 µg/mL), showing inhibition values similar to the tested standard (Amphotericin B). The metabolites present in the DCM fraction were then separated using chromatographic techniques: open column packed with silica and high performance liquid chromatography on a semi-preparative scale. Six substances were isolated, 4 of them from the classes of flavones: apigenin, 5- methoxy-chrysin, chrysin and acacetin and two dimeric flavonoids: brachydins A and C, identified by UV, NMR and UPLC-QTOF-HRMS. Among the isolates, 5-methoxy chrysin and brachydin-C showed the best cytotoxicity values against the promastigotes of Leishmania amazonensis, with IC50 values of 18.90 and 14.17 µg/mL, respectively.These chemical characterization steps contributed to the discussion of the genus and species of the studied plant, since most of the published studies refer to the roots of Arrabidaea brachypoda. Finally, the results obtained from this study show the potential biological effect of Arrabidaea brachypoda flowers as a possible pharmacological agent. |
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ROCHA, Claudia Quintino dahttp://lattes.cnpq.br/5609489233382242OLIVEIRA JÚNIOR, Raimundo Gonçalves dehttp://lattes.cnpq.br/5851751752528670GONÇALVES, Renato Sonchinihttp://lattes.cnpq.br/9191121610414514ROCHA, Claudia Quintino dahttp://lattes.cnpq.br/5609489233382242http://lattes.cnpq.br/8350879441314360ROSÁRIO, Marcelino Santos do2023-01-31T16:48:47Z2023-01-05ROSÁRIO, Marcelino Santos do. Isolamento, caracterização química e avaliação do potencial anti-leishmania das flores de Arrabidaea brachypoda (DC) Bureau. 2023. 107 f. Dissertação (Programa de Pós-Graduação em Química/CCET) - Universidade Federal do Maranhão, São Luís, 2023.https://tedebc.ufma.br/jspui/handle/tede/tede/4509Leishmaniasis is characterized as a protozoal infection transmitted through the blood meal of a sandfly. The drugs used in the treatment have a series of side effects, high cost, high toxicity and difficulty in administration. Natural products then appear as an alternative to conventional treatment. Among them, there is Arrabidaea brachypoda, which is a shrub native to the cerrado and commonly used by the Brazilian population for the treatment of various diseases. Previous studies performed on hydroethanolic extract showed that the roots of the plant are rich in dimeric flavonoids, which act as possible therapeutic agents. The objective of this work was to study the antileishmanial activity of the extract and fractions of the flowers of Arrabidaea brachypoda, as well as the isolation and chemical characterization of active compounds. The extract was obtained by the percolation method with ethanol/water (7:3) and partitioned with dichloromethane (DCM) and ethyl acetate (AcOEt). To investigate the chemical diversity of the extract and fractions of Arrabidaea brachypoda, the GNPS (Global Natural Products Molecular Networking) platform was used, making it possible to record 19 compounds from the classes of flavones, flavonols, flavanones, isoflavones, simple coumarin and cinnamic acid and their derivatives through the analysis of correspondences with the spectral libraries. The in vitro assay against promastigotes of Leishmania amazonensis indicated high activity for the dichloromethane fraction (IC50 = 21.50 µg/mL), showing inhibition values similar to the tested standard (Amphotericin B). The metabolites present in the DCM fraction were then separated using chromatographic techniques: open column packed with silica and high performance liquid chromatography on a semi-preparative scale. Six substances were isolated, 4 of them from the classes of flavones: apigenin, 5- methoxy-chrysin, chrysin and acacetin and two dimeric flavonoids: brachydins A and C, identified by UV, NMR and UPLC-QTOF-HRMS. Among the isolates, 5-methoxy chrysin and brachydin-C showed the best cytotoxicity values against the promastigotes of