Alcaloides e diidrochalconas de Metrodorea stipularis: química e bioatividade
Ano de defesa: | 2014 |
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Autor(a) principal: | |
Orientador(a): | |
Banca de defesa: | |
Tipo de documento: | Tese |
Tipo de acesso: | Acesso aberto |
Idioma: | por |
Instituição de defesa: |
Universidade Federal de São Carlos
|
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química - PPGQ
|
Departamento: |
Não Informado pela instituição
|
País: |
BR
|
Palavras-chave em Português: | |
Área do conhecimento CNPq: | |
Link de acesso: | https://repositorio.ufscar.br/handle/ufscar/6307 |
Resumo: | This work was based on bioactivity-guided study of five plants ( Galipea jasminiflora , Esenbeckia febrifuga, Esenbeckia grandiflora , Metrodorea stipularis and Zanthoxylum Fagara ) from Rutaceae family using the enzyme cruzain from Trypanosoma cruzi as target. The dichlorometane liquid-liquid partition from stems of M. stipularis were the most active one, and after a chromatographic study its fractions showed high enzymatic inhibition, so all fractions were submitted a chromatographic study aiming to isolate the secondary metabolites responsible for this inhibition. A number of compounds were isolated, among them: seven alkaloids , six coumarins, one steroid, and four dihydrochalcones, two alkaloids and three dihydrochalcones have been described for the first time. It was observed the presence of the dihydrochalcones in all active fractions indicating that has of compounds may be responsible for the activity of the extracts against cruzain. Due to the similarity of the cruzain with cathespsins B and L, and to further explore the bioactivity the isolated metabolites were also assayed in these enzymes. Four alkaloids as well two dihydrochalcones showed significant inhibition of cathepsin B, while dihydrochalcones showed to inhibition cathepsin L. Plants of this family are used in folk medicine for the treatment of malaria , so these compounds were also tested against Plasmodium falciparum parasite, and good activity was found for two dihydrochalcones. |
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Burger, Marcela Carmen de MeloVieira, Paulo Cezarhttp://genos.cnpq.br:12010/dwlattes/owa/prc_imp_cv_int?f_cod=K4781745U2http://lattes.cnpq.br/57190500360954912016-06-02T20:34:53Z2014-08-062016-06-02T20:34:53Z2014-04-04BURGER, Marcela Carmen de Melo. Alkaloids and dihydrochalcones from Metrodorea stipularis: chemistry and bioactivity. 2014. 171 f. Tese (Doutorado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2014.https://repositorio.ufscar.br/handle/ufscar/6307This work was based on bioactivity-guided study of five plants ( Galipea jasminiflora , Esenbeckia febrifuga, Esenbeckia grandiflora , Metrodorea stipularis and Zanthoxylum Fagara ) from Rutaceae family using the enzyme cruzain from Trypanosoma cruzi as target. The dichlorometane liquid-liquid partition from stems of M. stipularis were the most active one, and after a chromatographic study its fractions showed high enzymatic inhibition, so all fractions were submitted a chromatographic study aiming to isolate the secondary metabolites responsible for this inhibition. A number of compounds were isolated, among them: seven alkaloids , six coumarins, one steroid, and four dihydrochalcones, two alkaloids and three dihydrochalcones have been described for the first time. It was observed the presence of the dihydrochalcones in all active fractions indicating that has of compounds may be responsible for the activity of the extracts against cruzain. Due to the similarity of the cruzain with cathespsins B and L, and to further explore the bioactivity the isolated metabolites were also assayed in these enzymes. Four alkaloids as well two dihydrochalcones showed significant inhibition of cathepsin B, while dihydrochalcones showed to inhibition cathepsin L. Plants of this