Análise fitoquímica de Luehea divaricata (Martius) e Symplocos uniflora (Benth) - e suas potenciais atividades biológicas

Detalhes bibliográficos
Ano de defesa: 2022
Autor(a) principal: Cunha, Sabrina Bassaldua da lattes
Orientador(a): Morel, Ademir Farias lattes
Banca de defesa: Maldaner, Graciela, Moura, Neusa Fernandes de, Zanchet, Eliane Maria, Dornelles, Luciano
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/1/27122
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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spelling 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:Manancial - Repositório Digital da 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
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