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Previous issue date: 2015-02-20 / Amburana cearensis(Fr. All.) AC Smith (Fabaceae), popularly known as amburana de cheiro, cerejeira and cumaruis typical of the Caatinga and widely distributed in northeastern of Brazil. It is used in folk medicine to treat inflammations of the respiratory tract such as influenza, asthma and bronchitis. This work aimed the chemical investigation of the resin of Amburana cearensis and evaluate its antioxidant potential. Chromatographic profileanalysis using HPLC-DAD showed the presence of phenolic compounds. Chromatographic fractionation with Sephadex LH-20 followed by HPLC resulted in the isolation of twelve substances, comprising seven isoflavones identified as 7,8,3'- trihydroxy- 4'-methoxyisoflavone (Re-1), 7,8,3'-trihydroxy-6,4’-dimethoxyisoflavone (Re-2), 7,3'-dihydroxy-8,4'-dimethoxyisoflavone (Re-3) 7,3'-dihydroxy-4'-methoxyisoflavone (Re-4), 7,3'-dihydroxy-6,4'-dimethoxyisoflavona (Re-5), 3'-Hydroxy-7,8,4' trimethoxyisoflavone (Re-9) and 7,8,3',4'-tetramethoxyisoflavone (Re-12), one new isoflavonolignan identified as (2S,3S)-2,3-trans-3-(4’’-hydroxy-3’’,5’’-dimethoxyphenyl) – 8 – (3’-hydroxy-4’- methoxyphenyl)-2-hydroxymethyl-5-methoxy-2,3-dihydro - 7H-1,4 - dioxin [2,3h] chromen-7-one Re-7) and three chalcones identified as 2',3,4,4’-tetrahidroxi-trans-chalcone (Re-6), 2',4,4’-trihydroxy-3-methoxy-trans-chalcone (Re-11) and 2',4,4’-trihydroxy-trans-chalcone (Re-10) and a quinone identified as 3',4'-dimethoxy-1'- (7-methoxy-4-oxo-4H-romen-3-yl) benzo-2',5'-quinone (Re-8). The structures of these compounds were estabilished on the basis of 1D (1H and APT) and 2D (1H-1H COSY, HMQC, HMBC and NOESY) NMR spectroscopy. To evaluate the antioxidant potential of methanolic extract of the resin were carried out tests with DPPH, ABTS and the β-carotene / linoleic acid system. The test results showed that the resin showed promising activity antiradical front of DPPH (EC50 = 6.1 ± 0.06) and ABTS (EC50 = 10.42 ± 0.11), and good oxidation inhibitory activity across the β-carotene / linoleic acid system (69.09 ± 0.7, t = 60 min). / Amburana cearensis (Fr. All.) A.C. Smith (Fabaceae), popularmente conhecida como amburana de cheiro, cerejeira e cumaru é uma planta típica do bioma Caatinga com ampla distribuição no Nordeste brasileiro. É utilizada na medicina popular no tratamento de inflamações do trato respiratório como gripe, asma e bronquite. Este trabalho teve como objetivo realizar o estudo químico da resina de Amburana cearensis e avaliar seu potencial antioxidante. A análise do perfil cromatográfico por CLAE-DAD mostrou a presença de compostos fenólicos. O fracionamento cromatográfico em coluna com Sephadex LH-20 seguido do fracionamento em CLAE resultou no isolamento de doze substâncias, compreendendo sete isoflavonas identicadas como 7,8,3’- triidroxi- 4’-metoxiisoflavona (Re-1), 7,8,3’- triidroxi-6,4’-dimetoxiisoflavona (Re-2), 7,3’- diidroxi- 8,4’-dimetoxiisoflavona (Re-3), 7,3’- diidroxi- 4’-metoxiisoflavona (Re-4), 7,3’- diidroxi-6,4’-dimetoxiisoflavona (Re-5), 3’- Hidroxi- 7,8,4’-trimetoxiisoflavona (Re-9) e 7,8,3’,4’- tetrametoxiisoflavona (Re-12) e uma nova isoflavonolignana identificada como (2S,3S)-2,3-trans-3-(4’’-hidroxi-3’’,5’’-dimetoxifenil)-8-(3’-hidroxi-4’-metoxifenil)-2-hidroximetil-5-metoxi-2,3-di-hidro-7H-1,4-dioxino [2,3-h] cromen-7-ona (Re-7), três chalconas identificadas como 2’,3,4,4’–tetraidroxi-trans-chalcona (Re-6), 2’,4,4’-triidroxi-3-metoxi-trans-chalcona (Re-11) e 2’,4,4’–triidroxi-trans-chalcona (Re-10) e uma quinona identificada como 3’,4’-dimetoxi-1’-(7-metoxi-4-oxo-4H-romen-3-il)benzo-2’,5’-quinona (Re-8). As estruturas destes compostos foram estabelecidas com base em espectroscopia de RMN 1D (1H e APT) e 2D (1H-1H COSY, HMQC, HMBC e NOESY). Para avaliar o potencial antioxidante do extrato metanólico da resina foram realizados os ensaios com os radicais DPPH, ABTS e o sistema β-caroteno/ácido linoléico. Os resultados dos testes revelaram que a resina apresentou promissora atividade antirradicalar frente aos radicais DPPH (CE50 = 6,1 ± 0,06) e ABTS (CE50 = 10,42 ± 0,11), bem como boa atividade inibitória da oxidação frente ao sistema β-caroteno/ácido linoléico (69,09 ± 0,7; T= 60 min).
| Identifer | oai:union.ndltd.org:IBICT/oai:tede2:tede2/7032 |
| Date | 20 February 2015 |
| Creators | OLIVEIRA, Geane Pereira de |
| Contributors | SANTANA, Andréa Lopes Bandeira Delmiro, SILVA, Tania Maria Sarmento da, FREIRE, Kristerson Reinaldo de Luna, CAMARA, Celso de Amorim, SILVA, Girliane Regina da |
| Publisher | Universidade Federal Rural de Pernambuco, Programa de Pós-Graduação em Química, UFRPE, Brasil, Departamento de Química |
| 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 UFRPE, instname:Universidade Federal Rural de Pernambuco, instacron:UFRPE |
| Rights | info:eu-repo/semantics/openAccess |
| Relation | 1435648362225100898, 600, 600, 600, 3806416055457091030, 1571700325303117195 |
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