Chemical study of Croton floribundus Spreng (Euphorbiaceae)

Detalhes bibliográficos
Autor(a) principal: Paula Karina Santos UchÃa
Data de Publicação: 2011
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=6304
Resumo: The present work reports the chemical study of root barks from Croton floribundus Spreng, collected at Pacoti-CE. The phytochemical investigation of hexane extract lead to the isolation of three kaurene-type diterpenes, ent-kaur-16-en-19-oic acid, ent-kaur-16-en-6,19-diol and ent-16-hydroxykaur-11-en-19-oic acid, reported for the first time to the genus Croton. In addition, four trachylobane-type diterpenes were isolated and identified as ent-trachyloban-19-oic acid, ent-15-hydroxytrachyloban-19-oic acid, ent-trachyloban-19-ol and the ent-trachyloban-18,19-diol, which was described as a new compound. Two derivatives of ent-trachyloban-18,19-diol were prepared through acetylation and oxidation reactions, and were characterized as ent-18,19-diacetoxytrachylobane and ent-18-nortrachyloban-19-oic acid. Each of these isolated diterpenes were submited to cytotoxic activity using colon (HCT-8), breast (MDAMB-435) and brain (SF-295) cell lines, and the compounds ent-caur-16-en-6,19-diol and ent-18-nortrachyloban-19-oic acid showed moderated activity in preliminaries assays. The secondary metabolites were isolated through usual chromatography techniques, using thin layer chromatography, column chromatography and high performance liquid chromatography. The structure determination of the isolated compounds was performed through physical (melting point and optical rotation) and spectrometrical techniques, such as: infrared (IR), mass spectrometric (MS) and nuclear magnetic resonance (NMR), including bidimensional experiments, and comparison with the literature data.
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spelling info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisChemical study of Croton floribundus Spreng (Euphorbiaceae)Estudo QuÃmico de Croton floribundus Spreng (Euphorbiaceae)2011-07-21Mary Anne Sousa Lima32421508304http://lattes.cnpq.br/0781721524175361 Maria da ConceiÃÃo Ferreira de Oliveira97771430791JoÃo Henrique Silva Luciano88735176334http://lattes.cnpq.br/8169419101757061 02741945381http://lattes.cnpq.br/6024546630684507 Paula Karina Santos UchÃaUniversidade Federal do CearÃPrograma de PÃs-GraduaÃÃo em QuÃmica UFCBRQUIMICAThe present work reports the chemical study of root barks from Croton floribundus Spreng, collected at Pacoti-CE. The phytochemical investigation of hexane extract lead to the isolation of three kaurene-type diterpenes, ent-kaur-16-en-19-oic acid, ent-kaur-16-en-6,19-diol and ent-16-hydroxykaur-11-en-19-oic acid, reported for the first time to the genus Croton. In addition, four trachylobane-type diterpenes were isolated and identified as ent-trachyloban-19-oic acid, ent-15-hydroxytrachyloban-19-oic acid, ent-trachyloban-19-ol and the ent-trachyloban-18,19-diol, which was described as a new compound. Two derivatives of ent-trachyloban-18,19-diol were prepared through acetylation and oxidation reactions, and were characterized as ent-18,19-diacetoxytrachylobane and ent-18-nortrachyloban-19-oic acid. Each of these isolated diterpenes were submited to cytotoxic activity using colon (HCT-8), breast (MDAMB-435) and brain (SF-295) cell lines, and the compounds ent-caur-16-en-6,19-diol and ent-18-nortrachyloban-19-oic acid showed moderated activity in preliminaries assays. The secondary metabolites were isolated through usual chromatography techniques, using thin layer chromatography, column chromatography and high performance liquid chromatography. The structure determination of the isolated compounds was performed through physical (melting point and optical rotation) and spectrometrical techniques, such as: infrared (IR), mass spectrometric (MS) and nuclear magnetic resonance (NMR), including bidimensional experiments, and comparison with the literature data.O presente trabalho relata o estudo quÃmico das cascas da raiz de Croton floribundus Spreng, coletadas no municÃpio de Pacoti-CE. A investigaÃÃo fitoquÃmica do extrato hexÃnico de C. floribundus levou ao isolamento de trÃs diterpenos do tipo caureno, Ãcido ent-caur-16-en-19-Ãico, ent-caur-16-en-6,19-diol e Ãcido ent-16-hidroxicaur-11-en-19-Ãico, sendo os dois Ãltimos relatados pela primeira vez para o gÃnero Croton. AlÃm destes compostos, foram isolados quatro diterpenos do tipo traquilobano, identificados como sendo Ãcido ent-traquiloban-19-Ãico, Ãcido ent-15-hidroxitraquiloban-19-Ãico, ent-traquiloban-19-ol e o ent-traquiloban-18,19-diol, que nÃo possui registro na literatura. Foram preparados ainda dois derivados reacionais de carÃter inÃdito, obtidos atravÃs de reaÃÃes