Universidade Federal Do Rio De Janeiro Instituto De Química Programa De Pós-Graduação Em Ciência De Alimentos

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Universidade Federal Do Rio De Janeiro Instituto De Química Programa De Pós-Graduação Em Ciência De Alimentos UNIVERSIDADE FEDERAL DO RIO DE JANEIRO INSTITUTO DE QUÍMICA PROGRAMA DE PÓS-GRADUAÇÃO EM CIÊNCIA DE ALIMENTOS Compostos bioativos recuperados de farelo de soja (Glycine max) por extração aquosa: compostos fenólicos e peptídeos antimicrobianos e antitumorais Cyntia da Silva de Freitas Rio de Janeiro 2018 Cyntia da Silva de Freitas Compostos bioativos recuperados de farelo de soja (Glycine max) por extração aquosa: compostos fenólicos e peptídeos antimicrobianos e antitumorais Tese de Doutorado apresentada ao Programa de Pós-graduação em Ciência de Alimentos, Instituto de Química, Universidade Federal do Rio de Janeiro, como requisito parcial à obtenção do título de Doutor em Ciência de Alimentos. Orientadores: Profa .Dra . Vânia Margaret Flosi Paschoalin Prof. Dr. Eduardo Mere Del Aguila Dra. Patricia Ribeiro Pereira Rio de Janeiro 2018 Freitas, Cyntia da Silva de. Compostos bioativos recuperados de farelo de soja (Glycine max) por extração aquosa: compostos fenólicos e peptídeos antimicrobianos e antitumorais. / Cyntia da Silva de Freitas. – Rio de Janeiro: UFRJ, 2014. p., il. Tese (Doutorado em Ciência de Alimentos) – Universidade Federal do Rio de Janeiro, Instituto de Química, 2018. Orientadores: Eduardo Mere Del Aguila, Vânia Margaret Flosi Paschoalin e Patricia Ribeiro Pereira. 1. Glycine max. 2. Farelo da soja. 3. Peptídeos antimicrobianos. I. Del Aguila, Eduardo Mere. II. Paschoalin, Vânia Margaret Flosi. III. Pereira, Patricia Ribeiro. III. Universidade Federal do Rio de Janeiro. Programa de Pós Graduação em Ciência de Alimentos. IV. Título. Cyntia da Silva de Freitas COMPOSTOS BIOATIVOS RECUPERADOS DE FARELO DE SOJA (GLYCINE MAX) POR EXTRAÇÃO AQUOSA: COMPOSTOS FENÓLICOS E PEPTÍDEOS ANTIMICROBIANS E ANTITUMORAIS Profa. Dra. Vânia Margaret Flosi Paschoalin Prof. Dr. Eduardo Mere Del Aguila Dra. Patricia Ribeiro Pereira Tese de Doutorado apresentada ao Programa de Pós-graduação em Ciência de Alimentos, Instituto de Química, Universidade Federal do Rio de Janeiro, como requisito parcial à obtenção do título de Doutor em Ciência de Alimentos. Aprovada em: _______de Outubro de 2018. Aprovada por: ________________________________________________________ Profa.Dra. Vânia Margaret Flosi Paschoalin – IQ/UFRJ _______________________________________________________ Profa.Dra. Maria Alice Zarur Coelho – EQ/UFRJ _______________________________________________________ Prof.Dr.Carlos Conte Adam Junior _______________________________________________________ Profa.Dra. Mônica Ferreira Moreira – IQ/UFRJ _______________________________________________________ Profa.Dra. Ana Carolina Carvalho – UFRJ/Macaé Aos meus pais e avós, por toda dedicação, apoio, amor e força durante mais essa jornada. Principalmente à minha mãe e minha vó (Marly), às mulheres da minha vida que me ensinaram o que é força e sabedoria. “Do. Or do not. There is no try.” “Always pass on what you have learned.” Mestre Yoda Agradecimentos As agências de fomento CAPES, CNPQ e FAPERJ, pelo apoio financeiro concedido ao estudo. Ao Programa de Pós-graduação em Ciência de Alimentos - PPGCAL, pela oportunidade e conteúdo essencial transmitido. A professora Vânia Paschoalin por me receber no laboratório, pelas palavras de sabedoria, pelo apoio, dedicação, aconselhamento, que foram de grande importância para o meu crescimento acadêmica e pessoal. Ao Professor Eduardo Mere, pelo apoio, dedicação e paciência durante esse período. A Patricia Ribeiro Pereira, pela orientação, por ter sido meu braço direito e ter sido mais que orientadora, uma amiga. Foi um prazer inenarrável trabalhar com ela. Ao Giovani Verissimo pela parceria e valorosas discussões. A minha mãe Sandra e ao meu pai José, pois sempre acreditaram e investiram em mim sem duvidar. A minha avó Marly que sempre foi uma grande inspiração. Ao meu avô Amilton, por ter acreditado em mim. E a Bianca, por ter me apoiado e acreditado. Aos meus amigos de laboratório Diego Baião, Davi Vieira, Maria Fernanda, Anna Carolina Corrêa e Rafael Luiz, pela parceria, amizade, apoio, palavras de incêntivo e por proporcinarem muitos momentos de descontração e alegria. A toda minha famíla e amigos que me apoiaram nessa jornada. Resumo Freitas, Cyntia da Silva. Compostos bioativos recuperados de farelo de soja (Glycine max) por extração aquosa: Compostos fenólicos e peptídeos antimicrobianos e antitumorais. Rio de Janeiro, 2018. Tese (Doutorado em Ciência de Alimentos). Instituto de Química, Universidade Federal do Rio de Janeiro. A soja tem um potencial estratégico na segurança alimentar, além de ser uma fonte de proteínas e compostos bioativos para as necessidades humanas, como polifenóis e oligopeptídeos. Ambos os