Leishmania amazonensis, with IC50 values of 18.90 and 14.17 µg/mL, respectively.These chemical characterization steps contributed to the discussion of the genus and species of the studied plant, since most of the published studies refer to the roots of Arrabidaea brachypoda. Finally, the results obtained from this study show the potential biological effect of Arrabidaea brachypoda flowers as a possible pharmacological agent.A leishmaniose é caracterizada como uma infecção protozoária transmitida através do repasto sanguíneo de um flebotomíneo. Os fármacos utilizados no tratamento apresentam uma série de efeitos colaterais, alto custo, elevada toxicidade e dificuldade na administração. Surge então os produtos naturais como alternativa ao tratamento convencional. Dentre eles, tem-se Arrabidaea brachypoda, que é um arbusto nativo do cerrado e comumente utilizado pela população brasileira para o tratamento de diversas doenças. Estudos anteriores realizados em extrato hidroetanólico mostraram que as raízes da planta são ricas em flavonoides diméricos, os quais atuam como possíveis agentes terapêuticos. O objetivo neste trabalho foi estudar a atividade antileishmania do extrato e frações das flores de Arrabidaea brachypoda, bem como o isolamento e caracterização química de compostos ativos. O extrato foi obtido pelo método de percolação com etanol/água (7:3) e particionado com diclorometano (DCM) e acetato de etila (AcOEt). Para investigar a diversidade química do extrato e frações de Arrabidaea brachypoda utilizou-se a plataforma GNPS (Global Natural Products Molecular Networking), sendo possível anotar 19 compostos das classes das flavonas, flavonois, flavanonas, isoflavonas, cumarina simples e ácido cinâmico e seus derivados através da análise de correspondências com as bibliotecas espectrais. O ensaio in vitro contra formas promastigotas de Leishmania amazonensis indicou elevada atividade para a fração diclorometânica (CI50 = 21,50 µg/mL), evidenciando valores de inibição similares ao padrão testado (Anfotericina B). Foi então realizada a separação dos metabólitos presentes na fração DCM empregando técnicas cromatográficas: coluna aberta empacotada com sílica e cromatografia líquida de alta eficiência em escala semi preparativa. Foram isoladas 6 substâncias, sendo 4 delas das classes das flavonas: apigenina, 5-metóxi-crisina, crisina e acacetina e dois flavonóides diméricos: brachydinas A e C, identificadas por UV, RMN e UPLC-QTOF-HRMS. Dentre os isolados, a 5- metóxi-crisina e a brachydina-C apresentaram os melhores valores de citotoxicidade frente às formas promastigotas de Leishmania amazonensis, apresentando valores de CI50 de 18,90 e 14,17 µg/mL, respectivamente. Estas etapas de caracterização química contribuíram para a discussão do gênero e espécie da planta estudada, uma vez que grande parte dos estudos publicados se referem às raízes da Arrabidaea brachypoda. Por fim, os resultados obtidos a partir deste estudo evidenciam o potencial efeito biológico das flores de Arrabidaea brachypoda como possível agente farmacológico.Submitted by Daniella Santos (daniella.santos@ufma.br) on 2023-01-31T16:48:46Z No. of bitstreams: 1 MarcelinoRosário.pdf: 3192111 bytes, checksum: ff59efaf9d044a52c6e17389d9baed7a (MD5)Made available in DSpace on 2023-01-31T16:48:47Z (GMT). No. of bitstreams: 1 MarcelinoRosário.pdf: 3192111 bytes, checksum: ff59efaf9d044a52c6e17389d9baed7a (MD5) Previous issue date: 2023-01-05CNPqCAPESapplication/pdfporUniversidade Federal do MaranhãoPROGRAMA DE PÓS-GRADUAÇÃO EM QUÍMICA/CCETUFMABrasilDEPARTAMENTO DE QUÍMICA/CCETbignoniaceae;flavonoides;brachydinas;GNPS;leishmaniose;bignoniaceae;flavonoids;brachydinas;GNPS;QuímicaIsolamento, caracterização química e avaliação do potencial anti-leishmania das flores de Arrabidaea brachypoda (DC) BureauIsolation, chemical characterization and evaluation of the anti-leishmania potential of flowers of Arrabidaea