Investigação Química e Biológica de Bauhinia cheilantha (Bong.) Steud
Autor(a) principal: | |
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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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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 |
_version_ |
1813028863673892864 |