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Masterarbeit / Master's Thesis MASTERARBEIT / MASTER’S THESIS Titel der Masterarbeit / Title of the Master‘s Thesis “The Detection of caprylate produced by gut microbiota” verfasst von / submitted by András Gregor, BSc angestrebter akademischer Grad / in partial fulfilment of the requirements for the degree of Master of Science (MSc) Wien, 2017 Studienkennzahl lt. Studienblatt / A 066 838 degree programme code as it appears on the student record sheet: Studienrichtung lt. Studienblatt / Masterstudium Ernährungswissenschaften degree programme as it appears on the student record sheet: Betreut von / Supervisor: Univ.-Prof. Dr. Jürgen König Mitbetreut von / Co-Supervisor: Acknowledgement First, I would like to express my thanks to Univ.-Prof. Dr. Jürgen König and Univ.-Prof. Dr. Veronika Somoza for making it possible for me to do this Master thesis and for always being kind and helpful. Thank you, Dr. Kalina Duszka for your patience. You showed me how to work hard and motivated me when I was overwhelmed with the writing. Also, thank you for improving my personality, I appreciate it. Dr. Marc Pignitter, even when you were busy, you never minded spending (often more than enough) time on showing something or on talking something through. Because of this, and the nice people in the group the working atmosphere was always very good. Thank you. Ohne Jessica gäbe diese Masterarbeit nicht. Danke für die Motivation, für die Unterstützung und dafür, dass du mich immer so gut verstanden hast. Mohu se spolehnout na tebe v pristich letech. Dankica. Isabella, I’d like to thank you for the tremendous help you have given me over the past few years. Ádám, thank you for your help. I hope you enjoyed it as much as I did and I also hope you are still willing to help me in the future! Thank you Nika for helping to have more diplomas in our family and thank you Cicó for the 10 years. Great thanks to all members of my family, my friends, and of course Mr. Handy who was always there for me. I Eidesstattliche Erklärung Hiermit erkläre ich, dass ich diese Masterarbeit selbstständig verfasst und keine anderen als die angegebenen Quellen und Hilfsmittel benutzt und die aus fremden Quellen direkt oder indirekt übernommenen Gedanken als solche kenntlich gemacht habe. Wien, 2017 II Index of Abbreviations 4-APEBA 4-(2-((4- bromophenethyl)dimethylammonio)ethoxy)benzenaminiumdibromide AA Amino Acid abWAT Abdominal white adipose tissue ACN Acetonitrile AD Autoimmune disease BAT Brown Adipose Tissue CBT Core body temperature CLA Conjugated linoleic acid CR Caloric restriction DPP Dipeptidyl peptidase dWAT Dorsal white adipose tissue EDC (N- (3-Dimethylaminopropyl) -N′- ethylcarbodiimide hydrochloride EDTA ethylenediaminetetraacetic acid ESI Electrospray ionization eWAT Epididymal white adipose tissue FA Fatty acid FFA Free Fatty Acid IGF Insulin-like growth factor LA Lauric Acid LCFA Long Chain Fatty Acid MCFA Middle Chain Fatty Acid LCT Long Chain Triglyceride MeOH Methanol MG Monoglyceride MCT Middle Chain Triglyceride MIC Minimum Inhibitory Concentration MO Microorganism III ND Neurodegenerative disease NHS N-Hydroxysuccinimide NK Natural killer PPAR Peroxisome Proliferator Activated Receptor ROS Reactive oxygen species SCFA Short Chain Fatty Acid STDO Caprylate analytical standard STDR Isotopically labelled caprylate TG Triglyceride UCP Uncoupling Protein WAT White Adipose Tissue IV Table of Content 1 Abstract................................................................ 1 2 Zusammenfassung ............................................... 3 3 Introduction ......................................................... 5 3.1 Caloric restriction ............................................................. 6 3.1.1 Positive Effects of CR .................................................. 7 3.1.2 Negative Effects of CR ................................................ 11 3.2 Caprylate ....................................................................... 12 3.2.1 Introduction .............................................................. 12 3.2.2 Where can caprylate be found? .................................... 13 3.2.3 MCTs’ occurrence in human nutrition, digestion, absorption, storage and metabolism ....................................... 13 3.2.4 Caprylate concentration in plasma and faeces ............... 16 3.2.5 Health advantages ..................................................... 16 3.3 Intestinal microbiome ...................................................... 20 3.3.1 Metabolic products ..................................................... 20 4 Materials and Methods ....................................... 22 4.1 Bedding and chow........................................................... 22 4.2 Materials ....................................................................... 