Investigação química e avaliação biológica de bauhinia pentandra (bong.) D.dietr.

Detalhes bibliográficos
Ano de defesa: 2020
Autor(a) principal: Silva, Horlando Carlota da
Orientador(a): Santiago, Gilvandete Maria Pinheiro
Banca de defesa: Não Informado pela instituição
Tipo de documento: Dissertação
Tipo de acesso: Acesso aberto
Idioma: por
Instituição de defesa: Não Informado pela instituição
Programa de Pós-Graduação: Não Informado pela instituição
Departamento: Não Informado pela instituição
País: Não Informado pela instituição
Área do conhecimento CNPq:
Link de acesso: http://repositorio.ufc.br/handle/riufc/75091
Resumo: The use of medicinal plants as a therapeutic resource is a popular knowledge that plays an important role in disease prevention and cure. Research has revealed that chemical constituents of plants of the genus Bauhinia exhibit various biological activities, such as acetylcholinesterase inhibitory, antibacterial, antibiotic modifier, cytotoxic, among others. However, there are still many species of this genus that need to be studied regarding the phytochemical profile. Thus, the present work reports the chemical and biological investigation of B. pentandra ethanolic stem extract (EEBPS), which resulted in the isolation and structural determination of eleven secondary metabolites: the mixture of steroids sitosterol and stigmasterol (BPC–1a and BPC–1b), two oxepin derivatives bauhiniastatin 1 (BPC–2) and bauhiniastatin 4 (BPC–3), seven 7,4'-dihydroxyflavan flavonoids (BPC–4), (2S)-liquiritigenin (BPC–5), (2S) - naringenin (BPC–6), isoliquiritigenin (BPC–7), poriol (BPC– 8), (-)-fisetinidol (BPC–9) and fisetin (BPC–10). It is noteworthy that BPC–8 is being described for the first time in the genus Bauhinia and with the exception of the steroid mixture, the other compounds are being reported for the first time in B. pentandra specie. The structures of the compounds were characterized by spectroscopic techniques such as IR, 1H and 13C NMR and retention times of standard HPLC samples, in addition to comparison with data described in the literature. Ethanolic extract (EEBPS), as well as isolated compounds BPC–2, BPC–3, BPC–4, BPC–5, BPC–6, BPC–7 and BPC–10 were evaluated as acetylcholinesterase inhibitors using the modified Ellman’s method. Among the evaluated substances, 7,4'-dihydroxyflavan (BPC–4) presented the best activity, with the inhibition halo diameter (0.9 cm) equal to that of eserine (reference standard). (-)-Fisetinidol (BPC–9) was evaluated for antibacterial activity and the modifying effect of antibiotic action on Staphylococcus aureus (SA1199-B and ATCC 25923), and Escherichia coli (ATCC 25922) strains, however, did not exhibit antibacterial activity against the bacteria tested, therefore presenting a minimum inhibitory concentration (MIC) value greater than 1024 µg/mL. It is noteworthy that in the combination of norfloxacin antibiotic with (-)-fisetinidol (BPC–9), it was possible to observe a reduction of its MIC value (1/4) 2 times to 32 µg/mL when compared with chlorpromazine (classic inhibitor), significance was observed, indicating that there was a reversal of bacterial resistance.
