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Molecular Simulation, Mixture Optimization and Experimental Validation in Carbonated Soft Drinks

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Molecular Simulation, Mixture Optimization and Experimental Validation in Carbonated Soft Drinks PONTIFICIA UNIVERSIDAD CATOLICA DE CHILE SCHOOL OF ENGINEERING ORGANOLEPTICAL PROPERTIES OF NATURAL, NON-CALORIC SWEETENERS: MOLECULAR SIMULATION, MIXTURE OPTIMIZATION AND EXPERIMENTAL VALIDATION IN CARBONATED SOFT DRINKS WALDO ANDRÉS ACEVEDO CASTILLO Thesis submitted to the Office of Graduate Studies in partial fulfillment of the requirements for the Degree of Doctor in Engineering Sciences Advisor: EDUARDO AGOSIN Santiago de Chile, November, 2017 2017, Waldo Andrés Acevedo Castillo PONTIFICIA UNIVERSIDAD CATOLICA DE CHILE SCHOOL OF ENGINEERING ORGANOLEPTICAL PROPERTIES OF NATURAL, NON-CALORIC SWEETENERS: MOLECULAR SIMULATION, MIXTURE OPTIMIZATION AND EXPERIMENTAL VALIDATION IN CARBONATED SOFT DRINKS WALDO ANDRÉS ACEVEDO CASTILLO Members of the Committee: EDUARDO AGOSIN T. RICARDO PÉREZ C. DANILO GONZÁLEZ N. JAVIER SÁINZ L. PIERO A. TEMUSSI JORGE VÁSQUEZ P. Thesis submitted to the Office of Graduate Studies in partial fulfillment of the requirements for the Degree of Doctor in Engineering Sciences Santiago de Chile, November, 2017 To my family, Ximena, Valentina and Sebastián. To my parent, Marlene and Sergio To my grandmother, Teresa To my brother, Aroldo i ACKNOWLEDGMENTS I would like to thank all people who have contributed to this work either in the research area or with everyday support. Many thanks also to everyone in the Biotechnology laboratory of the Chemical Engineering and Bioprocess Department and “Centro de Aromas y Sabores – DICTUC” for their friendship and for making the laboratory an agreeable place to work. I would like to express my sincere gratitude to my advisor, Professor Eduardo Agosin, for his continuous support, motivation, and patience, his valuable supervision, his sharp observations and good advice throughout this thesis. His 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. Also thanks to professors Piero A. Temussi, Danilo González, Javier Sáinz and Ricardo Pérez for their support in different stages of this thesis and for their comments and discussions to improve the final version of this manuscript and the oral presentation. In particular, I am grateful to Dr. Temussi for enlightening me the glance of research. Thanks to the Comisión Nacional de Investigación Científica y Tecnológica (CONICYT), the Vicerrectoría de Investigación (VRI) and Pontificia Universidad Católica de Chile for providing the necessary funding to make this research possible. Last but not the least, I would like to thank my wife, Ximena, and my children, Valentina and Sebastián, for supporting me spiritually throughout writing this thesis and my life in general. ii LIST OF PUBLICATIONS This thesis is based on the following publications. Acevedo, W.A, González-Nilo, F., Agosin, E. 2016. Docking and Molecular Dynamics Simulations of Steviol Glycosides – Human Bitter Receptors Interactions. Journal of Agricultural and Food Chemistry. 64, 7585 – 7596. Acevedo, W.A, Ramírez-Sarmiento, C., Agosin, E. 2017. Identifying the Interactions between Natural, Non-Caloric Sweeteners and the Human Sweet Receptor by Molecular Docking. (Submitted to Journal of Food Chemistry, Manuscript ID: FOODCHEM-S-17-0923) Acevedo, W.A, Capitaine, C., Rodríguez, R., Araya, I., González-Nilo, F., Pérez- Correa, R, Agosin, E. 2017. Selecting Optimal Mixtures of Natural Sweeteners for Carbonated Soft Drinks through Multi-objective Decision Modeling and Sensory Validation. (Submitted to Food Quality and Preference Journal. Manuscript ID: FQAP_2017_5 ) iii INDEX OF CONTENTS ACKNOWLEDGMENTS ......................................................................................... ii LIST OF PUBLICATIONS ...................................................................................... iii INDEX OF CONTENTS .......................................................................................... iv FIGURE INDEX ..................................................................................................... viii TABLE INDEX ........................................................................................................ xii ABREVIATION INDEX ........................................................................................ xiii ABSTRACT .............................................................................................................. xv RESUMEN ............................................................................................................. xviii 1. INTRODUCTION ............................................................................................ 1 1.1 Motivation .................................................................................................. 