Análise fitoquímica de Luehea divaricata (Martius) e Symplocos uniflora (Benth) - e suas potenciais atividades biológicas
Ano de defesa: | 2022 |
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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
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Departamento: |
Química
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País: |
Brasil
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Palavras-chave em Português: | |
Palavras-chave em Inglês: | |
Área do conhecimento CNPq: | |
Link de acesso: | http://repositorio.ufsm.br/handle/1/27122 |
Resumo: | Luehea divaricata (Malvaceae) and Symplocos uniflora (Symplocaceae), better known as “açoita-cavalo” and “sete sangrias”, respectively, are native Brazilian species from pampa biome with few reports in the literature. The phytochemical investigation of the stem bark of L. divaricata (Malvaceae) resulted in the isolation of seven compounds, two of which are friedelin triterpenes and a mixture of α- and β-amyrin, two flavonoids catechin and penta - hydroxyflavane and two steroids, β-sitosterol and glycosylated β-sitosterol. The study of the species Symplocos uniflora led to the isolation of six compounds, including bis(2-ethyl-heptyl) phthalate, lauric acid, benzoic acid, benzoate-2-methyl-heptyl, 4-hydroxy-3-methoxybenzaldehyde and tetradecan-1-ol, these being isolated for the first time in the species. The structures of the isolated metabolites were elucidated through 1H and 13C NMR, one and twodimensional, by melting point, in addition to comparison with standard sample when available and data available in the literature. The extract, fractions and compounds isolated from both species were tested for their biological activities. The antimicrobial activity test was performed using the microdilution plate method and standard strains of different microorganisms were used: four Gram-positive bacteria (Staphylococcus aureus (Sa), Enterococcus faecalis (Ef), Enterococcus ssp (E) and Bacillus subtilis (Bs), and nine Gram-negative bacteria Shigella sonnei (Ss), Escherichia coli (Ec), Salmonella typhimurium (St), Pseudomonas aeroginosa (Pa), Klebsiella pneumoniae (Kp), Morganella morganii (Mm), Salmonella enteritidis (Se ) and Proteus mirabilis (Pm) and nine fungi Candida albicans(Ca), Candida tropicalis (Ct), Candida krusei (Ck), Candida parapslosis (Cp), Cryptococcus neoformans (Cn), Cryptococcus gatti (Cg), Sacharomyces cerivisae (Sc) , Candida glabrata (Cg) and Candida dublienses (Cd) Crude methanolic extract, its fractions and isolated compounds obtained from acid-base and neutral fractionation of the species Luehea divaricata and Symplocos uniflora showed antibacterial activity against Gram-negative bacteria Pseudomonas aeroginosa with (MIC 50 between 15.6- 31.2µg/mL) and for Gram-positive bacteria Bacillus subtilis with (MIC 50) of 50µg/mL, and effective antifungal activity for the tested strains. The basic ethyl acetate and neutral ethyl acetate fractions of the Luehea divaricata species, when tested for their antioxidant capacity, showed promising results with IC50 values, lower than the BHT standard. This study focused on the evaluation of the ability to inhibit the formation of biofilm of the extracts, fractions and isolates were tested against bacteria (Klebsiella pneumoniae) and fungi (Candida krusei, Candida tropicalis, Cryptococcus gatti, Candida glabrata and Cryptococcus neoformans). The antibiofilm activity was relevant for the crude methanolic extract and the acidic ether fraction of L. divaricata, basic acetate and neutral acetate fractions of S. uniflora with inhibition percentage values between 57.10% to 61.00%, while for the The results were significant for the fungal strains tested. Thus, the phytochemical study and pharmacological activities of the compounds identified from the stem bark of L. divaricata and Symplocos uniflora expand the knowledge about chemotaxonomy, as well as justify its use in ethnopharmacology |
