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Production of Cynaropicrin Extracts from Cynara Cardunculus Leaves and Its Use for Development of Wound Dressing Films

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Production of Cynaropicrin Extracts from Cynara Cardunculus Leaves and Its Use for Development of Wound Dressing Films Teresa Isabel de Amoreira Sousa e Silva Brás MSc Engenharia Química e Bioquímica Production of cynaropicrin extracts from Cynara cardunculus leaves and its use for development of wound dressing films Dissertação para obtenção do Grau de Doutor em Engenharia Química e Bioquímica Orientador: Luísa Alexandra Graça Neves, Investigadora Auxiliar, Faculdade de Ciências e Tecnologia – Universidade Nova de Lisboa Co-orientadores: João Paulo Serejo Goulão Crespo, Professor Catedrático, Faculdade de Ciências e Tecnologia – Universidade Nova de Lisboa Maria de Fátima Pereira Duarte Ricardo, Investigadora Auxiliar, Centro de Biotecnologia Agrícola e Agro-Alimentar do Alentejo Júri: Presidente: Prof. Doutor José Paulo Barbosa Mota Arguente(s): Professor Doutor Armando Jorge Domingues Silvestre Professor Doutor Frederico Castelo Alves Ferreira Vogais: Professora Doutora Maria Manuela Estevez Pintado Professora Doutora Isabel Maria Rôla Coelhoso Professor Doutor Vítor Manuel Delgado Alves Doutora Luísa Alexandra Graça Neves Setembro de 2020 Production of cynaropicrin extracts from Cynara cardunculus leaves and its use for development of wound dressing films Copyright © Teresa Isabel de Amoreira Sousa e Silva Brás, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa. A Faculdade de Ciências e Tecnologia e a Universidade Nova de Lisboa têm o direito, perpétuo e sem limites geográficos, de arquivar e publicar esta dissertação através de exemplares impressos reproduzidos em papel ou de forma digital, ou por qualquer outro meio conhecido ou que venha a ser inventado, e de a divulgar através de repositórios científicos e de admitir a sua cópia e distribuição com objetivos educacionais ou de investigação, não comerciais, desde que seja dado crédito ao autor e editor. iii iv “All our dreams can come true, if we have the courage to pursue them.” Walt Disney v vi Acknowledgments Aos longos dos anos de desenvolvimento deste trabalho, várias foram as aprendizagens a nível profissional e pessoal, que me tornaram mais rica em todos os aspetos. Nada disto teria sido possível sem a existência de Pessoas e Instituições que me apoiaram e às quais serei eternamente grata. Quero começar por agradecer aos meus orientadores da FCT-UNL, Professor João Paulo Crespo e Doutora Luísa Neves, por me terem acolhido e decidido apoiar-me nesta caminhada. Ao Professor João Paulo, agradeço-lhe também toda a partilha de conhecimentos, a dedicação que teve, o espírito critico e os bons conselhos que me deu. À Doutora Luísa, um grande obrigada pela confiança de anos, que culminou com esta tese. Agradeço todo o apoio e por me ter permitido crescer tanto profissional como pessoalmente. Agradeço à Doutora Fátima Duarte, do CEBAL, a sua enorme dedicação ao meu doutoramento, por me ter aceite como sua aluna, por me ter integrado no seu grupo de investigação. Um gigante obrigada pelo seu empenho, a sua dedicação, a sua sabedoria e a sua enorme paciência comigo. Agradeço por, em motivos de maior aflição não me ter deixado desmotivar, me ter feito ver o lado positivo e seguir em frente, tendo feito de mim uma profissional mais competente e uma pessoa mais completa emocionalmente. À Professora Maria João Cabrita, do ICAAM, Universidade de Évora, agradeço a disponibilidade por me ter recebido no seu laboratório para a realização dos ensaios de Extração por Líquidos Pressurizados. À Professora Adelaide Oliveira, da Escola Superior Agrária, do Instituto Politécnico de Beja, agradeço a disponibilidade demonstrada para utilização do equipamento de extração por Microondas. Ao Professor Vítor Alves, do Instituto Superior de Agronomia, agradeço a disponibilidade para a realização dos ensaios de perfuração dos filmes. Agradeço também todo o apoio na interpretação dos dados obtidos e de toda a teoria inerente aos mesmos. Ao Professor Armando Silvestre e à Doutora Patricia Ramos, agradeço a disponibilidade para a realização dos ensaios CG-MS e LC-MS e toda a partilha de conhecimentos relativa à caracterização química dos extratos analisados. Agradeço à Dra Carla Brazinha, todo o apoio na avaliação económica. A paciência durante os telefonemas em tempos de pandemia, tendo a casa cheia de crianças, foi extraordinária. À Professora Andreia Gomes, o meu obrigada por me ter recebido na Universidade do Minho, para a realização dos ensaios da IL-6. Obrigada pelo excecional acolhimento em Braga, por todo o auxílio com os ensaios e pela total disponibilidade para a discussão dos resultados. vii Agradeço ao Doutor Jorge Mota Pereira e à Doutora Raquel Machado o terem cuidado do meu eu interior, da minha saúde mental, o interesse pelo meu trabalho, todas as palavras de incentivo e de confiança. Um obrigada especial à Catarina Gonçalves da Universidade do Minho, pelo auxilio na realização dos ensaios da IL-6. Obrigada por teres abdicado dos teus fins de semana quando estive em Braga para que eu pudesse realizar em tempo record os ensaios. Obrigada a todos no CEBAL, sem exceção. Cada