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spelling Silva, Horlando Carlota daSantiago, Gilvandete Maria Pinheiro2023-11-28T15:54:34Z2023-11-28T15:54:34Z2020SILVA, Horlando Carlota da. Investigação química e avaliação biológica de bauhinia pentandra (bong.) D.dietr. 2020. 143 f. Dissertação (Mestrado em Química) - Universidade Federal do Ceará, Fortaleza, 2020.http://repositorio.ufc.br/handle/riufc/75091The use of medicinal plants as a therapeutic resource is a popular knowledge that plays an important role in disease prevention and cure. Research has revealed that chemical constituents of plants of the genus Bauhinia exhibit various biological activities, such as acetylcholinesterase inhibitory, antibacterial, antibiotic modifier, cytotoxic, among others. However, there are still many species of this genus that need to be studied regarding the phytochemical profile. Thus, the present work reports the chemical and biological investigation of B. pentandra ethanolic stem extract (EEBPS), which resulted in the isolation and structural determination of eleven secondary metabolites: the mixture of steroids sitosterol and stigmasterol (BPC–1a and BPC–1b), two oxepin derivatives bauhiniastatin 1 (BPC–2) and bauhiniastatin 4 (BPC–3), seven 7,4'-dihydroxyflavan flavonoids (BPC–4), (2S)-liquiritigenin (BPC–5), (2S) - naringenin (BPC–6), isoliquiritigenin (BPC–7), poriol (BPC– 8), (-)-fisetinidol (BPC–9) and fisetin (BPC–10). It is noteworthy that BPC–8 is being described for the first time in the genus Bauhinia and with the exception of the steroid mixture, the other compounds are being reported for the first time in B. pentandra specie. The structures of the compounds were characterized by spectroscopic techniques such as IR, 1H and 13C NMR and retention times of standard HPLC samples, in addition to comparison with data described in the literature. Ethanolic extract (EEBPS), as well as isolated compounds BPC–2, BPC–3, BPC–4, BPC–5, BPC–6, BPC–7 and BPC–10 were evaluated as acetylcholinesterase inhibitors using the modified Ellman’s method. Among the evaluated substances, 7,4'-dihydroxyflavan (BPC–4) presented the best activity, with the inhibition halo diameter (0.9 cm) equal to that of eserine (reference standard). (-)-Fisetinidol (BPC–9) was evaluated for antibacterial activity and the modifying effect of antibiotic action on Staphylococcus aureus (SA1199-B and ATCC 25923), and Escherichia coli (ATCC 25922) strains, however, did not exhibit antibacterial activity against the bacteria tested, therefore presenting a minimum inhibitory concentration (MIC) value greater than 1024 µg/mL. It is noteworthy that in the combination of norfloxacin antibiotic with (-)-fisetinidol (BPC–9), it was possible to observe a reduction of its MIC value (1/4) 2 times to 32 µg/mL when compared with chlorpromazine (classic inhibitor), significance was observed, indicating that there was a reversal of bacterial resistance.A utilização de plantas medicinais como recurso terapêutico é um conhecimento popular que desempenha importante papel na prevenção e cura de doenças. Pesquisas revelaram que constituintes químicos de plantas do gênero Bauhinia exibem diversas atividades biológicas, tais como inibitória da acetilcolinesterase, antibacteriana, modificadora de antibióticos, citotóxica, dentre outras. No entanto, ainda existem muitas espécies desse gênero que precisam ser estudadas com relação ao perfil fitoquímico. Desta forma, o presente trabalho relata a investigação química e biológica do extrato etanólico do caule de B. pentandra (EECBP), que resultou no isolamento e determinação estrutural de onze metabólitos secundários: a mistura dos esteroides sitosterol e estigmasterol (BPC–1a e BPC–1b), dois derivados oxepínicos bauhiniastatina 1 (BPC–2) e bauhiniastatina 4 (BPC–3), sete flavonoides 7,4’-diidroxiflavana (BPC–4), (2S)-liquiritigenina (BPC–5), (2S)-naringenina (BPC–6), isoliquiritigenina (BPC–7), poriol (BPC–8), (-)-fisetinidol (BPC–9) e fisetina (BPC–10). Ressalta-se que BPC-8 está sendo descrito pela primeira vez no gênero Bauhinia e com exceção da mistura de esteroides, os demais compostos estão sendo relatados pela primeira vez na espécie B. pentandra. As estruturas das substâncias foram caracterizadas através de técnicas espectroscópicas, tais como IV, RMN de 1H e 13C e por tempos de retenção de amostras padrão em CLAE, além da comparação com dados descritos na literatura. O extrato etanólico (EEBPC), bem como os compostos isolados BPC–2, BPC–3, BPC–4, BPC–5, BPC–6, BPC-7 e BPC–10 foram avaliados como inibidores da acetilcolinesterase usando o método de Ellman modificado. Dentre as substâncias avaliadas, 7,4’-diidroxiflavana (BPC–4) apresentou a melhor atividade, com o diâmetro de halo de inibição (0,9 cm) igual ao da eserina (padrão de referência). (-)-Fisetinidol (BPC–9) foi avaliado quanto à atividade antibacteriana e o efeito modificador da ação antibiótica sobre cepas de Staphylococcus aureus (SA1199-B e ATCC 25923) e Escherichia coli (ATCC 25922), porém, não exibiu atividade antibacteriana frente às bactérias testadas, apresentando, portanto, valor de concentração inibitória mímima (CIM) maior que 1024 µg/mL. Vale ressaltar que na combinação do antibiótico norfloxacino com (-)-fisetinidol (BPC–9), foi possível observar redução de seu valor de CIM (1/4) em 2 vezes para 32 µg/mL. Quando comparado com a clorpromazina (inibidor clássico), observou-se significância, sendo isso um indicativo que houve reversão da resistência bacteriana.Investigação química e avaliação biológica de bauhinia pentandra (bong.) D.dietr.Chemical investigation and biological evaluation of bauhinia pentandra (bong.) D.dietr.info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisBauhinia pentandraFlavonoidsSteroidsOxepin derivativesBauhinia pentandraFlavonoidsSteroidsOxepin derivativesCNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICAinfo:eu-repo/semantics/openAccessporreponame:Repositório Institucional da Universidade Federal do Ceará (UFC)instname:Universidade Federal do Ceará (UFC)instacron:UFChttps://orcid.org/0000-0001-8996-6095http://lattes.cnpq.br/4909224491441153http://orcid.org/0000-0002-6832-8374http://lattes.cnpq.br/01072794534283852020-11-28ORIGINAL2020_dis_hcsilva.pdf2020_dis_hcsilva.pdfapplication/pdf6010537http://repositorio.ufc.br/bitstream/riufc/75091/3/2020_dis_hcsilva.pdf0e31131df4ff1c41a2b8f9718fcec8fcMD53LICENSElicense.txtlicense.txttext/plain; charset=utf-81748http://repositorio.ufc.br/bitstream/riufc/75091/4/license.txt8a4605be74aa9ea9d79846c1fba20a33MD54riufc/750912023-11-28 12:54:35.451oai:repositorio.ufc.br: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Repositório InstitucionalPUBhttp://www.repositorio.ufc.br/ri-oai/requestbu@ufc.br || repositorio@ufc.bropendoar:2023-11-28T15:54:35Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC)false
dc.title.pt_BR.fl_str_mv Investigação química e avaliação biológica de bauhinia pentandra (bong.) D.dietr.
dc.title.en.pt_BR.fl_str_mv Chemical investigation and biological evaluation of bauhinia pentandra (bong.) D.dietr.
title Investigação química e avaliação biológica de bauhinia pentandra (bong.) D.dietr.
spellingShingle Investigação química e avaliação biológica de bauhinia pentandra (bong.) D.dietr.
Silva, Horlando Carlota da
CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Bauhinia pentandra
Flavonoids
Steroids
Oxepin derivatives
Bauhinia pentandra
Flavonoids
Steroids
Oxepin derivatives
title_short Investigação química e avaliação biológica de bauhinia pentandra (bong.) D.dietr.
title_full Investigação química e avaliação biológica de bauhinia pentandra (bong.) D.dietr.
title_fullStr Investigação química e avaliação biológica de bauhinia pentandra (bong.) D.dietr.
title_full_unstemmed Investigação química e avaliação biológica de bauhinia pentandra (bong.) D.dietr.
title_sort Investigação química e avaliação biológica de bauhinia pentandra (bong.) D.dietr.
