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Phytochemical Characterization and Sensory Evaluation of Macropiper Excelsum

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Phytochemical Characterization and Sensory Evaluation of Macropiper Excelsum TECHNISCHE UNIVERSITÄT MÜNCHEN Lehrstuhl für Allgemeine Lebensmitteltechnologie Phytochemical Characterization and Sensory Evaluation of Macropiper excelsum Katja Obst Vollständiger Abdruck der von der Fakultät Wissenschaftszentrum Weihenstephan für Ernährung, Landnutzung und Umwelt (WZW) der Technischen Universität München zur Erlangung des akademischen Grades eines Doktors der Naturwissenschaften (Dr. rer. nat.) genehmigten Dissertation. Vorsitzender: Univ.-Prof. Dr. Peter Schieberle Prüfer der Dissertation: 1. Univ.-Prof. Dr. Karl-Heinz Engel 2. Univ.-Prof. Dr. Thomas Hofmann Die Dissertation wurde am 12.05.2014 bei der Technischen Universität München eingereicht und durch die Fakultät Wissenschaftszentrum Weihenstephan für Ernährung, Landnutzung und Umwelt (WZW) am 07.10.2014 angenommen. ACKNOWLEDGEMENTS First and foremost, I would like to thank Professor Dr. Karl-Heinz Engel for his valuable scientific advice, his enlightening comments, and his interest in the progress of my thesis. I would like to show my gratitude to Dr. Gerhard Krammer, Senior Vice President Research & Technology Flavor & Nutrition, for the provision of this fascinating research project and his great interest in my work. This thesis would not have been possible without the guidance and help of Dr. Jakob Ley, Director Ingredient Research. I sincerely appreciate his excellent supervision, his ideas and proposals, as well as his encouragement. Thank you also for your confidence in my work and the possibilities to present the results of my thesis to the scientific community in many talks and poster sessions at various meetings. I would like to convey my sincerest gratitude to Dr. Katharina Reichelt, Natural Product Chemistry/Functional Flavor Solutions, for her perpetual help in all phases of this work. I highly appreciate her outstanding enthusiasm and her motivation. Katharina, thank you also very much for the late discussion sessions, your great support during writing up my thesis, and the endless supply of cookies and chocolate. I give my cordial thanks to the team of Symrise Ingredient Research, Petra Hoffmann-Lücke, Maria Blings, and Gisela Kunze, for their helpfulness in the everyday laboratory routine and the enjoyable working atmosphere. I highly appreciate the support of Dr. Michael Backes, his valuable scientific advice concerning synthetic chemistry and the great discussions. My special thanks go to Susanne Paetz and Susanne Mundt for sharing their expert knowledge in sensory analysis and their exceptional assistance in the innumerable tasting sessions. I would also like to thank the flavorists Kathrin Langer, Thomas Riess, and Rüdiger Hupe for their support in sensory evaluation and helpful suggestions during the last three years. Thank you also to Rüdiger Wittlake, Thomas Begemann, and Ingo Eikenberg for carrying out the LC-MS measurements, Regina Beier for her help in preparative HPLC, and Dr. Wiebke Zander and Beate Hartmann for NMR measurement and structure elucidation of the isolated molecules. I highly appreciate the work of Martin Heinemeyer, carrying out the LC Taste® fractionation, and of Stefan Brennecke, who has helped my so many times to get the FCPC running. Special thanks also to Birgit Kohlenberg, Markus Eggers, Lars Grohmann, and Iulia Poplacean for their support in GC and GC-MS analysis. Finally, I would like to thank all panelists who took part in the countless numbers of sensory sessions for their help and endurance. And last but not least, I would like to thank my friends at home, in Holzminden, and from all over Germany who have supported me in so many ways, and my parents for their infinite support, their love and encouragement. Ich bin froh, dass es Euch gibt! TABLE OF CONTENTS 1 ..... INTRODUCTION AND OBJECTIVES .............................................. 1 2 ..... BACKGROUND ......................................................................... 4 2.1 MECHANISM OF SENSORY PERCEPTION ............................................ 4 2.1.1 Signal Transduction in Taste Buds and Taste Cells .................................. 5 2.1.2 Structure and Function of Taste Receptors ............................................... 8 2.1.3 Trigeminally Active Compounds .............................................................. 12 2.1.4 Astringency Perception ........................................................................... 16 2.1.5 Reduction of Unpleasant Taste and Flavor ............................................. 19 2.2 PRINCIPLES OF SENSORY ANALYSIS ................................................ 21 2.2.1 Time-Intensity Measurements ................................................................. 