Estudo fitoquímico de Condalia buxifolia reissek: isolamento, determinação estrutural e atividades antimicrobianas
Ano de defesa: | 2020 |
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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 Santa Maria
Centro de Ciências Naturais e Exatas |
Programa de Pós-Graduação: |
Programa de Pós-Graduação em Química
|
Departamento: |
Química
|
País: |
Brasil
|
Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/22949 |
Resumo: | This work describes the phytochemical study of the Condalia buxifolia Reissek species, belonging to the Rhamnaceae family, and evaluation of the antimicrobial potencial of the extracts obtained and of the isolated metabolites for study of the ratio structure/activity. With the methanolic crude extract (EB) of the bark of the roots of Condalia buxifolia, acid-base fractionation was performed, obtaining basic ethereal fraction (FEB) and acidic etheric fraction (FEA). From the FEB a neutral cyclopeptide, scutianene X, five known cyclopeptide alkaloids scutianin B, scutianin D, frangulanine, condaline A and scutianine E were isolated and a new cyclopeptide alkaloid called condaline B. From the FEA, the phytosterols stigmasterol acetylglucoside and sitosterol--D-glucoside and a flavonoid of the catechin class, 4'-O-methyl-gallocatechin were isolated. From the leaves crude extract, a mixture of lupeol and -amirine triterpenes was isolated. In addition, the alkaloid condaline B was obtained synthetically from the transformation of condaline A. This transformation, in addition to confirming the structure, was important to attribute the stereochemistry of condaline B, as being the same of condaline A. The antimicrobial activity test it was carried out by the microdilution in plates method and standard strains of different microorganisms were used: six gram-positive bacterias, ten gram-negative bacterias and nine fungi. Of the cyclopeptide alkaloids, only condaline A and B had their antimicrobial potential evaluated for fungi and demonstrated good MIC against fungi Candida krusei and Cryptococcus gatti. The other alkaloids showed moderate MIC for gram-positive bacteria Staphylococcus aureus and gram-negative bacteria Morganella Morgani. The scutianin D alkaloid showed a good MIC for the gram-negative bacteria Pseudomonas aeroginosa. |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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2021-11-24T13:11:44Z2021-11-24T13:11:44Z2020-03-31http://repositorio.ufsm.br/handle/1/22949This work describes the phytochemical study of the Condalia buxifolia Reissek species, belonging to the Rhamnaceae family, and evaluation of the antimicrobial potencial of the extracts obtained and of the isolated metabolites for study of the ratio structure/activity. With the methanolic crude extract (EB) of the bark of the roots of Condalia buxifolia, acid-base fractionation was performed, obtaining basic ethereal fraction (FEB) and acidic etheric fraction (FEA). From the FEB a neutral cyclopeptide, scutianene X, five known cyclopeptide alkaloids scutianin B, scutianin D, frangulanine, condaline A and scutianine E were isolated and a new cyclopeptide alkaloid called condaline B. From the FEA, the phytosterols stigmasterol acetylglucoside and sitosterol--D-glucoside and a flavonoid of the catechin class, 4'-O-methyl-gallocatechin were isolated. From the leaves crude extract, a mixture of lupeol and -amirine triterpenes was isolated. In addition, the alkaloid condaline B was obtained synthetically from the transformation of condaline A. This transformation, in addition to confirming the structure, was important to attribute the stereochemistry of condaline B, as being the same of condaline A. The antimicrobial activity test it was carried out by the microdilution in plates method and standard strains of different microorganisms were used: six gram-positive bacterias, ten gram-negative bacterias and nine fungi. Of the cyclopeptide alkaloids, only condaline A and B had their antimicrobial potential evaluated for fungi and demonstrated good MIC against fungi Candida krusei and Cryptococcus gatti. The other alkaloids showed moderate MIC for gram-positive bacteria Staphylococcus aureus and gram-negative bacteria Morganella Morgani. The scutianin D alkaloid showed a good MIC for the gram-negative bacteria Pseudomonas aeroginosa.O presente trabalho descreve o estudo fitoquímico da espécie Condalia buxifolia Reissek, pertencente à família Rhamnaceae e avaliação do potencial antimicrobiano dos extratos obtidos e dos metabólitos isolados para estudo da