de acetilaÃÃo e oxidaÃÃo do diterpeno traquilobÃnico ent-traquiloban-18,19-diol, que foram caracterizados como sendo ent-18,19-diacetoxitraquilobano e Ãcido ent-18-nortraquiloban-19-Ãico. Todos os diterpenos isolados foram submetidos a testes de atividade citotÃxica, utilizando linhagens de cÃlulas tumorais de cÃlon (HCT-8), mama (MDAMB-435) e cÃrebro (SF-295), onde testes preliminares indicaram que os compostos ent-caur-16-en-6,19-diol e Ãcido ent-18-nortraquiloban-19-Ãico apresentaram moderada atividade. Os metabÃlitos secundÃrios foram isolados atravÃs de tÃcnicas cromatogrÃficas usuais, utilizando cromatografia em camada delgada, cromatografia em coluna e cromatografia lÃquida de alta eficiÃncia. A determinaÃÃo estrutural foi realizada atravÃs de mÃtodos fÃsicos (ponto de fusÃo e rotaÃÃo Ãptica) e do uso de tÃcnicas espectromÃtricas como: infravermelho (IV), espectrometria de massas (EM) e ressonÃncia magnÃtica nuclear de hidrogÃnio (RMN 1H) e carbono-13 (RMN 13C), incluindo experimentos bidimensionais (COSY, HSQC, HMBC, NOESY), alÃm de comparaÃÃo com dados da literatura.CoordenaÃÃo de AperfeiÃoamento de Pessoal de NÃvel Superiorhttp://www.teses.ufc.br/tde_busca/arquivo.php?codArquivo=6304application/pdfinfo:eu-repo/semantics/openAccessporreponame:Biblioteca Digital de Teses e Dissertações da UFCinstname:Universidade Federal do Cearáinstacron:UFC2019-01-21T11:19:15Zmail@mail.com -
dc.title.en.fl_str_mv Chemical study of Croton floribundus Spreng (Euphorbiaceae)
dc.title.alternative.pt.fl_str_mv Estudo QuÃmico de Croton floribundus Spreng (Euphorbiaceae)
title Chemical study of Croton floribundus Spreng (Euphorbiaceae)
spellingShingle Chemical study of Croton floribundus Spreng (Euphorbiaceae)
Paula Karina Santos UchÃa
QUIMICA
title_short Chemical study of Croton floribundus Spreng (Euphorbiaceae)
title_full Chemical study of Croton floribundus Spreng (Euphorbiaceae)
title_fullStr Chemical study of Croton floribundus Spreng (Euphorbiaceae)
title_full_unstemmed Chemical study of Croton floribundus Spreng (Euphorbiaceae)
title_sort Chemical study of Croton floribundus Spreng (Euphorbiaceae)
author Paula Karina Santos UchÃa
author_facet Paula Karina Santos UchÃa
author_role author
dc.contributor.advisor1.fl_str_mv Mary Anne Sousa Lima
dc.contributor.advisor1ID.fl_str_mv 32421508304
dc.contributor.advisor1Lattes.fl_str_mv http://lattes.cnpq.br/0781721524175361
dc.contributor.referee1.fl_str_mv Maria da ConceiÃÃo Ferreira de Oliveira
dc.contributor.referee1ID.fl_str_mv 97771430791
dc.contributor.referee2.fl_str_mv JoÃo Henrique Silva Luciano
dc.contributor.referee2ID.fl_str_mv 88735176334
dc.contributor.referee2Lattes.fl_str_mv http://lattes.cnpq.br/8169419101757061
dc.contributor.authorID.fl_str_mv 02741945381
dc.contributor.authorLattes.fl_str_mv http://lattes.cnpq.br/6024546630684507
dc.contributor.author.fl_str_mv Paula Karina Santos UchÃa
contributor_str_mv Mary Anne Sousa Lima
Maria da ConceiÃÃo Ferreira de Oliveira
JoÃo Henrique Silva Luciano
dc.subject.cnpq.fl_str_mv QUIMICA
topic QUIMICA
dc.description.sponsorship.fl_txt_mv CoordenaÃÃo de AperfeiÃoamento de Pessoal de NÃvel Superior
dc.description.abstract.por.fl_txt_mv The present work reports the chemical study of root barks from Croton floribundus Spreng, collected at Pacoti-CE. The phytochemical investigation of hexane extract lead to the isolation of three kaurene-type diterpenes, ent-kaur-16-en-19-oic acid, ent-kaur-16-en-6,19-diol and ent-16-hydroxykaur-11-en-19-oic acid, reported for the first time to the genus Croton. In addition, four trachylobane-type diterpenes were isolated and identified as ent-trachyloban-19-oic acid, ent-15-hydroxytrachyloban-19-oic acid, ent-trachyloban-19-ol and the ent-trachyloban-18,19-diol, which was described as a new compound. Two derivatives of ent-trachyloban-18,19-diol were prepared through acetylation and oxidation reactions, and were characterized as ent-18,19-diacetoxytrachylobane and ent-18-nortrachyloban-19-oic acid. Each of these isolated diterpenes were submited to cytotoxic activity using colon (HCT-8), breast (MDAMB-435) and brain (SF-295) cell lines, and the compounds ent-caur-16-en-6,19-diol and ent-18-nortrachyloban-19-oic acid showed moderated activity in preliminaries assays. The secondary metabolites were isolated through usual chromatography techniques, using thin layer chromatography, column chromatography and high performance liquid chromatography. The structure determination of the isolated compounds was performed through physical (melting point and optical rotation) and spectrometrical techniques, such as: infrared (IR), mass spectrometric (MS) and nuclear magnetic resonance (NMR), including bidimensional experiments, and comparison with the literature data.
