Extração, composição química e avaliação das atividades de inibição enzimática e antimicrobiana de Leonurus sibiricus L.
Autor(a) principal: | |
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Data de Publicação: | 2016 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Manancial - Repositório Digital da UFSM |
Texto Completo: | http://repositorio.ufsm.br/handle/1/10612 |
Resumo: | In this study, methanolic and acid methanolic extracts were prepared from the aerial parts of Leonurus sibiricus L. and six secondary metabolites were isolated: the triterpene squalene (28), the labdane-type diterpenoid leojaponin (29), the phytosterols β-sitosterol (30) and β-sitosterol glycosylated (32), the bis phthalate (2-ethylhexyl) (31) and the alkaloid leunurina (1), which are unprecedented in this species with the exception of alkaloid 1. These isolated compounds were tested to determine their antimicrobial activity and enzyme inhibition against to acetylcholinesterase (AChE) and proliloligopeptidase (POP) enzymes. The obtained results indicated moderate antimicrobial potential of the tested samples. The leojaponin diterpene (29) showed better results in the POP inhibition assay, with 72%. Regarding the assay of AChE enzyme, the metabolites tested demonstrated inhibition potential with percentages between 10-17%. Furthermore, in order to evaluate different methods of obtaining the methanolic and acid methanolic extracts, a serie of L. sibiricus extracts were prepared to compare yields, chromatographic profile and biological activities thereof. According to the observed results, the highest yield was obtained by hot extraction using reflux method and MeOH/HCl 1% as an extraction solvent (EB q-MeOH +, 21% yield). All acid extracts showed greater potential for enzyme inhibition, with the highest percentage obtained for the extracts from extraction assisted by ultrasound EB CHII-MeOH+ and CHI-MeOH+ (sonoreator like cup horn) and EB USII-MeOH+ (ultrasonic bath), with 91, 80 and 84% inhibition of POP enzyme, respectively. Considering the AChE, the highest percentages of inhibition were also obtained with extracts prepared by ultrasound technology (EB USI-MeOH and USI-MeOH+ with 34 and 38% of AChE inhibition, respectively). Moreover, it was carried out the extraction of essential oil from the fresh aerial parts of L. sibiricus to determine their chemical composition and biological activity. Three main constituents of the oil were identified: trans-caryophyllene (31.7%), α-humulene (18.53%) and γ-muuruleno (19.12%). The oil did not show satisfactory results for its biological activity in all performed tests. |
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Extração, composição química e avaliação das atividades de inibição enzimática e antimicrobiana de Leonurus sibiricus L.Extraction, chemical composition and evaluation of enzyme inhibition and antimicrobial activities of Leonurus sibiricus L.Leonurus sibiricus L.Atividades biológicasMetodologias de extraçãoÓleo essencialBiological activitiesExtraction methodologiesEssential oilCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAIn this study, methanolic and acid methanolic extracts were prepared from the aerial parts of Leonurus sibiricus L. and six secondary metabolites were isolated: the triterpene squalene (28), the labdane-type diterpenoid leojaponin (29), the phytosterols β-sitosterol (30) and β-sitosterol glycosylated (32), the bis phthalate (2-ethylhexyl) (31) and the alkaloid leunurina (1), which are unprecedented in this species with the exception of alkaloid 1. These isolated compounds were tested to determine their antimicrobial activity and enzyme inhibition against to acetylcholinesterase (AChE) and proliloligopeptidase (POP) enzymes. The obtained results indicated moderate antimicrobial potential of the tested samples. The leojaponin diterpene (29) showed better results in the POP inhibition assay, with 72%. Regarding the assay of AChE enzyme, the metabolites tested demonstrated inhibition potential with percentages between 10-17%. Furthermore, in order to evaluate different methods of obtaining the methanolic and acid methanolic extracts, a serie of L. sibiricus extracts were prepared to compare yields, chromatographic profile and biological activities thereof. According to the observed results, the highest yield was obtained by hot extraction using reflux method and MeOH/HCl 1% as an extraction solvent (EB q-MeOH +, 21% yield). All acid extracts showed greater potential for enzyme inhibition, with the highest percentage obtained for the extracts from extraction assisted by ultrasound EB CHII-MeOH+ and CHI-MeOH+ (sonoreator like cup horn) and EB USII-MeOH+ (ultrasonic bath), with 91, 80 and 84% inhibition of POP enzyme, respectively. Considering the AChE, the highest percentages of inhibition were also obtained