Conselho Nacional de Desenvolvimento CientÃfico e TecnolÃgico / Este trabalho relata o perfil quÃmico e farmacolÃgico de quatro espÃcies do gÃnero Senna Mill. â Senna gardneri, Senna georgica, Senna splendida e Senna macranthera var. pudibunda. Este estudo permitiu identificar 38 compostos diferentes de vÃrias classes, com destaque para os flavonoides, dentre os quais: galocatequina, epigalocatequina, (2R*,3S*,4S*,2ââR*,3ââS*)-guibourtinidol-(48)-catequina, quercetina glicoarabinose, taxifolina, isoramnetina, procianidina B1, miricetina e di-hidromiricetina. Todos esses compostos foram relatados pela primeira vez em espÃcies de Senna. AnÃlise quantitativa por cromatografia lÃquida de alta eficiÃncia (CLAE-DAD-ESI-MS) do material em estudo indicou o (E)- 3,3â,5,5â- tetra-hidroxi 4-metoxi estilbeno como majoritÃrio nas raÃzes de Senna georgica (6,14 g/Kg), S. gardneri (5,36 g/Kg) e S. splendida (19,23 g/kg). Nas raÃzes e no caule de S. macranthera var. pudibunda, a catequina foi o composto majoritÃrio com teores de 0,87 g/kg e 1,32g/kg, respectivamente. Nas folhas, a quercetina glicoarabinose foi o composto majoritÃrio nas espÃcies de S. gardineri (11,99g/kg) e S. splendida (3,24 g/kg), e a epigalocatequina, nas folhas de S. macranthera var. pudibunda (1,68 g/kg). O fracionamento cromatogrÃfico (CLAE) resultou na obtenÃÃo de seis compostos puros: (E)- 3, 3â, 5,5â- tetra-hidroxi 4-metoxi estilbeno, catequina, rutina, quercitrina, quercetina e (2R*,3S*,4S*,2'R*,3'S*)-guibourtinidol-(48)-catequina. A atividade antioxidante dos extratos e compostos puros foi analisada atravÃs das tÃcnicas de DHBA, DPPH, FRAP e ORAC, com resultados promissores para todas as amostras investigadas. Os extratos de S. georgica, S. macranthera var. pudibunda e S. gardneri apresentaram atividade anticolinesterÃsica e, para os ensaios enzimÃticos de inibiÃÃo da enzima conversora da angiotensina I, as folhas e raÃzes de S. gardneri apresentaram os melhores resultados. Os extratos das espÃcies de Senna nÃo apresentaram toxidade frente à Artemia salina e nem potencial leishmanicida. O estudo confirmou o potencial como fonte de compostos bioativos para as espÃcies de Senna estudadas. / This Thesis describes the chemical and pharmacologic profile of four species of the genus Senna Mill. Namely Senna gardneri, Senna georgica, Senna splendida and Senna macranthera var. pudibunda. In this study 38 different polyphenolic compounds of various classes, especially flavonoids were identified by HPLC-DAD-ESI-MS and NMR where possible. The flavonoids were identified as (+)-gallocatechin, (-)-epigallocatechin, 2R,3S,4S,2ââR,3ââS)-guibourtinidol-(48)-catechin, quercetin glucoarabinoside, taxifolin, isorhamnetin, procyanidin B1, myricetin and dihydromyricetin. All these compounds are reported for the first time in species of Senna. Quantitative analysis by HPLC showed that, in the material under study (E)-3, 3', 5, 5'-tetrahydroxy-4-methoxy stilbene was the major compound in the roots of Senna georgica (6.14 g/kg), Senna gardneri (5.36 g/kg) and Senna splendida (19.23 g/kg). In the roots and bark of Senna macranthera var. pudibunda, the flavonoid (+)-catechin was the major compound, with levels at 0.87 g/kg and 1.32g/kg, respectively. In the leaves of Senna gardineri and Senna splendida, the major compound was quercetin glucoarabinoside at 12.10 g/kg and 3.241g/kg respectively, and in the leaves of Senna macranthera var. pudibunda (-)-epigallocatechin at 1.68 g/kg. Chromatographic fractionation by semi-preparative HPLC resulted in the purification of six compounds: (E)-3, 3', 5, 5'-tetrahydroxy-4-methoxy stilbene, (+)-catechin, rutin, quercitrin, quercetin and (2R*,3S*,4S*,2''R*,3''S*)- guibourtinidol-(48)-catechin. The antioxidant capacity of the extracts and pure compounds was analyzed by the DPPH, FRAP, ORAC, and HPLC-based HX/XO assays,
with promising results for all samples investigated. Extracts of Senna georgica, macranthera var. pudibunda and gardneri displayed anticholinesterase activity and, inhibition of angiotensin converting enzyme-I. Extracts of the leaves and roots of Senna gardneri showed the best results. No toxicity of the extracts in the brine shrimp and leishmanicidal assays was evident. This study confirmed the potential of Senna species as a valuable source of bioactive polyphenolic compounds, which may augment their use in traditional Brazilian medicine.
| Identifer | oai:union.ndltd.org:IBICT/oai:www.teses.ufc.br:10079 |
| Date | 17 March 2015 |
| Creators | Irvila Ricarte de Oliveira |
| Contributors | Maria Goretti de Vasconcelos Silva, Maria Teresa Salles Trevisan, Marcos Carlos de Mattos, Edy Sousa de Brito, Jorge Mauricio David, Cristiane Pinto Oliveira |
| 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/doctoralThesis |
| 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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