GOIS, Roberto Wagner da Silva. Estudo químico e avaliação biológica de Bauhinia acuruana Moric. 2015. 218 f. Tese (Doutorado em química)- Universidade Federal do Ceará, Fortaleza-CE, 2015. / Submitted by Elineudson Ribeiro (elineudsonr@gmail.com) on 2016-10-11T17:25:31Z
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Previous issue date: 2015 / The present work reports the chemical research of the roots, stem and leaves from Bauhinia acuruana. In this study were obtained the extracts in hexane, ethyl acetate and methanol of the leaves and ethanol extracts of the roots and stems. The chromatographic fractionation of extracts allowed the isolation of sesquiterpenes 1β, 6α- dihydroxy 4-(14)-eudesmene (BA-1) and aromadendrane-4β,10α-diol (BA-2); the steroid glycosylated sitosterol (BA-4); the bibenzys 2-hydroxy-2’,3’,5’- trimethoxybybenzyl (BA-5) and 2-hydroxy-3’,5'-dimethoxybybenzyl (BA-6); the oxepin derivatives pacharin (BA-7) and bauhiniastatin 1 (BA-8); the flavonoids quercitrin (BA-3), (-)-fisetinidol (BA-9), (2R, 3S)-2-(3’,4’-dihydroxiphenyl)-5-methoxycroman-3,7-diol (BA-10), (2R,3S)-2-(3’,4’-dihydroxiphenyl)-5-methoxy-6-methylcroman-3,7-diol (BA-11) and astilbin (BA-13), as well as the steroidal mixture sitosterol and stigmasterol (BA-12). It is worth noting that the secondary metabolites BA-1 and BA-2 are unprecedented in the genus, while BA-5 and BA-11 unprecedented in the literature and BA-10 unpublished as natural product. The structures of the compounds were elucidated through spectroscopic techniques (IV, NMR 1D and 2D), mass spectrometry and comparison with data reported in literature. Ethanol extracts of the roots and of the stems were evalueted for antioxidant activity, showing significant activity at concentrations of 0.1 mg/mL and 1.0 mg/mL, respectively. BA-7 was evaluated for its larvicidal activity against Aedes aegypti and presented LC50 value of 78.9 ± 1.8 µg/mL. In addition, BA-5, BA-7, BA-8, BA-9, BA-10 and BA-11 were submitted to evaluation of cytotoxic activity and BA-5, BA-7 and BA-8 presented significant cytotoxic activity. / O presente trabalho relata a investigação química das raízes, do caule e das folhas de Bauhinia acuruana. Nesse estudo foram obtidos os extratos em hexano, em acetato de etila e em metanol das folhas e os extratos em etanol das raízes e do caule. O fracionamento cromatográfico destes extratos permitiu o isolamento dos sesquiterpenos 1β, 6α-diidróxi-4(14)-eudesmeno (BA-1), aromadendrano-4β,10α-diol (BA-2); do esteroide sitosterol glicosilado (BA-4); dos bibenzis 2-hidroxi-2’,3’,5’-trimetoxibibenzila (BA-5) e 2-hidroxi-3’,5’-dimetoxibibenzila (BA-6); dos derivados oxepínicos pacharina (BA-7) e bauhiniastatina 1 (BA-8); dos flavonoides quercitrina (BA-3), (-)-fisetinidol (BA-9), (2R, 3S)-2-(3’,4’-diidroxifenil)-5-metoxicromano-3,7-diol (BA-10), (2R, 3S)-2-(3’,4’-diidroxifenil)-5-metoxi-6-metilcromano-3,7-diol (BA-11) e astilbina (BA-13); bem como da mistura dos esteroides sitosterol e estigmasterol (BA-12). Cabe ressaltar que os metabólitos secundários BA-1 e BA-2 são inéditos no gênero, enquanto BA-5 e BA-11 são inéditos na literatura e BA-10 é inédito como produto natural. As estruturas dos compostos foram elucidadas através de técnicas espectroscópicas (IV, RMN 1D e 2D), espectrometria de massas e comparação com dados descritos na literatura. Os extratos em etanol das raízes e dos caules foram submetidos a testes de atividade antioxidante, apresentando atividades significativas nas concentrações de 0,1 mg/mL e 1,0 mg/mL. BA-7 foi avaliado quanto à sua atividade larvicida sobre Aedes aegypti e apresentou valor de CL50 igual a 78,9±1,8 µg/mL. Por outro lado, BA-5, BA-7, BA-8, BA-9, BA-10 e BA-11 foram submetidos à avaliação de atividade citotóxica frente a seis linhagens tumorais (HCT 116, SF 295, OVCAR, MCF-7, NCIH292 e HL60). BA-5, BA-7 e BA-8 apresentaram atividade citotóxica significativa.
| Identifer | oai:union.ndltd.org:IBICT/oai:www.repositorio.ufc.br:riufc/20127 |
| Date | January 2015 |
| Creators | Gois, Roberto Wagner da Silva |
| Contributors | Santiago, Gilvandete Maria Pinheiro |
| Source Sets | IBICT Brazilian ETDs |
| Language | Portuguese |
| Detected Language | English |
| Type | info:eu-repo/semantics/publishedVersion, info:eu-repo/semantics/doctoralThesis |
| Source | reponame:Repositório Institucional da UFC, instname:Universidade Federal do Ceará, instacron:UFC |
| Rights | info:eu-repo/semantics/openAccess |
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