Chemical and biological study of Bauhinia pulchella Benth

Detalhes bibliográficos
Autor(a) principal: Jarbas Lima de Carvalho
Data de Publicação: 2014
Tipo de documento: Dissertação
Idioma: por
Título da fonte: Biblioteca Digital de Teses e Dissertações da UFC
Texto Completo: http://www.teses.ufc.br/tde_busca/arquivo.php?codArquivo=13413
Resumo: This present work reports the chemical and biological analysis of the stem and leaves from Bauhinia pulchella. In this study, the ethanol extract from stems was obtained by maceration, subjected to chromatographic fractionation, leading to isolation of three flavonoids: (+)-3â,4â-dihydroxyphenyl-chroman-7-ol (BP-2), (-)-fisetinidol (BP-3) and (+)-epicatechin (BP-4); a mixture of triterpenes taraxerone and β-amyrenone (BP-1); a mixture of steroids sitosterol and stigmasterol (BP-5); and a bibenzyl named 2-hydroxy-3â,5â-dimethoxybibenzyl (BP-6). It is notewhorthy to mention that BP-1 and BP-4 substances are unprecedented in the genus, while BP-2 is unpublished. Chemical structures of secondary metabolites obtained were elucidated by 1H and 13C NMR; IR and MS associated with comparison of data described in the literature. Chemical composition of the essential oil from leaves of B. pulchella, obtained by hydrodistillation, was determined and quantified by gas chromatography-mass spectroscopy (GC/MS) and gas chromatography-flame ionization detector (GC/FID), which identified 95,68% of all constituents. α-pinene (23.89%); caryophyllene oxide (22.43%) and β-pinene (12.19%) were the major components. The essential oil was tested against Aedes aegypti larvae and showed LC50 value of 105.93 Â 1.48 μg/mL. The cytotoxic activity of essential oil was evaluated on human tumor cell lines (HL-60; MCF-7; NCI-H292 and HEP-2) was evaluated, showing IC50 values with confidence intervals of 9.941 (8.238 to 12.00), 53.05 (41.39 to 67.99), 48.98 (44.22 to 54.25) and 50.42 (42.47 to 59.87) μg/mL, respectively and the cell line HL-60 the most sensitive among the cells tested. This is the first report of the chemical study of Bauhinia pulchella, as well the investigation of larvicidal activity and cytotoxicity of the essential oil from its leaves.
id UFC_cf2c6014a1df4e77903a545e47b68e59
oai_identifier_str oai:www.teses.ufc.br:8969
network_acronym_str UFC
network_name_str Biblioteca Digital de Teses e Dissertações da UFC
spelling info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisChemical and biological study of Bauhinia pulchella BenthEstudo quÃmico e biolÃgico de Bauhinia pulchella Benth2014-12-08Gilvandete Maria Pinheiro Santiago11776650344Telma Leda Gomes de Lemos04511700320http://buscatextual.cnpq.br/buscatextual/visualizacv.jsp?id=K4783204Z7Jackson Nunes e Vasconcelos91652359320http://lattes.cnpq.br/3922991828253553 016493033http://lattes.cnpq.br/7175657155846384Jarbas Lima de CarvalhoUniversidade Federal do CearÃPrograma de PÃs-GraduaÃÃo em QuÃmica UFCBRFabaceae Bauhinia pulchella Ãleo essencial Atividade larvicida Atividade citotÃxica Triterpenos Flavonoides Bibenzil Esteroides Essential oil Larvicidal activity Cytotoxic activity Triterpenes Flavonoids Bibenzyl SteroidsQUIMICA ORGANICAThis present work reports the chemical and biological analysis of the stem and leaves from Bauhinia pulchella. In this study, the ethanol extract from stems was obtained by maceration, subjected to chromatographic fractionation, leading to isolation of three flavonoids: (+)-3â,4â-dihydroxyphenyl-chroman-7-ol (BP-2), (-)-fisetinidol (BP-3) and (+)-epicatechin (BP-4); a mixture of triterpenes taraxerone and β-amyrenone (BP-1); a mixture of steroids sitosterol and stigmasterol (BP-5); and a bibenzyl named 2-hydroxy-3â,5â-dimethoxybibenzyl (BP-6). It is notewhorthy to mention that BP-1 and BP-4 substances are unprecedented in the genus, while BP-2 is unpublished. Chemical structures of