O presente trabalho relata o estudo quÃmico das cascas da raiz de Croton floribundus Spreng, coletadas no municÃpio de Pacoti-CE. A investigaÃÃo fitoquÃmica do extrato hexÃnico de C. floribundus levou ao isolamento de trÃs diterpenos do tipo caureno, Ãcido ent-caur-16-en-19-Ãico, ent-caur-16-en-6,19-diol e Ãcido ent-16-hidroxicaur-11-en-19-Ãico, sendo os dois Ãltimos relatados pela primeira vez para o gÃnero Croton. AlÃm destes compostos, foram isolados quatro diterpenos do tipo traquilobano, identificados como sendo Ãcido ent-traquiloban-19-Ãico, Ãcido ent-15-hidroxitraquiloban-19-Ãico, ent-traquiloban-19-ol e o ent-traquiloban-18,19-diol, que nÃo possui registro na literatura. Foram preparados ainda dois derivados reacionais de carÃter inÃdito, obtidos atravÃs de reaÃÃes de acetilaÃÃo e oxidaÃÃo do diterpeno traquilobÃnico ent-traquiloban-18,19-diol, que foram caracterizados como sendo ent-18,19-diacetoxitraquilobano e Ãcido ent-18-nortraquiloban-19-Ãico. Todos os diterpenos isolados foram submetidos a testes de atividade citotÃxica, utilizando linhagens de cÃlulas tumorais de cÃlon (HCT-8), mama (MDAMB-435) e cÃrebro (SF-295), onde testes preliminares indicaram que os compostos ent-caur-16-en-6,19-diol e Ãcido ent-18-nortraquiloban-19-Ãico apresentaram moderada atividade. Os metabÃlitos secundÃrios foram isolados atravÃs de tÃcnicas cromatogrÃficas usuais, utilizando cromatografia em camada delgada, cromatografia em coluna e cromatografia lÃquida de alta eficiÃncia. A determinaÃÃo estrutural foi realizada atravÃs de mÃtodos fÃsicos (ponto de fusÃo e rotaÃÃo Ãptica) e do uso de tÃcnicas espectromÃtricas como: infravermelho (IV), espectrometria de massas (EM) e ressonÃncia magnÃtica nuclear de hidrogÃnio (RMN 1H) e carbono-13 (RMN 13C), incluindo experimentos bidimensionais (COSY, HSQC, HMBC, NOESY), alÃm de comparaÃÃo com dados da literatura.
description The present work reports the chemical study of root barks from Croton floribundus Spreng, collected at Pacoti-CE. The phytochemical investigation of hexane extract lead to the isolation of three kaurene-type diterpenes, ent-kaur-16-en-19-oic acid, ent-kaur-16-en-6,19-diol and ent-16-hydroxykaur-11-en-19-oic acid, reported for the first time to the genus Croton. In addition, four trachylobane-type diterpenes were isolated and identified as ent-trachyloban-19-oic acid, ent-15-hydroxytrachyloban-19-oic acid, ent-trachyloban-19-ol and the ent-trachyloban-18,19-diol, which was described as a new compound. Two derivatives of ent-trachyloban-18,19-diol were prepared through acetylation and oxidation reactions, and were characterized as ent-18,19-diacetoxytrachylobane and ent-18-nortrachyloban-19-oic acid. Each of these isolated diterpenes were submited to cytotoxic activity using colon (HCT-8), breast (MDAMB-435) and brain (SF-295) cell lines, and the compounds ent-caur-16-en-6,19-diol and ent-18-nortrachyloban-19-oic acid showed moderated activity in preliminaries assays. The secondary metabolites were isolated through usual chromatography techniques, using thin layer chromatography, column chromatography and high performance liquid chromatography. The structure determination of the isolated compounds was performed through physical (melting point and optical rotation) and spectrometrical techniques, such as: infrared (IR), mass spectrometric (MS) and nuclear magnetic resonance (NMR), including bidimensional experiments, and comparison with the literature data.
publishDate 2011
dc.date.issued.fl_str_mv 2011-07-21
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=6304
url http://www.teses.ufc.br/tde_busca/arquivo.php?codArquivo=6304
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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
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