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INVESTIGATING the ROLE of TOMATO PHYTOCHEMICALS THROUGH TARGETED and UNTARGETED METABOLOMICS DISSERTATION Presented in Partial F

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INVESTIGATING the ROLE of TOMATO PHYTOCHEMICALS THROUGH TARGETED and UNTARGETED METABOLOMICS DISSERTATION Presented in Partial F INVESTIGATING THE ROLE OF TOMATO PHYTOCHEMICALS THROUGH TARGETED AND UNTARGETED METABOLOMICS DISSERTATION Presented in Partial Fulfillment of the Requirements for the Degree Doctor of Philosophy in the Graduate School of The Ohio State University By Morgan Julienne Cichon Graduate Program in Food Science and Technology The Ohio State University 2015 Dissertation Committee: Steven J. Schwartz, Ph.D., Advisor Steven K. Clinton, M.D., Ph.D. Earl H. Harrison, Ph.D. Luis E. Rodriguez-Saona, Ph.D. Copyrighted by Morgan Julienne Cichon 2015 ABSTRACT Epidemiological studies have demonstrated a link between an increased consumption of tomatoes and a decreased risk of chronic diseases, such as cancer and cardiovascular disease. As the carotenoid lycopene is the predominant pigment in tomatoes and is an efficient singlet oxygen quencher, many have focused on lycopene as the main bioactive compound in tomatoes responsible for these observed health benefits. However, tomatoes contain many potential bioactive components and research has also suggested that some of the protective effects of tomatoes might be due to the combination of phytochemicals and their metabolites. Determining the biochemical changes tomato phytochemicals undergo and elicit in vivo is important for understanding the biological function of this fruit. The objective of this dissertation work was to utilize both targeted and untargeted metabolomics to investigate lycopene and other tomato phytochemicals in foods, preclinical models, and humans. One of the benefits of metabolomics is that it allows for continuity that is necessary in the area of functional food research. This technique can be applied first to chemically profile foods and then to profile biological samples collected from dietary interventions with those foods. The primary objective was accomplished ii through the metabolomic investigation of 1) lycopene oxidative metabolism in humans using 13C-labeled lycopene, 2) phytochemical differences between red and tangerine tomato juices intended for human clinical trials, and 3) the impact of lycopene and tomatoes on the plasma metabolome of mice. From this research, lycopene cis isomers and lycopene 1,2-epoxide were identified in plasma by mass spectrometry as potential oxidative metabolites, while nuclear magnetic resonance spectroscopy metabolomics experiments have suggested the presence of small, polar catabolites of lycopene in the urine. Red and tangerine tomato juices intended for use as functional foods in human clinical interventions with prostate cancer patients were found to differ significantly in a number of phytochemicals and metabolites. Many of these compounds have been shown to possess important antioxidant and biological activities and may contribute to the health promoting properties of tomato products in the diet. In mice, several tomato alkaloids were found to increase in plasma after the consumption of tomatoes. Results of this study also revealed that the red tomato fed mice had a unique metabolic profile compared to mice fed either tangerine tomatoes or low carotenoid tomatoes, suggesting differences in biological effect based on variety. This work demonstrates the utility of metabolomics in food science and nutrition research and supports continued investigation of the synergistic effects of tomato bioactive phytochemicals. iii Dedicated to my mom, Debra J. Trantolo iv ACKNOWLEDGMENTS First and foremost, I would like to thank my advisor, Dr. Steven J. Schwartz, for his unwavering support and guidance during all stages of my graduate studies. I appreciate the investment in my growth as a researcher and the exciting opportunity to work in an emerging field. I could not have asked for a better mentor. I would like to thank my committee members, Drs. Earl H. Harrison, Steven K. Clinton, and Luis E. Rodriguez-Saona, for their interest in my project and insightful comments along the way. A special thanks to Dr. Ken Riedl for teaching me everything I know about mass spectrometry. His analytical knowledge and expertise has certainly made me a better scientist. I would like to thank Lisa and Dan Wampler for their generous support of my research and commitment to the study of foods and health. Their philanthropy and kindness is inspiring. v Thank you to all of my lab members, past and present, for providing invaluable scientific advice and more importantly, much needed comic relief during late nights in the lab. Finally, I would like to thank my family for their encouragement during this journey and especially my mom for giving me my first dissertation to read and showing me that the possibilities are