Substâncias fenólicas de Helicteres eichleri K. SCHUM (Malvaceae sensu lato) e avaliação microbiológica de suas quinonas
Autor(a) principal: | |
---|---|
Data de Publicação: | 2022 |
Tipo de documento: | Dissertação |
Idioma: | por |
Título da fonte: | Biblioteca Digital de Teses e Dissertações da UFPB |
Texto Completo: | https://repositorio.ufpb.br/jspui/handle/123456789/23387 |
Resumo: | Natural products have been used to cure and treat various diseases since prehistoric times. These compounds have high structural diversity and arouse the interest of many researchers in the search for new bioactive molecules. Currently, microbial resistance caused by the inappropriate use of antibiotics was considered by the World Health Organization (WHO) a threat to the health of society, with a growing demand for new bioactive molecules from plants against bacterial resistance. Given the wide range of plant chemical structures, chemotaxonomic and biological knowledge of the genus Helicteres, this study sought to identify phytochemical and microbial potentials against 4 pathogenic bacterial strains, of substances isolated from Helicteres eichleri K. Schum, endemic to Brazil and popularly known as ―monkey smoke‖, family Sterculiaceae (Malvaceae sensu lato). For the phytochemical study, the crude ethanol extract was subjected to liquid-liquid chromatography, using Hex.; CH2Cl2; AcOEt; n-BuOH, obtaining their respective phases, in addition to the hydroalcoholic phase. The dichloromethane phase (20g) and the ethyl acetate phase (8g) were subjected to column chromatography using flash silica and/or C-18 cartridge and Sephadex-LH 20 as stationary phases. The antimicrobial activity of two isolated compounds (He-1 and He-2) was investigated against Staphylococcus aureus, Staphylococcus epidermidis, Klebsiella pneumoniae and Salmonella enterica typhimurium, by disk diffusion assay and by means of microdilution by determining the Minimum Inhibitory (MIC). The chromatographic process led to the isolation of four chemical constituents, whose chemical structures were defined by interpretation of 1H and 13C and two-dimensional NMR spectra, and comparisons with models in the literature. The isolated substances were two O-naphthoquinones, He-1: 4-methoxy-3,6,9-trimethyl-2,3-dihydrobenzo[de]chromene-7,8-dione (mansonone M) and He-2: 4-Hydroxy-3,6,9-trimethyl-2,3-dihydro-benzo[de]chromene-7,8-dione (mansonone H), a sulfated flavonoid, He-4: 7,4'-di -O-methyl-8-O-sulfate-isoscutellarein and a glycosylated flavonoid, He-5: kaempferol-3-O-β-D-(6‖-Ep-coumaroyl) glycopyranoside (tylyroside). The antimicrobial evaluation performed with the two sesquiterpene quinones showed that He-1 and He-2 showed antimicrobial activity against Staphylococcus aureus and Staphylococcus epidermidis, and He-1 showed low activity against Salmonella enterica typhimuriu. The four substances were isolated for the first time in the species, thus strengthening the phytochemical profile of the genus Helicteres and the O-naphthoquinones proved to be promising in terms of their antimicrobial activity. |
id |
UFPB_d71ce70a33621fcfa8751c4ad75bc936 |
---|---|
oai_identifier_str |
oai:repositorio.ufpb.br:123456789/23387 |
network_acronym_str |
UFPB |
network_name_str |
Biblioteca Digital de Teses e Dissertações da UFPB |
repository_id_str |
|
spelling |
Substâncias fenólicas de Helicteres eichleri K. SCHUM (Malvaceae sensu lato) e avaliação microbiológica de suas quinonasSterculiaceaeEstudo fitoquímicoFlavonoide sulfatadoNaftoquinonasAtividade antimicrobianaPhytochemical studySulfated flavonoidNaphthoquinonesAntimicrobian activityCNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIANatural products have been used to cure and treat various diseases since prehistoric times. These compounds have high structural diversity and arouse the interest of many researchers in the search for new bioactive molecules. Currently, microbial resistance caused by the inappropriate use of antibiotics was considered by the World Health Organization (WHO) a threat to the health of society, with a growing demand for new bioactive molecules from plants against