relação estrutura/atividade. Com o extrato bruto metanólico (EB) das cascas das raízes de Condalia buxifolia foi realizado fracionamento ácido-base e obtidas as frações etérea básica (FEB) e etérea ácida (FEA). Da FEB foram isolados um ciclopeptídeo neutro, scutianeno X, cinco alcaloides ciclopeptídicos já conhecidos scutianina B, scutianina D, frangulanina, condalina A e scutianina E, e um novo alcaloide ciclopeptídico denominado condalina B. Da FEA foram isolados os fitoesterois estigmasterol acetilglicosilado e -sitosterol glicosilado e um flavonoide da classe das catequinas, 4’-O-metil-galocatequina. Do extrato bruto das folhas foi isolada uma mistura dos triterpenos lupeol e -amirina. Adicionalmente, o alcaloide condalina B foi obtido sinteticamente a partir da transformação de condalina A. Essa transformação, além de confirmar a estrutura, foi importante para atribuir a estereoquímica da condalina B, como sendo a mesma da condalina A. O teste de atividade antimicrobiana foi realizado pelo método da microdiluição em placas e foram utilizadas cepas padrões de diferentes microorganismos: seis bactérias gram-positivas, dez bactérias gram-negativas e nove fungos. Dos alcaloides ciclopeptídicos somente condalina A e B tiveram seu potencial antimicrobiano avaliado para fungos e demonstraram boa CIM contra os fungos Candida krusei e Cryptococcus gatti. Os demais alcaloides apresentaram CIM moderada para bactéria gram-positiva Staphylococcus aureus e a gram-negativa Morganella Morgani. O alcaloide scutianina D apresentou boa CIM para a bactéria gram-negativa Pseudomonas aeroginosa.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESporUniversidade Federal de Santa MariaCentro de Ciências Naturais e ExatasPrograma de Pós-Graduação em QuímicaUFSMBrasilQuímicaAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessCondalia buxofoliaEstudo fitoquímicoAlcaloide ciclopeptidicoAtividade antimicrobianaPhytochemical studyCyclopeptide alkaloidAntimicrobial activityCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAEstudo fitoquímico de Condalia buxifolia reissek: isolamento, determinação estrutural e atividades antimicrobianasPhytochemical study of Condalia buxifolia reissek: isolation, structural determination and antimicrobial activitiesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisMorel, Ademir Fariashttp://lattes.cnpq.br/3554994385525333Dalcol, Ionara IrionMostardeiro, Marco AurelioCaro, Miguel Soriano BalpardaMaldaner, GracielaZanchet, Eliane Mariahttp://lattes.cnpq.br/9381250136955827Gehm, Adriana Zambenedetti1006000000006006006006006006008c99befa-f1b3-4afb-98b8-7fab46c3d493075b39ff-4d50-46ae-929f-422416df3b3c2c01e6d4-a21c-4d81-bd8c-5c4c289b62a16190e59b-afb1-46bf-8172-0091c19640253209cb7e-bf46-45b7-9ec0-d81b856e6a07ecdcf235-25a2-4a8b-bf5a-978935fd94daca2b5bc0-a577-4d5f-822b-b3821b6e2a34reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUIMICA_2020_GEHM_ADRIANA.pdfTES_PPGQUIMICA_2020_GEHM_ADRIANA.pdfTese de Doutoradoapplication/pdf7444811http://repositorio.ufsm.br/bitstream/1/22949/1/TES_PPGQUIMICA_2020_GEHM_ADRIANA.pdf2894d40b4bbc2184a80d86e32fbd6e2fMD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Estudo fitoquímico de Condalia buxifolia reissek: isolamento, determinação estrutural e atividades antimicrobianas |
dc.title.alternative.eng.fl_str_mv |
Phytochemical study of Condalia buxifolia reissek: isolation, structural determination and antimicrobial activities |
title |
Estudo fitoquímico de Condalia buxifolia reissek: isolamento, determinação estrutural e atividades antimicrobianas |
spellingShingle |
Estudo fitoquímico de Condalia buxifolia reissek: isolamento, determinação estrutural e atividades antimicrobianas Gehm, Adriana Zambenedetti Condalia buxofolia Estudo fitoquímico Alcaloide ciclopeptidico Atividade antimicrobiana Phytochemical study Cyclopeptide alkaloid Antimicrobial activity CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Estudo fitoquímico de Condalia buxifolia reissek: isolamento, determinação estrutural e atividades antimicrobianas |
title_full |
Estudo fitoquímico de Condalia buxifolia reissek: isolamento, determinação estrutural e atividades antimicrobianas |
title_fullStr |
Estudo fitoquímico de Condalia buxifolia reissek: isolamento, determinação estrutural e atividades antimicrobianas |
title_full_unstemmed |
Estudo fitoquímico de Condalia buxifolia reissek: isolamento, determinação estrutural e atividades antimicrobianas |
title_sort |
Estudo fitoquímico de Condalia buxifolia reissek: isolamento, determinação estrutural e atividades antimicrobianas |
author |
Gehm, Adriana Zambenedetti |