1 1.2 Taste Receptors .......................................................................................... 1 1.2.1 Sweetness Receptor ......................................................................... 1 1.2.2 Bitterness Receptor .......................................................................... 4 1.3 Natural, non-caloric sweeteners ................................................................. 5 1.3.1 Low-molecular-weight sweeteners .................................................. 6 1.3.2 Sweet proteins .................................................................................. 7 1.4 Optimal mixtures of sweeteners ................................................................ 9 1.5 Working hypothesis ................................................................................. 10 1.6 Objectives ................................................................................................ 10 1.7 Approach ................................................................................................. 11 2. CHAPTER I: DOCKING AND MOLECULAR DYNAMICS OF STEVIOL GLYCOSIDE - HUMAN BITTER RECEPTORS INTERACTIONS............................................................................................ 13 iv 2.1 Introduction .............................................................................................. 13 2.2 Materials and methods ............................................................................. 16 2.2.1 Template selection ......................................................................... 16 2.2.2 Modeling of bitter taste receptors .................................................. 16 2.2.3 Ligand preparation ......................................................................... 17 2.2.4 Molecular docking of "sweeeteners - bitter taste receptors" ......... 18 2.2.5 Mathematical modeling of the relationship between relative bitterness and the interaction paramter .......................................... 19 2.2.6 Analysis of protein - ligand interaction ......................................... 19 2.2.7 Molecular dynamics simulations ................................................... 20 2.2.8 Steered molecular dynamics simulations ....................................... 21 2.3 Results ...................................................................................................... 22 2.3.1 Modeling of taste receptors responsible for the bitterness of stevia .............................................................................................. 22 2.3.2 Molecular docking and binding site characterization .................... 23 2.3.3 Ligand - receptor molecular dynamics simulations ....................... 30 2.3.4 Steered molecular dynamics simulations ....................................... 31 2.4 Discussion ................................................................................................ 33 2.5 Acknowledgments ................................................................................... 36 3. CHAPTER II: IDENTIFYING THE INTERACTIONS BETWEEN NATURAL, NON-CALORIC SWEETENERS AND THE HUMAN SWEET RECEPTOR BY MOLECULAR DOCKING ....................................................... 37 3.1 Introduction .............................................................................................. 37 3.2 Materials and methods ............................................................................. 40 3.2.1 Template selection ......................................................................... 40 3.2.2 Modeling of sweet taste receptor ................................................... 40 3.2.3 Preparation of ligands .................................................................... 41 3.2.4 Molecular docking of "sweeeteners – sweet taste receptor" .......... 42 3.3 Results ...................................................................................................... 44 3.3.1 Modeling of sweet taste receptor ................................................... 44 v 3.3.2 Analisys of molecular docking ...................................................... 44 3.4 Discussion ................................................................................................ 49 3.5 Conclusions .............................................................................................. 51 3.6 Acknowledgments .................................................................................... 52 4. CHAPTER III: SELECTING OPTIMAL MIXTURES OF NATURAL SWEETENERS FOR CARBONATED SOFT DRINKS THROUGH MULTI-OBJECTIVE DECISION MODELING AND SENSORY VALIDATION ............................................................................................... 54 4.1 Introduction .............................................................................................
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