bacterial resistance. Given the wide range of plant chemical structures, chemotaxonomic and biological knowledge of the genus Helicteres, this study sought to identify phytochemical and microbial potentials against 4 pathogenic bacterial strains, of substances isolated from Helicteres eichleri K. Schum, endemic to Brazil and popularly known as ―monkey smoke‖, family Sterculiaceae (Malvaceae sensu lato). For the phytochemical study, the crude ethanol extract was subjected to liquid-liquid chromatography, using Hex.; CH2Cl2; AcOEt; n-BuOH, obtaining their respective phases, in addition to the hydroalcoholic phase. The dichloromethane phase (20g) and the ethyl acetate phase (8g) were subjected to column chromatography using flash silica and/or C-18 cartridge and Sephadex-LH 20 as stationary phases. The antimicrobial activity of two isolated compounds (He-1 and He-2) was investigated against Staphylococcus aureus, Staphylococcus epidermidis, Klebsiella pneumoniae and Salmonella enterica typhimurium, by disk diffusion assay and by means of microdilution by determining the Minimum Inhibitory (MIC). The chromatographic process led to the isolation of four chemical constituents, whose chemical structures were defined by interpretation of 1H and 13C and two-dimensional NMR spectra, and comparisons with models in the literature. The isolated substances were two O-naphthoquinones, He-1: 4-methoxy-3,6,9-trimethyl-2,3-dihydrobenzo[de]chromene-7,8-dione (mansonone M) and He-2: 4-Hydroxy-3,6,9-trimethyl-2,3-dihydro-benzo[de]chromene-7,8-dione (mansonone H), a sulfated flavonoid, He-4: 7,4'-di -O-methyl-8-O-sulfate-isoscutellarein and a glycosylated flavonoid, He-5: kaempferol-3-O-β-D-(6‖-Ep-coumaroyl) glycopyranoside (tylyroside). The antimicrobial evaluation performed with the two sesquiterpene quinones showed that He-1 and He-2 showed antimicrobial activity against Staphylococcus aureus and Staphylococcus epidermidis, and He-1 showed low activity against Salmonella enterica typhimuriu. The four substances were isolated for the first time in the species, thus strengthening the phytochemical profile of the genus Helicteres and the O-naphthoquinones proved to be promising in terms of their antimicrobial activity.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior - CAPESOs produtos naturais são utilizados para a cura e tratamento de diversas doenças desde os tempos pré-históricos. Esses compostos apresentam alta diversidade estrutural e despertam interesse de muitos pesquisadores na busca de novas moléculas bioativas. Atualmente a resistência microbiana causada pelo uso inadequado de antibióticos, foi considerada pela Organização Mundial da Saúde (OMS) uma ameaça à saúde da sociedade, havendo uma procura crescente por novas moléculas bioativas de plantas contra a resistência bacteriana. Diante da ampla gama de estruturas químicas vegetais, dos conhecimentos quimiotaxonômicos e biológicos do gênero Helicteres, buscou-se neste estudo os potenciais fitoquímicos e microbianos contra 4 linhagens bacterianas patogênicas, de substâncias isoladas de Helicteres eichleri K. Schum, endêmica do Brasil e conhecida popularmente como ―fumo-de-macaco‖, família Sterculiaceae (Malvaceae sensu lato). Para o estudo fitoquímico, o extrato etanólico bruto foi submetido à cromatografia líquido-líquido, utilizando Hex.; CH2Cl2; AcOEt; n-BuOH, obtendo-se suas respectivas fases, além da fase hidroalcoólica. A fase diclorometano (20g) e a fase acetato de etila (8g) foram submetidas a cromatografia em coluna utilizando sílica flash e/ou cartucho C-18 e Sephadex-LH 20, como fases estacionárias. A atividade antimicrobiana de dois compostos isolados (He-1 e He-2) foram investigadas frente a Staphylococcus aureus, Staphylococcus epidermidis, Klebsiella pneumoniae e Salmonella enterica typhimurium, por ensaio de disco difusão e por meio da de microdiluição por meio da determinação da Concentração Inibitória Mínima (CIM). O processo cromatográfico levou ao isolamento de quatro constituintes químicos, cujas estruturas químicas foram definidas por interpretação dos espectros de RMN 1H e 13C e bidimensionais, e