endless for women in science. vi VITA May 2010 .......................................................B.S. Chemistry; Economics, Summa Cum Laude, Emory University, Atlanta, GA September 2010 to present .............................Graduate Research Associate, Department of Food Science & Technology, The Ohio State University, Columbus, OH September 2010 to August 2011 ....................University Fellow, The Ohio State University, Columbus, OH January 2015 to present .................................Lisa and Dan Wampler Endowed Fellow for Foods and Health Research, Department of Food Science and Technology, The Ohio State University, Columbus, OH Publications Schwartz, S.J., Cooperstone, J.L., Cichon, M.J., von Elbe, J.H., Giusti, M.M. "Colorants." In Fennema’s Food Chemistry 5th Edition. Eds. Srinivasan Damodaran, Kirk L. Parkin, and Owen R. Fennema. Chichester, West Sussex, UK: Wiley-Blackwell. Accepted. vii Moran, N.E., Novotny, J.A., Cichon, M.J., Riedl, K.M., Rogers, R.B., Grainger, E.M., Schwartz, S.J., Erdman Jr, J.W., Clinton, S.K. Absorption and distribution kinetics of the 13C-labeled tomato carotenoid phytoene in healthy adults. J Nutr. Accepted. Moran, N.E., Cichon, M.J., Riedl, K.M., Grainger, E.M., Schwartz, S.J., Novotny, J.A., Erdman Jr, J.W., Clinton, S.K. Compartmental and non-compartmental modeling of 13C- lycopene absorption, isomerization, and distribution kinetics in healthy adults. Am J Clin Nutr. 2015. doi: 10.3945/ajcn.114.103143. Pumilia, G., Cichon, M.J., Cooperstone, J.L., Giuffrida, D., Dugo, G., Schwartz, S.J. Changes in chlorophylls, chlorophyll degradation products and lutein in pistachio kernels (Pistachia vera L.) during roasting. Food Res Int. 2014. 65(Part B): 193-198. Tan, S.H., Moran, N.E., Cichon, M.J., Riedl, K.M., Schwartz, S.J., Erdman Jr, J.W., Pearl, D.K., Thomas-Ahner, J.M., Clinton, S.K. Beta-carotene-9’,10’- oxygenase status modulates the impact of dietary tomato and lycopene on hepatic nuclear receptor-, stress-, and metabolism-related gene expression in mice. J Nutr. 2014. 144(4):431-439. Moran, N.E., Cichon, M.J., Novotny, J.A., Grainger, E.M., Riedl, K.M., Rogers, R.B., Schwartz, S.J., Erdman Jr, J.W., Clinton, S.K. 13C-phytoene from tomato cell suspension cultures for pharmacokinetic studies in healthy adults. FASEB J. 2014. 28:645.15. Moran, N.E., Cichon, M.J., Riedl, K.M., Grainger, E.M., Schwartz, S.J., Erdman Jr, J.W., Clinton, S.K. (2013). Pharmacokinetics of 13C-lycopene in healthy adults. FASEB J. 2013. 27:38.6. Kopec, R.E., Cooperstone, J.L., Cichon, M.J., Schwartz, S.J. "Analysis Methods of Carotenoids." In Analysis of Antioxidant-rich Phytochemicals. Eds. Zhimin Xu and Luke R. Howard. Chichester, West Sussex, UK: Wiley-Blackwell, 2012. 105-148. Hou Y., Xu, L., Cichon, M.J., Lense, S., Hardcastle, K.I., Hill, C.L. A New Family of Sandwich-Type Polytungstophosphates Containing Two Types of Metals in the Central Belt: M′2M2(PW9O34)212− (M′ = Na or Li, M = Mn2+, Co2+, Ni2+, and Zn2+). Inorg Chem. 2010. 49(9): 4125-4132. Fields of Study Major Field: Food Science and Technology viii TABLE OF CONTENTS Abstract ............................................................................................................................... ii Acknowledgments............................................................................................................... v Vita .................................................................................................................................... vii Table of Contents ............................................................................................................... ix List of Tables ................................................................................................................... xvi List of Figures ................................................................................................................. xvii Chapter 1: Literature Review .............................................................................................. 1 1.1 Tomatoes and Chronic Disease ............................................................................ 1 1.1.1.1 Prostate Cancer ...................................................................................... 1 1.2 Bioactive Tomato Phytochemicals ....................................................................... 4 1.2.1 Vitamins ........................................................................................................ 4 1.2.2 Phenolic Acids .............................................................................................. 5 1.2.3 Flavonoids ..................................................................................................... 6 1.2.4 Carotenoids ................................................................................................... 9 1.3 Lycopene Metabolism .......................................................................................
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