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TATIANA ZUCCOLOTTO.Pdf UNIVERSIDADE FEDERAL DO PARANÁ TATIANA ZUCCOLOTTO IDENTIFICAÇÃO DE CONSTITUINTES QUÍMICOS DE Baccharis organensis BAKER E AVALIAÇÃO DAS ATIVIDADES BIOLÓGICAS DOS EXTRATOS E FRAÇÕES DAS PARTES AÉREAS DE Baccharis aracatubaensis MALAG. E Baccharis organensis BAKER (ASTERACEAE) CURITIBA 2017 TATIANA ZUCCOLOTTO IDENTIFICAÇÃO DE CONSTITUINTES QUÍMICOS DE Baccharis organensis BAKER E AVALIAÇÃO DAS ATIVIDADES BIOLÓGICAS DOS EXTRATOS E FRAÇÕES DAS PARTES AÉREAS DE Baccharis aracatubaensis MALAG. E Baccharis organensis BAKER (ASTERACEAE) Tese apresentada ao Programa de Pós-Graduação em Ciências Farmacêuticas, Área de Insumos, Medicamentos e Correlatos, Setor de Ciências da Saúde, Universidade Federal do Paraná, como requisito parcial à obtenção do título de Doutor em Ciências Farmacêuticas. Orientador: Prof. Drª Francinete Ramos Campos CURITIBA 2017 Zuccolotto, Tatiana Identificação de constituintes químicos de Baccharis organensis Baker e avaliação das atividades biológicas dos extratos e frações das partes aéreas de Baccharis aracatubaensis Malag. e Baccharis organensis Baker (Asteraceae) / Tatiana Zuccolotto - Curitiba, 2017. 189 f. : il. (algumas color.) ; 30 cm Orientadora: Professora Dra. Francinete Ramos Campos Tese (doutorado) – Programa de Pós Graduação em Ciências Farmacêuticas, Setor de Ciências da Saúde. Universidade Federal do Paraná. Inclui bibliografia 1. Baccharis. 2. Antioxidante. 3. Óleos essenciais. 4. Terapêutica. 5. Espectrometria de massas. I. Campos, Francinete Ramos. II. Universidade Federal do Paraná. III. Título. CDD 615.321 “O valor das coisas não está no tempo que elas duram, mas na intensidade com que acontecem. Por isso, existem momentos inesquecíveis, coisas inexplicáveis e pessoas incomparáveis.” Fernando Pessoa AGRADECIMENTOS A Deus, por ter me dado o privilégio da realização deste trabalho, por sempre ter iluminado meu caminho e ter me dado forças para continuar e nunca desistir; Aos meus pais, Adair e Noely, pela confiança, carinho e dedicação. Por me mostrarem o significado de união, lealdade e honra; e por terem me dado todo o suporte e apoio nas minhas decisões. Amo-os incondicionalmente; À minha pequena Júlia, que sem saber ao certo, dividiu o tempo de convívio com a mãe e com esta tese. Obrigada pela alegria contagiante que me concede diariamente; Aos meus tios Décio e Suzete por me acolherem, acreditarem neste sonho e compartilharem momentos maravilhosos; À minha orientadora Profª Dra Francinete Ramos Campos. Foste muito mais que minha orientadora: uma grande amiga, companheira e incentivadora, mesmo nos momentos mais difíceis. Agradeço por todos os conselhos e pelos ensinamentos valiosos sobre a ciência e a vida; Ao Centro de Ressonância Magnética Nuclear da UFPR, em especial ao Prof. Dr. Andersson Barison pelos valiosos ensinamentos em RMN e à MSc. Lívia Dutra pela ajuda na elucidação das estruturas e pelas muitas análises de RMN; Ao Prof. Dr. Marcos José Salvador, do Instituto de Biologia Vegetal – UNICAMP, pelos ensinamentos e colaboração na realização das análises de CG-EM, ensaios de atividade antioxidante e por ter nos acolhidos no seu laboratório; Ao Prof. Dr. Fabio Seigi Murakami, do Laboratório de Controle de Qualidade II – UFPR, pelos ensinamentos e colaboração no teste de atividade antimicrobiana; À Prof. Dra. Jane Manfron Budel por sempre incentivar este trabalho e por todos os seus ensinamentos sobre Baccharis; Ao Prof. Dr. Roberto Pontarolo pelo apoio e por sempre incentivar a realização deste trabalho; Ao especialista em Baccharis, Dr. Gustavo Heiden, e ao Museu Botânico Municipal de Curitiba (MBM) pelo auxilio na identificação das espéciies; Aos amigos Allan, Elidiana, Estevan, Jane, Jaqueline, Letícia “black”, Leticia “white”, Paola e Rodrigo muito obrigada por estarem sempre presentes, seja cientificamente ou em programas improvisados, mas sempre tornando o trabalho muito melhor e mais divertido. É difícil lembrar de alguma situação onde vocês não se fizeram presentes. Ao meu amigo-irmão Estevan Bruginski, meu muito obrigada pela parceria, pela convivência e sobretudo, pela amizade. A todos os demais docentes do Departamento de Farmácia que contribuíram para minha formação; Ao Programa de Pós-Graduação em Ciências Farmacêuticas da UFPR por ter me concedido a oportunidade de crescimento profissional e pessoal; À CAPES (Coordenação de Aperfeiçoameno de Pessoal de Nível Superior) pela concessão da bolsa; Meus sinceros agradecimentos a todos que contribuíram direta ou indiretamente para a conclusão deste trabalho. Muito obrigada!! RESUMO Baccharis L. (Asteraceae) contém aproximadamente 400 espécies, sendo que 178 estão catalogadas no Brasil, principalmente nas regiões Sul, Sudeste e Centro-Oeste. Esse gênero tem sido descrito na literatura por apresentar