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CRISTIANE DA SILVA PAULA.Pdf UNIVERSIDADE FEDERAL DO PARANÁ CRISTIANE DA SILVA PAULA ESTUDO FITOQUÍMICO E PROPRIEDADES BIOLÓGICAS DAS FOLHAS DE Bauhinia ungulata L., Fabaceae CURITIBA 2014 CRISTIANE DA SILVA PAULA ESTUDO FITOQUÍMICO E PROPRIEDADES BIOLÓGICAS DAS FOLHAS DE Bauhinia ungulata L., Fabaceae Tese apresentada ao Programa de Pós Graduação em Ciências Farmacêuticas, Setor de Ciências da Saúde da Universidade Federal do Paraná, como requisito parcial para a obtenção do título de Doutor em Ciências Farmacêuticas. Orientadora: Dra. Marilis D. Miguel Co-orientador: Dr. Obdulio G. Miguel CURITIBA 2014 Paula, Cristiane da Silva Estudo fitoquímico e propriedades biológicas das folhas de Bauhinia ungulata L., Fabaceae / Cristiane da Silva Paula – Curitiba, 2014. 227 f. : il. (algumas color.) ; 30 cm Orientadora: Professora Dra. Marilis Dallarmi Miguel Coorientador: Professor Dr. Obdulio Gomes Miguel Tese (doutorado) – Programa de Pós-Graduação em Ciências Farmacêuticas, Setor de Ciências da Saúde, Universidade Federal do Paraná, 2014. Inclui bibliografia 1. Bauhinia ungulata. 2. Astilbina. 3. Engeletina. 4. Afzelina. I. Miguel, Marilis Dallarmi. II. Miguel, Obdulio Gomes. III. Universidade Federal do Paraná. IV. Título. CDD 615.32 AGRADECIMENTOS A DEUS, sempre presente nas horas mais difíceis me dando forças para entender as dificuldades e superá-las. Iluminou-me quando tudo escureceu e me insuflou a alma de serenidade e sabedoria sempre que precisei. A meus pais, meu marido e familiares, pelo grande apoio em todos os momentos de minha vida e por todos os seus ensinamentos. À Universidade Federal do Paraná, ao Programa de Pós-Graduação em Ciências Farmacêuticas pela oportunidade de realizar este trabalho. A Dra. Marilis Dallarmi Miguel e Dr. Obdúlio Gomes Miguel, pela orientação, dedicação, confiança e paciência nesses seis últimos anos, desde o mestrado. A todos os professores do programa de Pós Graduação em Ciências Farmacêuticas, pelos ensinamentos científicos e lições de vida. À Profa. Dra. Ana Luiza Lacava Lordello, Profa. Dra. Joice Cunha e ao Prof. Dr. Paulo Roberto Wunder pela parceria, excelente acolhimento e ensinamentos que foram muito importantes para o resultado final deste trabalho. Ao Departamento de Química e Bioquímica da UFPR, equipe do RMN do Institut de Chimie de Substances Naturelles e Prof Dr Didier Stien, de Gif-sur-Yvette, da França pela realização dos RMNs. Ao Departamento de Farmacologia da UFPR pelo acolhimento e possibilidade de realização dos experimentos “ in vivo ” e ao Biotério do setor de Ciências Biológicas da UFPR pelo fornecimento dos animais. À Professora Dra. Daniela de Almeida Cabrini e a mestranda Bruna Soley pela realização dos ensaios da mieloperoxidase. À Profa Dra Christiane Pienna Soares, Prof Dr Iguatemy Lourenço Brunetti e a doutoranda Thaís Moreira da pós graduação em "Biociências e Biotecnologia Aplicadas à Farmácia" da Universidade Estadual Paulista "Júlio de Mesquita Filho" - UNESP - Faculdade de Ciências Farmacêuticas - Departamento de Análises Clínicas, pela oportunidade de realização dos experimentos de citotoxicidade. Aos amigos Ana Flávia Schvabe Duarte, Ângela Souza, Cristiane Bezerra da Silva, Cristina Mayumi Miyazaki, Daniela Maria Soares de Oliveira, Fernanda Maria Marins Ocampos, Gislene Mari Fujiwara, Laura Lúcia Cogo, Luciane Dalarmi, Maria Christina Verdam, Maria Fernanda Arruda, Mariana Saragioto Krause, Marileda Zucheto, Milena Kalegari, Pedro Zanin, Ranieri Campos, Vanessa Cantelli, Vinícius Bednarczuk de Oliveira, Profa. Dra. Josiane de Fátima Gaspari Dias, Profa. Dra. Sandra Zanin, Prof. Dr. Vitor Alberto Kerber, que de diversas formas contribuíram para a realização deste trabalho. A Professora. Dra. Janaina Menezes Zanoveli, alunos de doutorado, mestrado e IC do departamento de farmacologia da UFPR que em várias situações nos socorreram auxiliando nos experimentos. As alunas de IC Ayla Jacomel Kowalczuk Ferreira e Letícia Milani pelo auxílio nos experimentos da Imunologia. Ao Paulo Diniz do laboratório de farmacotécnica pelo apoio e disponibilidade constante e a Maria da Graça da Central Analítica sempre simpática e amiga, pelo grande apoio técnico, auxiliando em todas as necessidades. Agradeço também a CAPES/REUNI pelo suporte financeiro e bolsa de estudo. RESUMO Este trabalho teve como objetivo realizar o estudo fitoquímico e biológico do extrato etanólico, frações e compostos isolados provenientes das folhas de Bauhinia ungulata L. (Fabaceae). As folhas secas foram submetidas aos ensaios farmacopeicos de determinação de água e cinzas totais. Extrato aquoso e etanólico foram submetidos a análise fitoquímica preliminar. O extrato etanólico foi particionado obtendo-se as frações hexano, clorofórmio, acetato de etila e residual. A fração acetato de etila foi