Fitoquímica, atividades antimicrobiana e de inibição enzimática de Erythrina crista-galli (Fabaceae) e Valeriana polystachya (Caprifoliaceae) e obtenção de derivados de metabólitos de V. polystachya.
Autor(a) principal: | |
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Data de Publicação: | 2018 |
Tipo de documento: | Tese |
Idioma: | por |
Título da fonte: | Manancial - Repositório Digital da UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/14918 |
Resumo: | The disorders that affect the central nervous system and infectious diseases are among the pathologies that affect the world's population and grow more and more. Thus, the search for compounds that are potentially more effective and less cytotoxic to the human body is a constant in scientific research, mainly seeking in the nature bioactive substances that can be used in the treatment of diseases or that serve as prototypes for the development of new synthetic drugs. In this context, a phytochemical and pharmacological study was carried out with the species E. crista-galli (Fabaceae) and V. polystachya (Caprifoliaceae), native to the Pampa Biome. The pharmacological potential of these species was evaluated through antimicrobial activity tests against a collection of pathogenic microorganisms and enzymatic inhibition against the enzymes acetylcholinesterase (AChE) and prolyl oligopeptidase (POP). Plants of the genus Erythrina are large producers of erythrin alkaloids and used in folk medicine to treat various diseases due to its sedative, antidepressant, anticonvulsant properties and also in the treatment of antimicrobial infections, among others. A new (erythratidine N-oxide, 99) and five already known alkaloids were isolated from the stem bark of E. crista-galli. The antimicrobial action of this species was attributed mainly to the alkaloid erysotrine (15) that inhibited the growth of C.krusei fungus (MIC of 12.5 μg/ml). 15 and 99 showed inhibitors of POP activity with percentages of 77.0 (IC50 89.5 μM) and 50.6%, respectively. The genus Valeriana is known for its anxiolytic, sedative and sleep inducing effects. The bioguided isolation by the enzymatic assays of extracts and fractions prepared from the roots and rhizomes of V. polystachya, resulted in eighteen compounds, three of them unpublished in the literature, being the iridoids valtral D (102), IIHD-acevaltrate (104) and polistachin A (109). Results of enzyme inhibition revealed three POP, 102, valtrate (77) and baldrinal (49) inhibitors with IC50 of 5.3, 7.9 and 175.3 μM, respectively. The antimicrobial activity assays showed compounds with significant antimicrobial action (MICs 6.2-25 μg/ml) and antifungal (MICs between ˂ 1.5-25 μg/ml). In addition, some compounds were submitted to structural modifications, which resulted in ten derivatives, which were evaluated for antimicrobial action and enzymatic inhibitory activity against AChE and POP. A comparison of the chromatographic profile was also carried out between the V. polystachya and commercial V. officinalis species, showing that some extracts and fractions of both species have the same constituents. |
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Fitoquímica, atividades antimicrobiana e de inibição enzimática de Erythrina crista-galli (Fabaceae) e Valeriana polystachya (Caprifoliaceae) e obtenção de derivados de metabólitos de V. polystachya.Phychochemistry, antimicrobial activities and enzymatic inhibition of Erythrina crista-galli (Fabaceae) and Valeriana polystachya (Caprifoliaceae) and obtaining metabolites derivatives from V. polystachya.Erythrina crista-galliAlcaloidesValeriana polystachyaIridoidesAtividade antimicrobianaAcetilcolinesteraseProlil oligopeptidaseAlkaloidsIridoidsAntimicrobial activityAcetylcholinesteraseProlyl oligopeptidaseCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAThe disorders that affect the central nervous system and infectious diseases are among the pathologies that affect the world's population and grow more and more. Thus, the search for compounds that are potentially more effective and less cytotoxic to the human body is a constant in scientific research, mainly seeking in the nature bioactive substances that can be used in the treatment of diseases or that serve as prototypes for the development of new synthetic drugs. In this context, a