brachypoda (DC) Bureauinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisinfo:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações da UFMAinstname:Universidade Federal do Maranhão (UFMA)instacron:UFMAORIGINALMarcelinoRosário.pdfMarcelinoRosário.pdfapplication/pdf3192111http://tedebc.ufma.br:8080/bitstream/tede/4509/2/MarcelinoRos%C3%A1rio.pdfff59efaf9d044a52c6e17389d9baed7aMD52LICENSElicense.txtlicense.txttext/plain; charset=utf-82255http://tedebc.ufma.br:8080/bitstream/tede/4509/1/license.txt97eeade1fce43278e63fe063657f8083MD51tede/45092023-01-31 13:48:47.039oai:tede2: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Biblioteca Digital de Teses e Dissertaçõeshttps://tedebc.ufma.br/jspui/PUBhttp://tedebc.ufma.br:8080/oai/requestrepositorio@ufma.br||repositorio@ufma.bropendoar:21312023-01-31T16:48:47Biblioteca Digital de Teses e Dissertações da UFMA - Universidade Federal do Maranhão (UFMA)false |
dc.title.por.fl_str_mv |
Isolamento, caracterização química e avaliação do potencial anti-leishmania das flores de Arrabidaea brachypoda (DC) Bureau |
dc.title.alternative.eng.fl_str_mv |
Isolation, chemical characterization and evaluation of the anti-leishmania potential of flowers of Arrabidaea brachypoda (DC) Bureau |
title |
Isolamento, caracterização química e avaliação do potencial anti-leishmania das flores de Arrabidaea brachypoda (DC) Bureau |
spellingShingle |
Isolamento, caracterização química e avaliação do potencial anti-leishmania das flores de Arrabidaea brachypoda (DC) Bureau ROSÁRIO, Marcelino Santos do bignoniaceae; flavonoides; brachydinas; GNPS; leishmaniose; bignoniaceae; flavonoids; brachydinas; GNPS; Química |
title_short |
Isolamento, caracterização química e avaliação do potencial anti-leishmania das flores de Arrabidaea brachypoda (DC) Bureau |
title_full |
Isolamento, caracterização química e avaliação do potencial anti-leishmania das flores de Arrabidaea brachypoda (DC) Bureau |
title_fullStr |
Isolamento, caracterização química e avaliação do potencial anti-leishmania das flores de Arrabidaea brachypoda (DC) Bureau |
title_full_unstemmed |
Isolamento, caracterização química e avaliação do potencial anti-leishmania das flores de Arrabidaea brachypoda (DC) Bureau |
title_sort |
Isolamento, caracterização química e avaliação do potencial anti-leishmania das flores de Arrabidaea brachypoda (DC) Bureau |
author |
ROSÁRIO, Marcelino Santos do |
author_facet |
ROSÁRIO, Marcelino Santos do |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
ROCHA, Claudia Quintino da |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/5609489233382242 |
dc.contributor.referee1.fl_str_mv |
OLIVEIRA JÚNIOR, Raimundo Gonçalves de |
dc.contributor.referee1Lattes.fl_str_mv |
http://lattes.cnpq.br/5851751752528670 |
dc.contributor.referee2.fl_str_mv |
GONÇALVES, Renato Sonchini |
dc.contributor.referee2Lattes.fl_str_mv |
http://lattes.cnpq.br/9191121610414514 |
dc.contributor.referee3.fl_str_mv |
ROCHA, Claudia Quintino da |
dc.contributor.referee3Lattes.fl_str_mv |
http://lattes.cnpq.br/5609489233382242 |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/8350879441314360 |
dc.contributor.author.fl_str_mv |
ROSÁRIO, Marcelino Santos do |
contributor_str_mv |
ROCHA, Claudia Quintino da OLIVEIRA JÚNIOR, Raimundo Gonçalves de GONÇALVES, Renato Sonchini ROCHA, Claudia Quintino da |
dc.subject.por.fl_str_mv |
bignoniaceae; flavonoides; brachydinas; GNPS; leishmaniose; |
topic |
bignoniaceae; flavonoides; brachydinas; GNPS; leishmaniose; bignoniaceae; flavonoids; brachydinas; GNPS; Química |
dc.subject.eng.fl_str_mv |
bignoniaceae; flavonoids; brachydinas; GNPS; |
dc.subject.cnpq.fl_str_mv |
Química |
description |