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2022-11-28T12:08:29Z2022-11-28T12:08:29Z2022-08-28http://repositorio.ufsm.br/handle/1/27122Luehea divaricata (Malvaceae) and Symplocos uniflora (Symplocaceae), better known as “açoita-cavalo” and “sete sangrias”, respectively, are native Brazilian species from pampa biome with few reports in the literature. The phytochemical investigation of the stem bark of L. divaricata (Malvaceae) resulted in the isolation of seven compounds, two of which are friedelin triterpenes and a mixture of α- and β-amyrin, two flavonoids catechin and penta - hydroxyflavane and two steroids, β-sitosterol and glycosylated β-sitosterol. The study of the species Symplocos uniflora led to the isolation of six compounds, including bis(2-ethyl-heptyl) phthalate, lauric acid, benzoic acid, benzoate-2-methyl-heptyl, 4-hydroxy-3-methoxybenzaldehyde and tetradecan-1-ol, these being isolated for the first time in the species. The structures of the isolated metabolites were elucidated through 1H and 13C NMR, one and twodimensional, by melting point, in addition to comparison with standard sample when available and data available in the literature. The extract, fractions and compounds isolated from both species were tested for their biological activities. The antimicrobial activity test was performed using the microdilution plate method and standard strains of different microorganisms were used: four Gram-positive bacteria (Staphylococcus aureus (Sa), Enterococcus faecalis (Ef), Enterococcus ssp (E) and Bacillus subtilis (Bs), and nine Gram-negative bacteria Shigella sonnei (Ss), Escherichia coli (Ec), Salmonella typhimurium (St), Pseudomonas aeroginosa (Pa), Klebsiella pneumoniae (Kp), Morganella morganii (Mm), Salmonella enteritidis (Se ) and Proteus mirabilis (Pm) and nine fungi Candida albicans(Ca), Candida tropicalis (Ct), Candida krusei (Ck), Candida parapslosis (Cp), Cryptococcus neoformans (Cn), Cryptococcus gatti (Cg), Sacharomyces cerivisae (Sc) , Candida glabrata (Cg) and Candida dublienses (Cd) Crude methanolic extract, its fractions and isolated compounds obtained from acid-base and neutral fractionation of the species Luehea divaricata and Symplocos uniflora showed antibacterial activity against Gram-negative bacteria Pseudomonas aeroginosa with (MIC 50 between 15.6- 31.2µg/mL) and for Gram-positive bacteria Bacillus subtilis with (MIC 50) of 50µg/mL, and effective antifungal activity for the tested strains. The basic ethyl acetate and neutral ethyl acetate fractions of the Luehea divaricata species, when tested for their antioxidant capacity, showed promising results with IC50 values, lower than the BHT standard. This study focused on the evaluation of the ability to inhibit the formation of biofilm of the extracts, fractions and isolates were tested against bacteria (Klebsiella pneumoniae) and fungi (Candida krusei, Candida tropicalis, Cryptococcus gatti, Candida glabrata and Cryptococcus neoformans). The antibiofilm activity was relevant for the crude methanolic extract and the acidic ether fraction of L. divaricata, basic acetate and neutral acetate fractions of S. uniflora with inhibition percentage values between 57.10% to 61.00%, while for the The results were significant for the fungal strains tested. Thus, the phytochemical study and pharmacological activities of the compounds identified from the stem bark of L. divaricata and Symplocos uniflora expand the knowledge about chemotaxonomy, as well as justify its use in ethnopharmacologyLuehea divaricata (Malvaceae) e Symplocos uniflora (Symplocaceae), mais conhecidas como açoita-cavalo e sete sangrias, respectivamente, são espécies brasileiras nativas do bioma pampa com poucos relatos na literatura. A investigação fitoquímica das cascas do caule de L. divaricata (Malvaceae) resultou no isolamento de sete compostos, sendo dois triterpenos friedelina e uma mistura de α- e β-amirina, dois flavonoides catequina e penta-hidroxiflavano e dois esteroides o β-sitosterol e β-sitosterol glicosilado. O estudo da espécie Symplocos uniflora levou ao isolamento de seis compostos, entre eles o ftalato de bis (2-etil-heptila), ácido láurico, ácido benzoico, benzoato-2-metil-heptila, 