Protective Activity of Phytochemicals from Natural Extracts

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Protective Activity of Phytochemicals from Natural Extracts Elena Valeria Girlus Degree in Biochemistry Protective activity of phytochemicals from natural extracts Dissertation to obtain a Master Degree in Biochemistry for Health Supervisor: Regina Menezes Echaniz, Ph.D, IBET/ITQB-UNL Co-Supervisor: Ana Alexandra Figueiredo Matias, Ph.D, IBET/ITQB-UNL January 2016 Elena Valeria Girlus Degree in Biochemistry Protective activity of phytochemicals from natural extracts Dissertation to obtain a Master Degree in Biochemistry for Health Supervisor: Regina Menezes Echaniz, Ph.D, IBET/ITQB-UNL Co-Supervisor: Ana Alexandra Figueiredo Matias, Ph.D, IBET/ITQB-UNL Júri: Presidente: Doutor Pedro Matias Arguente: Doutora Margarida Archer Vogal: Doutora Anabela Raymundo ITQB January 2016 Protective activity of phytochemicals from natural extracts Copyright Elena Girlus, ITQB/UNL, UNL O Instituto de Tecnologia Química e Biológica António Xavier 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 credito ao autor e editor. Acknowledgments Quero agradecer a todas as pessoas do laboratório de Disease and Stress Biology e do laboratório Nutraceuticals and Delivery, em especial à Dra. Regina Menezes, Dra. Cláudia Santos, Dra. Ana Matias e Dra. Catarina Duarte, por me terem dado a oportunidade de trabalhar nos dois grupos, e pelo apoio e disponibilidade ao longo destes meses. Obrigada por me incentivarem em continuar pois sem isso não teria conseguido chegar até aqui, e obrigada por todas as vezes em que me disseram que vai correr bem quando estava desanimada, foi muito importante ouvir isso! Muito obrigada à Carolina Jardim, Inês Costa e Gonçalo Garcia que me acompanharam mais de perto e que me ajudaram a conseguir acabar este trabalho, obrigada mesmo. Carolina obrigada por teres puxado por mim e por todos os conselhos! Muito obrigada pelo apoio e amizade Inês Figueira, Andreia Gomes, Diana Macedo, Joel Guerra, Joana Pereira, Ana Margarida Nunes, Sónia Moita. Muito obrigada à Ana Nunes por me ter acompanhado e por me ter introduzido aos conhecimentos e métodos para eu avançar com o meu trabalho, e a todas as pessoas do laboratório, Joana Poejo, Inês Silva, Agostinho Alexandre, Liliana Rodrigues, Daniel Lopes, Vanessa Gonçalves, Cátia Carmo, Catarina Maia pela disponibilidade em me esclarecerem as dúvidas que foram surgindo ao longo do trabalho. Obrigada também à Dra. Rosário Bronze, à Elsa e Andreia pela disponibilidade em analisar as minhas amostras. Tive um enorme prazer em conhecer-vos e poder trabalhar com vocês. Obrigada por tudo! Obrigada Tiago Matos, Francisco Oliveira e André Preto pela vossa amizade, por me darem força para continuar e por todos os momentos de descontração. Obrigada por estares ao meu lado e por todo o apoio que me tens dado Luís Batalha! Muito obrigada aos meus pais, sem vocês não teria sido possível ter conseguido tudo o que sou hoje, obrigada pelo esforço, apoio e confiança durante estes anos todos! Obrigada especialmente à minha mãe pela tua força! I II Abstract The rise in the incidence of neurodegenerative diseases leads to an increased demand for the development of alternative therapeutic strategies. Phytochemicals have proved beneficial effects for human health, exerting protective roles towards several diseases including neurodegenerative disorders. Thus, the search for new bioactivities is a field in constant growth. The beet and fruits belonging to Opuntia spp. are rich in betalains and phenolic compounds, which confer several benefits to human health such as regulators of antioxidant and anti-inflammatory responses as well as potential protective effect for chronic diseases. The objectives of this study were the optimization of solid-liquid extractions of beets, purple and yellow fruits of Opuntia spp. in order to obtain extracts enriched in betalains (betacyanins and betaxanthinas) and (poly)phenols. The beetroot purified fraction was selected as the matrix displaying higher contents of betalains and (poly)phenols, and bioactivities for key processes associated with neurodegenerative diseases (Parkinson's disease, Amyotrophic Lateral Sclerosis, Huntington's and Alzheimer's) were assessed using humanized yeast models. As chronic inflammation is a common pathological process associated with neurodegeneration, the potential anti-inflammatory properties of the beetroot purified fraction were also evaluated using a yeast model Crz1/NFAT activation. Although the beetroot phytochemicals did not reveal significant protective activities for amyloidogenic processes associated with these diseases, they showed a