family are used in folk medicine for the treatment of malaria , so these compounds were also tested against Plasmodium falciparum parasite, and good activity was found for two dihydrochalcones.Este trabalho baseou-se no estudo bioguiado de cinco plantas (Galipea jasminiflora, Esenbeckia febrifuga, Esenbeckia grandiflora, Metrodorea stipularis e Zanthoxylum fagara) pertencentes a família Rutaceae utilizando como alvo a enzima cruzaína de Trypanosoma cruzi. A partição diclorometânica dos caules de M. stipularis proveniente da partição líquido-líquido do extrato etanólico foi a mais ativa e após estudo cromatográfico suas frações apresentaram inibições enzimáticas muito alta. Assim foram todas estudadas cromatograficamente a fim de se isolar os metabólitos secundários responsáveis por esta inibição. Neste estudo isolou-se 18 compostos (7 alcaloides, 6 cumarinas, 1 esteroide, e 4 diidrochalconas), sendo cinco inéditos na literatura até o momento (2 alcaloides e 3 diidrochalconas). Observou-se a presença das diidrochalconas em todas as frações ativas e na enzima alvo cruzaína, as substâncias desta classe de metabolitos foram as que apresentaram as maiores inibições. Estes fatos indicam que elas podem ser as responsáveis pela inibição encontrada nas frações. Devido à similaridade da cruzaína com as catepsinas B e L, os metabolitos isolados foram ensaiados nestas enzimas e quatro alcaloides assim como duas diidrochalconas apresentaram significativa inibição na catepsina B, e duas diidrochalconas na catepsina L. Como plantas desta família são utilizadas pela medicina popular no tratamento de malária, estes compostos foram também ensaiados no Plasmodium falciparum, parasita causador da doença e os resultados de duas diidrochalconas foram satisfatórios.Universidade Federal de Minas Geraisapplication/pdfporUniversidade Federal de São CarlosPrograma de Pós-Graduação em Química - PPGQUFSCarBRAlcalóidesDiidrochalconasChagas, Doença deMaláriaCâncerCIENCIAS EXATAS E DA TERRA::QUIMICAAlcaloides e diidrochalconas de Metrodorea stipularis: química e bioatividadeAlkaloids and dihydrochalcones from Metrodorea stipularis: chemistry and bioactivityinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisinfo:eu-repo/semantics/openAccessreponame:Repositório Institucional da UFSCARinstname:Universidade Federal de São Carlos (UFSCAR)instacron:UFSCARORIGINAL6031.pdfapplication/pdf4687769https://{{ getenv "DSPACE_HOST" "repositorio.ufscar.br" }}/bitstream/ufscar/6307/1/6031.pdf0dcc9e7d60a8899699a162ecb357f433MD51TEXT6031.pdf.txt6031.pdf.txtExtracted texttext/plain0https://{{ getenv "DSPACE_HOST" "repositorio.ufscar.br" }}/bitstream/ufscar/6307/4/6031.pdf.txtd41d8cd98f00b204e9800998ecf8427eMD54THUMBNAIL6031.pdf.jpg6031.pdf.jpgIM Thumbnailimage/jpeg9351https://{{ getenv "DSPACE_HOST" "repositorio.ufscar.br" }}/bitstream/ufscar/6307/5/6031.pdf.jpg7fde7dce1ab1d07a2230940657e11fc1MD55ufscar/63072020-03-23 19:47:04.921oai:repositorio.ufscar.br:ufscar/6307Repositório InstitucionalPUBhttps://repositorio.ufscar.br/oai/requestopendoar:43222023-05-25T12:51:06.882261Repositório Institucional da UFSCAR - Universidade Federal de São Carlos (UFSCAR)false |
dc.title.por.fl_str_mv |
Alcaloides e diidrochalconas de Metrodorea stipularis: química e bioatividade |
dc.title.alternative.eng.fl_str_mv |
Alkaloids and dihydrochalcones from Metrodorea stipularis: chemistry and bioactivity |
title |
Alcaloides e diidrochalconas de Metrodorea stipularis: química e bioatividade |
spellingShingle |
Alcaloides e diidrochalconas de Metrodorea stipularis: química e bioatividade Burger, Marcela Carmen de Melo Alcalóides Diidrochalconas Chagas, Doença de Malária Câncer CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Alcaloides e diidrochalconas de Metrodorea stipularis: química e bioatividade |
title_full |
Alcaloides e diidrochalconas de Metrodorea stipularis: química e bioatividade |
title_fullStr |
