Please use this identifier to cite or link to this item: http://www.repositorio.ufc.br/handle/riufc/32590
Title in Portuguese: Prospecção química e farmacológica dos extratos de Cordia glazioviana Taub. e Cordia oncocalyx Taub.
Title: Chemical and pharmacological prospecting of extracts of Cordia glazioviana Taub. and Cordia oncocalyx Taub.
Author: Silva, Ana Karine Oliveira da
Advisor(s): Pessoa, Otília Deusdênia Loiola
Keywords: Cordia glazioviana
Cordia oncocalyx
Inibição neurogênica
Atividade citotóxica
Benzoquinonas
Issue Date: 2017
Abstract in Portuguese: Neste trabalho é descrita a investigação química dos extratos etanólicos dos caules de Cordia glazioviana Taub. e Cordia oncocalyx Taub. (Boraginaceae), árvores típicas do nordeste do Brasil. A partir de C. glazioviana foram isolados quatro sesquiterpenos [10,12-diidróxibisabolol (1), hamanasal A (2), 1β,6β-diidróxi-7-epi-eudesm-3-eno (3) e 1β,6β-dihidróxi-7-epi-eudesm-4(15)-eno (4)], um meroterpeno fenólico [didehidroconicol (5)], cinco hidroquinonas [rel-5α-formila-1,4-diidróxi-8aβ-metil-5,6,7,8,8a,9,10,10a-octahidro-10-antracenona (6), 12,16-diepóxi-1,4-diidróxi-globiferina (7), (2E)-3’,8’-diidróxi-3’-7’-dimetilnona-1’,6’-dienil-1,4-benzenodiol (8), cordiaquinol D (9) e rel-1,4-diidróxi-8α,llα;9α,11α-diepóxi-2-metóxi-8aβ-metil-5,6,7,8,8a,9,10,10a-octahidro-10-antracenona (20)] e duas quinonas [2-metóxi-7-metil-(6→4’)-1’-hidróxi-dihidropiran-l,4-naftalenodiona (10) e oncocalyxona A (15)]. Os compostos 6, 7, 8, 9 e 10 estão sendo relatados pela primeira vez na literatura. De C. oncocalyx foram isoladas sete quinonas [rel-10β,11β-epóxi-11β-etóxi-8α-hidróxi-2-metóxi-8aβ-metil-5α,6,7,8,8a,9,10,10aβ-octahidro-1,4-antracendiona (11), rel-10β,11β-epóxi-2,11β-dimetóxi-8α-hidróxi-8aβ-metil-5α,6,7,8,8a,9,10,10aβ-octahidro-1,4-antracendiona (12), 11α-oncocalyxona D (13), rel-10β,11β-epóxi-8α,5-diidróxi-2-metóxi-8aβ-metil-5,6,7,8,8a,9,10,10aβ-octahidro-1,4-antracendiona (14), oncocalyxona A (15), 6-formila-2-metóxi-9-metil-1,4-fenantrenodiona (16) e oncocalyxona B (22)] e cinco hidroquinonas [rel-1,4,8α-triidróxi-5-furanil-2-metóxi-8aβ-metil-6,7,8,8a,9,10-hexahidro-10-antracenona (17), rel-10α,11α-epóxi-8α,11β-diidróxi-8aβ-metil-5β,6,7,8,8a,9,10,10aβ-octahidro-1,4-antraceno diol (18), rel-9α,11α-epóxi-1,4,8α-triidróxi-2-metóxi-8aβ-metil-5,6,7,8,8a,9,10,10aβ-octahidro-10-antracenona (19), rel-1,4-diidróxi-8α,llα;9α,11α-diepóxi-2-metóxi-8aβ-metil-5,6,7,8,8a,9,10,10a-octahidro-10-antracenona (20) e rel-1,4,8α-triidróxi-5-carboxietil-2-metóxi-8aβ-metil-6,7,8,8a,9,10-hexahidro-10-antracenona (21)]. Os compostos 11, 12, 14, 17 e 21 são novos. As estruturas de todas as substâncias isoladas foram elucidadas através de métodos espectroscópicos (IV, RMN de 1H e 13C 1D e 2D e EMAR), além de comparação com dados disponíveis na literatura. As substâncias isoladas de C. oncocalyx foram submetidas ao ensaio de inibição neurogênica e respectivos tipos de receptores. Sete deles foram ativos (11, 14, 15, 16, 17, 19 e 22) e seus efeitos revertidos principalmente por prometazina e yohimbina. Os compostos isolados de C. glazioviana foram submetidos a teste de citotoxicidade frente a células de adenocarcinoma de cólon, dos quais apenas o cordiaquinol D (9) foi significativamente ativo apresentando CI50 de 0,8.
