Investigação Química e Biológica de Bauhinia cheilantha (Bong.) Steud

Detalhes bibliográficos
Autor(a) principal: Silva, Ana Maria Amaral
Data de Publicação: 2018
Tipo de documento: Dissertação
Idioma: por
Título da fonte: Repositório Institucional da Universidade Federal do Ceará (UFC)
Texto Completo: http://www.repositorio.ufc.br/handle/riufc/36301
Resumo: The present work reports the chemical and biological study of the fresh leaves essential oil (OEBC) and the ethanolic extract from the roots of Bauhinia cheilantha (EEBCR). The essential oil (OEBC) has been obtained by hydrodistillation, and 97.84% of its constituents were identified. (E)-cariophilene (21.65%) and α-pinene (11.74%) were the major constituents. The study of the fixed constituents resulted in the isolation and structural determination of nine secondary metabolites: the oxepinic derivatives pacharina (BCR-1) and bauhiniastatin 1 (BCR-2), the triterpenes cycloartenone (BCR-3) and taraxerol (BCR-6), the flavonoids fisetinidol (BCR-5) and the mixture of dihydroquercetin and 2-(3',4'-dihydroxyphenyl)-5-methoxychroman-3,7-diol (BCR-4) and the bibenzis 3,5-dimethoxy- 4-methyl-2'-hydroxybibenzyl (BCR-7) and 3,5,6-trimethoxy-4-methyl-2'-hydroxybibenzyl (BCR-8). It is noteworthy that BCR-3 is being described for the first time in the Bauhinia genus and BCR-8 is being reported for the first time in the literature. Structures of isolated secondary metabolites were elucidated by 1 H and 13 C NMR, IR and MS, together with the comparison with the data described in the literature. The hexane (FHBCR), dichloromethane (FDBCR), ethyl acetate (FABCR) and methanolic (FMBCR) fractions, obtained from the chromatographic treatment of the ethanolic extract from roots (EEBCR), as well as the essential oil of the fresh leaves of B. cheilantha (OEBC) were evaluated for their cytotoxicity on human tumor cell lines HL-60 (promyelocytic leukemia), NCI-H292 (lung carcinoma) and MCF-7 (breast carcinoma), and IC50 values were obtained with their respective confidence intervals 8.6 (5.9 – 12.6), 33.08 (29.1 – 37.5), and 18.3 (16.0 – 21.0) for the OEBC and 7.6 (6,1 – 9.4), 5.4 (4.2 – 6.9) and 2.7 (1.9 – 3.7) for FDBCR, the active samples. The ethanolic extract from roots (EEBCR), the four fractions mentioned (FHBCR, FDBCR, FABCR and FMBCR) and essential oil (OEBC) were submitted to evaluation of the activity on third stage larvae of Aedes aegypti, however, only the essential oil (OEBC) showed to be active, with a LC50 value corresponding to 40.84 ± 0.87 μg / mL.
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spelling Investigação Química e Biológica de Bauhinia cheilantha (Bong.) SteudChemical and Biological Research of Bauhinia Cheilantha (Bong.) SteudBauhinia cheilanthaÓleo essencialOxepinasTriterpenosThe present work reports the chemical and biological study of the fresh leaves essential oil (OEBC) and the ethanolic extract from the roots of Bauhinia cheilantha (EEBCR). The essential oil (OEBC) has been obtained by hydrodistillation, and 97.84% of its constituents were identified. (E)-cariophilene (21.65%) and α-pinene (11.74%) were the major constituents. The study of the fixed constituents resulted in the isolation and structural determination of nine secondary metabolites: the oxepinic derivatives pacharina (BCR-1) and bauhiniastatin 1 (BCR-2), the triterpenes cycloartenone (BCR-3) and taraxerol (BCR-6), the flavonoids fisetinidol (BCR-5) and the mixture of dihydroquercetin and 2-(3',4'-dihydroxyphenyl)-5-methoxychroman-3,7-diol (BCR-4) and the bibenzis 3,5-dimethoxy- 4-methyl-2'-hydroxybibenzyl (BCR-7) and 3,5,6-trimethoxy-4-methyl-2'-hydroxybibenzyl (BCR-8). It is noteworthy that BCR-3 is being described for the first time in the Bauhinia genus and BCR-8 is being reported for the first time in the literature. Structures of isolated secondary metabolites were elucidated by 1 H and 13 C NMR, IR and MS, together with the comparison with the data described in the literature. The hexane (FHBCR), dichloromethane (FDBCR), ethyl acetate (FABCR) and methanolic (FMBCR) fractions, obtained from the chromatographic treatment of the ethanolic extract from roots (EEBCR), as well as the