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Downloads/Drugs/Guidances/Ucm070107.Pdf DEVELOPMENT AND VALIDATION OF METHODS FOR THE INVESTIGATION OF WINE STILBENOIDS by RYAN KURTIS MOSS B.Sc., University of British Columbia, 2011 A THESIS SUBMITTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF MASTER OF SCIENCE in THE COLLEGE OF GRADUATE STUDIES Chemistry THE UNIVERSITY OF BRITISH COLUMBIA (Okanagan) September 2014 © Ryan Kurtis Moss, 2014 Abstract Stilbenoids are secondary plant metabolites responsible for the protection of grape vine from bacterial and fungal infection. Red wine has been shown to be a major source of these compounds in the human diet, where they display an array of health benefits. The first goal of our study was to develop and validate a robust and selective method for quantification of the major stilbenoids in red and white wine using ultra-high-performance liquid chromatography coupled with electrospray ionization/quadrupole time-of-flight mass spectrometry (UHPLC-ESI-Q-TOF). Both isomers of resveratrol and piceid were quantified externally using authentic standards, while piceatannol was quantified in trans-piceid equivalents. Due to the minimal amount of sample preparation and the short method runtime, results were obtained rapidly and with low expenditure of energy, chemicals, and labor. The method was validated with respect to linearity, limit of detection (LOD), limit of quantification (LOQ), accuracy, intra- and inter-day precision and stability. All six stilbene monomers were quantified in 44 British Columbian wines; the highest total stilbene concentration in an individual wine was 28.81 mg/L in Pinot Noir, while the average across all wines was 8.49 ± 6.25 mg/L. Another method was developed for separation, identification and semi-quantification of all derivatives of resveratrol that are present in wine. ii A total of 41 (both known and novel) stilbenoids were detected in extracted red wine. In addition to the well-known monomeric stilbenes, several resveratrol-resveratrol homodimers (m/z 453.1344), resveratrol-piceatannol heterodimers (m/z 469.1293) and piceatannol- piceatannol homodimers (m/z 485.1236) were detected. Modified dimers of resveratrol were also detected. Multiple trimers of resveratrol (m/z 679.1978) were detected for the first time in red wine, as well as some known and some novel stilbenoid tetramers (m/z 905.2604). A solid-phase extraction (SPE) method was developed for quantification of the stilbenoid oligomers in red wines. The monomers and oligomers in red wine from the Okanagan Valley (Cabernet Sauvignon, Merlot and Pinot Noir) and Québec (Maréchal Foch, Marquette, Sabrevois, St.Croix, and Frontenac) wines were semi-quantified as using this method. The highest concentration of total stilbenoids was 10.67 mg/L in Pinot Noir with an overall average of 3.32 ± 2.86 mg/L in all wines. iii Preface All of the optimization, sample preparation and analysis using ultra-high performance liquid chromatography, coupled with quadupole time-of-flight mass spectrometry were performed on the University of British Columbia, Okanagan campus (UBCO) by Ryan Moss. Many of the standards used in this study were synthesized at The University of Adelaide, School of Agriculture, Food and Wine in Dr. Dennis Taylor’s lab, by Qinyong Mao. The study was designed by Dr. Cédric Saucier, Dr. Dennis Taylor, and Ryan Moss. A manuscript containing the identification of numerous stilbenoid derivatives, many newly discovered in wine, was prepared primarily by Ryan Moss with editorial assistance from Dr. Saucier. The manuscript was published in Rapid Communications in Mass Spectrometry in May 2013. The same results were presented in a poster presentation at the 2013 annual American Society of Mass Spectrometry in June 2013. iv Table of Contents Abstract ......................................................................................................................................................... ii Preface ......................................................................................................................................................... iv Table of Contents .......................................................................................................................................... v List of Tables ............................................................................................................................................. viii List of Figures .............................................................................................................................................. ix List of Abbreviations .................................................................................................................................. xii Acknowledgements .................................................................................................................................... xiv CHAPTER 1 – INTRODUCTION ............................................................................................................... 1 1.1 General Polyphenols ........................................................................................................................... 1 1.1.1 Stilbenes ....................................................................................................................................... 5 1.1.2 Metabolism and Biosynthesis of Stilbenes in Vitis vinifera. ........................................................ 6 1.1.3 Medical and Health Benefits of Stilbenes .................................................................................. 11 1.2 Instrumentation Background ............................................................................................................. 12 1.2.1 Ultra High Performance Liquid Chromatography ..................................................................... 12 1.2.1 General Mass Spectrometry ....................................................................................................... 14 1.2.1.1 Electrospray Ionization ....................................................................................................... 17 1.2.1.2 Quadrupole-Time-of-Flight (Q-TOF) Mass Analyzer ........................................................ 19 1.3 Identification and Quantification of Stilbenoids in Wine Using Mass Spectrometry ....................... 22 1.4 Research Objectives .......................................................................................................................... 24 1.5 Hypotheses & Rationale ................................................................................................................... 24 1.6 Significance of study ......................................................................................................................... 26 CHAPTER 2 – DEVELOPMENT OF A VALIDATED METHOD FOR QUANTIFICATION OF MONOMERIC STILBENES IN WINE ..................................................................................................... 27 2.1 Synopsis ............................................................................................................................................ 27 2.2 Experimental ..................................................................................................................................... 28 2.2.1 Test Samples .............................................................................................................................. 28 2.2.2 Reagents and Materials .............................................................................................................. 28 2.2.3 Calibration Standards ................................................................................................................. 28 2.2.4 UHPLC-ESI-Q-TOF Analysis ................................................................................................... 30 2.2.5 Validation ................................................................................................................................... 32 v 2.2.5.1 Linearity, Limits of Detection and Quantification .............................................................. 32 2.2.5.2 Intra-, Inter-day Repeatability, and Stability ....................................................................... 33 2.2.5.3 Recovery ............................................................................................................................. 33 2.3 Results & Discussion ........................................................................................................................ 35 2.3.1 Optimization of UHPLC-ESI-Q-TOF and Analysis .................................................................. 35 2.3.1.1 Optimization of UHPLC Parameters .................................................................................. 35 2.3.1.2 Optimization of ESI-Q-TOF Parameters ............................................................................ 37 2.3.2 Validation ................................................................................................................................... 43 2.3.2.1 Specificity ........................................................................................................................... 43 2.3.2.2 Calibration Curves .............................................................................................................. 45 2.3.2.3 Linearity, Limits of Detection, and Quantification ............................................................. 48 2.3.2.4 Precision, Stability, and Recovery .....................................................................................
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