Abstract: In this work, the chemical investigation of the ethanol extracts of the stems of Cordia glazioviana Taub. and Cordia oncocalyx Taub. (Boraginaceae), typical trees of the northeastern of Brazil, are described. From C. glazioviana were isolated four sesquiterpenes [10,12-dihydroxybisabolol (1), hamanasal A (2), 1β,6β-dihydroxy-7-epi-eudesm-3-ene (3), and 1β,6β-dihydroxy-7-epi-eudesm-4(15)-ene (4)], one phenolic meroterpene [didehydroconicol (5)], five hydroquinones [rel-1,4-dihydroxy-5α-formyl-8aβ-methyl-5,6,7,8,8a,9,10,10a-octahydro-10-anthracenone (6), 12,16-diepoxy-1,4-dihydroxy-globiferin (7), (2E)-3’,8’-dihydroxy-3’-7’-dimethylnona-1’,6’-dienyl-1,4-benzene diol (8), cordiaquinol D (9) and rel-1,4-dihydroxy-8α,11α;9α,11α-diepoxy-2-methoxy-8aβ-methyl-5,6,7,8,8a,9,10,10a-octahydro-10-antracenone (20)] and two quinones (2-methoxy-7-methyl-(6→4’)-1’-hydroxy-dihydropyran-l,4-naphthalenedione (10) and oncocalyxone A (15)]. Compounds 6, 7, 8, 9 and 10 are described for the first time. From C. oncocalyx were isolated seven quinones [rel-10β,11β-epoxy-11β-ethoxy-8α-hydroxy-2-methoxy-8aβ-methyl-5α,6,7,8,8a,9,10aβ-octahydro-1,4-anthracendione (11), rel-10β,11β-epoxy-2,11β-dimethoxy-8α-hydroxy-8aβ-methyl-5α,6,7,8, 8a,9,10,10aβ-octahydro-1,4-anthracendione (12), 11α-Oncocalyxone D (13), rel-10β,11β-epoxy-8α,5-dihydroxy-2-methoxy-8aβ-methyl-5,6,7,8,8a,9,10,10aβ-octahydro-1,4-anthracendione (14), oncocalyxone A (15), 6-formyl-2-methoxy-9-methyl-1,4-phenanthrendione (16) and oncocalyxone B (22)] and five hydroquinones [rel-1,4,8α-trihydroxy-5-furanyl-2-methoxy-8aβ-methyl-6,7,8,8a,9,10-hexahydro-10-anthracenone (17), rel-10α,11α-epoxy-8α,11β-dihydroxy-8aβ-methyl-5β,6,7,8,8a,9,10,10aβ-octahydro-1,4-anthracenediol (18), rel-9α,11α-epoxy-1,4,8α-trihydroxy-2-methoxy-8aβ-methyl-5,6,7,8,8a, 9,10,10aβ-octahydro-10-anthracenone (19), rel-8α,11α;9α,11α-diepoxy-1,4-dihydroxy-2-methoxy-8aβ-methyl-5,6,7,8,8a,9,10-10aβ-octahydro-10-anthracenone (20) and rel-1,4,8α-trihydroxy-5-carboxyethyl-2-methoxy-8aβ-methyl-6,7,8,8a,9,10-hexahydro-10-anthracenone (21)]. Compounds 11, 12, 14, 17 and 21 are new. The structures of all isolated compounds were elucidated using spectroscopic methods (IR, 1H and 13C NMR, and HRESIMS), and comparison with data available in the literature. All isolated compounds from C. oncocalyx were screened on the neurogenic inhibition and respective receptors. Seven of them were active (11, 14, 15, 16, 17, 19 and 22), being particularly reverted by promethazine and yohimbin. The isolated compounds of C. glazioviana were tested against the colon adenocarcinoma cancer cell line, from which cordiaquinol D (9) was strongly active, with IC50 0.8.
Description: SILVA, Ana Karine Oliveira da. Prospecção química e farmacológica dos extratos de Cordia glazioviana Taub. e Cordia oncocalyx Taub. 2017. 248 f. Tese (Doutorado em Química) - Universidade Federal do Ceará, Fortaleza, 2017.
URI: http://www.repositorio.ufc.br/handle/riufc/32590
metadata.dc.type: Tese
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