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1 Musterseite Im C5-Format Für Winword Comprehensive Analysis of Cocoa Lipidomics – unraveling the unknown chemistry of cocoa butter by Diana Sirbu a Thesis submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Chemistry Approved Dissertation Committee Prof. Dr. Nikolai Kuhnert, Jacobs University Bremen, Germany Prof. Dr. Matthias Ullrich, Jacobs University Bremen, Germany Dr. Frédéric Depypere, Barry Callebaut Lebbeke-Wieze, Belgium Date of Defense: June 1st, 2018 Department of Life Sciences and Chemistry Sirbu Diana 20331305 Ph. D. Thesis 07.09.2018 I dedicated this thesis to my family for their encouragement, lifelong support and inconditional love. Table of contents Preface ............................................................................................................................................................... I Abstract ........................................................................................................................................................... III List of abbreviations........................................................................................................................................ VI List of figures ............................................................................................................................................... VIII List of tables .................................................................................................................................................. XV Chapter 1: .......................................................................................................................................................... 1 1 Introduction .................................................................................................................................................... 1 1.1 Lipidomics ............................................................................................................................................. 1 1.1.1 General concept of Lipidomics........................................................................................................... 1 1.1.2 Lipid classification and functions ....................................................................................................... 1 1.1.3 Experimental approaches in lipidomics research................................................................................ 5 1.1.4 Plant lipidomics .................................................................................................................................. 7 1.1.5 Lipidomics and food science .............................................................................................................. 8 1.2 Theobroma cacao – from bean to bar .................................................................................................... 9 1.2.1 History, origin, and cocoa varieties .................................................................................................... 9 1.2.2 Agriculture ....................................................................................................................................... 10 1.2.3 Post-harvesting treatments ................................................................................................................ 11 1.2.4 Factory production process ............................................................................................................... 12 1.2.5 Economic impact and health benefits ............................................................................................... 15 Chapter 2: ........................................................................................................................................................ 21 2 Review on cocoa lipidomics – state of knowledge and future needs ........................................................... 21 Abstract ........................................................................................................................................................... 22 2.1 Introduction ......................................................................................................................................... 23 2.2 From cocoa tree to cocoa butter ........................................................................................................... 24 2.3 Quality criteria of cocoa butter ............................................................................................................ 29 2.4 Chemical composition background and significance ........................................................................... 30 2.4.1 Cocoa fat content .............................................................................................................................. 30 2.4.2 Fatty acids composition .................................................................................................................... 31 2.4.3 Triacylglycerol composition ............................................................................................................. 34 2.4.4 Minor components ............................................................................................................................ 40 2.5 Correlation of chemical composition with the physical properties of cocoa butter ............................. 42 2.5.1 Cocoa butter polymorphism ............................................................................................................. 43 2.5.2 Crystallization and melting behavior ................................................................................................ 45 2.5.3 Influence of the origin – softness assessment ................................................................................... 47 2.6 Cocoa butter alternatives ..................................................................................................................... 48 2.7 Conclusions ......................................................................................................................................... 48 2.8 Aim of the thesis .................................................................................................................................. 49 Chapter 3: ........................................................................................................................................................ 61 3 Exploring cocoa lipid classes ....................................................................................................................... 61 Abstract ........................................................................................................................................................... 61 3.1 Introduction ......................................................................................................................................... 62 3.2 Material and Methods .......................................................................................................................... 64 3.2.1 Chemicals and reagents .................................................................................................................... 64 3.2.2 Preparation of the seed sample ......................................................................................................... 64 3.2.3 Thin layer chromatography (TLC) ................................................................................................... 65 3.2.4 Solid phase extraction (SPE) ............................................................................................................ 65 3.2.5 Silica gel column chromatography ................................................................................................... 66 3.2.6 HPLC chromatographic conditions .................................................................................................. 66 3.2.7 Mass spectrometry detection ............................................................................................................ 66 3.3 Results and discussion ......................................................................................................................... 67 3.3.1 Extraction optimization .................................................................................................................... 67 3.3.2 TLC lipid profile .............................................................................................................................. 70 3.3.3 Separation of lipid classes ................................................................................................................ 73 3.4 Conclusions ......................................................................................................................................... 76 Chapter 4: ....................................................................................................................................................... 79 4 Characterization of triacylglycerols in unfermented cocoa beans by HPLC-ESI mass spectrometry .......... 79 Abstract ........................................................................................................................................................... 80 4.1 Introduction ......................................................................................................................................... 81 4.2 Material and methods .........................................................................................................................
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