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Universidade Federal Do Ceará Centro De Ciências Departamento De Bioquímica E Biologia Molecular Programa De Pós-Graduação Em Bioquímica UNIVERSIDADE FEDERAL DO CEARÁ CENTRO DE CIÊNCIAS DEPARTAMENTO DE BIOQUÍMICA E BIOLOGIA MOLECULAR PROGRAMA DE PÓS-GRADUAÇÃO EM BIOQUÍMICA PROSPECÇÃO MOLECULAR E ANÁLISE FUNCIONAL DE SHORT- PEPTIDES VEGETAIS THIAGO LUSTOSA JUCÁ FORTALEZA-CE Abril de 2014 iii THIAGO LUSTOSA JUCÁ PROSPECÇÃO MOLECULAR E ANÁLISE FUNCIONAL DE SHORT- PEPTIDES VEGETAIS Tese apresentada ao Departamento de Bioquímica e Biologia Molecular da Universidade Federal do Ceará, como parte dos requisitos para obtenção do título de Doutor em Bioquímica. Área de concentração: Bioquímica Vegetal. Orientador: Prof. Dr. Márcio Viana Ramos Co-Orientadora: Profa. Dra. Ana Cristina de Oliveira Monteiro Moreira FORTALEZA-CE Abril de 2014 ii iii PROSPECÇÃO MOLECULAR E ANÁLISE FUNCIONAL DE SHORT- PEPTIDES VEGETAIS Tese apresentada ao Departamento de Bioquímica e Biologia Molecular da Universidade Federal do Ceará, como parte dos requisitos para obtenção do título de Doutor em Bioquímica. Área de concentração: Bioquímica Vegetal. Tese aprovada em: 03 / 04 / 2014. BANCA EXAMINADORA Prof. Dr. Márcio Viana Ramos (Orientador) Universidade Federal do Ceará (UFC) Profa. Dra. Ana Cristina de Oliveira Monteiro Moreira (Co-Orientadora) Universidade de Fortaleza (UNIFOR) Prof. Dr. Edilberto Rocha Silveira (Examinador) Universidade Federal do Ceará (UFC) Prof. Dr. Cleverson Diniz Teixeira de Freitas (Examinador) Universidade Federal do Ceará (UFC) Profa. Dra. Patrícia Maria Guedes Paiva (Examinadora) Universidade Federal de Pernanbuco (UFPE) iii DEDICATÓRIA Dedico esta tese à minha família (“Jucá e Cunha”), pelo apoio incondicional! Em especial, gostaria de dedicar à minha esposa Muciana, pelo amor incondicional, pela leitura e correção minuciosa da escrita da tese, e a meus dois tesouros: Ana Beatriz e Ana Alice, amos vocês! iv AGRADECIMENTOS INSTITUCIONAIS Este trabalho foi realizado com o suporte das seguintes instituições: . Universidade Federal do Ceará (UFC): - Através do Laboratório de Plantas Laticíferas, coordenado pelo Professor Dr. Márcio Viana Ramos, do Departamento de Bioquímica e Biologia Molecular. - Através do Centro Nordestino de Aplicação e Uso da Ressonância Magnética Nuclear, coordenado pelo Dr. Professor Edilberto Rocha Silveira, do Departamento de Química Orgânica e Inorgânica. Universidade de Fortaleza (Unifor): - Através do Laboratório de Desenvolvimento de Fármacos, coordenado pela Professora Dra. Ana Cristina de Oliveira Monteiro Moreira e pelo Professor Dr. Renato Azevedo Moreira do Centro de Ciências da Saúde; . Instituto de Física de São Carlos (USP): - Na pessoa da Professora Dra. Leila Maria Beltramini e do Dr. José Luiz de Souza Lopes, do grupo de Biofísica Molecular Sérgio Mascarenhas; . Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES) . Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq) v AGRADECIMENTOS PESSOAIS Ao meu orientador, Professor Márcio Viana Ramos. Aceitou orientar-me quando eu pensava seriamente em desistir do doutorado. Aceitou e apoiou incondicionalmente a idéia de trabalhar com peptídeos vegetais de plantas laticíferas. Gostaria de agradecer o voto de confiança depositado em mim e no meu trabalho, e dizer que nesses quase quatros anos de convívio, eu encontrei exatamente aquilo que eu buscava em um orientador, daí minha admiração e respeito. Muito obrigado! À Professora Ana Cristina Monteiro Moreira por ter recebido de braços abertos no seu laboratório, até então, “um estranho”. A professora Cristina não só me deu oportunidades (sem medir esforços), como me inseriu na família do Bloco F e do laboratório F-66. Ao professor Renato Moreira, uma figura adimirável, sempre disposto a ajudar e a ensinar. Para mim foi uma honra ter o convívio diário desses dois professores e ter presenciado bem de perto a chegada do Dudu. Muito obrigado! Ao Professor Edilberto Rocha Silveira, por ter me recebido tão bem em seu laboratório, sendo sempre muito solícito. É um exemplo de dedicação para com seus alunos e com a Universidade Federal do Ceará; Ao professor Cleverson Diniz Teixeira de Freitas por gentilmente aceitar participar da banca examinadora deste trabalho de doutorado. Obrigado pelas importantes considerações para a melhoria deste trabalho; À professora Patrícia Maria Guedes Paiva por gentilmente aceitar participar da banca examinadora deste trabalho de doutorado; À Professora Leila Maria Beltramini e ao Dr. José Luiz de Souza Lopes pelo suporte experimental nos experimentos de dicroísmo circular; Aos amigos do F66: Frederico Moreno (peça chave, sem a qual esta tese não aconteceria, por ter me dado oportunidades e ensinado bastante); Felipe Sousa (pela amizade sólida, apoio e grande ajuda nesses quase quatro anos de doutorado); Leonardo