potential anti-inflammatory activity as revealed by the great potential to attenuate Crz1/NFAT activation. The most abundant compound present in beet extract, betanin (pure standard), was used to infer whether the potential of the beetroot purified fraction to modulate Crz1/NFAT activation was associated with betalains compounds, revealing that was not the case. Possibly, the phenolic compounds present in this fraction exert the potential anti-inflammatory effects observed or maybe the synergistic action between betalains and (poly)phenols are in the ground of the bioactivity displayed by the beetroot phytochemicals. Keywords: Natural extracts, Betalains, (Poly)phenols, Neuroprotection, Anti-inflammatory activity III IV Resumo O aumento na incidência de doenças neurodegenerativas tem levado a um aumento da demanda para o desenvolvimento de estratégias terapêuticas alternativas. Os fitoquímicos têm revelado efeitos benéficos para a saúde humana, exercendo funções de proteção para várias doenças, incluindo doenças neurodegenerativas. Assim, a procura de novas bioatividades é um campo em crescimento constante. A beterraba e frutos pertencentes a Opuntia spp. são ricos em compostos fenólicos e betalaínas, os quais conferem vários benefícios para a saúde humana, tais como a regulação de respostas antioxidantes e anti-inflamatórias, assim como efeitos protetores potenciais para doenças crónicas. Os objetivos deste estudo foram a otimização da extração sólido-líquido de beterraba, frutos roxos e amarelos de Opuntia spp. de modo a obter extratos enriquecidos em betalaínas (betacianinas e betaxantinas) e (poli)fenóis. A fração purificada de beterraba foi selecionada como a matriz exibindo teores de betalaínas e (poli)fenóis mais elevados. As bioatividades desta matriz para processos-chave associadas a doenças neurodegenerativas (doença de Parkinson, Esclerose Lateral Amiotrófica, Huntington e Alzheimer) foram avaliadas utilizando modelos humanizados de levedura. Como a inflamação crónica é um processo patológico comum associado à neurodegeneração, as potenciais propriedades anti-inflamatórias da fração de beterraba purificada foram também avaliadas usando um modelo de levedura de ativação do fator de transcrição Crz1/NFAT. Embora os fitoquímicos da beterraba não tenham revelado atividades de proteção significativas para processos amiloidogénicos associados a estas doenças, eles mostraram uma potencial atividade anti-inflamatória conforme revelado pelo grande potencial para atenuar a ativação Crz1/NFAT. O composto mais abundante presente no extrato de beterraba, betanina (padrão puro), foi usado para inferir se o potencial da fração de beterraba purificada para modular a ativação Crz1/NFAT estava associado às betalaínas, revelando que este não era o caso. Possivelmente, os compostos fenólicos presentes nesta fração exercem os efeitos protetores observados ou talvez a ação sinérgica entre betalaínas e (poli)fenóis estejam na base das propriedades protetoras exibidas pelos fitoquímicos da beterraba. Palavras-chave: Extratos naturais, Betalaínas, (Poli)fenóis, Neuroprotecção, Atividade anti- inflamatória V VI Index Page 1) Introduction ……………………………………………………………………………………….. 1 1.1) Phytochemicals ………………………………………………………………………………… 1 1.2) Beetroot (Beta vulgaris)………………………………………………………………………… 4 1.3) Opuntia spp. fruits ……………………………………………………………………………… 5 1.4) Neurodegenerative diseases ……………………………………………………………………. 6 1.5) Inflammation …………………………………………………………………………………… 7 1.6) Yeast as a discovery platform for therapeutic compounds ……………………………………... 9 1.7) Objectives ……………………………………………………………………………………... 10 2) Materials and Methods …………………………………………………………………………... 11 2.1) Samples and extracts preparation ……………………………………………………………… 11 2.2) Solid Phase Extraction (SPE) ………………………………………………………………….. 13 2.3) Extracts characterization ……………………………………………………………………… 13 2.3.1) Betalain determination ………………………………………………………………….. 13 2.3.2) Total phenolic content (TPC) determination ……………………………………………. 14 2.3.3) Oxygen radical absorbance capacity (ORAC) ………………………………………….. 14 2.4) Sucrose, D-fructose and D-glucose assay procedure ………………………………………….. 15 2.5) Strains and plasmids …………………………………………………………………………... 15 2.6) Yeast media and reagents ……………………………………………………………………… 16 2.7) Growth conditions …………………………………………………………………………….. 16 2.8) Growth curves ………………………………………………………………………………… 17 2.9) β-galactosidase assays ………………………………………………………………………... 17 2.10) Statistical analyses …………………………………………………………………………… 18 3) Results and Discussion ………………………………………………………………………… 19 3.1) Extracts chemical characterization ……………………………………………………………. 19 3.1.1) Betalain
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