with extracts prepared by ultrasound technology (EB USI-MeOH and USI-MeOH+ with 34 and 38% of AChE inhibition, respectively). Moreover, it was carried out the extraction of essential oil from the fresh aerial parts of L. sibiricus to determine their chemical composition and biological activity. Three main constituents of the oil were identified: trans-caryophyllene (31.7%), α-humulene (18.53%) and γ-muuruleno (19.12%). The oil did not show satisfactory results for its biological activity in all performed tests.Conselho Nacional de Desenvolvimento Científico e TecnológicoNo presente trabalho foram preparados os extratos metanólico e metanólico ácido das partes aéreas de Leonurus sibiricus L. e isolados seis metabólitos secundários: o triterpeno esqualeno (28), o diterpeno do tipo labdano leojaponina (29), os fitoesteróis β-sitosterol (30) e β-sitosterol glicosilado (32), o ftalato de bis (2-etilexila) (31) e o alcaloide leonurina (1), inéditos nesta espécie com excessão do alcaloide 1. Estes compostos isolados foram testados a fim de se determinar suas atividades antimicrobiana e de inibição enzimática frente às enzimas acetilcolinesterase (AChE) e prolil oligopeptidase (POP). Os resultados obtidos indicaram moderado potencial antimicrobiano das amostras testadas. O diterpeno leojaponina (29) apresentou melhor resultado no ensaio de inibição da POP, com 72%. Com relação ao ensaio de inibição da enzima AChE, os metabólitos testados demonstraram um potencial de inibição com percentuais entre 10-17%. Além disso, objetivando-se avaliar diferentes métodos de obtenção dos extratos brutos metanólico e metanólico ácido foram preparados uma série de extratos de L. sibiricus a pequena escala a fim de se comparar rendimentos, perfis cromatográficos e atividades biológicas dos mesmos. De acordo com os resultados observados, o maior rendimento foi obtido através da extração a quente utilizando refluxo e MeOH/HCl 1% como solvente de extração (EB q-MeOH+; com 21% de rendimento). Todos os extratos ácidos apresentaram maior potencial de inibição enzimática, sendo os maiores percentuais obtidos para os extratos provenientes de extrações asistidas por ultrassom EB CHII-MeOH+ e CHI-MeOH+ (sonoreator do tipo cup horn ) e USII-MeOH+(banho ultrassonico), com 91, 80 e 84% de inibição da enzima POP, respectivamente. Em relação a AChE, os maiores percentuais de inibição também foram obtidos com os extratos preparados por tecnologia de ultrassom (EB USI-MeOH e USI-MeOH+ com 34 e 38% de inibição da AChE, respectivamente). Realizou-se ainda a extração do óleo essencial das partes aéreas frescas de L. sibiricus a fim de determinar sua composição química e atividade biológica. Foram identificados três constituintes principais do óleo: trans-cariofileno (31,7%), α-humuleno (18,53%) e γ-muuruleno (19,12%). O óleo não apresentou resultados satisfatórios quando a sua atividade biológica, em todos os testes realizados.Universidade Federal de Santa MariaBRQuímicaUFSMPrograma de Pós-Graduação em QuímicaDalcol, Ionara Irionhttp://lattes.cnpq.br/9769548819312192Ethur, Eduardo Mirandahttp://lattes.cnpq.br/0536800052883688Mostardeiro, Marco Aureliohttp://lattes.cnpq.br/6195396264565980Zachow, Lucimara Lais2017-05-182017-05-182016-02-25info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisapplication/pdfapplication/pdfZACHOW, Lucimara Lais. Extraction, chemical composition and evaluation of enzyme inhibition and antimicrobial activities of Leonurus sibiricus L.. 2016. 123 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2016.http://repositorio.ufsm.br/handle/1/10612porinfo:eu-repo/semantics/openAccessreponame:Manancial - Repositório Digital da UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSM2022-05-02T20:04:30Zoai:repositorio.ufsm.br:1/10612Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufsm.br/ONGhttps://repositorio.ufsm.br/oai/requestatendimento.sib@ufsm.br||tedebc@gmail.comopendoar:2022-05-02T20:04:30Manancial - Repositório Digital da UFSM - Universidade Federal de Santa Maria (UFSM)false |
dc.title.none.fl_str_mv |
Extração, composição química e avaliação das atividades de inibição enzimática e antimicrobiana de Leonurus sibiricus L. Extraction, chemical composition and evaluation of enzyme inhibition and antimicrobial activities of Leonurus sibiricus L. |
title |
Extração, composição química e avaliação das atividades de inibição enzimática e antimicrobiana de Leonurus sibiricus L. |
spellingShingle |
Extração, composição química e avaliação das atividades de inibição enzimática e antimicrobiana de Leonurus sibiricus L. Zachow, Lucimara Lais Leonurus sibiricus L. Atividades biológicas Metodologias de extração Óleo essencial Biological activities Extraction methodologies Essential oil CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Extração, composição química e avaliação das atividades de inibição enzimática e antimicrobiana de Leonurus sibiricus L. |