22 4.2.1 Equipment ................................................................ 22 4.2.2 Accessories ............................................................... 23 4.3 Reagents ....................................................................... 24 4.3.1 Chemicals ................................................................. 24 V 4.3.2 Preparation of solvents .............................................. 25 4.3.3 Eluent ..................................................................... 25 4.4 Animals and experimental protocol ................................... 26 4.4.1 Tissue collection ....................................................... 27 4.5 NMR ............................................................................. 28 4.6 Plasma caprylate detection .............................................. 28 4.6.1 Sample preparation ................................................... 30 4.6.2 Measurement with HPLC-MS/MS ................................. 32 4.6.3 Validation ................................................................ 33 4.6.4 Precursor ion ............................................................ 36 4.6.5 Quantifier and Qualifier ............................................. 37 4.6.6 Statistical analysis .................................................... 39 5 Results ............................................................... 40 5.1 Bedding ........................................................................ 40 5.2 Starting meal ................................................................ 43 5.3 Glucose ........................................................................ 44 5.4 Body weight .................................................................. 45 5.5 Weight of the organs ...................................................... 46 5.6 Calorimetry ................................................................... 48 5.7 HPLC-MS/MS detection of caprylate in plasma ................... 50 5.7.1 Optimization of caprylate detection ............................. 50 5.7.2 Selectivity ................................................................ 51 5.7.3 Limit of quantification/detection .................................. 52 5.7.4 Plasma caprylate concentration .................................. 53 5.7.5 Further optimization .................................................. 54 VI 5.8 NMR .............................................................................. 57 6 Discussion .......................................................... 60 7 Conclusion .......................................................... 64 8 References ......................................................... 66 VII Figures Figure 1: Caprylate. ................................................................. 12 Figure 2: Intestinal fatty acid absorption. .................................... 14 Figure 3: Possible mechanisms of the antibacterial effects of FFA. .. 19 Figure 4: Pipetting scheme for establishing the method for derivatization. ......................................................................... 29 Figure 5: Scheme for hydrolyzation, extraction and derivatization. 31 Figure 6: A variety of product ions for caprylate.. ......................... 33 Figure 7: Electrospray ionisation and ion source overview. ............ 36 Figure 8: Triple quadrupole mass spectrometer............................ 37 Figure 9: Major fragmentations of the adduct of 4-APEBA and caprylate. ................................................................................ 38 Figure 10: Bedding eaten. ......................................................... 40 Figure 11: Fiber eatin in g/day. .................................................. 42 Figure 12: Total fiber intake. ..................................................... 42 Figure 13: Start meal. .............................................................. 43 Figure 14: Fasting glucose levels. ............................................... 44 Figure 15: BW changes of CR mice. ............................................ 45 Figure 16: Total BW loss in %. ................................................... 46 Figure 17: Cecum weight.. ........................................................ 47 Figure 18: Stomach weight.. ..................................................... 47 Figure 19: Sum sWAT. .............................................................. 48 Figure 20:Average calorie content/g. .......................................... 49 Figure 21: Daily calorie content of feces. ..................................... 49 Figure 22: Caprylate bound to 4-APEBA. ..................................... 50 Figure 23: Caprylate has a retention time at 19.4. ....................... 51 Figure 24: Isotopically labeled caprylate
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