22 2.3 MACROPIPER EXCELSUM .................................................................... 23 2.4 EXTRACTION, PURIFICATION AND ISOLATION TECHNIQUES ......... 28 2.4.1 Extraction Techniques - Pressurized Solvent Extraction ......................... 28 2.4.2 Sensory-Guided Analysis ........................................................................ 30 2.4.2.1 Aroma Analysis using Gas Chromatography-Olfactometry (GC-O) ......... 30 2.4.2.2 Taste Analysis ......................................................................................... 32 2.4.3 Fast Centrifugal Partition Chromatography (FCPC) ................................ 35 2.4.3.1 Principle of Countercurrent Chromatography .......................................... 35 2.4.3.2 Selection of Solvent Systems for FCPC .................................................. 39 3 ..... MATERIAL AND METHODS .......................................................... 41 3.1 MATERIAL .............................................................................................. 41 3.1.1 Chemicals ............................................................................................... 41 3.1.2 Plant Material .......................................................................................... 43 3.2 TECHNICAL EQUIPMENT ...................................................................... 44 3.3 METHODS .............................................................................................. 47 3.3.1 Extraction of Plant Material ..................................................................... 47 3.3.1.1 Preparation of a Pentane/Diethyl Ether Extract of M. excelsum .............. 47 3.3.1.2 Preparation of an Ethanol/Water Extract of M. excelsum ........................ 47 3.3.1.3 Preparation of Extracts using the SpeedExtractor ................................... 47 3.3.2 Methods for Volatile Analysis of the n-Pentane-Diethyl Ether Extract ..... 48 3.3.3 High Temperature Liquid-Chromatographic Separation of the Ethanol/Water Extract ............................................................................. 49 3.3.4 Fast Centrifugal Partition Chromatography ............................................. 49 3.3.4.1 Selection of a Solvent System ................................................................. 49 3.3.4.2 FCPC – Fractionation of the Ethanol/Water Extract of M. excelsum ....... 49 3.3.5 Preparative HPLC ................................................................................... 50 3.3.6 Liquid Chromatography – Mass Spectrometry ........................................ 52 3.3.7 Gas Chromatography - Mass Spectrometry Direct Inlet .......................... 52 3.3.8 Sensory Analysis ..................................................................................... 53 3.3.8.1 General Conditions .................................................................................. 53 3.3.8.2 Sensory Analysis of High-Temperature Liquid-Chromatography Fractions ................................................................................................................. 53 3.3.8.3 Flavor Language ..................................................................................... 54 3.3.8.4 Pre-Tests for Masking Trials .................................................................... 54 3.3.8.5 Intensity Variation Descriptive Methodology (IVDM) ............................... 55 3.3.8.6 Statistical Analysis ................................................................................... 56 4 ..... RESULTS AND DISCUSSION ....................................................... 57 4.1 MACROPIPER EXCELSUM .................................................................... 57 4.1.1 Volatile Compounds in M. excelsum ....................................................... 57 4.1.2 Non-Volatile Compounds in M. excelsum ................................................ 60 4.1.2.1 Authentication and Comparison with Piper methysticum ......................... 61 4.1.2.2 Sensory-Guided Analysis of the Non-Volatile Compounds via HTLC ...... 62 4.1.2.3 Identification of Compounds in M. excelsum Extract by Comparison of Reference Molecules ............................................................................... 65 4.1.2.4 Fast Centrifugal Partition Chromatography (FCPC) of M. excelsum Extract ................................................................................................................. 67 4.1.2.5 Isolation of Compounds from FCPC Fractions via Preparative HPLC ..... 70 4.1.2.6 Structure Elucidation of Isolated Compounds via NMR Spectroscopy .... 76 4.1.2.7 Comparison of the Contents of Non-Volatile Comounds in Different Parts of the M. excelsum Plant ....................................................................... 103 4.1.3 Sensory Evaluation of the Compounds Identifid in M. excelsum ........... 106
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