secondary metabolites obtained were elucidated by 1H and 13C NMR; IR and MS associated with comparison of data described in the literature. Chemical composition of the essential oil from leaves of B. pulchella, obtained by hydrodistillation, was determined and quantified by gas chromatography-mass spectroscopy (GC/MS) and gas chromatography-flame ionization detector (GC/FID), which identified 95,68% of all constituents. α-pinene (23.89%); caryophyllene oxide (22.43%) and β-pinene (12.19%) were the major components. The essential oil was tested against Aedes aegypti larvae and showed LC50 value of 105.93  1.48 μg/mL. The cytotoxic activity of essential oil was evaluated on human tumor cell lines (HL-60; MCF-7; NCI-H292 and HEP-2) was evaluated, showing IC50 values with confidence intervals of 9.941 (8.238 to 12.00), 53.05 (41.39 to 67.99), 48.98 (44.22 to 54.25) and 50.42 (42.47 to 59.87) μg/mL, respectively and the cell line HL-60 the most sensitive among the cells tested. This is the first report of the chemical study of Bauhinia pulchella, as well the investigation of larvicidal activity and cytotoxicity of the essential oil from its leaves.O presente trabalho relata o estudo quÃmico e biolÃgico do caule e das folhas de Bauhinia pulchella. Nesse estudo, o extrato etanÃlico do caule, obtido por maceraÃÃo, foi submetido a fracionamento cromatogrÃfico levando ao isolamento de trÃs flavonoides (+)-3â-4âdiidroxifenil-cromano-7-ol (BP-2), (-)-fisetinidol (BP-3) e (+)-epicatequina (BP-4); da mistura de triterpenos taraxerona e β-amirenona (BP-1); da mistura de esteroides sitosterol e estigmasterol (BP-5) e de um bibenzil denominado 2-hidrÃxi-3â-5â-dimetoxibibenzila (BP-6). Cabe ressaltar que as substÃncias BP-1 e BP-4 sÃo inÃditas no gÃnero, enquanto BP-2 à inÃdita na literatura. As estruturas dos metabÃlitos secundÃrios isolados foram elucidadas por RMN 1H e 13C; IV e EM, juntamente com a comparaÃÃo com os dados descritos na literatura. A composiÃÃo quÃmica do Ãleo essencial das folhas de B. pulchella, obtido por hidrodestilaÃÃo, foi determinada e quantificada por cromatografia gasosa acoplada à espectrometria de massas (CG-EM) e detector de ionizaÃÃo por chama (CG-DIC), sendo, portanto, identificados 95,68% dos seus constituintes: α-pineno (23,89%), Ãxido de cariofileno (22,43%) e β-pineno (12,19%) foram os constituintes majoritÃrios. O Ãleo essencial teve sua atividade larvicida sobre Aedes aegypti avaliada, sendo obtido um valor de CL50 igual a 105,93  1,48 μg/mL. O poder citotÃxico do Ãleo essencial foi avaliado sobre as linhagens tumorais humanas HL-60, MCF-7, NCI-H292 e HEP-2, sendo obtidos valores de CI50 e intervalos de confianÃa iguais a 9,941 (8,238 a 12,00); 53,05 (41,39 a 67,99); 48,98 (44,22 a 54,25) e 50,42 (42,47 a 59,87) μg/mL, respectivamente, sendo a linhagem celular HL-60 a mais sensÃvel dentre as cÃlulas testadas. Este à o primeiro relato do estudo quÃmico de Bauhinia pulchella, bem como da investigaÃÃo da atividade larvicida e citotÃxica do Ãleo essencial de suas folhas.Conselho Nacional de Desenvolvimento CientÃfico e TecnolÃgicohttp://www.teses.ufc.br/tde_busca/arquivo.php?codArquivo=13413application/pdfinfo:eu-repo/semantics/openAccessporreponame:Biblioteca Digital de Teses e Dissertações da UFCinstname:Universidade Federal do Cearáinstacron:UFC2019-01-21T11:27:41Zmail@mail.com -
dc.title.en.fl_str_mv Chemical and biological study of Bauhinia pulchella Benth
dc.title.alternative.pt.fl_str_mv Estudo quÃmico e biolÃgico de Bauhinia pulchella Benth
title Chemical and biological study of Bauhinia pulchella Benth
spellingShingle Chemical and biological study of Bauhinia pulchella Benth
Jarbas Lima de Carvalho
Fabaceae
Bauhinia pulchella
Ãleo essencial
Atividade larvicida
Atividade citotÃxica
Triterpenos
Flavonoides
Bibenzil
Esteroides
Essential oil
Larvicidal activity
Cytotoxic activity
