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Universidade Federal Da Paraíba UNIVERSIDADE FEDERAL DA PARAÍBA CENTRO DE CIÊNCIAS DA SAÚDE LABORATÓRIO DE TECNOLOGIA FARMACÊUTICA PROGRAMA DE PÓS-GRADUAÇÃO EM PRODUTOS NATURAIS E SINTÉTICOS BIOATIVOS HARLEY DA SILVA ALVES NOVOS FLAVONÓIDES MONOTERPÊNICOS E OUTROS CONSTITUINTES QUÍMICOS ISOLADOS DE ESPÉCIES DE Piper (PIPERACEAE) JOÃO PESSOA – PB 2008 HARLEY DA SILVA ALVES NOVOS FLAVONÓIDES MONOTERPÊNICOS E OUTROS CONSTITUINTES QUÍMICOS ISOLADOS DE ESPÉCIES DE Piper (PIPERACEAE) Tese Apresentada ao Programa de Pós-Graduação em Produtos Naturais e Sintéticos Bioativos do Laboratório de Tecnologia Farmacêutica, Universidade Federal da Paraíba, como requisito para a obtenção do título de Doutor em Produtos Naturais e Sintéticos Bioativos, área de concentração Farmacoquímica. ORIENTADORA: PROFa. Dra. MARIA CÉLIA DE OLIVEIRA CHAVES João Pessoa – PB 2008 A474n Alves, Harley da Silva. Novos flavonóides monoterpênicos e outros constituintes químicos isolados de espécies de Piper(PIPERACEAE) / Harley da Silva Alves. - - João Pessoa : [s.n.], 2008. 325 f : il. Orientadora: Maria Célia de Oliveira Chaves. Tese (Doutorado) – UFPB /CCS. 1.Produtos naturais. 2.Farmoquímica. 3.Piper(PIPERACEAE). UFPB/BC CDU: 547.9(043) HARLEY DA SILVA ALVES NOVOS FLAVONÓIDES MONOTERPÊNICOS E OUTROS CONSTITUINTES QUÍMICOS ISOLADOS DE ESPÉCIES DE Piper (PIPERACEAE) BANCA EXAMINADORA Profª. Dra. Maria Célia de Oliveira Chaves (Universidade Federal da Paraíba) Orientadora Profª Dra. Márcia Ortiz Mayo Marques (Instituto Agronômico de Campinas-SP) Examinadora externa Profa Dra. Danielly Albuquerque da Costa (Universidade Federal de Campina Grande-PB) Examinadora externa Profª. Dra. Maria de Fátima Vanderlei de Souza (Universidade Federal da Paraíba) Examinadora interna Profª. Dra. Antonia Lúcia de Souza (Universidade Federal da Paraíba) Examinadora interna A meus pais e irmãos pelo incondicional e inigualável desvelo e apoio que sempre me ofereceram e são, sem dúvida alguma, co- responsáveis por mais esse êxito: Carlos, Edna, Hussein, Hoardy e Carolina. A Fernanda Fernandes, pelo carinho e compreensão depositada, em virtude da distância que se fez necessária nesta caminhada. Ao povo brasileiro. AGRADECIMENTOS A professora Maria Célia de Oliveira Chaves, não apenas pelos ensinamentos científicos e éticos que serão de total proveito em toda a minha carreira acadêmica, mas também por me mostrar uma paixão pela ciência que se vê em poucos, motivada mesmo diante das condições precárias que se é fazer pesquisa no país A todos os meus professores da pós-graduação que passaram parte de seus saberes para a edificação de minha intelectualidade. A meus tios e primos que me acolheram por um bom tempo e me trataram como um igual: Edmar, Salete, Bruno, Viviane e Lorena. A todos os meus colegas e agora amigos de turma e de laboratório, que unidos se ajudam a superar o drama existencial que, creio eu, aflige boa parte das pessoas que fazem pós-graduação: Irinaldo, Jackson, Karla, Aldeídia, Enrique, Juliannely, Túlio, Rossana, Raissa, Josimar, Rita, Josean, Roosevelt, Rafael, Marcelo, George, Caroline, Danielle, Anna Claúdia, Gabriela, Roberto, Kristerson, Ticiano, Antonio, Kiriaki, Ionaldo, Xirley, Marcílio, Wermesson, Fernando e Alessandra. Ao amigo, que mesmo longe, foi um idealizador junto comigo dessa empreitada: Fabiano. A Stanley Juan Chávez, novo amigo e que me auxiliou em algumas reações químicas e nas ―broncas‖ do computador (tem que formatar!!!). Aos professores da banca de qualificação que contribuíram no engrandecimento dessa tese: Profo. Davi Antas e Silva, Profa. Maria de Fátima Vanderlei de Souza e Profa. Antonia Lúcia de Souza. Ao Profo. José Maria Barbosa Filho pela disposição em contribuir com esse trabalho científico. Ao Profo. Edilberto, Daniel, Renata e ao CENAUREMN pela obtenção de espectros de RMN e acolhimento na UFC. Aos técnicos do LTF que são essenciais no andamento de nossas pesquisas: Vicente Carlos, Sócrates Golzio, Alexsandro, Ataíde, Wellington e Nonato. A Maria das Graças Zoghbi e Sr. Ferdinando pelo fornecimento do material botânico. Ao professor Raimundo Braz Filho pelo auxílio na elucidação de alguns compostos. Aos professores Celso Câmara e Tânia Sarmento pela disponibilidade de reagentes. Aos professores do Departamento de Fisiologia e Patologia, pela convivência agradável, em especial a professora Regina. A todos os meus amigos e familiares que além de me apoiarem, apesar da enorme distância que se fez entre nós nesses últimos anos, em virtude da falta de tempo que se acomete, não me fizeram esquecer que existe vida do outro lado da muralha da Universidade. Todos sempre se fazem presente em minha mente. A todos os outros funcionários do LTF, principalmente àqueles que tentam fazer a ―máquina andar‖. A todos que de alguma forma contribuíram na