author Silva, Horlando Carlota da
author_facet Silva, Horlando Carlota da
author_role author
dc.contributor.author.fl_str_mv Silva, Horlando Carlota da
dc.contributor.advisor1.fl_str_mv Santiago, Gilvandete Maria Pinheiro
contributor_str_mv Santiago, Gilvandete Maria Pinheiro
dc.subject.cnpq.fl_str_mv CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
topic CNPQ::CIENCIAS EXATAS E DA TERRA::QUIMICA
Bauhinia pentandra
Flavonoids
Steroids
Oxepin derivatives
Bauhinia pentandra
Flavonoids
Steroids
Oxepin derivatives
dc.subject.ptbr.pt_BR.fl_str_mv Bauhinia pentandra
Flavonoids
Steroids
Oxepin derivatives
dc.subject.en.pt_BR.fl_str_mv Bauhinia pentandra
Flavonoids
Steroids
Oxepin derivatives
description The use of medicinal plants as a therapeutic resource is a popular knowledge that plays an important role in disease prevention and cure. Research has revealed that chemical constituents of plants of the genus Bauhinia exhibit various biological activities, such as acetylcholinesterase inhibitory, antibacterial, antibiotic modifier, cytotoxic, among others. However, there are still many species of this genus that need to be studied regarding the phytochemical profile. Thus, the present work reports the chemical and biological investigation of B. pentandra ethanolic stem extract (EEBPS), which resulted in the isolation and structural determination of eleven secondary metabolites: the mixture of steroids sitosterol and stigmasterol (BPC–1a and BPC–1b), two oxepin derivatives bauhiniastatin 1 (BPC–2) and bauhiniastatin 4 (BPC–3), seven 7,4'-dihydroxyflavan flavonoids (BPC–4), (2S)-liquiritigenin (BPC–5), (2S) - naringenin (BPC–6), isoliquiritigenin (BPC–7), poriol (BPC– 8), (-)-fisetinidol (BPC–9) and fisetin (BPC–10). It is noteworthy that BPC–8 is being described for the first time in the genus Bauhinia and with the exception of the steroid mixture, the other compounds are being reported for the first time in B. pentandra specie. The structures of the compounds were characterized by spectroscopic techniques such as IR, 1H and 13C NMR and retention times of standard HPLC samples, in addition to comparison with data described in the literature. Ethanolic extract (EEBPS), as well as isolated compounds BPC–2, BPC–3, BPC–4, BPC–5, BPC–6, BPC–7 and BPC–10 were evaluated as acetylcholinesterase inhibitors using the modified Ellman’s method. Among the evaluated substances, 7,4'-dihydroxyflavan (BPC–4) presented the best activity, with the inhibition halo diameter (0.9 cm) equal to that of eserine (reference standard). (-)-Fisetinidol (BPC–9) was evaluated for antibacterial activity and the modifying effect of antibiotic action on Staphylococcus aureus (SA1199-B and ATCC 25923), and Escherichia coli (ATCC 25922) strains, however, did not exhibit antibacterial activity against the bacteria tested, therefore presenting a minimum inhibitory concentration (MIC) value greater than 1024 µg/mL. It is noteworthy that in the combination of norfloxacin antibiotic with (-)-fisetinidol (BPC–9), it was possible to observe a reduction of its MIC value (1/4) 2 times to 32 µg/mL when compared with chlorpromazine (classic inhibitor), significance was observed, indicating that there was a reversal of bacterial resistance.
publishDate 2020
dc.date.issued.fl_str_mv 2020
dc.date.accessioned.fl_str_mv 2023-11-28T15:54:34Z
dc.date.available.fl_str_mv 2023-11-28T15:54:34Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/masterThesis
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dc.identifier.citation.fl_str_mv SILVA, Horlando Carlota da. Investigação química e avaliação biológica de bauhinia pentandra (bong.) D.dietr. 2020. 143 f. Dissertação (Mestrado em Química) - Universidade Federal do Ceará, Fortaleza, 2020.
dc.identifier.uri.fl_str_mv http://repositorio.ufc.br/handle/riufc/75091
identifier_str_mv SILVA, Horlando Carlota da. Investigação química e avaliação biológica de bauhinia pentandra (bong.) D.dietr. 2020. 143 f. Dissertação (Mestrado em Química) - Universidade Federal do Ceará, Fortaleza, 2020.
url http://repositorio.ufc.br/handle/riufc/75091
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