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UNIVERSIDADE FEDERAL DE SÃO PAULO Instituto De Ciências UNIVERSIDADE FEDERAL DE SÃO PAULO Instituto de Ciências Ambientais, Químicas e Farmacêuticas Estudo químico e avaliação da atividade antimicrobiana dos óleos essenciais extraídos das espécies Pimenta dioica (Myrtaceae) e Chenopodium ambrosioides (Amaranthaceae) Clerlune PHANORD Diadema 2016 UNIVERSIDADE FEDERAL DE SÃO PAULO Instituto de Ciências Ambientais, Químicas e Farmacêuticas Clerlune PHANORD Estudo químico e avaliação da atividade antimicrobiana dos óleos essenciais extraídos das espécies Pimenta dioica (Myrtaceae) e Chenopodium ambrosioides (Amaranthaceae) Dissertação apresentada como exigência parcial para obtenção do título de Mestre em Ciências, ao Programa de Pós Graduação em Biologia Química do Instituto de Ciências Ambientais, Químicas e Farmacêuticas da Universidade Federal de São Paulo – Campus Diadema Orientadora: Dra. Patricia Sartorelli Diadema 2016 Clerlune PHANORD Estudo químico e avaliação da atividade antimicrobiana dos óleos essenciais extraídos das espécies Pimenta dioica (Myrtaceae) e Chenopodium ambrosioides (Amaranthaceae) 96 p. Dissertação de mestrado (Programa de Pós-graduação em Biologia Química) – Universidade Federal de São Paulo Orientadora: Patricia Sartorelli 1. Pimenta dioica. 2.Chenopodium ambrosioides .3.Óleo essencial. 4. Constituintes químicos. 5.Atividade antimicrobiana Diadema 2016 i DEDICAÇÃO Este trabalho de estudo é dedicado a: Minha mãe Sra. Clernius PHANORD nasceu Dalida DONATIEN Meu pai Sr. Clernius PHANORD Meu irmão John Wadner Kerson PHANORD ii AGRADECIMENTOS Em primeiro lugar devo dizer obrigado ao meu grande Jeová Deus Todo Poderoso por sua misericórdia e graça por mim. Sem a sua vontade este trabalho não seria realizado. Um muito obrigado aos meus queridos pais Clernius PHANORD e Dalida DONATIEN PHANORD por toda a devoção e sacrifícios que eles fizeram pela minha educação, minha felicidade e aquilo que sou. Eu agradeço a OEA/OEA-GCUB PAEC que oferece as bolsas por meio de programa de mobilidade estudantil onde fui contemplada para receber esta oportunidade entre milhares de candidatos. Meu agradecimento pelo Governo do Brasil e MEC para formação de qualidade que recebi durante este período. Eu agradeço a Reitoria da Universidade Federal de São Paulo, também por esta oportunidade de formação com qualidade, que recebi durante os anos de pós graduação. Eu agradeço aos Coordenadores do Programa de Biologia Química – Carla Maximo Prado e João Henrique Lago - por me receberem com alegria neste Mestrado. Na verdade, este trabalho é o resultado também da dedicação, boa vontade e sacrifíciode vários profissionais, amigos e colegas a quem também, agradeço pela ajuda prestada. A minha Orientadora, Profª. Dra. Patrícia Sartorelli. Você me acolheu em seu laboratório para compartilhar a sua experiência científica e profissional. Sou especialmente grata que você concordou em dirigir-me ao final desta pesquisa. A sua disponibilidade a cada dia e o tempo gasto para corrigir esta grande obra foi de fundamental importância para mim. A todos os professores do Labiorg um grande obrigado pela sua cooperação. A todos os professores do laboratório LIMIC, Renata Pascom, Marcelo Afonso Vallim. Vocês contribuíram para a realização desta pesquisa e permitiram um trabalho e bioensaios em excelentes condições. Um agradecimento a Professora Célia Além por sua ajuda na coleta das plantas. Um agradecimento à Professora Marisi Gomes Soares por toda ajuda e esforço dedicados na realização das análises de GC-MS. iii Para os meus colegas e amigos labiorg: Ana Carvalho, Nara Oshiro, Geanne Conserva, Fernanda Samara, Simone Grecco, Anderson Ueno, Pedro Henrique Ferreira Arato, Kaio Souza, Patrícia Dias, Flavia Rie Hasegawa, Luciana Grus, Pamela Laura Noemy Ramirez, Natalia Quintiliano, Vinicius Londero, Thiago Rahal, Bianca Novais, Viviane de Mello Veneza, Augusto Leonardo Dos Santos, Deborah Sessa, Emerson Alves de Oliveria, Silmara, Waldemar. Vocês me deram a oportunidade de fazer este trabalho em uma atmosfera amigável, onde o sorriso e apoio de bom grado estiveram comigo até o final deste trabalho. Obrigado pela sinceridade, apoio, discussões construtivas e sugestões. Vocês contribuíram para o sucesso deste trabalho. Ao companheirismo dos colegas do laboratório LIMC: Natalia, Camilia, Thais, Aline, Ricardo, kervin, João e Amanda meu sincero agradecimento. Ao meu irmão Jhon Wadner Kerson PHANORD, que mesmo à distância, sempre me motivou e me deu o apoio necessário em tempo útil. Suas preocupações têm contribuído em grande parte para o sucesso deste trabalho. À Marc-Donald ANGRAND pelo incentivo e apoio, que contribuíram para a realização deste trabalho. A minha família que simples preocupada comigo especialmente meus tios wilna PHANORD MERCIER e Idalien