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Vanessa Ariana Azevedo Vieira Utilização De Solventes Alternativos

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Vanessa Ariana Azevedo Vieira Utilização De Solventes Alternativos Universidade de Aveiro Departamento de Química 2019 Vanessa Ariana Utilização de solventes alternativos para a extração Azevedo Vieira de compostos bioativos de Juglans regia L. Using alternative solvents for the extraction of bioactive compounds from Juglans regia L. Universidade de Aveiro Departamento de Química 2019 Vanessa Ariana Utilização de solventes alternativos para a extração Azevedo Vieira de compostos bioativos de Juglans regia L. Using alternative solvents for the extraction of bioactive compounds from Juglans regia L. Tese apresentada à Universidade de Aveiro para cumprimento dos requisitos necessários à obtenção do grau de Doutor em Engenharia Química, realizada sob a orientação científica do Professor Doutor João Manuel da Costa e Araújo Pereira Coutinho, Professor Catedrático do Departamento de Química da Universidade de Aveiro, da Professora Doutora Maria Olga de Amorim e Sá Ferreira, Professora Adjunta da Escola Superior de Tecnologia e Gestão do Instituto Politécnico de Bragança, e Professora Doutora Isabel Cristina Fernandes Rodrigues Ferreira, Professora Coordenadora-Principal da Escola Superior Agrária do Instituto Politécnico de Bragança. Apoio financeiro do POCTI no âmbito O doutoramento agradece o apoio financeiro da FCT e do FSE no âmbito do III do III Quadro Comunitário de Apoio. Quadro Comunitário de Apoio (SFRH/BD/108487/2015). Este trabalho foi desenvolvido no âmbito dos projetos: CICECO-Instituto de Materiais de Aveiro, Refª. FCT UID/CTM/50011/2019, financiado por fundos nacionais através da FCT/MCTES; CIMO, Refª. UID/AGR/00690/2019, financiado por fundos nacionais e europeus; Laboratório Associado LSRE-LCM - UID/EQU/50020/2019 - financiado por fundos nacionais através da FCT/MCTES (PIDDAC); Project AllNat, Refº. POCI-01-0145-FEDER-030463 (PTDC/EQU-EPQ/30463/2017), financiado por fundos FEDER através do COMPETE2020 – Programa Operacional Competitividade e Internacionalização (POCI), Portugal 2020 e por fundos nacionais através da FCT/MCTES. Ao João o júri Presidente Professor Doutor João de Lemos Pinto Professor Catedrático da Universidade de Aveiro Doutora Maria Arminda Costa Alves Professora Catedrática da Universidade do Porto Doutor Jesus Simal-Gandra Professor Catedrático da Universidade de Vigo Doutor Simão Pedro de Almeida Pinho Professor Coordenador do Instituto Politécnico de Bragança Doutora Mara Guadalupe Freire Martins Investigadora Coordenadora em regime laboral da Universidade de Aveiro Doutora Maria Olga de Amorim e Sá Professora Adjunta do Instituto Politécnico de Bragança agradecimentos Primeiramente, dirijo os meus agradecimentos aos meus orientadores. Obrigada pela oportunidade que me deram, pela vossa compreensão, apoio, tempo e paciência. Prof. João Coutinho, muito obrigada por me ensinar a olhar para tudo com outros olhos, muitas das vezes a fazer-me sentir “enorme” mas sempre mostrando que o caminho é em frente. Prof. Olga, obrigada pelo carinho, tempo dedicado, palavras de encorajamento e, sobretudo, por abraçar esta aventura. Prof. Isabel, obrigada por TUDO. Obrigada por estar sempre ao meu lado, por essa objetividade que torna tudo simples e atingível, por alimentar o amor à ciência. Gostaria também de agradecer a todos que os que colaboraram direta ou indiretamente neste percurso, pelo auxílio e partilha de conhecimento, contribuindo para o desenvolvimento destes trabalhos que tenho a oportunidade de apresentar. Em particular, quero agradecer à Dra. Lillian Barros pelo ser especial que é, por seguir cada passo dado e ser uma fonte de soluções. Também quero agradecer generosidade dos “parceiros” Dr. Ricardo C. Calhelha e Dr. Miguel A. Prieto. Um bem-haja a todos! Naturalmente, um carinhoso agradecimento terá que ser dirigido aos meus colegas e amigos dos grupos de investigação PATh, BioChemCore e LSRE- CIMO. Obrigado por serem bons companheiros! Um obrigado especial a todos os amigos, por me encorajarem, por festejarem vitórias... por estarem sempre lá. Obrigada Josy, Cristina, Sónia, Rita, Carlitos e a toda a equipa de ACSP dos SAMS – Centro Sul e Ilhas. Para terminar, quero agradecer à minha família. Aos meus pais por fazerem de mim quem sou. Ao meu irmão por todo o amor e cumplicidade. Aos meus segundos pais. Ao João. palavras-chave Juglans regia L., compostos fenólicos, extratos bioativos, solventes alternativos resumo As plantas e os seus resíduos resultantes das indústrias agro-florestal e alimentar são uma potencial fonte de compostos bioativos. Neste contexto, revela-se de grande importância a caracterização química e bioquímica dos extratos de diversas matrizes vegetais avaliando a sua bioatividade em várias dimensões (antioxidante, anti-inflamatória, antimicrobiana, antitumoral, entre