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Asteraceae) E Determinação Da Atividade Antifúngica

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Asteraceae) E Determinação Da Atividade Antifúngica UNIVERSIDADE FEDERAL DO RIO GRANDE DO SUL FACULDADE DE FARMÁCIA PROGRAMA DE PÓS-GRADUAÇÃO EM CIÊNCIAS FARMACÊUTICAS Análise química de espécies de Pterocaulon (Asteraceae) e determinação da atividade antifúngica Ana Cristina Stein Porto Alegre, 2005. ii UNIVERSIDADE FEDERAL DO RIO GRANDE DO SUL FACULDADE DE FARMÁCIA PROGRAMA DE PÓS-GRADUAÇÃO EM CIÊNCIAS FARMACÊUTICAS Análise química de espécies de Pterocaulon (Asteraceae) e determinação da atividade antifúngica Dissertação apresentada por Ana Cristina Stein para obtenção do grau de mestre em Ciências Farmacêuticas Orientadora: Profa. Dra. Gilsane Lino von Poser Porto Alegre, 2005. iii Dissertação apresentada ao Programa de Pós-Graduação em Ciências Farmacêuticas da Universidade Federal do Rio Grande do Sul e aprovada em 23.06.2005, pela Comissão Examinadora, constituída por: Prof. Dr. Alexandre de Barros Falcão Ferraz Universidade Luterana do Brasil Profa. Dra. Raquel Bridi Universidade Federal do Rio Grande do Sul Profa. Dra. Renata Pereira Limberguer Universidade Federal do Rio Grande do Sul S819a Stein, Ana Cristina Análise química de espécies de Pterocaulon (Asteraceae) e determinação da atividade antifúngica / Ana Cristina Stein. – Porto Alegre : UFRGS, 2005. - 164 p.: il. Dissertação (mestrado). UFRGS. Faculdade de Farmácia. Progra- ma de Pós-graduação em Ciências Farmacêuticas. 1. Pterocaulon. 2. Asteraceae. 3. Cumarinas 4. Quitoco. 5. Atividade antifúngica. I. Poser, Gilsane Lino von. II. Título. CDU: 615.322: 582.998.2 Bibliotecária responsável: Margarida Maria C. F. Ferreira-CRB10/480 iv "A mente que se abre a uma nova idéia jamais voltará ao seu tamanho original" (Albert Einstein) v vi Agradecimentos À Profa. Dra. Gilsane Lino von Poser (a Gil) pela orientação, amizade, carinho, confiança e estímulo para ir além As minhas queridas colegas Paulinha, Dani Fritz, Carol e Dani Albring pelos momentos inesquecíveis de trabalho, companheirismo e amizade cultivados neste tempo em que passamos juntas As amigas, bolsistas e futuras farmacêuticas Ju, Kênia, Simone e Bruna pela paciência, empenho e interesse Ao Prof. Dr. Alexandre Ferraz, pelo incentivo, colaboração, apoio e amizade Aos colegas e amigos Ana Lúcia, Camila, Marina, Paulinho, Leo, Dudu, Rogério, Tati, Melissa, Nael e Raquel pela parceria e momentos de descontração Aos professores deste Curso de Pós-Graduação pelos ensinamentos passados Ao CNPQ, pelo apoio financeiro Ao botânico Prof Dr. Nelson Matzembacker pela coleta e identificação das espécies em estudo À Profa. Dra. Suzana Zacchino e ao laboratório de microbiologia da Faculdade de Ciências Bioquímicas e Farmacêuticas da Universidade Nacional de Rosário (Rosário, Argentina) pelos ensaios de atividade antifúngica realizados Ao botânico e farmacêutico Luis Fernando Paiva Lima pela coleta e identificação das espécies e colaboração nos estudos taxonômicos do gênero Ao Prof. Dr. Jan Schripsema da Universidade Estadual do Norte Fluminense (RJ), pela obtenção dos espectros de RMN de 1H e 13C À Faculdade de Farmácia da Universidade de Picardie Jules Verne (Amiens, França) pela disponibilização de equipamento para obtenção dos espectros de RMN de 1H e 13C À Simone, ao Caiçara e à Luana pelo carinho, amizade e acolhida À Nina e ao Artur, que mesmo à distância, sempre me incentivaram As minhas grandes e inseparáveis amigas Déia, Fran e Márcia que sempre apoiaram e me deram força para chegar até aqui Ao meu Lucas, pelo carinho e amor, e por ser um constante exemplo de força e determinação para seguir adiante Aos meus manos Ale, Ange e Renan, por tudo. Aos meus pais, pela vida, dedicação, amor e apoio incondicionais, e por serem meu admirável exemplo de vida a seguir. vii SUMÁRIO 1. INTRODUÇÃO................................................................................................... 12 2. OBJETIVOS....................................................................................................... 16 3. REVISÃO BIBLIOGRÁFICA............................................................................... 18 3.1 ASPECTOS BOTÂNICOS................................................................................ 19 3.1.1 Taxonomia..................................................................................................... 19 3.1.2 Morfologia...................................................................................................... 21 3.1.2.1 Gênero Pterocaulon................................................................................... 21 3.1.2.1.1 Pterocaulon alopecuroides...................................................................... 22 3.1.2.1.2 Pterocaulon polystachyum...................................................................... 24 3.1.2.1.3 Pterocaulon balansae……………………………………………………….. 