Alcaloides e diidrochalconas de Metrodorea stipularis: química e bioatividade |
title_full_unstemmed |
Alcaloides e diidrochalconas de Metrodorea stipularis: química e bioatividade |
title_sort |
Alcaloides e diidrochalconas de Metrodorea stipularis: química e bioatividade |
author |
Burger, Marcela Carmen de Melo |
author_facet |
Burger, Marcela Carmen de Melo |
author_role |
author |
dc.contributor.authorlattes.por.fl_str_mv |
http://lattes.cnpq.br/5719050036095491 |
dc.contributor.author.fl_str_mv |
Burger, Marcela Carmen de Melo |
dc.contributor.advisor1.fl_str_mv |
Vieira, Paulo Cezar |
dc.contributor.advisor1Lattes.fl_str_mv |
http://genos.cnpq.br:12010/dwlattes/owa/prc_imp_cv_int?f_cod=K4781745U2 |
contributor_str_mv |
Vieira, Paulo Cezar |
dc.subject.por.fl_str_mv |
Alcalóides Diidrochalconas Chagas, Doença de Malária Câncer |
topic |
Alcalóides Diidrochalconas Chagas, Doença de Malária Câncer CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.cnpq.fl_str_mv |
CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work was based on bioactivity-guided study of five plants ( Galipea jasminiflora , Esenbeckia febrifuga, Esenbeckia grandiflora , Metrodorea stipularis and Zanthoxylum Fagara ) from Rutaceae family using the enzyme cruzain from Trypanosoma cruzi as target. The dichlorometane liquid-liquid partition from stems of M. stipularis were the most active one, and after a chromatographic study its fractions showed high enzymatic inhibition, so all fractions were submitted a chromatographic study aiming to isolate the secondary metabolites responsible for this inhibition. A number of compounds were isolated, among them: seven alkaloids , six coumarins, one steroid, and four dihydrochalcones, two alkaloids and three dihydrochalcones have been described for the first time. It was observed the presence of the dihydrochalcones in all active fractions indicating that has of compounds may be responsible for the activity of the extracts against cruzain. Due to the similarity of the cruzain with cathespsins B and L, and to further explore the bioactivity the isolated metabolites were also assayed in these enzymes. Four alkaloids as well two dihydrochalcones showed significant inhibition of cathepsin B, while dihydrochalcones showed to inhibition cathepsin L. Plants of this family are used in folk medicine for the treatment of malaria , so these compounds were also tested against Plasmodium falciparum parasite, and good activity was found for two dihydrochalcones. |
publishDate |
2014 |
dc.date.available.fl_str_mv |
2014-08-06 2016-06-02T20:34:53Z |
dc.date.issued.fl_str_mv |
2014-04-04 |
dc.date.accessioned.fl_str_mv |
2016-06-02T20:34:53Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/doctoralThesis |
format |
doctoralThesis |
status_str |
publishedVersion |
dc.identifier.citation.fl_str_mv |
BURGER, Marcela Carmen de Melo. Alkaloids and dihydrochalcones from Metrodorea stipularis: chemistry and bioactivity. 2014. 171 f. Tese (Doutorado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2014. |
dc.identifier.uri.fl_str_mv |
https://repositorio.ufscar.br/handle/ufscar/6307 |
identifier_str_mv |
BURGER, Marcela Carmen de Melo. Alkaloids and dihydrochalcones from Metrodorea stipularis: chemistry and bioactivity. 2014. 171 f. Tese (Doutorado em Ciências Exatas e da Terra) - Universidade Federal de São Carlos, São Carlos, 2014. |
url |
https://repositorio.ufscar.br/handle/ufscar/6307 |
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Universidade Federal de São Carlos |
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Programa de Pós-Graduação em Química - PPGQ |
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UFSCar |
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BR |
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Universidade Federal de São Carlos |
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