Leishmaniasis is characterized as a protozoal infection transmitted through the blood meal of a sandfly. The drugs used in the treatment have a series of side effects, high cost, high toxicity and difficulty in administration. Natural products then appear as an alternative to conventional treatment. Among them, there is Arrabidaea brachypoda, which is a shrub native to the cerrado and commonly used by the Brazilian population for the treatment of various diseases. Previous studies performed on hydroethanolic extract showed that the roots of the plant are rich in dimeric flavonoids, which act as possible therapeutic agents. The objective of this work was to study the antileishmanial activity of the extract and fractions of the flowers of Arrabidaea brachypoda, as well as the isolation and chemical characterization of active compounds. The extract was obtained by the percolation method with ethanol/water (7:3) and partitioned with dichloromethane (DCM) and ethyl acetate (AcOEt). To investigate the chemical diversity of the extract and fractions of Arrabidaea brachypoda, the GNPS (Global Natural Products Molecular Networking) platform was used, making it possible to record 19 compounds from the classes of flavones, flavonols, flavanones, isoflavones, simple coumarin and cinnamic acid and their derivatives through the analysis of correspondences with the spectral libraries. The in vitro assay against promastigotes of Leishmania amazonensis indicated high activity for the dichloromethane fraction (IC50 = 21.50 µg/mL), showing inhibition values similar to the tested standard (Amphotericin B). The metabolites present in the DCM fraction were then separated using chromatographic techniques: open column packed with silica and high performance liquid chromatography on a semi-preparative scale. Six substances were isolated, 4 of them from the classes of flavones: apigenin, 5- methoxy-chrysin, chrysin and acacetin and two dimeric flavonoids: brachydins A and C, identified by UV, NMR and UPLC-QTOF-HRMS. Among the isolates, 5-methoxy chrysin and brachydin-C showed the best cytotoxicity values against the promastigotes of Leishmania amazonensis, with IC50 values of 18.90 and 14.17 µg/mL, respectively.These chemical characterization steps contributed to the discussion of the genus and species of the studied plant, since most of the published studies refer to the roots of Arrabidaea brachypoda. Finally, the results obtained from this study show the potential biological effect of Arrabidaea brachypoda flowers as a possible pharmacological agent. |
publishDate |
2023 |
dc.date.accessioned.fl_str_mv |
2023-01-31T16:48:47Z |
dc.date.issued.fl_str_mv |
2023-01-05 |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/masterThesis |
format |
masterThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
ROSÁRIO, Marcelino Santos do. Isolamento, caracterização química e avaliação do potencial anti-leishmania das flores de Arrabidaea brachypoda (DC) Bureau. 2023. 107 f. Dissertação (Programa de Pós-Graduação em Química/CCET) - Universidade Federal do Maranhão, São Luís, 2023. |
dc.identifier.uri.fl_str_mv |
https://tedebc.ufma.br/jspui/handle/tede/tede/4509 |
identifier_str_mv |
ROSÁRIO, Marcelino Santos do. Isolamento, caracterização química e avaliação do potencial anti-leishmania das flores de Arrabidaea brachypoda (DC) Bureau. 2023. 107 f. Dissertação (Programa de Pós-Graduação em Química/CCET) - Universidade Federal do Maranhão, São Luís, 2023. |
url |
https://tedebc.ufma.br/jspui/handle/tede/tede/4509 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
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application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal do Maranhão |
dc.publisher.program.fl_str_mv |
PROGRAMA DE PÓS-GRADUAÇÃO EM QUÍMICA/CCET |
dc.publisher.initials.fl_str_mv |
UFMA |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
DEPARTAMENTO DE QUÍMICA/CCET |
publisher.none.fl_str_mv |
Universidade Federal do Maranhão |
dc.source.none.fl_str_mv |
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Biblioteca Digital de Teses e Dissertações da UFMA |
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