várias propriedades biológicas, tais como atividade antioxidante, anti-inflamatória, citotóxica, leishmanicida, tripanocida, anti-hipertensiva, hipoglicemiante, diurética, digestiva e antimicrobiana. Tendo em vista o potencial terapêutico do gênero, o presente trabalho teve como objetivos caracterizar os constituintes químicos e avaliar as atividades antioxidante e antimicrobiana de B. aracatubaensis Malag. e B. organensis Baker. Os indivíduos masculinos e femininos, de ambas as espécies, foram coletados no município de Piraquara-PR, durante o período de floração. A partir do material botânico coletado foram separadas as inflorescências de B. aracatubaensis e B. organensis para extração do óleo essencial. Este foi obtido através de hidrodestilação em aparelho de Clevenger modificado e os constituintes químicos foram identificados por CG-EM. Foi possível identificar um total de 25 compostos para B. aracatubaensis e 32 para B. organensis. Os componentes majoritários (masc./fem.) de B. aracatubaensis foram -muuroleno (21,4/23,9%), biciclogermacreno (21,4/21,7%), - cariofileno (10,9/12,7%), -cadineno (6,6/8,2%) e limoneno (5,5% apenas para o indivíduo masculino). Já em B. organensis foram identificados como majoritários (masc./fem.), viridiflorol (23,0/11,9%), biciclogermacreno (15,2/15,1%), -muuroleno (6,8/10,4%), epiglobulol (7,4/6,4%). Os compostos -cadinol e curcufenol (7,5% e 5,9%, respectivamente) foram majoritários somente para os indivíduos masculinos de B. organensis. Os extratos brutos foram obtidos a partir da extração hidroalcoólica das folhas de B. aracatubaensis e B. organensis, sendo indivíduos masculinos (Ba-M e Bo-M) e femininos (Ba-F e Bo-F), respectivamente. A análise de espectros de RMN de 1H dos extratos masculinos e femininos, de ambas as espécies, apresentaram perfil químico muito semelhante. Assim os extratos Ba-F e Bo-F foram fracionados por procedimentos cromatográficos e as frações de Bo-F analisadas por técnicas de RMN de 1H e espectrometria de massas, resultando na identificação de 19 substâncias: 3- (3,4,5-trimetoxifenil)-prop-2-en-1-al, ácido trans-ferúlico, 1-etoxietil-3,5-dimetoxi-4- hidroxifenol, siringaldeído, cafeato de etila, cirsimaritina, hispidulina, apigenina, ácido trans-isoferúlico, ferulato de etila, ácido siríngico, ácido cafeico, álcool siríngico, 8- metoxi apigenina, cafeato de 4’-O--D-glucopiranosil-3’,5’-dimetoxibenzila, kaempferol, ácido 3,5-dicafeoilquínico, escopoletina e ácido tricafeoilquínico. Também foram realizadas avaliação in vitro das atividades antioxidante (DPPH e ORACFL) e antimicrobiana (técnica de microdiluição) dos óleos essenciais, extratos e frações de ambas as espécies. Todas as amostras apresentaram atividade antioxidante promissora. No ensaio antimicrobiano os extratos e frações apresentaram atividade que variou de moderada a fraca, entretanto, os óleos essenciais não apresentaram atividade antimicrobiana frente aos micro-organismos testados. Palavras-chave: Baccharis, atividade biológica, RMN, CG-EM, espectrometria de massas. ABSTRACT Baccharis L. (Asteraceae) contains approximately 400 species, of that 178 are cataloged in Brazil, mainly in the Sul, Sudeste, and Centro-Oeste regions. This genus has been described in the literature due the several biological properties, such as antioxidant, anti-inflammatory, cytotoxic, leishmanicidal, trypanocidal, antihypertensive, hypoglycemic, diuretic, digestive, and antimicrobial. Considering the therapeutic potential of the genus, the present work had as objectives to characterize the chemical constituents and to evaluate the antioxidant and antimicrobial activities of the B. aracatubaensis Malag. and B. organensis Baker. The male and female individuals of both species were collected in the municipality of Piraquara-PR, during the flowering period. The inflorescences of B. aracatubaensis and B. organensis were extracted to obtain the essential oils. The was obtained by hydrodistillation in a modified Clevenger apparatus and the chemical constituents were identified by GC- MS. It was possible to identify a total of 25 compounds for B. aracatubaensis and 32 for B. organensis. The major components (male / female) of B. aracatubaensis were - muurolene (21.4 / 23.9%), bicyclogermacrene (21.4 / 21.7%), -caryophyllene (10.9 / 12), -cadinene (6.6 / 8.2%) and limonene (5.5% for male subjects only). In the B. organensis, the majorities (male / female), viridiflorol (23.0 / 11.9%), bicyclogermacrene (15.2 / 15.1%), γ-muurolene (6,8 / 10.4%), epiglobulol (7.4 / 6.4%). The compounds -cadinol and curcufenol (7.5% and 5.9%, respectively) were predominant only for male individuals of B. organensis. The crude extracts were obtained from the hydroalcoholic extraction of the leaves of B. aracatubaensis and B. organensis, being male
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