submetida à cromatografia em coluna e cromatografia líquida de alta eficiência e compostos isolados foram identificados por ressonância magnética nuclear. O extrato etanólico e frações foram submetidos aos ensaios de toxicidade frente a Artemia salina ; atividade hemolítica; doseamento de fenóis totais pelo método de Folin Ciocalteou; às atividades antioxidantes pelos métodos de fosfomolibdênio, DPPH e TBARS; alelopática determinado interferência das amostras sobre germinação, crescimento, conteúdo de clorofila e respiração, utilizando com espécies alvo a Lactuca sativa e Alium cepa e antibacteriana por meio de concentração inibitória mínima. O extrato etanólico foi submetido a ensaios farmacológicos de nocicepção induzida pela formalina, contorções abdominais induzidas por ácido acético, teste da placa quente, edema de pata induzido por carragenina, medida da atividade enzimática da mieloperoxidase e análise histológica e campo aberto em modelos in vivo . Os compostos isolados foram submetidos aos ensaios imunológicos utilizando neutrófilos humanos e de citotoxicidade por redução do MTT frente a linhagem celular SiHa de câncer de cólo de útero. Os resultados das análises farmacopeicas demostraram que o material utilizado no estudo encontra-se dentro dos parâmetros estabelecidos. Na análise fitoquímica preliminar foram detectados alguns grupamentos que serviram de guias para o isolamento principalmente de flavonoides. Da fração acetato de etila foram isolados os compostos astilbina, quercetina, engeletina, afzelina e canferol. Nos ensaios biológicos não foram observadas toxicidade sobre a Artemia salina e hemolítica nos modelos testados. Com relação ao teor de fenóis totais todas as amostras possuem estes compostos em sua constituição com destaque para FAE que apresentou teores elevados. Com relação a atividade antioxidante no ensaio do fosfomolibdênio, DPPH e TBARS destacou-se a FAE com resultados semelhantes aos padrões utilizados. No ensaio alelopático as amostras demostraram potencial fitotóxico variáveis nas duas espécies utilizadas como alvo influenciando os parâmetros avaliados. Não foi observada atividade antibacteriana das amostras frente as bactérias testadas. O extrato etanólico apresentou atividade antinociceptiva e anti-inflamatória frente aos modelos utilizados. Os isolados quercetina, engeletina e canferol monstraram-se ativadores de neutrófilos. Os compostos isolados não apresentaram citotoxicidade frente as células da linhagem SiHA nas concentrações utilizadas. Os resultados revelam atividade antioxidante, alelopática, antinociceptiva, anti-inflamatória do extrato e imunossupressora de compostos das folhas de Bauhinia ungulata . Palavras-chave: Bauhinia ungulata . Astilbina. Engeletina. Afzelina. ABSTRACT This work aimed to carry out the phytochemical and biological studies of the extract ethanolic, fractions and isolated compounds from the leaves of Bauhinia ungulata L. (Fabaceae ). The dried leaves were subjected to pharmacopoeial tests to determine water and ashes. Aqueous and ethanolic extract were subjected to preliminary phytochemical analysis. The ethanol extract was partitioned obtaining the fractions hexane, chloroform , ethyl acetate and the remaining residual. The ethyl acetate fraction was subjected to column chromatography and high performance liquid chromatography and isolated compounds identified by nuclear magnetic resonance. The ethanolic extract and fractions were subjected to testing for toxicity against Artemia salina ; hemolytic activity; determination of total phenols by Folin Ciocalteou, the antioxidant activities by methods phosphomolybdenum, DPPH and TBARS; allelopathic interference of samples given on germination, growth, chlorophyll content and respiration using to target the species Lactuca sativa and Allium cepa and antibacterial by minimum inhibitory concentration. The ethanol extract was subjected to pharmacological testing of nociception formalin-induced and writhing induced by acetic acid, hot plate test, paw edema induced by carrageenan, measure the enzymatic activity of myeloperoxidase, histological analysis and open field in models in vivo. The isolated compounds were tested for immunological assays using human neutrophils and cytotoxicity by MTT reduction compared to SiHa cell line of cervical cancer. The results for pharmacopoeial analysis showed that the material used in the study are within established parameters. Preliminary phytochemical analysis of some groups that served as guides for the isolation of mainly flavonoides were detected. The ethyl acetate fraction were isolated astilbin, quercetin, engeletin, afzelin and kaempferol. In biological tests on the Artemia salina and hemolytic activity models the samples showed no activity. With respect to total phenols all
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