4-hidroxi-3-metoxi-benzaldeído e tetradecan-1-ol, sendo estes, isolados pela primeira vez na espécie. As estruturas dos metabólitos isolados foram elucidadas através de RMN 1H e 13C, uni e bidimensionais, por ponto de fusão, além de comparação com amostra-padrão quando existente e dados disponíveis na literatura. O extrato, as frações e os compostos isolados de ambas as espécies foram testados quanto à suas atividades biológicas. O teste de atividade antimicrobiana foi realizado pelo método da microdiluição em placas e foram utilizadas cepas padrões de diferentes microorganismos: quatro bactérias Gram-positivas (Staphylococcus aureus (Sa), Enterococcus faecalis (Ef), Enterococcus ssp (E) e Bacillus subtilis (Bs), e nove bactérias Gram-negativas Shigella sonnei (Ss), Escherichia coli (Ec), Salmonella typhimurium (St), Pseudomonas aeroginosa (Pa), Klebsiella pneumoniae (Kp), Morganella morganii (Mm), Salmonella enteritidis (Se) e Proteus mirabilis (Pm) e nove fungosCandida albicans (Ca), Candida tropicalis (Ct), Candida krusei (Ck), Candida parapslosis (Cp), Cryptococcus neoformans (Cn), Cryptococcus gatti (Cg), Sacharomyces cerivisae (Sc), Candida glabrata (Cg) e Candida dublienses (Cd). Extrato bruto metanólico, suas frações e compostos isolados obtidos no fracionamento ácido-base e neutro das espécies Luehea divaricata e Symplocos uniflora apresentaram atividade antibacteriana frente a bactéria Gram-negativa Pseudomonas aeroginosa com (CIMs 50 entre 15,6-31,2µg/mL) e para bactéria Gram-positiva Bacillus subtilis com (CIM 50) de 50µg/mL, e atividade antifúngica efetivas para as cepas testadas. As frações acetato de etila básica e acetato de etila neutra da espécie Luehea divaricata quando testada a sua capacidade antioxidante, apresentaram resultados promissores com valores de CI50, menores que o padrão BHT. Este estudo focou-se na avaliação da capacidade de inibir a formação de biofilme dos extratos, frações e isolados foram testados frente a bactéria (Klebsiella pneumoniae) e fungos (Candida krusei, Candida tropicalis, Cryptococcus gatti, Candida glabrata e Cryptococcus neoformans).A atividade antibiofilme foi relevante para o extrato bruto metanólico e a fração etérea ácida de L. divaricata, frações acetato básica e acetato neutra de S. uniflora com valores de porcentual de inibição entre 57,10% a 61,00%, enquanto para as cepas fúngicas testadas os resultados foram significativos. Dessa forma, o estudo fitoquímico e das atividades farmacológicas dos compostos identificados da casca do caule de L. divaricata e S. uniflora ampliam os conhecimentos alusivos à quimiotaxonomia, bem como justifica seu uso na etnofarmacologia.Conselho Nacional de Pesquisa e Desenvolvimento Científico e Tecnológico - CNPqporUniversidade 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/openAccessAçoita cavaloSete sangriasMetabólitos secundáriosAtividade antioxidanteAtividade antimicrobianaAtividade antibiofilmeSecondary metabolitesAntioxidant activityAntimicrobial activityAntibiofilm activityCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAAnálise fitoquímica de Luehea divaricata (Martius) e Symplocos uniflora (Benth) - e suas potenciais atividades biológicasPhytochemical analysis of Luehea divaricata (Martius) and Symplocos uniflora (Benth) - and their potential biological activitiesinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/doctoralThesisMorel, Ademir Fariashttp://lattes.cnpq.br/3554994385525333Dalcol, Ionara IrionMaldaner, GracielaMoura, Neusa Fernandes deZanchet, Eliane MariaDornelles, Lucianohttp://lattes.cnpq.br/0418913324318445Cunha, Sabrina Bassaldua da1006000000006006006006006006006006008c99befa-f1b3-4afb-98b8-7fab46c3d49366b13ae1-3591-41b0-87ff-c441858341582c01e6d4-a21c-4d81-bd8c-5c4c289b62a1b0db7504-a42c-44d0-b7f0-992c14108c1a24bb05e9-ab5c-4992-b51a-839d83a4893393c45b93-3c5c-4de3-a200-3c1877d329cc6f6ca89d-dfdf-41bb-9190-ea786a030c67reponame:Biblioteca Digital de Teses e Dissertações do UFSMinstname:Universidade Federal de Santa Maria (UFSM)instacron:UFSMORIGINALTES_PPGQUÍMICA_2022_CUNHA_SABRINA.pdfTES_PPGQUÍMICA_2022_CUNHA_SABRINA.pdfTese de doutoradoapplication/pdf2478388http://repositorio.ufsm.br/bitstream/1/27122/1/TES_PPGQU%c3%8dMICA_2022_CUNHA_SABRINA.pdf06ccb1fc5d64310681401858610546c5MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; 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dc.title.por.fl_str_mv |