24 3.2 ASPECTOS ETNOFARMACOLÓGICOS........................................................ 27 3.3 ASPECTOS BIOLÓGICOS E FARMACOLÓGICOS....................................... 28 3.3.1 Atividade antimicrobiana............................................................................... 28 3.3.2 Atividade antiviral.......................................................................................... 29 3.3.3 Atividades citotóxica e antiproliferativa......................................................... 29 3.3.4 Atividade inseticida....................................................................................... 31 3.3.5 Outras atividades investigadas..................................................................... 31 3.4 COMPOSIÇÃO QUÍMICA DE ESPÉCIES DE PTEROCAULON..................... 32 3.5 ASPECTOS QUIMIOTAXONÔMICOS............................................................. 42 3.6 CUMARINAS.................................................................................................... 43 3.6.1 Aspectos químicos........................................................................................ 43 3.6.2 Propriedades farmacológicas das cumarinas............................................... 44 3.6.2.1 Atividade antimicrobiana............................................................................ 44 3.6.2.2 Atividade antiinflamatória........................................................................... 45 3.6.2.3 Atividade antitumoral.................................................................................. 45 3.6.2.4 Fototoxicidade............................................................................................ 46 3.6.2.5 Outras atividades....................................................................................... 47 3.6.2.6 O papel das cumarinas como fitoalexinas.................................................. 48 4. MATERIAL E MÉTODOS................................................................................... 50 4.1 MATERIAL VEGETAL...................................................................................... 51 4.2 SOLVENTES E REAGENTES......................................................................... 51 4.3 PREPARAÇÃO DOS EXTRATOS................................................................... 52 viii 4.3.1 Extratos para análise do perfil cromatográfico das espécies de Pterocaulon........................................................................................................... 52 4.3.2 Extratos para análise fitoquímica.................................................................. 52 4.3.3 Extratos para análise da atividade antifúngica.............................................. 53 4.3.3.1 Preparação dos extratos brutos................................................................. 53 4.3.3.2 Preparação das frações............................................................................. 53 4.4 ANÁLISE CROMATOGRÁFICA....................................................................... 53 4.4.1 Extratos diclorometano de superfície foliar................................................... 53 4.4.2 Extratos submetidos a avaliação da atividade antifúngica............................ 54 4.5 ISOLAMENTO E IDENTIFICAÇÃO DAS SUBSTÂNCIAS............................... 54 4.5.1 Métodos cromatográficos empregados para o isolamento........................... 54 4.5.2 Elucidação estrutural..................................................................................... 54 4.6 AVALIAÇÃO DA ATIVIDADE ANTIFÚNGICA.................................................. 55 4.6.1 Microorganismos e meios............................................................................. 55 4.6.2 Testes de susceptibilidade antifúngica............................................................ 55 5. RESULTADOS E DISCUSSÃO............................................................................ 57 5.1 ANÁLISE QUÍMICA............................................................................................. 58 5.1.1 Análise e isolamento das substâncias............................................................. 58 5.1.1.1 P. alopecuroides .......................................................................................... 58 5.1.1.2 P. polystachyum............................................................................................ 59 5.1.1.3 P. balansae…………………………………………………………………......... 59 5.1.2 Identificação das cumarinas…………………………………….......................... 59 5.1.2.1 P. alopecuroides........................................................................................... 60 5.1.2.1.1 Composto PA1 .........................................................………………………. 60 5.1.2.1.2 Composto PA2..........................................................................................
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