FundaÃÃo Cearense de Apoio ao Desenvolvimento Cientifico e TecnolÃgico / O trabalho relata a investigaÃÃo quÃmica dos extratos das raÃzes de Cordia multispicata e Cordia globosa. Para o isolamento dos compostos foram utilizadas tÃcnicas cromatogrÃficas clÃssicas, tais como: cromatografia em coluna aberta e do tipo âflashâ, cromatografia por exclusÃo molecular e cromatografia lÃquida de alta eficiÃncia. A investigaÃÃo quÃmica do extrato hexÃnico de C. multispicata resultou no isolamento de duas naftoquinonas terpÃnicas conhecidas, as cordiaquinonas B e J, alÃm da naftoquinona inÃdita 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 etanÃlico das raÃzes de C. globosa foram isoladas duas hidroquinonas terpÃnicas 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 Ãster N-benzoil-L-fenilalaninato de N-benzoil-2-amino-3-fenilpropila foi tambÃm isolado. A citotoxicidade dos novos compostos foi avaliada frente a trÃs linhagens de cÃlulas tumorais: OVCAR-8 (ovÃrio), SF-295 (glioblastoma) e HCT-116 (cÃlon). Os compostos foram fracamente ativos com valores de IC50 > 5 μg/mL. A determinaÃÃo estrutural das substÃncias isoladas foi realizada atravÃs de mÃtodos espectromÃtricos: IR, EMAR and RMN 1H and 13C, incluindo tÃcnicas bidimensionais (COSY, HSQC, HMBC), alÃm de comparaÃÃo com dados disponÃveis na literatura, sempre que disponÃveis. / 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 âflashâ 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 > 5Âg/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.
| Identifer | oai:union.ndltd.org:IBICT/oai:www.teses.ufc.br:6908 |
| Date | 14 March 2013 |
| Creators | Ana Karine Oliveira da Silva |
| Contributors | OtÃlia DeusdÃnia Loiola Pessoa, Daniel Esdras de Andrade Uchoa, Francisco Arnaldo Viana |
| Publisher | Universidade Federal do CearÃ, Programa de PÃs-GraduaÃÃo em QuÃmica, UFC, BR |
| Source Sets | IBICT Brazilian ETDs |
| Language | Portuguese |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/masterThesis |
| Format | application/pdf |
| Source | reponame:Biblioteca Digital de Teses e Dissertações da UFC, instname:Universidade Federal do Ceará, instacron:UFC |
| Rights | info:eu-repo/semantics/openAccess |
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