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Universidade Estadual De Campinas UNIVERSIDADE ESTADUAL DE CAMPINAS FACULDADE DE ENGENHARIA DE ALIMENTOS GRAZIELLE NÁTHIA NEVES The use of clean technologies to obtain bioactive compounds from unripe genipap fruit (Genipa americana L.) Uso de tecnologias limpas para a obtenção de compostos bioativos do jenipapo verde (Genipa americana L.) CAMPINAS – SP 2019 GRAZIELLE NÁTHIA NEVES The use of clean technologies to obtain bioactive compounds from unripe genipap fruit (Genipa americana L.) Uso de tecnologias limpas para a obtenção de compostos bioativos do jenipapo verde (Genipa americana L.) Thesis presented to the School of Food Engineering of the University of Campinas in partial fulfillment of the requirements for the degree of Doctor in Food Engineering. Tese apresentada à Faculdade de Engenharia de Alimentos da Universidade Estadual de Campinas como parte dos requisitos exigidos para a obtenção do título de Doutora em Engenharia de Alimentos. Supervisor: Maria Angela Almeida Meireles Petenate ESTE TRABALHO CORRESPONDE À VERSÃO FINAL DA TESE DEFENDIDA PELA ALUNA GRAZIELLE NÁTHIA NEVES, E ORIENTADA PELA PROFA. DRA. MARIA ANGELA ALMEIDA MEIRELES PETENATE CAMPINAS – SP 2019 Agência(s) de fomento e nº(s) de processo(s): CAPES, 001 ORCID: https://orcid.org/0000-0003-4561-7779 Ficha catalográfica Universidade Estadual de Campinas Biblioteca da Faculdade de Engenharia de Alimentos Claudia Aparecida Romano - CRB 8/5816 Neves, Grazielle Náthia, 1988- N414u NevThe use of clean technologies to obtain bioactive compounds from unripe genipap (Genipa americana L.) / Grazielle Náthia Neves. – Campinas, SP : [s.n.], 2018. NevOrientador: Maria Angela de Almeida Meireles Petenate. NevTese (doutorado) – Universidade Estadual de Campinas, Faculdade de Engenharia de Alimentos. Nev1. Genipa americana L.. 2. Corantes naturais. 3. Iridoides. 4. Tecnologias emergente. I. Petenate, Maria Angela de Almeida Meireles. II. Universidade Estadual de Campinas. Faculdade de Engenharia de Alimentos. III. Título. Informações para Biblioteca Digital Título em outro idioma: Uso de tecnologias limpas para a obtenção de compostos bioactivos do jenipapo verde (Genipa americana L.) Palavras-chave em inglês: Genipa americana L. Natural colorants Iridoids Emerging technologies Área de concentração: Engenharia de Alimentos Titulação: Doutora em Engenharia de Alimentos Banca examinadora: Maria Angela de Almeida Meireles Petenate [Orientador] Fabiana Queiroz Julian Martínez Irede Angela Lucini Dalmolin Milena Martelli Tosi Data de defesa: 15-03-2018 Programa de Pós-Graduação: Engenharia de Alimentos Powered by TCPDF (www.tcpdf.org) EXAMINATION BOARD Profa. Dra. Maria Angela Almeida Meireles Petenate FEA / UNICAMP Presidente Profa. Dra. Fabiana Queiroz DCA - UFLA Membro titular Prof. Dr. Julian Martínez FEA - UNICAMP Membro titular Profa. Dra. Irede Angela Lucini Dalmolin UFTPR - Francisco Beltrão Membro titular Profa. Dra. Milena Martelli Tosi USP - Pirassununga Membro titular Ata da defesa com as respectivas assinaturas dos membros encontra-se no SIGA/Sistema de Fluxo de Dissertação/Tese e na Secretaria do Programa da Unidade. DEDICATION To all my family, especially my Mother for never measuring efforts so that I could realize my dreams, for the love granted throughout my journey and for supporting all my decisions. A toda minha família, em especial minha Mãe por nunca medir esforços para que eu pudesse realizar meus sonhos, pelo amor concedido ao longo de toda minha jornada e por apoiar todas as minhas decisões. I dedicate this work... Eu dedico este trabalho... “Talvez não tenha conseguido fazer o melhor, mas lutei para que o melhor fosse feito. Não sou o que deveria ser, mas graças a Deus, não sou o que era antes”. Marthin Luther King ACKNOWLEDGMENTS This thesis becomes a reality with the kind support and help of many individuals. For this reason, I offer my sincere thanks: Foremost, I want to thank GOD, who has always given me the strength, peace of my mind, good health and wisdom to face all the challenges. I would like to express my sincere gratitude to my advisor Profa. M. Angela A. Meireles for the continuous support of my Ph.D. study and related research, for her patience, motivation, and immense knowledge. Her guidance helped me in all the time of research and writing of this thesis. I could not have imagined having a better advisor and mentor for my Ph.D. study. My sincere thanks also goes to Dra. Renata Vardanega, for her generosity and patience in sharing all knowledge with me. Without her precious support, it would not be possible to conduct this research. I'm lucky to have met you on my way. Thank you. I would like to thank my friends Paulo and Suellen for being by my side during all the post-graduation. I thank my fellow labmates, Gislaine, Eric, Pedro, Júlio, Abel, Tahmasb, Julia, Isabel, Monique, in for the stimulating discussions, for the days we were working together before deadlines, and for all the fun we have had in the last three years. Also I thank all my friends of the University of Campinas. I would