compostos foram recuperados após a extração aquosa do farelo de soja, um subproduto do refino do óleo de soja. As isoflavonas predominantes são genistina, daidzina, glicitina e malonilgenistina e suas formas glicosídicas exibiram uma bioacessibilidade global próxima a 75%. Outros dezesseis fenólicos com alta bioacessibilidade foram identificados e o ácido cafeico, ácido 5-CQA e hesperidina foram os mais predominantes. O extrato aquoso não apresentou citotoxicidade para células murinas saudáveis, mas apresentou bioatividades como a capacidade antioxidante, que foi aumentada após digestão gástrica in vitro, inibição da peroxidação lipídica, quando comparado a antioxidantes naturais e sintéticos, e atividade antimicrobiana contra patógenos alimentares Gram-positivas e Gram- negativas. Tais atividades biológicas podem ser atribuídas não apenas à presença de polifenóis, mas também a oligopeptídeos, especialmente peptídeos antimicrobianos (PAM). Para avaliar a participação de PAMs na atividade antimicrobiana, os oligopeptídeos foram fracionados por meio de membrana de ultrafiltração com ponto de 10kDa e cromatografia de filtração em gel a partir do extrato aquoso de farelo de soja. Duas frações ricas em peptídeos e com baixo teor de compostos fenólicos - F1 e F2 - exibiram atividade antimicrobiana superior em comparação com o extrato total e foram capazes de inibir a proliferação de céluas de glioblastoma humano, confirmando que contribuem ou são responsáveis por tal atividade. A espectrometria de massa de F1 e F2 seguida de triagem com cinco algoritmos deu origem a doze candidatos a peptídeos antimicrobianos que estavam encriptados, principalmente, em subunidades alfa e alfa-prime da β-conglicinina com massas moleculares variando de 718,42 a 4872,43 Da. Estudos de alinhamento revelaram dois domínios em subunidades da β-conglicinina que contêm os candidatos a PAMs. A estrutura tridimensional da região contendo os dois domínios foi determinada pela primeira vez, revelando predominância de estrutura em alfa-hélice. A produção em larga escala e o uso de peptídeos multifuncionais e compostos fenólicos é uma aplicação inovadora do conceito de bioeconomia circular, valorizando o subproduto agroindustrial. Palavras-chave: Farelo de soja, polifenóis, isoflavonas, bioacessibilidade, peptídeos antimicrobianos e antitumorais, modelagem molecular. Abstract Freitas, Cyntia da Silva. Bioactive compounds recovered from soybean meal (Glycine max) by aqueous extraction: Phenolic compounds and antimicrobial and antitumor peptides. Rio de Janeiro, 2018. Tese (Doutorado em Ciência de Alimentos). Instituto de Química, Universidade Federal do Rio de Janeiro. Soybean has a strategic potential in food security besides being a source of protein and functional bioactives for human needs, such as polyphenols and oligopeptides. Both compounds were recovered after aqueous extraction of soybean meal, a by-product of soy oil refining. The predominant isoflavones are Genistin, daidzin, glycitinand malonylgenistin and their glicosidic forms exhibited an overall bioaccessibility near 75%. Additional sixteen phenolics with high bioacessibility were identified and caffeic acid, 5-CQA acid and hesperidin were the most predominant. The aqueous extract showed no cytotoxicity to healthy murine cells while maintained bioactivities such as antioxidant capacity, that was enhanced after in vitro gastric digestion, inhibition of lipid peroxidation, when compared to natural and synthetic food antioxidants, and antimicrobial activity to gram-positive and gram-negative foodborne pathogens. Biologycal activities can be attributed not only to the presence of polyphenols but also to oligopeptides, especially antimicrobial peptides (AMP). To evaluate the participation of AMPs in the antimicrobial activity, oligopeptides were fractionated by 10kDa-cutoff ultrafiltration membrane followed by gel filtration chromatography of soybean meal aqueous extract. Two peptide-rich and low- polyphenol fractions – F1 and F2 – exhibited superior antimicrobial activity compared with the whole extract and was able to inhibited human glioblastoma proliferation, confirming they contribute or are responsible for the activity. Mass spectrometry of F1 and F2 followed by screening with five algorithms gave rise to twelve antimicrobial peptide candidates which were mainly encrypted in alpha and alpha-prime subunits of β-conglycinin with molecular masses ranging from 718.42 to 4872.43 Da. Alignment studies revealed two domains in β-conglycinin subunits that contain AMP candidates. Three dimensional structure of the region containing both domains was determined for the first time, revealing predominance of alpha-helix. The production inlarge scale and the use of multifunctional peptides as well as polyphenols is an innovative application of the concept of circular bioeconomy, valuing the agro-industrial
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