DONATIEN Aos meus amigos André Andy, Nicole Pinotte Rodriques, Jessica Fernanda Helena, Pierre Jacque-Elie, Harold Corantin, Ingrid Candido Garafolo, Bien-aime Ronald, Abbe Tosa, Fleurmont Antoine. Um grande obrigado por vosso apoio, lealdade e sinceridade. Às funcionárias da Secretaria da UNIFESP, Fátima e Nazareth. Ao Núcleo de Apoio ao Estudante (NAE), Rose Adriana, Cláudia Luisa Verônica. A Prfa Dra Luciana Chagas Caperuto, Cristina Viana Niero, Julio Oliveirae a todos os professores que participaram de meu mestrado e formação em biologiaquímica, um grande obrigado a todos vocês. Um agradecimento a todos aqueles que contribuíram de alguma forma para realizar este trabalho de estudo. iv RESUMO Atualmente as doenças infecciosas continuam sendo um dos mais sérios problemas de saúde pública e têm causado muitas mortes. Segundo a OMS, as doenças infecciosas causaram 14,7 milhões de mortes em 2001, ou 26% da mortalidade mundial total. Desde a descoberta da penicilina por Alexander Fleming em 1928, muitos antibióticos estão disponíveis em farmácias, porém apesar da existência desses antibióticos, as doenças infecciosas, em vez de ser completamente erradicadas estão reaparecendo e também novas doenças infecciosas vêm surgindo. As causas deste problema são diversas: existem poucos antibióticos específicos disponíveis, o tratamento custa muito caro, e o mais preocupante: os microrganismos estão cada vez mais resistentes aos antibióticos. Por isso, como contribuição para a descoberta de novos antibióticos, o presente estudo teve por objetivo encontrar novas substâncias que possam ser protótipos de fármacos antimicrobianos, ou, pelo menos, um meio eficaz e de baixo custo para combater estes patógenos. Desta forma, foi proposto o estudo químico dos óleos essenciais das espécies Pimenta dioica (Myrtaceae) e Chenopodium ambrosioides (Amaranthaceae), bem como a avaliação da atividade antimicrobiana frente a várias linhagens de bactérias e leveduras. Os compostos majoritários do óleo essencial de P. dioica foram os fenilpropanóides eugenol e chavicol além do monoterpeno mirceno, enquanto que para C. ambrosioides foram os monoterpenos ascaridol e terpineno. Com relação à atividade antimicrobiana, as linhagens testadas apresentaram sensibilidade para o óleo essencial de P. dioica e para o composto isolado eugenol, exceto para Pseudomonas aeruginosa. O CIM90 para os dois óleos variou de 0,25 mg/mL para Enterococcus faecalis e 1mg/mL para todas as bactérias testadas. A mesma concentração foi válida para o óleo essencial de P. dioica e para eugenol, sendo que para eugenol, só os Cryptococcus testados apresentaram sensibilidade de 0,5 mg/mL para o CIM90. Com relação ao óleo de C. ambrosioides e do componente principal ascaridol, os dois foram ativos só pra E.coli, com CIM90 de 2 mg/mL. Com relação às linhagens de fungos testados, o óleo de C. ambrosioides e o monoterpeno ascaridol foram ativos para todas as linhagens testadas. O CIM90 para ó óleo bruto de C. ambrosioides foi de 0,25 mg/mL para todas as candidas testadas, sendo que em C. albicans o resultado foi positivo em 0,50mg/mL, assim como para os Cryptococcus testados. O ascaridol apresentou CIM90 de 0,25 mg/mL para todas as linhagens de candidas, exceto em C. krusi que foi de 0,5mg/ml e no caso dos Cryptococcus,o CIM90 foi de 1 mg/mL. v ABSTRACT Currently infectious diseases remain one of the most serious public health problems and have caused many deaths. According to OMS, infectious diseases caused 14.7 million deaths in 2001, or 26% of total world mortality. Since the discovery of penicillin by Alexander Fleming in 1928, many antibiotics are available in pharmacies, but despite the existence of these antibiotics, infectious diseases, instead of being completely eradicated are reappearing and also new infectious diseases have emerged. The causes of this problem are diverse: there are few specific antibiotics available, the treatment is very expensive, and the most disturbing: the microorganisms are increasingly resistant to antibiotics. Therefore, as a contribution to the discovery of new antibiotics, this study aimed to find new substances that might be prototypes of antimicrobial drugs, or at least an effective and low cost to fight these pathogens. Thus, the chemical study was proposed of the essential oils of the species Pimenta dioica (Myrtaceae) and Chenopodium ambrosioides (Amaranthaceae), and the evaluation of antimicrobial activity against various strains of bacteria and yeast. The majority of essential oil compounds of P. dioica were phenylpropanoids eugenol and chavicol beyond monoterpene myrcene, whereas for C. ambrosioides were monoterpenes: ascaridol and terpinene. Regarding the antimicrobial activity, the tested strains showed sensitivity to the essential oil of P. dioica and the
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