essential oil of the fresh leaves of B. cheilantha (OEBC) were evaluated for their cytotoxicity on human tumor cell lines HL-60 (promyelocytic leukemia), NCI-H292 (lung carcinoma) and MCF-7 (breast carcinoma), and IC50 values were obtained with their respective confidence intervals 8.6 (5.9 – 12.6), 33.08 (29.1 – 37.5), and 18.3 (16.0 – 21.0) for the OEBC and 7.6 (6,1 – 9.4), 5.4 (4.2 – 6.9) and 2.7 (1.9 – 3.7) for FDBCR, the active samples. The ethanolic extract from roots (EEBCR), the four fractions mentioned (FHBCR, FDBCR, FABCR and FMBCR) and essential oil (OEBC) were submitted to evaluation of the activity on third stage larvae of Aedes aegypti, however, only the essential oil (OEBC) showed to be active, with a LC50 value corresponding to 40.84 ± 0.87 μg / mL.O presente trabalho relata o estudo químico e biológico do óleo essencial das folhas frescas (OEBC) e do extrato etanólico das raízes de Bauhinia cheilantha (EEBCR). Do óleo essencial (OEBC), obtido por hidrodestilação, foram identificados 97,84% dos seus constituintes, sendo o (E)-cariofileno (21,65%) e α-pineno (11,74%), os constituintes majoritários. O estudo dos constituintes fixos resultou no isolamento e determinação estrutural de nove metabólitos secundários: os derivados oxepínicos pacharina (BCR-1) e bauhiniastatina 1 (BCR-2), os triterpenos cicloartenona (BCR-3) e taraxerol (BCR-6), os flavonóides fisetinidol (BCR-5) e a mistura de diidroquercetina e de 2-(3’,4’-diidroxifenil)-5-metoxicromano-3,7-diol (BCR-4) e os bibenzis 3,5-dimetoxi-4-metil-2’-hidroxibibenzil (BCR-7) e 3,5,6-trimetoxi-4-metil-2’-hidroxibibenzil (BCR-8). Vale ressaltar que BCR-3 está sendo descrita pela primeira vez no gênero Bauhinia e BCR-8 está sendo relatada pela primeira vez na literatura. As estruturas dos metabólitos secundários isolados foram elucidadas por RMN 1H e 13C; IV e EM, juntamente com a comparação com os dados descritos na literatura. As frações hexânica (FHBCR), diclorometano (FDBCR), acetato de etila (FABCR) e metanólica (FMBCR), obtidas do tratamento cromatográfico do extrato etanólico das raízes (EEBCR), assim como o óleo essencial das folhas frescas de B. cheilantha (OEBC) foram avaliadas quanto à citotoxidade sobre as linhagens tumorais humanas HL-60 (leucemia promielocítica), NCI-H292 (carcinoma de pulmão) e MCF-7 (carcinoma de mama), sendo obtidos valores de CI50, com seus respectivos intervalos de confiança iguais a 8,6 (5,9 – 12,6), 33,08 (29,1 – 37,5), e 18,3 (16,0 – 21,0) para o OEBC e 7,6 (6,1 – 9,4), 5,4 (4,2 – 6,9) e 2,7 (1,9 – 3,7) para a FDBCR, únicas amostras ativas. O extrato etanólico das raízes (EEBCR), as quatro frações citadas (FHBCR, FDBCR, FABCR e FMBCR) e o óleo essencial (OEBC) foram submetidos à avaliação da atividade sobre larvas de terceiro estágio de Aedes aegypti, no entanto, somente o óleo essencial (OEBC) mostrou-se ativo, com valor de CL50 correspondente a 40,84 ± 0,87 µg/mL.Santiago, Gilvandete Maria PinheiroSilva, Ana Maria Amaral2018-10-04T19:56:28Z2018-10-04T19:56:28Z2018info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisapplication/pdfSILVA, Ana Maria Amaral. Investigação Química e Biológica de Bauhinia Cheilantha (Bong.) Steud. 2018. 176 f. Dissertação (Mestrado em Química) - Universidade Federal do Ceará, Fortaleza, 2018.http://www.repositorio.ufc.br/handle/riufc/36301porreponame:Repositório Institucional da Universidade Federal do Ceará (UFC)instname:Universidade Federal do Ceará (UFC)instacron:UFCinfo:eu-repo/semantics/openAccess2020-06-19T19:34:41Zoai:repositorio.ufc.br:riufc/36301Repositório InstitucionalPUBhttp://www.repositorio.ufc.br/ri-oai/requestbu@ufc.br || repositorio@ufc.bropendoar:2024-09-11T18:34:54.080465Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC)false
dc.title.none.fl_str_mv Investigação Química e Biológica de Bauhinia cheilantha (Bong.) Steud
Chemical and Biological Research of Bauhinia Cheilantha (Bong.) Steud
title Investigação Química e Biológica de Bauhinia cheilantha (Bong.) Steud
spellingShingle Investigação Química e Biológica de Bauhinia cheilantha (Bong.) Steud
Silva, Ana Maria Amaral
Bauhinia cheilantha
Óleo essencial
Oxepinas
Triterpenos
title_short Investigação Química e Biológica de Bauhinia cheilantha (Bong.) Steud
