SILVA, A. K. O.; PESSOA, O. D. L. 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. / Submitted by José Jairo Viana de Sousa (jairo@ufc.br) on 2014-10-15T20:26:52Z No. of bitstreams: 1 2013_dis_akosilva.pdf: 5357295 bytes, checksum: 7cf7ea0232c8130d7dc69e9a9d4ecbd4 (MD5) / Approved for entry into archive by José Jairo Viana de Sousa(jairo@ufc.br) on 2015-11-24T20:05:34Z (GMT) No. of bitstreams: 1 2013_dis_akosilva.pdf: 5357295 bytes, checksum: 7cf7ea0232c8130d7dc69e9a9d4ecbd4 (MD5) / Made available in DSpace on 2015-11-24T20:05:34Z (GMT). No. of bitstreams: 1 2013_dis_akosilva.pdf: 5357295 bytes, checksum: 7cf7ea0232c8130d7dc69e9a9d4ecbd4 (MD5) Previous issue date: 2013 / 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. / 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.

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.