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An Abstract of the Thesis Of AN ABSTRACT OF THE DISSERTATION OF Mei Song for the degree of Doctor of Philosophy in Food Science and Technology presented on June 8, 2017. Title: Free Monoterpene Isomer Profiles in White Wine: Effect of Grape Variety, Region and Style and Impact on Odor Perception Abstract approved: _____________________________________________________________________ Elizabeth Tomasino Monoterpenes are important volatile compounds to the aroma of many white wines. Many monoterpenes are chiral and found in wine as different isomers. These isomers (also known as enantiomers) are non-superimposable mirror images of each other, maintain the same molecular structure and in many instances possess different sensory characteristics. Much research in wine has investigated the contents of monoterpenes, but has largely overlooked the monoterpene enantiomer profiles and important roles of the different monoterpene enantiomers in wine. Monoterpene enantiomer profiles in grapes and final wine are due to many factors, including genotype (grape variety), climate, temperature, soil type and winemaking technique. These compounds are of great interest to wine as they are related to the unique sensory identity of varietal wine. The aim of the project was to: firstly develop a robust and valid method for monoterpene enantiomer identification and quantitation, secondly investigate the effect of grape variety, growing region and wine style on the profiles of monoterpene enantiomers, thirdly determine the important role of monoterpene isomer profiles in wine matrix and evaluate the effect of interactions between monoterpenes and other wine components on odor perception of wine. The study presented the comprehensive exploration of monoterpene enantiomers (S-(-)-limonene, R-(+)-limonene, (2R,4S)-(+)-cis-rose oxide, (2S,4R)-(-)-cis-rose oxide, (2R,4R)-(-)-trans-rose oxide, (2S,4S)-(+)-trans-rose oxide, (2R,5R)-(+)-trans-linalool oxide, (2R,5S)-(-)-cis-linalool oxide, (2S,5S)-(-)-trans-linalool oxide, (2S,5R)-(+)-cis- linalool oxide, R-(-)-linalool, S-(+)-linalool, S-(-)-α-terpineol, R-(+)-α-terpineol, and R- (+)-β-citronellol) in white wines from different grape varieties using head-space solid phase micro-extraction-multidimensional GC-MS (HS-SPME-MDGC-MS). In addition, it presented for the first time the varietal differences from monoterpene enantiomers and enantiomer fractions which were calculated by dividing the first eluting enantiomer by the total enantiomers of each compound (enantiomer pairs). Despite heterogeneity in vintages, regions, and styles, varietal wines could be clearly differentiated. Results have expanded upon the current knowledge of varietal distinctiveness based on isomer profiles and enantiomeric fraction. Riesling wines possess very diverse flavors as the composition of grapes, can be altered by environmental characteristics and viticultural practices. Moreover, Riesling wines carry more stylistic variability in terms of residual sugar content, than any other major international white grape variety. Our study found that chiral monoterpene profiles and enantiomer fractions could be important factors to classify Riesling wines according to their geographical origin and style. Sensory discrimination tests were performed to elucidate the interactions between monoterpene isomers at low concentrations and other wine components. The results imply that a combination of enhancing and suppression effects occur and impact the perception of monoterpene isomer profiles in Pinot gris wines. Furthermore, the effects of same monoterpene profiles differed according to the matrices, displaying the many interactions that occur and affect sensory perception. The study on chiral monoterpenes in white wine not only expands our knowledge on monoterpene isomer analysis and distribution, but it provides information for varietal quality, by offering an objective measure of flavor quality. Additionally we have shown that when investigating sensory perception it is important to use a matrix as close to the original product and we further support that aroma compounds found at concentrations below their known perception thresholds can effect aroma perception. ©Copyright by Mei Song June 8, 2017 All Rights Reserved Free Monoterpene Isomer Profiles in White Wine: Effect of Grape Variety, Region and Style and Impact on Odor Perception by Mei Song A DISSERTATION submitted to Oregon State University in partial fulfillment of the requirements for the degree of Doctor of Philosophy Presented June 8, 2017 Commencement June 2017 Doctor of Philosophy dissertation of Mei Song presented on June 8, 2017 APPROVED: _____________________________________________________________________ Major Professor, representing Food Science & Technology _____________________________________________________________________ Head of the Department of Food Science & Technology _____________________________________________________________________ Dean of the Graduate School I understand that my dissertation will become part of the permanent collection of Oregon State University libraries. My signature below authorizes release of my dissertation to any reader upon request. _____________________________________________________________________ Mei Song, Author ACKNOWLEDGEMENTS I would like to acknowledge all those people who have supported and helped me so much throughout my PhD program. I would like to express the deepest appreciation to my advisor, Dr. Elizabeth Tomasino, without her invaluable guidance and constant help this dissertation would not have been possible. She provided recommendations and instructions but also gave me intellectual freedom in my work, supported my attendance at various conferences, encouraged my scholarships application, and demanded a high quality of work has made me more independent and confident and enabled me to finish this dissertation effectively. I am also very grateful to all committee members. Thanks to Dr. Claudio Fuentes for his encouragement and supervisory role on my statistical analysis during the study. My thanks also go out to Dr. Michael Qian for his invaluable advice and feedback on my research design. I greatly appreciate the support from Dr. James Osborne on Pinot gris winemaking for my sensory study. A special thank goes to Dr. Benjamin Philmus, who was willing to serve as GCR in my final defense at the last moment. My deep appreciation goes out to Nadine Skyllingstad for her assistance with my sensory panels, and bottling of wine. Many thanks to Ying Xia, Athena Loos, Akira Kurniawan Ishii, and Hongyan Yu for their help with wine sampling and the residual sugar analysis in all of the wines investigated; Samuel Hoffman, Kiyomi Ide, Chase E Jutzi, Anthony Le, and Vaishnavi Trivedi for their help with the sensory analysis in this study. In addition, thanks to my lab mates, Pallavi Mohekar, Jack Twilley, Anthony Sereni and Quynh Phan for their friendship, help and support. Many thanks go out to Dr. Robert McGorrin, Linda Hoyer, Linda Dunn, Holly Templeton, Debby Yacas, and Christina Hull for their support and help during my PhD program. I would also like to say a heartfelt thank you to my parents, in-laws and younger sister for always believing in me, supporting and encouraging me, dedicating their time taking care of my kids, providing the emotional support I needed to complete my dissertation. To them, I am eternally grateful. Finally, I would like to thank my husband, Qing Yan who has been by my side throughout this PhD. He was always there cheering me up, listening to me, giving me suggestions through the good times and bad times. And thanks to my darling Ethan and Christoph for being such good little kids, made me the happiest mom in the world. This dissertation would not have been possible without their warm love and endless support. CONTRIBUTION OF AUTHORS Chapter 1: Mei Song wrote Chapter 1 with revision from Dr. Elizabeth Tomasino. Chapter 2: Dr. Elizabeth Tomasino and Mei Song conceived and designed the study. Acquisition, analysis and interpretation of data were performed by Mei Song. Dr. Elizabeth Tomasino and Mei Song participated in drafting the manuscript with revision from Dr. Elizabeth Tomasino. Chapter 3: Dr. Elizabeth Tomasino and Mei Song conceived and designed the study. Acquisition, analysis and interpretation of data were performed by Mei Song. Mei Song drafted the manuscript with revision from Dr. Elizabeth Tomasino and Dr. Claudio Fuentes. Chapter 4: Dr. Elizabeth Tomasino and Mei Song conceived and designed the study. Acquisition, analysis and interpretation of data were performed by Mei Song. Mei Song drafted the manuscript with revision from Dr. Elizabeth Tomasino and Dr. Claudio Fuentes. Chapter 5: Dr. Elizabeth Tomasino, Dr. James Osborne and Mei Song conceived and designed the study. Acquisition, analysis and interpretation of data were performed by Mei Song. Mei Song drafted the manuscript with revision from Dr. Elizabeth Tomasino and Dr. Claudio Fuentes. Chapter 6: Mei Song wrote chapter 6 with revision from Dr. Elizabeth Tomasino. TABLE OF CONTENTS Page CHAPTER 1: Introduction ..............................................................................................................1 1.1. Monoterpene chemistry ............................................................................................................3 1.1.1. General structure ............................................................................................................3 1.1.1.1. Acyclic monoterpenes .........................................................................................3
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