comparações com modelos da literatura. As substâncias isoladas foram duas O-naftoquinonas, He-1: 4-metoxi-3,6,9-trimetil-2,3-di-hidrobenzo [de] cromeno-7, 8-diona (mansonona M) e He-2 :4-Hidroxi-3,6,9-trimetil-2,3-di-hidro-benzo [de] cromeno-7,8-diona (mansonona H), um flavonóide sulfatado He-4: 7,4’-di-O-metil-8-O-sulfato-isoscutelareina e um flavonoide glicosilado He-5: canferol-3-O-β-D-(6‖-E-p-coumaroil) glicopiranosídeo (tilirosídeo). A avaliação antimicrobiana realizada com as duas quinonas sesquiterpênicas, demonstrou que He-1 e He-2 apresentou atividade antimicrobiana frente a Staphylococcus aureus e Staphylococcus epidermidis, e He-1 apresentou baixa atividade contra Salmonella enterica typhimuriu. As quatro substâncias foram isoladas pela primeira vez na espécie, fortalecendo assim o perfil fitoquímico do gênero Helicteres e as O-naftoquinonas demonstraram-se promissoras quanto a sua atividade antimicrobiana.Universidade Federal da ParaíbaBrasilFarmacologiaPrograma de Pós-Graduação em Produtos Naturais e Sintéticos BioativosUFPBSouza, Maria de Fátima Vanderlei dehttp://lattes.cnpq.br/6609504592713876Silva, Camila Macaúbas da2022-07-11T16:57:15Z2022-04-232022-07-11T16:57:15Z2022-02-24info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesishttps://repositorio.ufpb.br/jspui/handle/123456789/23387porAttribution-NoDerivs 3.0 Brazilhttp://creativecommons.org/licenses/by-nd/3.0/br/info:eu-repo/semantics/openAccessreponame:Biblioteca Digital de Teses e Dissertações da UFPBinstname:Universidade Federal da Paraíba (UFPB)instacron:UFPB2022-08-09T12:47:47Zoai:repositorio.ufpb.br:123456789/23387Biblioteca Digital de Teses e Dissertaçõeshttps://repositorio.ufpb.br/PUBhttp://tede.biblioteca.ufpb.br:8080/oai/requestdiretoria@ufpb.br|| diretoria@ufpb.bropendoar:2022-08-09T12:47:47Biblioteca Digital de Teses e Dissertações da UFPB - Universidade Federal da Paraíba (UFPB)false |
dc.title.none.fl_str_mv |
Substâncias fenólicas de Helicteres eichleri K. SCHUM (Malvaceae sensu lato) e avaliação microbiológica de suas quinonas |
title |
Substâncias fenólicas de Helicteres eichleri K. SCHUM (Malvaceae sensu lato) e avaliação microbiológica de suas quinonas |
spellingShingle |
Substâncias fenólicas de Helicteres eichleri K. SCHUM (Malvaceae sensu lato) e avaliação microbiológica de suas quinonas Silva, Camila Macaúbas da Sterculiaceae Estudo fitoquímico Flavonoide sulfatado Naftoquinonas Atividade antimicrobiana Phytochemical study Sulfated flavonoid Naphthoquinones Antimicrobian activity CNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIA |
title_short |
Substâncias fenólicas de Helicteres eichleri K. SCHUM (Malvaceae sensu lato) e avaliação microbiológica de suas quinonas |
title_full |
Substâncias fenólicas de Helicteres eichleri K. SCHUM (Malvaceae sensu lato) e avaliação microbiológica de suas quinonas |
title_fullStr |
Substâncias fenólicas de Helicteres eichleri K. SCHUM (Malvaceae sensu lato) e avaliação microbiológica de suas quinonas |
title_full_unstemmed |
Substâncias fenólicas de Helicteres eichleri K. SCHUM (Malvaceae sensu lato) e avaliação microbiológica de suas quinonas |
title_sort |
Substâncias fenólicas de Helicteres eichleri K. SCHUM (Malvaceae sensu lato) e avaliação microbiológica de suas quinonas |
author |
Silva, Camila Macaúbas da |
author_facet |
Silva, Camila Macaúbas da |
author_role |
author |
dc.contributor.none.fl_str_mv |
Souza, Maria de Fátima Vanderlei de http://lattes.cnpq.br/6609504592713876 |
dc.contributor.author.fl_str_mv |
Silva, Camila Macaúbas da |
dc.subject.por.fl_str_mv |
Sterculiaceae Estudo fitoquímico Flavonoide sulfatado Naftoquinonas Atividade antimicrobiana Phytochemical study Sulfated flavonoid Naphthoquinones Antimicrobian activity CNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIA |
topic |
Sterculiaceae Estudo fitoquímico Flavonoide sulfatado Naftoquinonas Atividade antimicrobiana Phytochemical study Sulfated flavonoid Naphthoquinones Antimicrobian activity CNPQ::CIENCIAS BIOLOGICAS::FARMACOLOGIA |
description |