um de vocês teve um papel importante durante estes anos, cada um à sua maneira. Um especial Obrigada a todos no Grupo de Compostos Bioativos, os que atualmente estão e os que estiveram durante esta aventura. Maria Castro, obrigada por tudo! Obrigada por todos os conhecimentos transmitidos sobre cultura de células animais. Por me teres atendido o telefone quando tinha dúvidas inacabáveis. Mas, agradeço-te principalmente toda a amizade, todo o companheirismo e toda a fé que tiveste e tens em mim. Ana Paulino, muito obrigada pelo teu carinho, amizade, confiança e palavras ternurentas para comigo, durante esta longa caminhada. Agradeço também todo o apoio no laboratório, sem dúvida importante. À minha querida Daniela Rosa, agradeço a amizade, o carinho, as brincadeiras, as músicas animadas, o estar presente, o “estar lá”. Agradeço o teres aparecido de uma forma mais constante na minha vida, o nunca me teres deixado baixar a cabeça, me teres aturado as lamurias e a celebração das vitórias com a mesma euforia como se fossem tuas. Agradeço também, mas não menos importante, toda a ajuda ao nível da microbiologia e ao nível da recolha de amostras durante os ensaios de fracionamento. À Ivone Torrado, agradeço a enorme amizade. Lado a lado comigo nesta caminhada de doutoramentos, tenho-te a agradecer os inúmeros conselhos, as inúmeras partilhas de possíveis soluções, a enorme criatividade. Agradeço por todo o apoio, dentro e fora do laboratório, e emocional. Agradeço por teres estado sempre lá, mesmo quando tudo foi difícil. Agradeço o teres apanhado as lágrimas, o teres motivado imensas gargalhadas, o teres celebrado as vitorias e ensinado a desvalorizar as derrotas. Obrigada pelo grande companheirismo. À minha irmã, cunhado e sobrinhos, agradeço todo o apoio e compreensão por ter ido tão pouco ao Porto nesta caminhada. Aos meus sogros, desejo agradecer o terem sido um pilar para os meus filhos, permitindo que eu muitas vezes estivesse ausente. Aos meus pais, a educação e o amor que fizeram de mim a mulher que sou hoje. À minha mãe, agradeço toda a preocupação, todo o apoio dado, mesmo estando tão longe. Ao meu pai, presente no meu coração dia após dia, agradeço a herança genética da persistência, da resiliência e da superação. Tenho a certeza que estejas onde estiveres estás orgulhoso de mim. viii Ao meu marido, Hugo e aos meus filhos, Inês e Diogo, agradeço-vos o facto de existirem na minha vida. Agradeço o fazerem de mim, uma mulher e mãe mais completa. Hugo agradeço-te todo o apoio, todas as questões pertinentes, toda a paciência, todo o ânimo, todo o amor, companheirismo. Inês e Diogo, a vocês agradeço a paciência que tiveram das muitas vezes que tive que dizer que precisava trabalhar e as vezes que estive ausente. Agradeço-vos o tornarem os meus dias cinzentos, em dias arco-íris. Agradeço cada beijo, cada abraço, cada ternura, cada carinho nada disto fazia sentido sem vocês na minha vida. ix x Abstract Natural compounds derived from plants are presently an alternative for the discovery of new effective drugs, from which new products may be developed, potentially overcoming the current limitations of synthetic compounds for use in pharma and biomedical applications. This thesis concerns the design and production of cynaropicrin enriched extracts from leaves of Cynara cardunculus, and their application in a chitosan matrix as wound dressing for anti- inflammatory drug delivery. The design and production of cynaropicrin enriched extracts was performed considering the use of environmentally friendly extraction methodologies and biocompatible solvents. Selection of solvent and the extraction methodology took into consideration their effect upon cynaropicrin extraction yield, as well as energy expenditure and other operating costs. Among conventional and non- conventional extraction methodologies, ultrasound assisted extraction combined with ethanol presented the best results regarding the cynaropicrin extraction yield (55.00 mg/g Dry Weight) and energy expenditure (0.027 kWh/gcynaropicrin). Applied for the first time for cynaropicrin extraction from C. cardunculus leaves, ultrasound assisted extraction was firstly optimized regarding the pulse effect on cynaropicrin extraction yield. Comparatively to continuous mode, pulse mode (duty cycle of 25%) presented a reduction on energy consumption/gcynaropicrin, as well as a better temperature control being selected and further optimized with a response surface methodology, using the Box-Behnken design model. The results obtained confirm the applicability of the response surface methodology for optimization of cynaropicrin extraction by pulsed ultrasound assisted extraction, from C. cardunculus. Aiming the increase of the extract biological potential, fractionation of the optimized extract was performed by membrane processes. A Duramem® 200 membrane was selected for the retention of cynaropicrin while low molecular weight compounds, such as glucose and fructose, were removed by diananofiltration (after 5 diavolumes). As a result of the diananofiltration process, a global removal of 93.0% of glucose and 95.6% of fructose was obtained. An increase of the extract biological potential was achieved, when tested with a Bj5-ta human normal fibroblast cell line.
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