phytochemical and pharmacological study was carried out with the species E. crista-galli (Fabaceae) and V. polystachya (Caprifoliaceae), native to the Pampa Biome. The pharmacological potential of these species was evaluated through antimicrobial activity tests against a collection of pathogenic microorganisms and enzymatic inhibition against the enzymes acetylcholinesterase (AChE) and prolyl oligopeptidase (POP). Plants of the genus Erythrina are large producers of erythrin alkaloids and used in folk medicine to treat various diseases due to its sedative, antidepressant, anticonvulsant properties and also in the treatment of antimicrobial infections, among others. A new (erythratidine N-oxide, 99) and five already known alkaloids were isolated from the stem bark of E. crista-galli. The antimicrobial action of this species was attributed mainly to the alkaloid erysotrine (15) that inhibited the growth of C.krusei fungus (MIC of 12.5 μg/ml). 15 and 99 showed inhibitors of POP activity with percentages of 77.0 (IC50 89.5 μM) and 50.6%, respectively. The genus Valeriana is known for its anxiolytic, sedative and sleep inducing effects. The bioguided isolation by the enzymatic assays of extracts and fractions prepared from the roots and rhizomes of V. polystachya, resulted in eighteen compounds, three of them unpublished in the literature, being the iridoids valtral D (102), IIHD-acevaltrate (104) and polistachin A (109). Results of enzyme inhibition revealed three POP, 102, valtrate (77) and baldrinal (49) inhibitors with IC50 of 5.3, 7.9 and 175.3 μM, respectively. The antimicrobial activity assays showed compounds with significant antimicrobial action (MICs 6.2-25 μg/ml) and antifungal (MICs between ˂ 1.5-25 μg/ml). In addition, some compounds were submitted to structural modifications, which resulted in ten derivatives, which were evaluated for antimicrobial action and enzymatic inhibitory activity against AChE and POP. A comparison of the chromatographic profile was also carried out between the V. polystachya and commercial V. officinalis species, showing that some extracts and fractions of both species have the same constituents.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqOs distúrbios que acometem o sistema nervoso central e as doenças infecciosas estão entre as patologias que afetam a população mundial e crescem cada vez mais. Assim, a busca de compostos potencialmente mais eficazes e menos citotóxicos ao organismo humano são uma constante na pesquisa científica, buscando-se principalmente na natureza substâncias bioativas que possam ser utilizadas na terapêutica de doenças ou que sirvam de protótipos para o desenvolvimento de novos medicamentos sintéticos. Nesse contexto, realizou-se um estudo fitoquímico e farmacológico com as espécies E. crista-galli (Fabaceae) e V. polystachya (Caprifoliaceae), nativas do Bioma Pampa. O potencial farmacológico destas espécies foi avaliado através de ensaios de atividades antimicrobiana frente à uma coleção de microrganismos patogênicos e de inibição enzimática frente às enzimas acetilcolinesterase (AChE) e prolil oligopeptidase (POP). Plantas do gênero Erythrina são grandes produtoras de alcaloides eritrínicos e utilizadas na medicina popular para tratar diversas enfermidades, devido às suas propriedades sedativas, antidepressivas, anticonvulsivantes e também no tratamento de infecções antimicrobianas, entre outras. Um novo (eritratidina N-óxido, 99) e cinco alcaloides já conhecidos foram isolados a partir das cascas do caule de E. crista-galli. A ação antimicrobiana desta espécie foi atribuída principalmente ao alcaloide erisotrina (15) que inibiu o crescimento do fungo C. krusei (CIM de 12,5 μg/ml). 