Estudo químico de espécies de Cordia (Boraginaceae): Cordia multispicata (Cham.) e Cordia globosa (Jacq.)
Autor(a) principal: | |
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Data de Publicação: | 2013 |
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/14111 |
Resumo: | This work reports the chemical investigation of the hexane extracts from the roots of Cordia multispicata and Cordia globosa species. For the compounds isolation were used classic chromatographic techniques, such as open and “flash” chromatography on column over silica gel, molecular exclusion on sephadex LH-20 and High Performance Liquid Cromatography in reverse phase. The chemical investigation of the hexane extract of C. multispicata lead to the isolation of two known terpenoid naphthoquinones, the cordiaquinones B and J. In addition, the new naphthoquinone 6-[10-(12,12,16-trimethyl-7- oxabicyclo[2.2.1]hept-2-yl]-2,3-dihydroxy-1,4-naphthalenedione, which was designed cordiaquinone P. From the hexane extract of C. globosa were isolated two uncommon terpenec hydroquinones, (4bE,6Z,8E)-1,4-dihydroxy-9a,10-dihydro-10,12-epoxy-5- methylbenzo[a]azulen-12-one and 4bZ,6Z,8E)-1-hydroxy-9a,10-dihydro-4,11:10,12- diepoxy-benzo[a]-azulen-11,12-dione, both reported for the first time. The Nbenzoylphenylalaninyl-N-benzoyl-2-amino-3-phenylpropyl was also isolated. The cytotoxic potential of the new compounds were evaluated against three tumor cell lines OVCAR-8 (ovarium), SF-295 (glioblastoma) and HCT-116 (colon). The compounds were weakly active showing IC50 values > 5µg/mL. The structural elucidation was performed by spectrometric methods: IR, HRMS and 1H and 13C NMR, including bidimensional techniques (COSY, HSQC and HMBC), in addition to comparison with literature data, whenever available. |
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Estudo químico de espécies de Cordia (Boraginaceae): Cordia multispicata (Cham.) e Cordia globosa (Jacq.)Study of chemical species Cordia (Boraginaceae): Cordia multispicata (Cham.) and Cordia globosa (Jacq.)Cordia multispicataCordia globosaThis work reports the chemical investigation of the hexane extracts from the roots of Cordia multispicata and Cordia globosa species. For the compounds isolation were used classic chromatographic techniques, such as open and “flash” chromatography on column over silica gel, molecular exclusion on sephadex LH-20 and High Performance Liquid Cromatography in reverse phase. The chemical investigation of the hexane extract of C. multispicata lead to the isolation of two known terpenoid naphthoquinones, the cordiaquinones B and J. In addition, the new naphthoquinone 6-[10-(12,12,16-trimethyl-7- oxabicyclo[2.2.1]hept-2-yl]-2,3-dihydroxy-1,4-naphthalenedione, which was designed cordiaquinone P. From the hexane extract of C. globosa were isolated two uncommon terpenec hydroquinones, (4bE,6Z,8E)-1,4-dihydroxy-9a,10-dihydro-10,12-epoxy-5- methylbenzo[a]azulen-12-one and 4bZ,6Z,8E)-1-hydroxy-9a,10-dihydro-4,11:10,12- diepoxy-benzo[a]-azulen-11,12-dione, both reported for the first time. The Nbenzoylphenylalaninyl-N-benzoyl-2-amino-3-phenylpropyl was also isolated. The cytotoxic potential of the new compounds were evaluated against three tumor cell lines OVCAR-8 (ovarium), SF-295 (glioblastoma) and HCT-116 (colon). The compounds were weakly active showing IC50 values > 5µg/mL. The structural elucidation was performed by spectrometric methods: IR, HRMS and 1H and 13C NMR, including bidimensional techniques (COSY, HSQC and HMBC), in addition to comparison with literature data, whenever available.O trabalho relata a investigação química dos extratos das raízes de Cordia multispicata e Cordia globosa. Para o isolamento dos compostos foram utilizadas técnicas cromatográficas clássicas, tais como: cromatografia em coluna aberta e do tipo “flash”, cromatografia por exclusão molecular e cromatografia líquida de alta eficiência. A investigação química do extrato hexânico de C. multispicata resultou no isolamento de duas naftoquinonas terpênicas conhecidas, as cordiaquinonas B e J, além da naftoquinona inédita 6-[10-(12,12,16-trimetil-7-oxabiciclo[2.2.1]hept-2-ila]-2,3-dihidroxi-1,4-naftalenodiona, a qual foi denominada de cordiaquinona P. Do extrato etanólico das raízes de C. globosa foram isoladas duas hidroquinonas terpênicas incomuns: (4bE,6Z,8E)-1,4-dihidroxi-9a,10-dihidro-10,12-epoxi-5-etilbenzo[a]azulen-12-ona e (4bZ,6Z,8E)-1-hidroxi-9a,10-dihidro-4,11:10,12-diepoxi-benzo[a]-azulen-11,12-diona, ambas relatadas pela primeira vez. O éster N-benzoil-L-fenilalaninato de N-benzoil-2-amino-3-fenilpropila foi também isolado. A citotoxicidade dos novos compostos foi avaliada frente a três linhagens de células tumorais: OVCAR-8 (ovário), SF-295 (glioblastoma) e HCT-116 (cólon). Os compostos foram fracamente ativos com valores de IC50 > 5 μg/mL. A determinação estrutural das substâncias isoladas foi realizada através de métodos espectrométricos: IR, EMAR and RMN 1H and 13C, incluindo técnicas bidimensionais (COSY, HSQC, HMBC), além de comparação com dados disponíveis na literatura, sempre que disponíveis.Pessoa, Otília Deusdênia LoiolaSilva, Ana Karine Oliveira da2015-11-24T20:05:34Z2015-11-24T20:05:34Z2013info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/masterThesisapplication/pdfSILVA, A. K. O. Estudo químico de espécies de Cordia (Boraginaceae): Cordia multispicata (Cham.) e Cordia globosa (Jacq.) 2013. 