Análise fitoquímica de Luehea divaricata (Martius) e Symplocos uniflora (Benth) - e suas potenciais atividades biológicas |
dc.title.alternative.eng.fl_str_mv |
Phytochemical analysis of Luehea divaricata (Martius) and Symplocos uniflora (Benth) - and their potential biological activities |
title |
Análise fitoquímica de Luehea divaricata (Martius) e Symplocos uniflora (Benth) - e suas potenciais atividades biológicas |
spellingShingle |
Análise fitoquímica de Luehea divaricata (Martius) e Symplocos uniflora (Benth) - e suas potenciais atividades biológicas Cunha, Sabrina Bassaldua da Açoita cavalo Sete sangrias Metabólitos secundários Atividade antioxidante Atividade antimicrobiana Atividade antibiofilme Secondary metabolites Antioxidant activity Antimicrobial activity Antibiofilm activity CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
title_short |
Análise fitoquímica de Luehea divaricata (Martius) e Symplocos uniflora (Benth) - e suas potenciais atividades biológicas |
title_full |
Análise fitoquímica de Luehea divaricata (Martius) e Symplocos uniflora (Benth) - e suas potenciais atividades biológicas |
title_fullStr |
Análise fitoquímica de Luehea divaricata (Martius) e Symplocos uniflora (Benth) - e suas potenciais atividades biológicas |
title_full_unstemmed |
Análise fitoquímica de Luehea divaricata (Martius) e Symplocos uniflora (Benth) - e suas potenciais atividades biológicas |
title_sort |
Análise fitoquímica de Luehea divaricata (Martius) e Symplocos uniflora (Benth) - e suas potenciais atividades biológicas |
author |
Cunha, Sabrina Bassaldua da |
author_facet |
Cunha, Sabrina Bassaldua da |
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 |
Maldaner, Graciela |
dc.contributor.referee2.fl_str_mv |
Moura, Neusa Fernandes de |
dc.contributor.referee3.fl_str_mv |
Zanchet, Eliane Maria |
dc.contributor.referee4.fl_str_mv |
Dornelles, Luciano |
dc.contributor.authorLattes.fl_str_mv |
http://lattes.cnpq.br/0418913324318445 |
dc.contributor.author.fl_str_mv |
Cunha, Sabrina Bassaldua da |
contributor_str_mv |
Morel, Ademir Farias Dalcol, Ionara Irion Maldaner, Graciela Moura, Neusa Fernandes de Zanchet, Eliane Maria Dornelles, Luciano |
dc.subject.por.fl_str_mv |
Açoita cavalo Sete sangrias Metabólitos secundários Atividade antioxidante Atividade antimicrobiana Atividade antibiofilme |
topic |
Açoita cavalo Sete sangrias Metabólitos secundários Atividade antioxidante Atividade antimicrobiana Atividade antibiofilme Secondary metabolites Antioxidant activity Antimicrobial activity Antibiofilm activity CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
dc.subject.eng.fl_str_mv |
Secondary metabolites Antioxidant activity Antimicrobial activity Antibiofilm activity |
dc.subject.cnpq.fl_str_mv |
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA |
description |
Luehea divaricata (Malvaceae) and Symplocos uniflora (Symplocaceae), better known as “açoita-cavalo” and “sete sangrias”, respectively, are native Brazilian species from pampa biome with few reports in the literature. The phytochemical investigation of the stem bark of L. divaricata (Malvaceae) resulted in the isolation of seven compounds, two of which are friedelin triterpenes and a mixture of α- and β-amyrin, two flavonoids catechin and penta - hydroxyflavane and two steroids, β-sitosterol and glycosylated β-sitosterol. The study of the species Symplocos uniflora led to the isolation of six compounds, including bis(2-ethyl-heptyl) phthalate, lauric acid, benzoic acid, benzoate-2-methyl-heptyl, 4-hydroxy-3-methoxybenzaldehyde and tetradecan-1-ol, these being isolated for the first time in the species. The structures of the isolated metabolites were elucidated through 1H and 13C NMR, one and twodimensional, by melting point, in addition to comparison with standard sample when available