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Universidade Federal De Ouro Preto Escola De Farmácia Pós-Graduação Em Ciências Farmacêuticas Química E Farmacologia De Substâncias Bioativas E Medicamentos

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Universidade Federal De Ouro Preto Escola De Farmácia Pós-Graduação Em Ciências Farmacêuticas Química E Farmacologia De Substâncias Bioativas E Medicamentos UNIVERSIDADE FEDERAL DE OURO PRETO ESCOLA DE FARMÁCIA PÓS-GRADUAÇÃO EM CIÊNCIAS FARMACÊUTICAS QUÍMICA E FARMACOLOGIA DE SUBSTÂNCIAS BIOATIVAS E MEDICAMENTOS ESTÊVÃO AUGUSTO MAIA AMÂNCIO ESTUDO FITOQUÍMICO DE EXTRATOS ETANÓLICOS DE ESPÉCIES DO GÊNERO JACARANDA (BIGNONIACEAE) OCORRENTES NO ESTADO DE MINAS GERAIS E AVALIAÇÃO DA ATIVIDADE CITOTÓXICA. OURO PRETO - MG 2019 ESTÊVÃO AUGUSTO MAIA AMÂNCIO ESTUDO FITOQUÍMICO DE EXTRATOS ETANÓLICOS DE ESPÉCIES DO GÊNERO JACARANDA (BIGNONIACEAE) OCORRENTES NO ESTADO DE MINAS GERAIS E AVALIAÇÃO DA ATIVIDADE CITOTÓXICA. Dissertação apresentada ao Programa de Pós-graduação em Ciências Farmacêuticas CIPHARMA da Universidade Federal de Ouro Preto, como requisito parcial para obtenção do título de mestre em Ciências Farmacêuticas. Orientador: Prof. Dr. Geraldo Célio Brandão OURO PRETO - MG 2019 A484e Amâncio, Estêvão Augusto Maia. Estudo fitoquímico de extratos etanólicos de espécies do gênero Jacaranda (Bignoniaceae) ocorrentes no Estado de Minas Gerais e avaliação da atividade citotóxica. [manuscrito] / Estêvão Augusto Maia Amâncio. - 2019. 162f.: il.: color; grafs; tabs. Orientador: Prof. Dr. Geraldo Célio Brandão. Dissertação (Mestrado) - Universidade Federal de Ouro Preto. Escola de Farmácia. Departamento de Farmácia. Programa de Pós-Graduação em Ciências Farmacêuticas. Área de Concentração: Fármacos e Medicamentos. 1. Flavonoides. 2. Citotoxicidade. 3. Compostos fenólicos. 4. Jacaranda. I. Brandão, Geraldo Célio. II. Universidade Federal de Ouro Preto. III. Titulo. CDU: 615.3 Catalogação: www.sisbin.ufop.br Dedico este trabalho aos familiares em especial meus pais, Gisele, Samuel e aos amigos que sempre me incentivaram nesta caminhada. AGRADECIMENTOS Agradeço inicialmente a meus pais por terem investido em minha educação e este é o legado mais importante que podemos deixar para nossos descendentes. Muito obrigado a todos os familiares sejam os de sangue ou escolhidos por opção, em especial a minha esposa Gisele que, diante das dificuldades enfrentadas devido a minhas escolhas, sempre deu o suporte necessário para mais esta conquista pessoal; muitas vezes a minha ausência é unicamente pensando no futuro do nosso maior tesouro chamado Samuel, um dia espero ser compreendido por todos vocês. Ao orientador desta pesquisa o Prof. Dr. Geraldo Célio Brandão, pela orientação prestada, pelas correções, incentivo, disponibilidade e apoio que sempre demonstrou e principalmente por entender minhas ausências justificadas pelo trabalho e família. Um salve a todos os amigos e que de uma forma direta ou indireta, contribuíram, ou auxiliaram na elaboração do presente estudo. Sejam os amigos do Laboratório de Química Medicinal e Bioensaios por ajudarem a dividir o fardo de pesquisar no Brasil com recursos mínimos e improvisações, aliado as boas risadas do convívio diário. Aos colegas da Firma (PRF) pelas trocas de plantão para que eu conseguisse assistir as aulas e realizar os experimentos. Aos amigos e companheiros de corrida conquistados nos últimos anos por serem minha válvula de escape realizando uma atividade física e conseguindo manter um pouco de sanidade nessa vida louca. Por fim aos amigos de infância e de boteco por compreenderem minha ausência, especialmente nesses últimos 2 anos. Agradecimento especial as agências de fomento FAPEMIG, CAPES, CNPq, PROPP- UFOP pelo aporte financeiro e ao CIPHARMA/UFOP pela oportunidade de qualificação profissional. Por último e não menos importante que os demais, agradeço a Deus por ser minha fonte de apego quando tudo parecia perdido. Uma pessoa que tem fé e acredita em algo superior consegue suportar melhor os percalços da vida. Enfim, quero demonstrar o meu agradecimento, a todos aqueles que, de um modo ou de outro, tornaram possível a realização da presente dissertação. Com vocês, queridos, divido a alegria desta experiência, deixando o meu sincero e profundo muito obrigado! “Navegar é preciso se não a rotina te cansa…” (O Rappa) RESUMO Extratos de plantas são matrizes complexas compostas por diferentes tipos de metabólitos bioativos, dos quais se destacam os agentes anticancerígenos. O gênero Jacaranda é bem conhecido por seu uso na indústria madeireira e como plantas ornamentais. Além disso, na medicina, espécies de Jacaranda têm sido tradicionalmente utilizadas no tratamento de afecções da pele, doenças venéreas, leishmanioses, resfriados, reumatismo e também são utilizadas no tratamento de diversos tipos de câncer. Oito espécies do gênero Jacaranda (J. brasiliana, J. caroba, J. cuspidifolia, J. macrantha, J. micrantha, J. mimosifolia, J. paucifoliata e