author_facet |
Gehm, Adriana Zambenedetti |
author_role |
author |
dc.contributor.advisor1.fl_str_mv |
Morel, Ademir Farias |
dc.contributor.advisor1Lattes.fl_str_mv |
http://lattes.cnpq.br/3554994385525333 |
dc.contributor.advisor-co1.fl_str_mv |
Dalcol, Ionara Irion |
dc.contributor.referee1.fl_str_mv |
Mostardeiro, Marco Aurelio |
dc.contributor.referee2.fl_str_mv |
Caro, Miguel Soriano Balparda |
dc.contributor.referee3.fl_str_mv |
Maldaner, Graciela |
dc.contributor.referee4.fl_str_mv |
Zanchet, Eliane Maria |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/9381250136955827 |
dc.contributor.author.fl_str_mv |
Gehm, Adriana Zambenedetti |
contributor_str_mv |
Morel, Ademir Farias Dalcol, Ionara Irion Mostardeiro, Marco Aurelio Caro, Miguel Soriano Balparda Maldaner, Graciela Zanchet, Eliane Maria |
dc.subject.por.fl_str_mv |
Condalia buxofolia Estudo fitoquímico Alcaloide ciclopeptidico Atividade antimicrobiana |
topic |
Condalia buxofolia Estudo fitoquímico Alcaloide ciclopeptidico Atividade antimicrobiana Phytochemical study Cyclopeptide alkaloid Antimicrobial activity CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Phytochemical study Cyclopeptide alkaloid Antimicrobial activity |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
This work describes the phytochemical study of the Condalia buxifolia Reissek species, belonging to the Rhamnaceae family, and evaluation of the antimicrobial potencial of the extracts obtained and of the isolated metabolites for study of the ratio structure/activity. With the methanolic crude extract (EB) of the bark of the roots of Condalia buxifolia, acid-base fractionation was performed, obtaining basic ethereal fraction (FEB) and acidic etheric fraction (FEA). From the FEB a neutral cyclopeptide, scutianene X, five known cyclopeptide alkaloids scutianin B, scutianin D, frangulanine, condaline A and scutianine E were isolated and a new cyclopeptide alkaloid called condaline B. From the FEA, the phytosterols stigmasterol acetylglucoside and sitosterol--D-glucoside and a flavonoid of the catechin class, 4'-O-methyl-gallocatechin were isolated. From the leaves crude extract, a mixture of lupeol and -amirine triterpenes was isolated. In addition, the alkaloid condaline B was obtained synthetically from the transformation of condaline A. This transformation, in addition to confirming the structure, was important to attribute the stereochemistry of condaline B, as being the same of condaline A. The antimicrobial activity test it was carried out by the microdilution in plates method and standard strains of different microorganisms were used: six gram-positive bacterias, ten gram-negative bacterias and nine fungi. Of the cyclopeptide alkaloids, only condaline A and B had their antimicrobial potential evaluated for fungi and demonstrated good MIC against fungi Candida krusei and Cryptococcus gatti. The other alkaloids showed moderate MIC for gram-positive bacteria Staphylococcus aureus and gram-negative bacteria Morganella Morgani. The scutianin D alkaloid showed a good MIC for the gram-negative bacteria Pseudomonas aeroginosa. |
publishDate |
2020 |
dc.date.issued.fl_str_mv |
2020-03-31 |
dc.date.accessioned.fl_str_mv |
2021-11-24T13:11:44Z |
dc.date.available.fl_str_mv |
2021-11-24T13:11:44Z |
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.uri.fl_str_mv |
http://repositorio.ufsm.br/handle/1/22949 |
url |
http://repositorio.ufsm.br/handle/1/22949 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 600 600 600 600 600 |
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dc.rights.driver.fl_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Attribution-NonCommercial-NoDerivatives 4.0 International http://creativecommons.org/licenses/by-nc-nd/4.0/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.publisher.program.fl_str_mv |
Programa de Pós-Graduação em Química |
dc.publisher.initials.fl_str_mv |
UFSM |
dc.publisher.country.fl_str_mv |
Brasil |
dc.publisher.department.fl_str_mv |
Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Centro de Ciências Naturais e Exatas |
dc.source.none.fl_str_mv |
reponame:Biblioteca Digital de Teses e Dissertações do UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
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Universidade Federal de Santa Maria (UFSM) |
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UFSM |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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Biblioteca Digital de Teses e Dissertações do UFSM |
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