like to thank Ari for the daily help, patience and friendship. I would like to thank the members of the examining committee, for the relevant contribution to the improvement of this work. I would like to thank CAPES for the financial support. Last but not the least, I would like to thank my family in particular my mom for providing me with unfailing support and continuous encouragement throughout my years of study and through the process of researching and writing this thesis. In a way, I will take you all with me wherever I go, always with affection and gratitude. RESUMO Atualmente, o uso de corantes sintéticos predomina sobre os naturais em virtude do menor custo e sua maior estabilidade. Porém, o uso a longo prazo desses aditivos sintéticos pode acarretar sérios danos à saúde humana. Nesta perspectiva, os corantes naturais têm ganhado força e desafiado as indústrias a desenvolverem processos que garantam produtos naturais com estabilidade, viabilidade técnica e econômica, qualidade e segurança. O jenipapo verde (Genipa americana L.), um fruto nativo do Brasil, tem se destacado como uma boa fonte para a obtenção da um corante azul natural. Sendo assim, este trabalho propõe o uso do jenipapo verde para obtenção de um pigmento azul natural inexistente na indústria brasileira através de tecnologias de extração limpas e ambientalmente amigáveis. Isso porque este fruto é rico em genipina, uma substância que é capaz de produzir a cor azul. Com o intuito de quantificar a genipina e o geniposídeo, compostos responsáveis pala formação da cor azul no jenipapo, foi desenvolvido um método de cromatografia líquida simples e rápido que, com 13 minutos de corrida, permitiu separar estes compostos de forma eficiente em termos da resolução, seletividade e simetria dos picos. Em seguida, foi estudada a extração de diferentes partes do jenipapo verde utilizando etanol pressurizado. Os resultados obtidos neste estudo mostraram que a temperatura e as partes do fruto estudadas exercem grande influência na recuperação dos iridoides genipina e geniposídeo. A interação entre a pressão e as partes do fruto apenas influenciaram na recuperação do geniposídeo. O endocarpo e o fruto inteiro se destacaram como fontes para a obtenção de genipina, enquanto o mesocarpo e a casca se mostraram excelentes fontes para a recuperação de geniposídeo. Com o intuito de otimizar a extração do corante azul do jenipapo foi estudada a extração de genipina utilizando líquidos pressurizados (PLE), solvente a baixa pressão (LPSE) e prensagem a frio seguida por extração a baixa pressão (Press+LPSE). Neste estudo, os efeitos do solvente de extração (água e etanol), da temperatura (40, 50 e 60 °C) e da pressão (0,1, 2, 5 e 8 MPa) foram investigados, e apenas o solvente afetou significativamente a extração de genipina. O processo LPSE permitiu recuperar, em 25 minutos, 79 mg de genipina/g de jenipapo, enquanto o processo Press+LPSE recuperou neste mesmo tempo 83 mg de genipina/g de jenipapo. Além disso, o processo Press+LPSE recuperou mais de 90% do total de genipina em menos de 6 minutos. Ainda neste estudo, foi realizado uma avaliação econômica dos processos LPSE e Press+LPSE. Apesar de ambos os processos se mostrarem viáveis nos diferentes cenários analisados, o processo Press+LPSE apresentou maior viabilidade econômica com um tempo de retorno do investimento inferior a um ano. Com o intuito de recuperar os compostos apolares do jenipapo verde, a extração utilizando dióxido de carbono supercrítico foi empregada. Neste estudo, os efeitos de temperatura (40 e 60 °C) e da pressão (15, 20, 25, 30 e 35 MPa) foram investigados, e apenas a pressão e a interação entre pressão e temperatura influenciaram no rendimento da extração. A melhor condição para a extração via SFE (extração com fluido supercrítico) foi 40 °C e 30 MPa. Os principais ácidos graxos encontrados neste extrato foram linoleico (13 ± 1 mg/g de jenipapo) e linolênico (2.2 ± 0.2 mg/g de jenipapo). Finalmente, o processo integrado foi estudado, no qual em um primeiro estágio foi obtido um extrato rico em ácidos graxos e num segundo estágio foi obtido um extrato rico em genipina (71± 6 mg/g de jenipapo). A etapa prévia de SFE não exerceu papel importante na LPSE, pois não possibilitou maior rendimento do composto genipina. Os processos desenvolvidos nesta tese mostraram-se tecnicamente eficientes na obtenção de um extrato que pode ser usado como um corante azul natural com propriedades funcionais pela indústria de alimentos, nutracêutica e de cosméticos. Palavras-chave: Genipa americana L., corantes naturais, iridoides, tecnologias emergentes. ABSTRACT Currently, the use of synthetic colorants predominates over the natural ones due to the lower cost and its greater stability. However, the long-term use of these synthetic additives can cause serious damage to human health. In this perspective, natural colorants have gained strength and challenged industries to develop processes that guarantee natural products with stability, technical and economic viability, quality and safety.
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