J. puberula), colhidas no estado de Minas Gerais – Brasil, tiveram suas partes anatômicas utilizadas na preparação de extratos brutos e analisadas em triagem fitoquímica preliminar por cromatografia de camada delgada (CCD). Os extratos etanólicos foram caracterizados por cromatografia líquida de alta eficiência acoplada à detecção de arranjo de diodos (CLAE-DAD) e Cromatografia de ultra eficiência acoplada a espectrometria de massas (CLUE-EM) com técnica de ionização por eletropulverização (ESI). Além disso, a citotoxicidade dos extratos etanólicos foi avaliada nas linhagens celulares MRC-5, HeLa, Hep G2 e TOV-21G pelo método colorimétrico do MTT. A técnica CLUE/DAD/ESI/EM resultou na identificação de oito feniletanoides como verbascosídeo e derivados, além de quatorze flavonoides, como quercetina, naringenina, luteolina, apigenina, bem como seus derivados glicosilados. Dos quinze extratos etanólicos testados, oito apresentaram atividade citotóxica (CC50) significativa nas linhagens celulares testadas. Também foi detectada uma redução moderada da viabilidade das células tumorais testadas em comparação à linhagem celular normal (MRC-5), especialmente para as linhagens HeLa, HepG2 e TOV-21G. Em conclusão, os dados sugerem que alguns dos extratos etanólicos estudados de espécies de Jacaranda podem ser potenciais fontes de substâncias com atividade antineoplásicas. Estudos futuros envolvendo o fracionamento desses extratos e isolamento de substâncias ativas, bem como ensaios in vivo e testes clínicos, poderão prover informações para a elucidação dos mecanismos de ação e emprego dos mesmos como fármacos anticancerígenos. Palavras chave: feniletanoides, flavonoides, CLAE-DAD-ESI/EMn, citotoxicidade, MTT, Jacaranda. ABSTRACT Plant extracts are complex matrices composed by different types of bioactive metabolites, especially anticancer agents. The genus Jacaranda is well known for its use in the timber industry and as an ornamental plant. Furthermore, in medicine, Jacaranda species have been traditionally used in the treatment of skin infections, venereal diseases, common colds, leishmaniasis, rheumatism, besides several types of cancer. Eight species of the genus Jacaranda (J. brasiliana, J. caroba, J. cuspidifolia, J. macrantha, J. micrantha, J. mimosifolia, J. paucifoliata and J. puberula), were collected in the State of Minas Gerais - Brazil, They had their anatomical parts used in the preparation of crude extracts and analyzed in preliminary phytochemical screening by thin layer chromatography (TLC). The ethanolic extracts were characterized by high performance liquid chromatography coupled with detector diode array (HPLC-DAD) and ultra high-performance liquid chromatography coupled to mass spectrometry (UPLC-MS) with electrospray ionization (ESI) technique. In addition, the cytotoxicity of the ethanolic extracts was evaluated in MRC-5, HeLa, Hep G2 and TOV-21G cell lines through the MTT colorimetric assay. The technique UPLC/DAD/ESI/MS resulted in the identification of eight phenylethanoids as verbascoside and derivatives, as well fourteen flavonoids, such as quercetin, naringenin, luteolin, apigenin and glycosylated derivatives. Eight ethanolic extracts tested, presented significant cytotoxic activity (CC50) in the cell lines. A moderate reduction in viability of the tumor cells tested compared to the normal cell line (MRC-5) was also detected, especially for tumor cells lines HeLa, HepG2 and TOV-21G. In conclusion, the data suggest that some ethanolic extracts studied of Jacaranda species can be potential sources of substances with antineoplastic activities. Additional studies involving the fractionation of these extracts and isolation of active substances, as well as in vivo and clinical assays, will be able to provide information towards the elucidation of their mechanism of action and usage as anticancer drugs. Keywords: Phenylethanoids, flavonoids, UPLC-DAD-ESI/MS, cytotoxicity, MTT, Jacaranda. LISTA DEFIGURAS Figura 1: Jacaranona e verbascosídeo ........................................................................... 14 Figura 2: Triterpenos isolados de J. mimosifolia.......................................................... 15 Figura 3: Flavonoides encontrados em J. decurrens ..................................................... 15 Figura 4: Triterpenos isolados de J. decurrens ............................................................. 16 Figura 5: Todos os novos medicamentos aprovados no período de 1981-2014 ........... 16 Figura 6: O que é o câncer? ........................................................................................... 19 Figura 7: Características do câncer revisadas ................................................................ 20 Figura 8: Distribuição proporcional dos dez tipos de câncer mais incidentes estimados para 2018 por sexo, exceto pele não melanoma ............................................................. 21 Figura 9: Jacaranda caroba – A. ramo com
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