and data available in the literature. The extract, fractions and compounds isolated from both species were tested for their biological activities. The antimicrobial activity test was performed using the microdilution plate method and standard strains of different microorganisms were used: four Gram-positive bacteria (Staphylococcus aureus (Sa), Enterococcus faecalis (Ef), Enterococcus ssp (E) and Bacillus subtilis (Bs), and nine Gram-negative bacteria Shigella sonnei (Ss), Escherichia coli (Ec), Salmonella typhimurium (St), Pseudomonas aeroginosa (Pa), Klebsiella pneumoniae (Kp), Morganella morganii (Mm), Salmonella enteritidis (Se ) and Proteus mirabilis (Pm) and nine fungi Candida albicans(Ca), Candida tropicalis (Ct), Candida krusei (Ck), Candida parapslosis (Cp), Cryptococcus neoformans (Cn), Cryptococcus gatti (Cg), Sacharomyces cerivisae (Sc) , Candida glabrata (Cg) and Candida dublienses (Cd) Crude methanolic extract, its fractions and isolated compounds obtained from acid-base and neutral fractionation of the species Luehea divaricata and Symplocos uniflora showed antibacterial activity against Gram-negative bacteria Pseudomonas aeroginosa with (MIC 50 between 15.6- 31.2µg/mL) and for Gram-positive bacteria Bacillus subtilis with (MIC 50) of 50µg/mL, and effective antifungal activity for the tested strains. The basic ethyl acetate and neutral ethyl acetate fractions of the Luehea divaricata species, when tested for their antioxidant capacity, showed promising results with IC50 values, lower than the BHT standard. This study focused on the evaluation of the ability to inhibit the formation of biofilm of the extracts, fractions and isolates were tested against bacteria (Klebsiella pneumoniae) and fungi (Candida krusei, Candida tropicalis, Cryptococcus gatti, Candida glabrata and Cryptococcus neoformans). The antibiofilm activity was relevant for the crude methanolic extract and the acidic ether fraction of L. divaricata, basic acetate and neutral acetate fractions of S. uniflora with inhibition percentage values between 57.10% to 61.00%, while for the The results were significant for the fungal strains tested. Thus, the phytochemical study and pharmacological activities of the compounds identified from the stem bark of L. divaricata and Symplocos uniflora expand the knowledge about chemotaxonomy, as well as justify its use in ethnopharmacology |
publishDate |
2022 |
dc.date.accessioned.fl_str_mv |
2022-11-28T12:08:29Z |
dc.date.available.fl_str_mv |
2022-11-28T12:08:29Z |
dc.date.issued.fl_str_mv |
2022-08-28 |
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/1/27122 |
url |
http://repositorio.ufsm.br/handle/1/27122 |
dc.language.iso.fl_str_mv |
por |
language |
por |
dc.relation.cnpq.fl_str_mv |
100600000000 |
dc.relation.confidence.fl_str_mv |
600 600 600 600 600 600 600 600 |
dc.relation.authority.fl_str_mv |
8c99befa-f1b3-4afb-98b8-7fab46c3d493 66b13ae1-3591-41b0-87ff-c44185834158 2c01e6d4-a21c-4d81-bd8c-5c4c289b62a1 b0db7504-a42c-44d0-b7f0-992c14108c1a 24bb05e9-ab5c-4992-b51a-839d83a48933 93c45b93-3c5c-4de3-a200-3c1877d329cc 6f6ca89d-dfdf-41bb-9190-ea786a030c67 |
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 |
instname_str |
Universidade Federal de Santa Maria (UFSM) |
instacron_str |
UFSM |
institution |
UFSM |
reponame_str |
Biblioteca Digital de Teses e Dissertações do UFSM |
collection |
Biblioteca Digital de Teses e Dissertações do UFSM |
bitstream.url.fl_str_mv |
http://repositorio.ufsm.br/bitstream/1/27122/1/TES_PPGQU%c3%8dMICA_2022_CUNHA_SABRINA.pdf http://repositorio.ufsm.br/bitstream/1/27122/2/license_rdf http://repositorio.ufsm.br/bitstream/1/27122/3/license.txt |
bitstream.checksum.fl_str_mv |
06ccb1fc5d64310681401858610546c5 4460e5956bc1d1639be9ae6146a50347 2f0571ecee68693bd5cd3f17c1e075df |
bitstream.checksumAlgorithm.fl_str_mv |
MD5 MD5 MD5 |
repository.name.fl_str_mv |
Biblioteca Digital de Teses e Dissertações do UFSM - Universidade Federal de Santa Maria (UFSM) |
repository.mail.fl_str_mv |
atendimento.sib@ufsm.br||tedebc@gmail.com |
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1793240168027652096 |