15 e 99 mostraram-se inibidores da atividade de POP com percentuais de 77,0 (IC50 89,5 μM) e 50,6%, respectivamente. O gênero Valeriana é conhecido por seus efeitos ansiolíticos, sedativos e indutores do sono. O isolamento bioguiado pelos ensaios enzimáticos dos extratos e frações preparados das raízes e rizomas de V. polystachya resultou em dezoito compostos, três destes inéditos na literatura, sendo os iridoides valtral D (102), IIHD-acevaltrato (104) e polistachina A (109). Os resultados de inibição enzimática revelaram três inibidores da POP, 102, valtrato (77) e baldrinal (49) com IC50 de 5,3, 7,9 e 175,3 μM, respectivamente. Os ensaios de atividade antimicrobiana mostraram compostos com significativa ação antimicrobiana (MICs 6,2-25 μg/ml) e antifúngica (MICs entre ˂ 1,5-25 μg/ml). Além disso, alguns compostos foram submetidos à modificações estruturais, que resultaram na obtenção de dez derivados, os quais foram avaliados quanto a ação antimicrobiana e atividade inibitória enzimática frente à AChE e POP. Uma comparação de perfil cromatográfico também foi realizado entre as espécies V. polystachya e V. officinalis comercial, mostrando que alguns extratos e frações de ambas espécies possuem os mesmos constituintes.Universidade Federal de Santa MariaBrasilQuímicaUFSMPrograma de Pós-Graduação em QuímicaCentro de Ciências Naturais e ExatasDalcol, Ionara Irionhttp://lattes.cnpq.br/9769548819312192Morel, Ademir Fariashttp://lattes.cnpq.br/3554994385525333Mostardeiro, Marco Aureliohttp://lattes.cnpq.br/6195396264565980Dornelles, Lucianohttp://lattes.cnpq.br/7629319262073140Tiburski Neto, Alexandrehttp://lattes.cnpq.br/0251925499442617Ilha, Viniciushttp://lattes.cnpq.br/3882671719676564Ávila, Janaína Medeiros de2018-11-23T14:44:22Z2018-11-23T14:44:22Z2018-07-18info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisapplication/pdfhttp://repositorio.ufsm.br/handle/1/14918porAttribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSM2022-05-18T20:08:53Zoai:repositorio.ufsm.br:1/14918Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2022-05-18T20:08:53Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.none.fl_str_mv |
Fitoquímica, atividades antimicrobiana e de inibição enzimática de Erythrina crista-galli (Fabaceae) e Valeriana polystachya (Caprifoliaceae) e obtenção de derivados de metabólitos de V. polystachya. Phychochemistry, antimicrobial activities and enzymatic inhibition of Erythrina crista-galli (Fabaceae) and Valeriana polystachya (Caprifoliaceae) and obtaining metabolites derivatives from V. polystachya. |
title |
Fitoquímica, atividades antimicrobiana e de inibição enzimática de Erythrina crista-galli (Fabaceae) e Valeriana polystachya (Caprifoliaceae) e obtenção de derivados de metabólitos de V. polystachya. |
spellingShingle |
Fitoquímica, atividades antimicrobiana e de inibição enzimática de Erythrina crista-galli (Fabaceae) e Valeriana polystachya (Caprifoliaceae) e obtenção de derivados de metabólitos de V. polystachya. Ávila, Janaína Medeiros de Erythrina crista-galli Alcaloides Valeriana polystachya Iridoides Atividade antimicrobiana Acetilcolinesterase Prolil oligopeptidase Alkaloids Iridoids Antimicrobial activity Acetylcholinesterase Prolyl oligopeptidase CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Fitoquímica, atividades antimicrobiana e de inibição enzimática de Erythrina crista-galli (Fabaceae) e Valeriana polystachya (Caprifoliaceae) e obtenção de derivados de metabólitos de V. polystachya. |
title_full |
Fitoquímica, atividades antimicrobiana e de inibição enzimática de Erythrina crista-galli (Fabaceae) e Valeriana polystachya (Caprifoliaceae) e obtenção de derivados de metabólitos de V. polystachya. |
title_fullStr |
Fitoquímica, atividades antimicrobiana e de inibição enzimática de Erythrina crista-galli (Fabaceae) e Valeriana polystachya (Caprifoliaceae) e obtenção de derivados de metabólitos de V. polystachya. |
title_full_unstemmed |
Fitoquímica, atividades antimicrobiana e de inibição enzimática de Erythrina crista-galli (Fabaceae) e Valeriana polystachya (Caprifoliaceae) e obtenção de derivados de metabólitos de V. polystachya. |
title_sort |
Fitoquímica, atividades antimicrobiana e de inibição enzimática de Erythrina crista-galli (Fabaceae) e Valeriana polystachya (Caprifoliaceae) e obtenção de derivados de metabólitos de V. polystachya. |
author |
Ávila, Janaína Medeiros de |
author_facet |
Ávila, Janaína Medeiros de |
author_role |
author |
dc.contributor.none.fl_str_mv |
Dalcol, Ionara Irion http://lattes.cnpq.br/9769548819312192 Morel, Ademir Farias http://lattes.cnpq.br/3554994385525333 Mostardeiro, Marco Aurelio http://lattes.cnpq.br/6195396264565980 Dornelles, Luciano http://lattes.cnpq.br/7629319262073140 Tiburski Neto, Alexandre http://lattes.cnpq.br/0251925499442617 Ilha, Vinicius http://lattes.cnpq.br/3882671719676564 |
dc.contributor.author.fl_str_mv |
Ávila, Janaína Medeiros de |
dc.subject.por.fl_str_mv |