Triterpenes
Flavonoids
Bibenzyl
Steroids
QUIMICA ORGANICA
title_short Chemical and biological study of Bauhinia pulchella Benth
title_full Chemical and biological study of Bauhinia pulchella Benth
title_fullStr Chemical and biological study of Bauhinia pulchella Benth
title_full_unstemmed Chemical and biological study of Bauhinia pulchella Benth
title_sort Chemical and biological study of Bauhinia pulchella Benth
author Jarbas Lima de Carvalho
author_facet Jarbas Lima de Carvalho
author_role author
dc.contributor.advisor1.fl_str_mv Gilvandete Maria Pinheiro Santiago
dc.contributor.advisor1ID.fl_str_mv 11776650344
dc.contributor.referee1.fl_str_mv Telma Leda Gomes de Lemos
dc.contributor.referee1ID.fl_str_mv 04511700320
dc.contributor.referee1Lattes.fl_str_mv http://buscatextual.cnpq.br/buscatextual/visualizacv.jsp?id=K4783204Z7
dc.contributor.referee2.fl_str_mv Jackson Nunes e Vasconcelos
dc.contributor.referee2ID.fl_str_mv 91652359320
dc.contributor.referee2Lattes.fl_str_mv http://lattes.cnpq.br/3922991828253553
dc.contributor.authorID.fl_str_mv 016493033
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/7175657155846384
dc.contributor.author.fl_str_mv Jarbas Lima de Carvalho
contributor_str_mv Gilvandete Maria Pinheiro Santiago
Telma Leda Gomes de Lemos
Jackson Nunes e Vasconcelos
dc.subject.por.fl_str_mv Fabaceae
Bauhinia pulchella
Ãleo essencial
Atividade larvicida
Atividade citotÃxica
Triterpenos
Flavonoides
Bibenzil
Esteroides
topic Fabaceae
Bauhinia pulchella
Ãleo essencial
Atividade larvicida
Atividade citotÃxica
Triterpenos
Flavonoides
Bibenzil
Esteroides
Essential oil
Larvicidal activity
Cytotoxic activity
Triterpenes
Flavonoids
Bibenzyl
Steroids
QUIMICA ORGANICA
dc.subject.eng.fl_str_mv Essential oil
Larvicidal activity
Cytotoxic activity
Triterpenes
Flavonoids
Bibenzyl
Steroids
dc.subject.cnpq.fl_str_mv QUIMICA ORGANICA
dc.description.sponsorship.fl_txt_mv Conselho Nacional de Desenvolvimento CientÃfico e TecnolÃgico
dc.description.abstract.por.fl_txt_mv This present work reports the chemical and biological analysis of the stem and leaves from Bauhinia pulchella. In this study, the ethanol extract from stems was obtained by maceration, subjected to chromatographic fractionation, leading to isolation of three flavonoids: (+)-3â,4â-dihydroxyphenyl-chroman-7-ol (BP-2), (-)-fisetinidol (BP-3) and (+)-epicatechin (BP-4); a mixture of triterpenes taraxerone and β-amyrenone (BP-1); a mixture of steroids sitosterol and stigmasterol (BP-5); and a bibenzyl named 2-hydroxy-3â,5â-dimethoxybibenzyl (BP-6). It is notewhorthy to mention that BP-1 and BP-4 substances are unprecedented in the genus, while BP-2 is unpublished. Chemical structures of secondary metabolites obtained were elucidated by 1H and 13C NMR; IR and MS associated with comparison of data described in the literature. Chemical composition of the essential oil from leaves of B. pulchella, obtained by hydrodistillation, was determined and quantified by gas chromatography-mass spectroscopy (GC/MS) and gas chromatography-flame ionization detector (GC/FID), which identified 95,68% of all constituents. α-pinene (23.89%); caryophyllene oxide (22.43%) and β-pinene (12.19%) were the major components. The essential oil was tested against Aedes aegypti larvae and showed LC50 value of 105.93 Â 1.48 μg/mL. The cytotoxic activity of essential oil was evaluated on human tumor cell lines (HL-60; MCF-7; NCI-H292 and HEP-2) was evaluated, showing IC50 values with confidence intervals of 9.941 (8.238 to 12.00), 53.05 (41.39 to 67.99), 48.98 (44.22 to 54.25) and 50.42 (42.47 to 59.87) μg/mL, respectively and the cell line HL-60 the most sensitive among the cells tested. This is the first report of the chemical study of Bauhinia pulchella, as well the investigation of larvicidal activity and cytotoxicity of the essential oil from its leaves.