title_full |
Extração, composição química e avaliação das atividades de inibição enzimática e antimicrobiana de Leonurus sibiricus L. |
title_fullStr |
Extração, composição química e avaliação das atividades de inibição enzimática e antimicrobiana de Leonurus sibiricus L. |
title_full_unstemmed |
Extração, composição química e avaliação das atividades de inibição enzimática e antimicrobiana de Leonurus sibiricus L. |
title_sort |
Extração, composição química e avaliação das atividades de inibição enzimática e antimicrobiana de Leonurus sibiricus L. |
author |
Zachow, Lucimara Lais |
author_facet |
Zachow, Lucimara Lais |
author_role |
author |
dc.contributor.none.fl_str_mv |
Dalcol, Ionara Irion http://lattes.cnpq.br/9769548819312192 Ethur, Eduardo Miranda http://lattes.cnpq.br/0536800052883688 Mostardeiro, Marco Aurelio http://lattes.cnpq.br/6195396264565980 |
dc.contributor.author.fl_str_mv |
Zachow, Lucimara Lais |
dc.subject.por.fl_str_mv |
Leonurus sibiricus L. Atividades biológicas Metodologias de extração Óleo essencial Biological activities Extraction methodologies Essential oil CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
topic |
Leonurus sibiricus L. Atividades biológicas Metodologias de extração Óleo essencial Biological activities Extraction methodologies Essential oil CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
In this study, methanolic and acid methanolic extracts were prepared from the aerial parts of Leonurus sibiricus L. and six secondary metabolites were isolated: the triterpene squalene (28), the labdane-type diterpenoid leojaponin (29), the phytosterols β-sitosterol (30) and β-sitosterol glycosylated (32), the bis phthalate (2-ethylhexyl) (31) and the alkaloid leunurina (1), which are unprecedented in this species with the exception of alkaloid 1. These isolated compounds were tested to determine their antimicrobial activity and enzyme inhibition against to acetylcholinesterase (AChE) and proliloligopeptidase (POP) enzymes. The obtained results indicated moderate antimicrobial potential of the tested samples. The leojaponin diterpene (29) showed better results in the POP inhibition assay, with 72%. Regarding the assay of AChE enzyme, the metabolites tested demonstrated inhibition potential with percentages between 10-17%. Furthermore, in order to evaluate different methods of obtaining the methanolic and acid methanolic extracts, a serie of L. sibiricus extracts were prepared to compare yields, chromatographic profile and biological activities thereof. According to the observed results, the highest yield was obtained by hot extraction using reflux method and MeOH/HCl 1% as an extraction solvent (EB q-MeOH +, 21% yield). All acid extracts showed greater potential for enzyme inhibition, with the highest percentage obtained for the extracts from extraction assisted by ultrasound EB CHII-MeOH+ and CHI-MeOH+ (sonoreator like cup horn) and EB USII-MeOH+ (ultrasonic bath), with 91, 80 and 84% inhibition of POP enzyme, respectively. Considering the AChE, the highest percentages of inhibition were also obtained with extracts prepared by ultrasound technology (EB USI-MeOH and USI-MeOH+ with 34 and 38% of AChE inhibition, respectively). Moreover, it was carried out the extraction of essential oil from the fresh aerial parts of L. sibiricus to determine their chemical composition and biological activity. Three main constituents of the oil were identified: trans-caryophyllene (31.7%), α-humulene (18.53%) and γ-muuruleno (19.12%). The oil did not show satisfactory results for its biological activity in all performed tests. |
publishDate |
2016 |
dc.date.none.fl_str_mv |
2016-02-25 2017-05-18 2017-05-18 |
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.uri.fl_str_mv |
ZACHOW, Lucimara Lais. Extraction, chemical composition and evaluation of enzyme inhibition and antimicrobial activities of Leonurus sibiricus L.. 2016. 123 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2016. http://repositorio.ufsm.br/handle/1/10612 |
identifier_str_mv |
ZACHOW, Lucimara Lais. Extraction, chemical composition and evaluation of enzyme inhibition and antimicrobial activities of Leonurus sibiricus L.. 2016. 123 f. Dissertação (Mestrado em Química) - Universidade Federal de Santa Maria, Santa Maria, 2016. |
url |
http://repositorio.ufsm.br/handle/1/10612 |
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 |
dc.format.none.fl_str_mv |
application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
Universidade Federal de Santa Maria BR Química UFSM Programa de Pós-Graduação em Química |
publisher.none.fl_str_mv |
Universidade Federal de Santa Maria BR Química UFSM Programa de Pós-Graduação em Química |
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_ |
1805922083919626240 |