Erythrina crista-galli Alcaloides Valeriana polystachya Iridoides Atividade antimicrobiana Acetilcolinesterase Prolil oligopeptidase Alkaloids Iridoids Antimicrobial activity Acetylcholinesterase Prolyl oligopeptidase CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
topic |
Erythrina crista-galli Alcaloides Valeriana polystachya Iridoides Atividade antimicrobiana Acetilcolinesterase Prolil oligopeptidase Alkaloids Iridoids Antimicrobial activity Acetylcholinesterase Prolyl oligopeptidase CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
The disorders that affect the central nervous system and infectious diseases are among the pathologies that affect the world's population and grow more and more. Thus, the search for compounds that are potentially more effective and less cytotoxic to the human body is a constant in scientific research, mainly seeking in the nature bioactive substances that can be used in the treatment of diseases or that serve as prototypes for the development of new synthetic drugs. In this context, a phytochemical and pharmacological study was carried out with the species E. crista-galli (Fabaceae) and V. polystachya (Caprifoliaceae), native to the Pampa Biome. The pharmacological potential of these species was evaluated through antimicrobial activity tests against a collection of pathogenic microorganisms and enzymatic inhibition against the enzymes acetylcholinesterase (AChE) and prolyl oligopeptidase (POP). Plants of the genus Erythrina are large producers of erythrin alkaloids and used in folk medicine to treat various diseases due to its sedative, antidepressant, anticonvulsant properties and also in the treatment of antimicrobial infections, among others. A new (erythratidine N-oxide, 99) and five already known alkaloids were isolated from the stem bark of E. crista-galli. The antimicrobial action of this species was attributed mainly to the alkaloid erysotrine (15) that inhibited the growth of C.krusei fungus (MIC of 12.5 μg/ml). 15 and 99 showed inhibitors of POP activity with percentages of 77.0 (IC50 89.5 μM) and 50.6%, respectively. The genus Valeriana is known for its anxiolytic, sedative and sleep inducing effects. The bioguided isolation by the enzymatic assays of extracts and fractions prepared from the roots and rhizomes of V. polystachya, resulted in eighteen compounds, three of them unpublished in the literature, being the iridoids valtral D (102), IIHD-acevaltrate (104) and polistachin A (109). Results of enzyme inhibition revealed three POP, 102, valtrate (77) and baldrinal (49) inhibitors with IC50 of 5.3, 7.9 and 175.3 μM, respectively. The antimicrobial activity assays showed compounds with significant antimicrobial action (MICs 6.2-25 μg/ml) and antifungal (MICs between ˂ 1.5-25 μg/ml). In addition, some compounds were submitted to structural modifications, which resulted in ten derivatives, which were evaluated for antimicrobial action and enzymatic inhibitory activity against AChE and POP. A comparison of the chromatographic profile was also carried out between the V. polystachya and commercial V. officinalis species, showing that some extracts and fractions of both species have the same constituents. |
publishDate |
2018 |
dc.date.none.fl_str_mv |
2018-11-23T14:44:22Z 2018-11-23T14:44:22Z 2018-07-18 |
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/1/14918 |
url |
http://repositorio.ufsm.br/handle/1/14918 |
dc.language.iso.fl_str_mv |
por |
language |
por |
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.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Brasil Química UFSM Programa de Pós-Graduação em Química Centro de Ciências Naturais e Exatas |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria Brasil Química UFSM Programa de Pós-Graduação em Química Centro de Ciências Naturais e Exatas |
dc.source.none.fl_str_mv |
reponame:Manancial - Repositório Digital da UFSM instname:Universidade Federal de Santa Maria (UFSM) instacron:UFSM |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
instacron_str |
UFSM |
institution |
UFSM |
reponame_str |
Manancial - Repositório Digital da UFSM |
collection |
Manancial - Repositório Digital da UFSM |
repository.name.fl_str_mv |
Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
atendimento.sib@ufsm.br||tedebc@gmail.com |
_version_ |
1805922170006667264 |