elaboração desse projeto científico. Ao CNPq, pelo auxílio na forma de bolsa de pesquisa. SUMÁRIO LISTA DE ABREVIATURAS, FÓRMULAS E SÍMBOLOS.............................................. V LISTA DE FIGURAS............................................................................................................ VII LISTA DE QUADROS.......................................................................................................... XX LISTA DE ESQUEMAS........................................................................................................ XXI LISTA DE TABELAS........................................................................................................... XXII RESUMO............................................................................................................................... XXV ABSTRACT........................................................................................................................... XXVI 1 - INTRODUÇÃO................................................................................................................ 1 2 – OBJETIVOS..................................................................................................................... 8 2.1 – Geral............................................................................................................................... 9 2.2 – Específicos..................................................................................................................... 9 3 – FUNDAMENTAÇÃO TEÓRICA................................................................................... 10 3 – Aspectos botânicos............................................................................................................ 11 3.1 – Ordem Piperales............................................................................................................. 11 3.2 – Descrição botânica da família Piperaceae Baill............................................................. 11 3.3 – Gênero Piper Linnaeus.................................................................................................. 12 3.4 – Distribuição geográfica de espécies da família Piperaceae no mundo.......................... 13 3.5 – Classificação taxonômica das espécies de piper estudadas nesta pesquisa, segundo Cronquist (1946)..................................................................................................................... 13 3.6 – Considerações sobre Piper carniconnectivum C. DC.................................................... 14 3.7 – Constituintes químicos isolados de Piper glandulosissimum........................................ 15 3.8 – Constituintes químicos isolados de Piper montealegreanum........................................ 16 4 – COMPOSTOS FENÓLICOS: CONSIDERAÇÕES GERAIS......................................... 17 4.1 – Flavonóides.................................................................................................................... 19 4.1 – Conceitos gerais............................................................................................................. 19 4.1.2 – Distribuição e localização........................................................................................... 20 4.1.3 – Importância dos flavonóides para os vegetais............................................................ 20 4.1.4 – Atividades biológicas dos flavonóides....................................................................... 21 4.1.5 – Aspectos químicos...................................................................................................... 22 4.1.6 – Classes dos flavonóide............................................................................................... 25 4.1.7 - Possível rota biossintética para os flavonóides........................................................... 27 4.2 – Flavonóides isolados no gênero Piper........................................................................... 32 4.2.1 – Diidrochalconas (1) e chalconas (2)........................................................................... 32 4.2.2 - Flavanonas (3)……………………............................................................................ 38 4.2.3 – Flavonas (4)................................................................................................................ 41 4.3 - Flavonoides monoterpênicos ......................................................................................... 44 4.4 – Espectrometria de massas de flavonóides..................................……..……………...... 45 4.5 - Considerações sobre as outras classes de constituintes químicos isolados de Piper montealegreanum e Piper carniconnectivum ........................................................................ 47 4.5.1
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