Natural products have been used to cure and treat various diseases since prehistoric times. These compounds have high structural diversity and arouse the interest of many researchers in the search for new bioactive molecules. Currently, microbial resistance caused by the inappropriate use of antibiotics was considered by the World Health Organization (WHO) a threat to the health of society, with a growing demand for new bioactive molecules from plants against bacterial resistance. Given the wide range of plant chemical structures, chemotaxonomic and biological knowledge of the genus Helicteres, this study sought to identify phytochemical and microbial potentials against 4 pathogenic bacterial strains, of substances isolated from Helicteres eichleri K. Schum, endemic to Brazil and popularly known as ―monkey smoke‖, family Sterculiaceae (Malvaceae sensu lato). For the phytochemical study, the crude ethanol extract was subjected to liquid-liquid chromatography, using Hex.; CH2Cl2; AcOEt; n-BuOH, obtaining their respective phases, in addition to the hydroalcoholic phase. The dichloromethane phase (20g) and the ethyl acetate phase (8g) were subjected to column chromatography using flash silica and/or C-18 cartridge and Sephadex-LH 20 as stationary phases. The antimicrobial activity of two isolated compounds (He-1 and He-2) was investigated against Staphylococcus aureus, Staphylococcus epidermidis, Klebsiella pneumoniae and Salmonella enterica typhimurium, by disk diffusion assay and by means of microdilution by determining the Minimum Inhibitory (MIC). The chromatographic process led to the isolation of four chemical constituents, whose chemical structures were defined by interpretation of 1H and 13C and two-dimensional NMR spectra, and comparisons with models in the literature. The isolated substances were two O-naphthoquinones, He-1: 4-methoxy-3,6,9-trimethyl-2,3-dihydrobenzo[de]chromene-7,8-dione (mansonone M) and He-2: 4-Hydroxy-3,6,9-trimethyl-2,3-dihydro-benzo[de]chromene-7,8-dione (mansonone H), a sulfated flavonoid, He-4: 7,4'-di -O-methyl-8-O-sulfate-isoscutellarein and a glycosylated flavonoid, He-5: kaempferol-3-O-β-D-(6‖-Ep-coumaroyl) glycopyranoside (tylyroside). The antimicrobial evaluation performed with the two sesquiterpene quinones showed that He-1 and He-2 showed antimicrobial activity against Staphylococcus aureus and Staphylococcus epidermidis, and He-1 showed low activity against Salmonella enterica typhimuriu. The four substances were isolated for the first time in the species, thus strengthening the phytochemical profile of the genus Helicteres and the O-naphthoquinones proved to be promising in terms of their antimicrobial activity. |
publishDate |
2022 |
dc.date.none.fl_str_mv |
2022-07-11T16:57:15Z 2022-04-23 2022-07-11T16:57:15Z 2022-02-24 |
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 |
https://repositorio.ufpb.br/jspui/handle/123456789/23387 |
url |
https://repositorio.ufpb.br/jspui/handle/123456789/23387 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.rights.driver.fl_str_mv |
Attribution-NoDerivs 3.0 Brazil http://creativecommons.org/licenses/by-nd/3.0/br/ info:eu-repo/semantics/openAccess |
rights_invalid_str_mv |
Attribution-NoDerivs 3.0 Brazil http://creativecommons.org/licenses/by-nd/3.0/br/ |
eu_rights_str_mv |
openAccess |
dc.publisher.none.fl_str_mv |
Universidade Federal da Paraíba Brasil Farmacologia Programa de Pós-Graduação em Produtos Naturais e Sintéticos Bioativos UFPB |
publisher.none.fl_str_mv |
Universidade Federal da Paraíba Brasil Farmacologia Programa de Pós-Graduação em Produtos Naturais e Sintéticos Bioativos UFPB |
dc.source.none.fl_str_mv |
reponame:Biblioteca Digital de Teses e Dissertações da UFPB instname:Universidade Federal da Paraíba (UFPB) instacron:UFPB |
instname_str |
Universidade Federal da Paraíba (UFPB) |
instacron_str |
UFPB |
institution |
UFPB |
reponame_str |
Biblioteca Digital de Teses e Dissertações da UFPB |
collection |
Biblioteca Digital de Teses e Dissertações da UFPB |
repository.name.fl_str_mv |
Biblioteca Digital de Teses e Dissertações da UFPB - Universidade Federal da Paraíba (UFPB) |
repository.mail.fl_str_mv |
diretoria@ufpb.br|| diretoria@ufpb.br |
_version_ |
1801842995893370880 |