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CHANGES in COMPOSITION and BIOLOGICAL ACTIVITY of the PHENOLIC COMPOUNDS from Ribes Magellanicum and Ribes Punctatum AFTER in Vi

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CHANGES in COMPOSITION and BIOLOGICAL ACTIVITY of the PHENOLIC COMPOUNDS from Ribes Magellanicum and Ribes Punctatum AFTER in Vi UNIVERSIDAD DE TALCA INSTITUTO DE QUIMICA DE RECURSOS NATURALES CHANGES IN COMPOSITION AND BIOLOGICAL ACTIVITY OF THE PHENOLIC COMPOUNDS FROM Ribes magellanicum AND Ribes punctatum AFTER in vitro GASTROINTESTINAL DIGESTION AND COLONIC FERMENTATION ALBERTO JAVIER BURGOS EDWARDS TESIS PARA OPTAR AL GRADO DE: DOCTOR EN CIENCIAS, MENCIÓN INVESTIGACIÓN Y DESARROLLO DE PRODUCTOS BIOACTIVOS Director Dr. Guillermo Schmeda Hirschmann Talca, 2019 i CONSTANCIA La Dirección del Sistema de Bibliotecas a través de su unidad de procesos técnicos certifica que el autor del siguiente trabajo de titulación ha firmado su autorización para la reproducción en forma total o parcial e ilimitada del mismo. Talca, 2019 Vicerrectoría Académica | Dirección de Bibliotecas ii Changes in composition and biological activity of the phenolic compounds from Ribes magellanicum and Ribes punctatum after in vitro gastrointestinal digestion and colonic fermentation Cambios en la composición y actividad biológica de los compuestos fenólicos de Ribes magellanicum y Ribes punctatum posterior a la digestión gastrointestinal y fermentación colónica in vitro Alberto Javier Burgos Edwards Fecha inicio Tesis: Enero 2016 Fecha término Tesis: Octubre 2019 Director de Tesis: Guillermo Schmeda Hirschmann, Universidad de Talca, Instituto de Química de Recursos Naturales, Casilla 747, Talca, Chile. Email: [email protected] Integrantes de la comisión de Tesis: 1. Dr. Ramiro Araya Maturana, Universidad de Talca. 2. Dr. Sergio Wehinger Wehinger, Universidad de Talca. 3. Dr. Camilo López Alarcón, Pontificia Universidad Católica de Chile. i Acknowledgments To PIEI-QUIM-BIO program from Universidad de Talca for financial support. CONICYT for the doctoral grant PFCHA Doctorado Nacional 2015-21151561 (April 2015- January 2019). To my family for always being by my side along this path, despite the distance. To my best friend Laura Lascano for giving me her unconditional support, especially in the difficult times. Prof. Guillermo Schmeda-Hirschmann and Cristina Theoduloz, for sharing with me their knowledge, experiences and advices, allowing me to develop this work. To Mrs. Irene Manrriquez and Mr. Sergio Reyes for their teachings and support day by day. To my good friends and lab mates Daniel Mieres, Javier Antileo, Jean Paulo de Andrade, Verónica Olate, Samanta Thomas, Felipe Jimenez, Liudis Pino, Victoria Nina, and Sergio Reyes for their advice and help every time I needed them. To the entire Instituto de Quimica de Recursos Naturales, for their goodwill in helping me. I would like to thank Prof. Mar Larrosa and the members of the Nutrition, Microbiota and Health Group (Arantxa Fernández, Laura Martin, Natalia Moracho, Cristina Vitores, Goyi Montalvo, Beatriz Lucas and Jose García) from the Faculty of Biomedical Sciences of the European University of Madrid, for their help in the development of this Thesis. To my former Professors Esteban Ferro, Nelson Alvarenga, María Eugenia Flores, María Luisa Kennedy, and Javier Barúa, who encouraged me to follow this path. To Olga Coronel and all my dear friends in Asunción that supported me from the distance. To my dear friends in Talca Viviana Donoso, Carolina Ojeda, and Jefferson Romero. Thank you very much. ii iii General index Abstract ...............................................................................................................................................2 Chapter 1 ............................................................................................................................................4 Introduction ........................................................................................................................................4 1.1. Phenolic compounds ...............................................................................................................4 1.1.1. Overview ............................................................................................................................4 1.1.2. Biosynthesis .......................................................................................................................5 1.1.3. Classification ......................................................................................................................7 1.1.4. Metabolism ......................................................................................................................12 1.1.5. Biological effects .............................................................................................................14 1.2. Currants and gooseberries (Ribes spp.) .................................................................................17 1.3. In vitro methodologies for the evaluation of the digestion process ........................................25 1.3.1. Overview ..........................................................................................................................25 1.3.2. Simulated gastric and intestinal digestion models ...........................................................27 1.3.3. Simulated colonic fermentation models ...........................................................................30 1.4. Analysis of phenolic compounds ............................................................................................32 1.4.1. Extraction .........................................................................................................................32 1.4.2. Samples pre-treatment ......................................................................................................33 1.4.3. Phenolic profiling by HPLC-DAD and HPLC-ESI-MS/MS ...........................................34 1.5. In vitro methods for biological activity evaluation .................................................................35 1.5.1. Antioxidant activity..........................................................................................................35 1.5.2. Inhibition of metabolic syndrome-related enzymes .........................................................36 1.5.3. Anti-inflammatory activity ..............................................................................................37 1.5.4. Prebiotic activity ..............................................................................................................38 Hypothesis .....................................................................................................................................40 Objectives......................................................................................................................................41 1. General objective ...................................................................................................................41 2. Specific objectives .................................................................................................................41 Chapter 2 ..........................................................................................................................................43 Materials and Methods ....................................................................................................................43 iv 2.1. Reagents and solvents .............................................................................................................43 2.2. Samples collection ..................................................................................................................45 2.3. Sample processing ..................................................................................................................46 2.3.1. Fruits extraction ...............................................................................................................46 2.3.2. Phenolic-enriched extract (PEE) obtention ......................................................................47 2.4. In vitro gastrointestinal tract experiments ...............................................................................47 2.4.1. Simulated gastrointestinal digestion (GID) ......................................................................47 2.4.2. Simulated colonic fermentation conditions ......................................................................48 2.5. Chromatographic analyses ......................................................................................................50 2.5.1. HPLC-DAD analyses of GID samples .............................................................................50 2.5.2. HPLC-DAD analyses of fermented samples ....................................................................51 2.5.3. Identification by HPLC-ESI-MS/MSn .............................................................................51 2.6. Total flavonoid (TF) and total phenolic (TP) content .............................................................52 2.7. Antioxidant activity ................................................................................................................53 2.7.1. Discoloration of the DPPH radical ...................................................................................53 2.7.2. Ferric reducing antioxidant power (FRAP) ......................................................................53 2.7.3. Trolox equivalent antioxidant capacity (TEAC) ..............................................................54 2.7.4. Cupric-reducing antioxidant power (CUPRAC) ..............................................................54 2.7.5. Superoxide anion scavenging capacity ............................................................................54
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