O presente trabalho relata o estudo quÃmico e biolÃgico do caule e das folhas de Bauhinia pulchella. Nesse estudo, o extrato etanÃlico do caule, obtido por maceraÃÃo, foi submetido a fracionamento cromatogrÃfico levando ao isolamento de trÃs flavonoides (+)-3â-4âdiidroxifenil-cromano-7-ol (BP-2), (-)-fisetinidol (BP-3) e (+)-epicatequina (BP-4); da mistura de triterpenos taraxerona e β-amirenona (BP-1); da mistura de esteroides sitosterol e estigmasterol (BP-5) e de um bibenzil denominado 2-hidrÃxi-3â-5â-dimetoxibibenzila (BP-6). Cabe ressaltar que as substÃncias BP-1 e BP-4 sÃo inÃditas no gÃnero, enquanto BP-2 à inÃdita na literatura. As estruturas dos metabÃlitos secundÃrios isolados foram elucidadas por RMN 1H e 13C; IV e EM, juntamente com a comparaÃÃo com os dados descritos na literatura. A composiÃÃo quÃmica do Ãleo essencial das folhas de B. pulchella, obtido por hidrodestilaÃÃo, foi determinada e quantificada por cromatografia gasosa acoplada à espectrometria de massas (CG-EM) e detector de ionizaÃÃo por chama (CG-DIC), sendo, portanto, identificados 95,68% dos seus constituintes: α-pineno (23,89%), Ãxido de cariofileno (22,43%) e β-pineno (12,19%) foram os constituintes majoritÃrios. O Ãleo essencial teve sua atividade larvicida sobre Aedes aegypti avaliada, sendo obtido um valor de CL50 igual a 105,93  1,48 μg/mL. O poder citotÃxico do Ãleo essencial foi avaliado sobre as linhagens tumorais humanas HL-60, MCF-7, NCI-H292 e HEP-2, sendo obtidos valores de CI50 e intervalos de confianÃa iguais a 9,941 (8,238 a 12,00); 53,05 (41,39 a 67,99); 48,98 (44,22 a 54,25) e 50,42 (42,47 a 59,87) μg/mL, respectivamente, sendo a linhagem celular HL-60 a mais sensÃvel dentre as cÃlulas testadas. Este à o primeiro relato do estudo quÃmico de Bauhinia pulchella, bem como da investigaÃÃo da atividade larvicida e citotÃxica do Ãleo essencial de suas folhas.
description This present work reports the chemical and biological analysis of the stem and leaves from Bauhinia pulchella. In this study, the ethanol extract from stems was obtained by maceration, subjected to chromatographic fractionation, leading to isolation of three flavonoids: (+)-3â,4â-dihydroxyphenyl-chroman-7-ol (BP-2), (-)-fisetinidol (BP-3) and (+)-epicatechin (BP-4); a mixture of triterpenes taraxerone and β-amyrenone (BP-1); a mixture of steroids sitosterol and stigmasterol (BP-5); and a bibenzyl named 2-hydroxy-3â,5â-dimethoxybibenzyl (BP-6). It is notewhorthy to mention that BP-1 and BP-4 substances are unprecedented in the genus, while BP-2 is unpublished. Chemical structures of secondary metabolites obtained were elucidated by 1H and 13C NMR; IR and MS associated with comparison of data described in the literature. Chemical composition of the essential oil from leaves of B. pulchella, obtained by hydrodistillation, was determined and quantified by gas chromatography-mass spectroscopy (GC/MS) and gas chromatography-flame ionization detector (GC/FID), which identified 95,68% of all constituents. α-pinene (23.89%); caryophyllene oxide (22.43%) and β-pinene (12.19%) were the major components. The essential oil was tested against Aedes aegypti larvae and showed LC50 value of 105.93 Â 1.48 μg/mL. The cytotoxic activity of essential oil was evaluated on human tumor cell lines (HL-60; MCF-7; NCI-H292 and HEP-2) was evaluated, showing IC50 values with confidence intervals of 9.941 (8.238 to 12.00), 53.05 (41.39 to 67.99), 48.98 (44.22 to 54.25) and 50.42 (42.47 to 59.87) μg/mL, respectively and the cell line HL-60 the most sensitive among the cells tested. This is the first report of the chemical study of Bauhinia pulchella, as well the investigation of larvicidal activity and cytotoxicity of the essential oil from its leaves.
publishDate 2014
dc.date.issued.fl_str_mv 2014-12-08
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/masterThesis
status_str publishedVersion
format masterThesis
dc.identifier.uri.fl_str_mv http://www.teses.ufc.br/tde_busca/arquivo.php?codArquivo=13413
url http://www.teses.ufc.br/tde_busca/arquivo.php?codArquivo=13413
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
dc.publisher.none.fl_str_mv Universidade Federal do CearÃ
dc.publisher.program.fl_str_mv Programa de PÃs-GraduaÃÃo em QuÃmica
dc.publisher.initials.fl_str_mv UFC
dc.publisher.country.fl_str_mv BR
publisher.none.fl_str_mv Universidade Federal do CearÃ
dc.source.none.fl_str_mv reponame:Biblioteca Digital de Teses e Dissertações da UFC
instname:Universidade Federal do Ceará
instacron:UFC
reponame_str Biblioteca Digital de Teses e Dissertações da UFC
collection Biblioteca Digital de Teses e Dissertações da UFC
instname_str Universidade Federal do Ceará
instacron_str UFC
institution UFC
repository.name.fl_str_mv -
repository.mail.fl_str_mv mail@mail.com
_version_ 1643295205340741632