Primo (pelo apoio e grande amizade); Marina Lobo (Pelo ótimo convívio, pessoa do bem, sempre solícita e disposta a ajudar); Antônio Neto (Pela amizadae, apoio, um cara 10); Célio Ribeiro (Pela vi amizade e ótimo convívio); Igor Sá (Pela amizade e ajuda); Márcio Cavalcante, Pedrinha Vasconcelos e Vinícius Oliveira (Pessoas do bem, obrigado pelo ótimo convívio). O meu muito obrigado às funcionárias do F-66 (Patrícia, Lia e Gil); À Carolina Viana, amiga desde os tempos de graduação passando pela pós-graduação, se mostrou muito presente e ajudou bastante durante o doutorado. À Bárbara Jéssica pela ajuda nos ensaios antifúngicos. À Patrícia Coelho e Nayara Coriolano, estudantes da Química, pela grande ajuda nos experimentos de RMN. Aos amigos Jefferson Oliveira e Edvar Júnior, pela grande amizade e mais uma vez pelas correções e sugestões na redação desta tese. Ao amigo Fabiano Texeira, por estar sempre presente nesses quatro anos e sempre ajudando da maneira que era possível. Ao Fábio Nogueira, amigo que sempre contribui bastante para minha formação científica e que nunca deixou de colaborar e estar disponível. Aos professores do Departameto de Bioquímica que contribuíram com minha formação acadêmica durante todos esses anos. Muito obrigado! vii “Nossas atitudes, nossa imaginária auto-importância, a ilusão de que nós temos alguma posição privilegiada no universo é desafiada por um pálido ponto azul chamado Terra, localizada na envolvente e grande escuridão cósmica.” Pálido ponto azul, 1994. Carl Sagan viii RESUMO Prospecção molecular e análise funcional de short-peptides vegetais Um número crescente de peptídeos isolados a partir dos mais diversos tecidos vegetais tem destacado essas moléculas como alvo potencial de estudo. Estes peptídeos apresentam uma grande diversidade funcional e, por isso, vem sendo descritos frequentemente na literatura científica dos últimos anos. No presente trabalho são relatadas a prospecção molecular e caracterização funcional de “short-peptides” vegetais. Inicialmente, o látex de Calotropis procera foi particionado, gerando cinco frações: hexânica (49,4%), diclorometano (5,2%), acetato de etila (2,0%), butanólica (2,1%) e aquosa (41,1%) (Capítulo 1). O perfil fitoquímico e as análises espectroscópicas mostraram que a fração diclorometano foi quimicamente a mais heterogênea. As frações diclorometano e acetato de etila apresentaram toxicidade in vitro contra linhagens de células tumorais (DL50 variando de 0,05 a 3,9 µg/mL) e, in vivo, contra o crustáceo Artemia salina (DL50 variando de 10,9 a 65,7 µg/mL). Estas mesmas frações apresentaram atividade antiinflamatória no modelo de peritonite induzida por carragenana em ratos, associadas a uma inibição da migração de neutrófilos de 67% (diclorometano) e 56% (acetato de etila). A reação positiva com tolidina e ninidrina sugere a presença de ciclopeptídeos na fração bioativa acetato de etila. No Capítulo 2, vinte e uma sequências primárias de peptídeos, oriundas da fração 1 de sementes de Jatropha curcas, foram deduzidas por meio de sequenciamento de novo e confirmadas através de buscas contra um banco de dados genômico de Jatropha. A comparação do padrão de fragmentação por MS/MS entre o íon duplamente carregado de m/z de 671,79, presente nas frações 1 e PII-C, e um peptídeo sintético, análogo àquele, mostrou que o uso de passos analíticos adicionais para a identificação e caracterização destes peptídeos não seria necessário. A ferramenta de busca BlastP mostrou que a sequência APTLSGGSVPRDAD apresenta homologia e está inserida no domínio conservado das proteínas de embriogênese tardia (LEA_6). No Capítulo 3, os dois peptídeos sintéticos análogos, linear (1342,44 g/mol) e cíclico (1324,44 g/mol), obtidos por síntese química em fase sólida, mostraram diferenças que caracterizam seus arranjos, quando comparados pelo padrão de fragmentação por MS/MS e mobilidade iônica. O estado de carga e o tempo de retenção foram similares, do ponto de vista físico- químico. Os estudos de dicroísmo circular mostraram a presença de um estado desordenado para os peptídeos. Os ensaios biológicos com os peptídeos não revelam sinais aparentes de atividade funcional, porém não se pode descartar a possibilidade de que modelos biológicos adicionais sejam testados. Os resultados advindos deste estudo geram novas perspectivas e servem de base para a realização de trabalhos subsequentes que tratem do isolamento e caracterização de peptídeos nas espécies Calotropis procera e Jatropha curcas. Palavras-chaves: Peptídeos vegetais; Calotropis procera; látex; Jatropha curcas, sementes. ix ABSTRACT Molecular prospecting and functional characterization of plant short-peptides An increasing number of peptides isolated from a range of tissue plants have highlighted these molecules as a potential study target. Those peptides demonstrate
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