title_full Investigação Química e Biológica de Bauhinia cheilantha (Bong.) Steud
title_fullStr Investigação Química e Biológica de Bauhinia cheilantha (Bong.) Steud
title_full_unstemmed Investigação Química e Biológica de Bauhinia cheilantha (Bong.) Steud
title_sort Investigação Química e Biológica de Bauhinia cheilantha (Bong.) Steud
author Silva, Ana Maria Amaral
author_facet Silva, Ana Maria Amaral
author_role author
dc.contributor.none.fl_str_mv Santiago, Gilvandete Maria Pinheiro
dc.contributor.author.fl_str_mv Silva, Ana Maria Amaral
dc.subject.por.fl_str_mv Bauhinia cheilantha
Óleo essencial
Oxepinas
Triterpenos
topic Bauhinia cheilantha
Óleo essencial
Oxepinas
Triterpenos
description The present work reports the chemical and biological study of the fresh leaves essential oil (OEBC) and the ethanolic extract from the roots of Bauhinia cheilantha (EEBCR). The essential oil (OEBC) has been obtained by hydrodistillation, and 97.84% of its constituents were identified. (E)-cariophilene (21.65%) and α-pinene (11.74%) were the major constituents. The study of the fixed constituents resulted in the isolation and structural determination of nine secondary metabolites: the oxepinic derivatives pacharina (BCR-1) and bauhiniastatin 1 (BCR-2), the triterpenes cycloartenone (BCR-3) and taraxerol (BCR-6), the flavonoids fisetinidol (BCR-5) and the mixture of dihydroquercetin and 2-(3',4'-dihydroxyphenyl)-5-methoxychroman-3,7-diol (BCR-4) and the bibenzis 3,5-dimethoxy- 4-methyl-2'-hydroxybibenzyl (BCR-7) and 3,5,6-trimethoxy-4-methyl-2'-hydroxybibenzyl (BCR-8). It is noteworthy that BCR-3 is being described for the first time in the Bauhinia genus and BCR-8 is being reported for the first time in the literature. Structures of isolated secondary metabolites were elucidated by 1 H and 13 C NMR, IR and MS, together with the comparison with the data described in the literature. The hexane (FHBCR), dichloromethane (FDBCR), ethyl acetate (FABCR) and methanolic (FMBCR) fractions, obtained from the chromatographic treatment of the ethanolic extract from roots (EEBCR), as well as the essential oil of the fresh leaves of B. cheilantha (OEBC) were evaluated for their cytotoxicity on human tumor cell lines HL-60 (promyelocytic leukemia), NCI-H292 (lung carcinoma) and MCF-7 (breast carcinoma), and IC50 values were obtained with their respective confidence intervals 8.6 (5.9 – 12.6), 33.08 (29.1 – 37.5), and 18.3 (16.0 – 21.0) for the OEBC and 7.6 (6,1 – 9.4), 5.4 (4.2 – 6.9) and 2.7 (1.9 – 3.7) for FDBCR, the active samples. The ethanolic extract from roots (EEBCR), the four fractions mentioned (FHBCR, FDBCR, FABCR and FMBCR) and essential oil (OEBC) were submitted to evaluation of the activity on third stage larvae of Aedes aegypti, however, only the essential oil (OEBC) showed to be active, with a LC50 value corresponding to 40.84 ± 0.87 μg / mL.
publishDate 2018
dc.date.none.fl_str_mv 2018-10-04T19:56:28Z
2018-10-04T19:56:28Z
2018
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 SILVA, Ana Maria Amaral. Investigação Química e Biológica de Bauhinia Cheilantha (Bong.) Steud. 2018. 176 f. Dissertação (Mestrado em Química) - Universidade Federal do Ceará, Fortaleza, 2018.
http://www.repositorio.ufc.br/handle/riufc/36301
identifier_str_mv SILVA, Ana Maria Amaral. Investigação Química e Biológica de Bauhinia Cheilantha (Bong.) Steud. 2018. 176 f. Dissertação (Mestrado em Química) - Universidade Federal do Ceará, Fortaleza, 2018.
url http://www.repositorio.ufc.br/handle/riufc/36301
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.source.none.fl_str_mv reponame:Repositório Institucional da Universidade Federal do Ceará (UFC)
instname:Universidade Federal do Ceará (UFC)
instacron:UFC
instname_str Universidade Federal do Ceará (UFC)
instacron_str UFC
institution UFC
reponame_str Repositório Institucional da Universidade Federal do Ceará (UFC)
collection Repositório Institucional da Universidade Federal do Ceará (UFC)
repository.name.fl_str_mv Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC)
repository.mail.fl_str_mv bu@ufc.br || repositorio@ufc.br
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