120 f. Dissertação (Mestrado em Química) - Centro de Ciências, Universidade Federal do Ceará, Fortaleza, 2013.http://www.repositorio.ufc.br/handle/riufc/14111porreponame:Repositório Institucional da Universidade Federal do Ceará (UFC)instname:Universidade Federal do Ceará (UFC)instacron:UFCinfo:eu-repo/semantics/openAccess2019-07-12T14:56:18Zoai:repositorio.ufc.br:riufc/14111Repositório InstitucionalPUBhttp://www.repositorio.ufc.br/ri-oai/requestbu@ufc.br || repositorio@ufc.bropendoar:2024-09-11T18:28:39.802507Repositório Institucional da Universidade Federal do Ceará (UFC) - Universidade Federal do Ceará (UFC)false |
dc.title.none.fl_str_mv |
Estudo químico de espécies de Cordia (Boraginaceae): Cordia multispicata (Cham.) e Cordia globosa (Jacq.) Study of chemical species Cordia (Boraginaceae): Cordia multispicata (Cham.) and Cordia globosa (Jacq.) |
title |
Estudo químico de espécies de Cordia (Boraginaceae): Cordia multispicata (Cham.) e Cordia globosa (Jacq.) |
spellingShingle |
Estudo químico de espécies de Cordia (Boraginaceae): Cordia multispicata (Cham.) e Cordia globosa (Jacq.) Silva, Ana Karine Oliveira da Cordia multispicata Cordia globosa |
title_short |
Estudo químico de espécies de Cordia (Boraginaceae): Cordia multispicata (Cham.) e Cordia globosa (Jacq.) |
title_full |
Estudo químico de espécies de Cordia (Boraginaceae): Cordia multispicata (Cham.) e Cordia globosa (Jacq.) |
title_fullStr |
Estudo químico de espécies de Cordia (Boraginaceae): Cordia multispicata (Cham.) e Cordia globosa (Jacq.) |
title_full_unstemmed |
Estudo químico de espécies de Cordia (Boraginaceae): Cordia multispicata (Cham.) e Cordia globosa (Jacq.) |
title_sort |
Estudo químico de espécies de Cordia (Boraginaceae): Cordia multispicata (Cham.) e Cordia globosa (Jacq.) |
author |
Silva, Ana Karine Oliveira da |
author_facet |
Silva, Ana Karine Oliveira da |
author_role |
author |
dc.contributor.none.fl_str_mv |
Pessoa, Otília Deusdênia Loiola |
dc.contributor.author.fl_str_mv |
Silva, Ana Karine Oliveira da |
dc.subject.por.fl_str_mv |
Cordia multispicata Cordia globosa |
topic |
Cordia multispicata Cordia globosa |
description |
This work reports the chemical investigation of the hexane extracts from the roots of Cordia multispicata and Cordia globosa species. For the compounds isolation were used classic chromatographic techniques, such as open and “flash” chromatography on column over silica gel, molecular exclusion on sephadex LH-20 and High Performance Liquid Cromatography in reverse phase. The chemical investigation of the hexane extract of C. multispicata lead to the isolation of two known terpenoid naphthoquinones, the cordiaquinones B and J. In addition, the new naphthoquinone 6-[10-(12,12,16-trimethyl-7- oxabicyclo[2.2.1]hept-2-yl]-2,3-dihydroxy-1,4-naphthalenedione, which was designed cordiaquinone P. From the hexane extract of C. globosa were isolated two uncommon terpenec hydroquinones, (4bE,6Z,8E)-1,4-dihydroxy-9a,10-dihydro-10,12-epoxy-5- methylbenzo[a]azulen-12-one and 4bZ,6Z,8E)-1-hydroxy-9a,10-dihydro-4,11:10,12- diepoxy-benzo[a]-azulen-11,12-dione, both reported for the first time. The Nbenzoylphenylalaninyl-N-benzoyl-2-amino-3-phenylpropyl was also isolated. The cytotoxic potential of the new compounds were evaluated against three tumor cell lines OVCAR-8 (ovarium), SF-295 (glioblastoma) and HCT-116 (colon). The compounds were weakly active showing IC50 values > 5µg/mL. The structural elucidation was performed by spectrometric methods: IR, HRMS and 1H and 13C NMR, including bidimensional techniques (COSY, HSQC and HMBC), in addition to comparison with literature data, whenever available. |
publishDate |
2013 |
dc.date.none.fl_str_mv |
2013 2015-11-24T20:05:34Z 2015-11-24T20:05:34Z |
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, A. K. O. Estudo químico de espécies de Cordia (Boraginaceae): Cordia multispicata (Cham.) e Cordia globosa (Jacq.) 2013. 120 f. Dissertação (Mestrado em Química) - Centro de Ciências, Universidade Federal do Ceará, Fortaleza, 2013. http://www.repositorio.ufc.br/handle/riufc/14111 |
identifier_str_mv |
SILVA, A. K. O. Estudo químico de espécies de Cordia (Boraginaceae): Cordia multispicata (Cham.) e Cordia globosa (Jacq.) 2013. 120 f. Dissertação (Mestrado em Química) - Centro de Ciências, Universidade Federal do Ceará, Fortaleza, 2013. |
url |
http://www.repositorio.ufc.br/handle/riufc/14111 |
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) |
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UFC |
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UFC |
reponame_str |
Repositório Institucional da Universidade Federal do Ceará (UFC) |
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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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1813028820227194880 |