outras), bem como a obtenção desses extratos através de processos mais eficientes, sustentáveis e seguros. Em particular, os compostos fenólicos representam a fração de metabolitos secundários de plantas mais amplamente extraída e reconhecida pela sua abundância e bioatividade. Nesta tese, estudou-se o perfil fitoquímico e a bioatividade de duas matrizes vegetais que se destacam como fontes naturais deste tipo de compostos: as folhas da nogueira e os mesocarpos da noz. Assim, após a caracterização química e bioativa da biomassa, otimizou-se o processo de extração de compostos fenólicos, aplicando um planeamento experimental e a metodologia de superfície de resposta, e utilizando etanol como solvente numa primeira fase. Depois, estudaram-se solventes alternativos aos solventes orgânicos voláteis, tais como alcanodióis e solventes eutécticos baseados em cloreto de colina e ácidos carboxílicos ou alcanodióis. Neste último caso, os extratos inseridos no solvente poderão ser utilizados como componentes de formulações com potencial aplicação nas indústrias alimentar, farmacêutica ou cosmética. Finalmente, a escolha dos solventes de extração e purificação de compostos fenólicos é realizada, em geral, de forma empírica, existindo pouca informação sobre a sua solubilidade em solventes orgânicos comuns. Neste sentido, considerou-se oportuno estudar a solubilidade de três ácidos aromáticosde enorme relevância no contexto das biorrefinarias. A modelação termodinâmica do equilíbrio sólido-líquido destas misturas foi efetuada com o modelo NRTL- SAC (Nonrandom Two-Liquid Segment Activity Coefficient) e o modelo de solvatação de Abraham, cujo carácter semi-preditivo permitirá simplificar a seleção preliminar de solventes para um determinado processo. keywords Juglans regia L., phenolic compounds, bioactive extracts, alternative solvents abstract Plants and its residues resulting from the agroforest and food industries are potential sources of bioactive compounds. In this context, it is of great importance to carry out the chemical and biochemical characterization of the extracts of various plant materials evaluating their bioactivity in different dimensions (antioxidant, anti-inflammatory, antimicrobial, anti-tumour, among others), as well as to obtain those extracts by designing more efficient, sustainable and safer processes. In particular, phenolic compounds represent the fraction of secondary metabolites of plants most widely extracted and recognized for their abundance and bioactivity. In this thesis, the phytochemical profile and bioactivity of two plant matrices that stand out as natural sources of this type of compounds were studied: the leaves of walnut trees and walnut green husks. Thus, after the chemical and bioactive characterization of the biomass, the extraction process of phenolic compounds was optimized, applying an experimental design assisted by response surface methodology, using ethanol as solvent in a first stage. After, alternative solvents to volatile organic solvents were studied, such as alkanediols and eutectic solvents based on choline chloride and carboxylic acids or alkanediols. In the latter case, the extracts incorporated in the solvent may be used as components of formulations with potential application in the food, pharmaceutical or cosmetic industries. Finally, the choice of solvents for the extraction and purification of phenolic compounds is generally performed empirically, as scarce information on their solubility in common organic solvents is available. Therefore, it was considered appropriate to study the solubility of three arotimatic acids of great relevance in the biorefinery context. The thermodynamic modelling of the solid-liquid equilibrium of these mixtures was performed using the NRTL-SAC model (Nonrandom Two-Liquid Segment Activity Coefficient) and the Abraham's solvation model, whose semi-predictive character will simplify the preliminary selection of solvents for a given process. List of Abbreviations ([M – H]–) Pseudomolecular ion 2D Two-dimensional 3D Three-dimensional 769-P Human kidney carcinoma cell line A1 Ethanol extract A10 Water extract A2 1,2-Ethanediol extract A3 1,2-Propanediol extract A4 1,3-Propanediol extract A-498 Human kidney carcinoma cell line A5 1,3-Butanediol extract A6 1,2-Pentanediol extract A7 1,5-Pentanediol extract A8 1,2-Hexanediol extract A9 Glycerol extract AAPH 2,2'-Azobis(2-amidinopropane)dihydrochloride ABTS 2,2'-Aazino-bis(3-ethylbenzothiazoline-6-sulphonic acid) ARD Average relative deviations AUC Area under the curve B1 Ethanol B10 Water B2 1,2-Ethanediol B3 1,2-Propanediol B4 1,3-Propanediol B5 1,3-Butanediol B6 1,2-Pentanediol B7 1,5-Pentanediol B8 1,2-Hexanediol B9 Glycerol BA Butyric acid Bt Betaine CA Carboxylic acids Caco-2 Human colorectal carcinoma cell line CC Choline chloride CCCD Circumscribed
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