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Chemopreventive Effects of Apiaceous Vegetables

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Chemopreventive Effects of Apiaceous Vegetables CHEMOPREVENTIVE EFFECTS OF APIACEOUS VEGETABLES, CRUCIFEROUS VEGETABLES, AND THEIR PHYTOCHEMICALS AGAINST DIETARY CARCINOGEN PHIP IN RAT COLON A DISSERTATION SUBMITTED TO THE FACULTY OF UNIVERSITY OF MINNESOTA BY JAE KYEOM KIM IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY ADVISER: SABRINA P. TRUDO JUNE 2013 © 2013 JAE KYEOM KIM -University of Minnesota ACKNOWLEDGEMENTS There are a number of people without whom this dissertation and my Ph. D. degree may not have been completed. First and foremost, I would like to express the deepest appreciation to my advisor, Dr. Sabrina P. Trudo. She always listened, was thoughtful and dedicated, and tried to be on the side of students. There is no doubt that this dissertation would not have been possible without her academic mentorship and guidance. Although I did get a chance to make small achievements during the degree, I never ever felt they are mine but ours. I am also grateful for Dr. Daniel D. Gallaher, who was co- principal investigator of the project. His vast experience in the field and positive attitude truly helped me to enjoy my journey. Thank you to my committee member Dr. Chi Chen, for his time to analyze samples and his feedback on the data. Working with him and his discussions allowed me to broaden my knowledge of the novel field, metabolomics. Also thanks to Dr. Fekadu Kassie for his insight and discussion of the project and dissertation. I am also thankful to Dr. Robert J. Turesky who provided the reference standard and helped with establishing key methods here. I would like to show appreciation to all of my colleagues and friends, Cindy Gallaher (laboratory mom), my best friend Drew Brockman, Marissa Warnert, Ana Dos Santos, Diane Nowak, Sang Yub Kim, Joanie Zhang, Noemia Strapazzon, Dr. Moon Yeon Youn, and Dr. Eui Cheol Shin. I was able to enjoy the time in the lab and had unforgettable memories with them. i I want to thank my mentors in Korea as well. Dr. Dong Hoon Shin, who is my ex-advisor for my master’s degree, provided a number of opportunities and showed his trust in me. I truly appreciate his guidance and warm advice. Dr. Young Jun Kim, who is my role- model, encouraged me to study abroad and pursue a doctoral degree. Although they were academic mentors, I never considered them just as academic advisors; it’s been always more than that. Especially, I would like to express my gratitude to my parents. Their unconditional love and dedication truly helped me to be motivated and move forward. Lastly, my love Tracy, thanks for being on my side and listening. As you did for me and my dreams, I will be always with you whenever you need me. ii DEDICATION I dedicate this dissertation to my father, Young Beom Kim and my mother, Young Sook Lee for their love and dedication throughout their lives. iii TABLE OF CONTENTS ACKNOWLEDGEMENTS .............................................................................................. i DEDICATION.................................................................................................................. iii TABLE OF CONTENTS ................................................................................................ iv LIST OF TABLES ............................................................................................................ x LIST OF FIGURES ......................................................................................................... xi CHAPTER 1. LITERATURE REVIEW ........................................................................ 1 Section 1-1. Diets and Colon Cancer Risk ...................................................................... 2 Colon cancer overview .............................................................................................. 2 Meat consumption and colon cancer ....................................................................... 3 Levels of HAA in foods ............................................................................................. 6 Mechanisms of PhIP formation .......................................................................... 7 Levels of PhIP exposure in humans .................................................................... 8 PhIP metabolism, mutagenicity, and colon cancer risk ........................................ 8 Metabolism of PhIP ............................................................................................ 9 Mutagenicity of PhIP and colon cancer risk ..................................................... 10 In vitro studies................................................................................................... 11 Animal studies .................................................................................................. 12 Human studies ................................................................................................... 14 Genetic alterations by PhIP ............................................................................... 16 DNA adducts and PhIP ..................................................................................... 18 Measurement of PhIP-DNA adducts ................................................................ 20 iv Section 1-2. Vegetable Intake and Cancer Prevention ................................................ 22 An overview of chemoprevention .......................................................................... 22 Cancer prevention through vegetable intake ....................................................... 22 Cruciferous vegetables and glucosinolates: evidence for chemoprevention ...... 24 Metabolism of glucosinolates and hydrolysis products .................................... 26 Cruciferous and phase I enzymes: CYP1A regulation ..................................... 28 Cruciferous and phase II enzymes: UGT and SULT regulation ....................... 31 Apiaceous vegetables and furanocoumarins: evidence for chemoprevention ... 33 Metabolism of furanocoumarins ....................................................................... 35 Apiaceous and phase I enzymes: CYP1A regulation ....................................... 36 Apiaceous and phase II enzymes: UGT and SULT regulation ......................... 37 Intact vegetables versus purified compounds....................................................... 38 Section 1-3. Metabolomics-Based Approaches ............................................................. 41 Overview .................................................................................................................. 41 Applications to nutritional sciences ....................................................................... 41 Metabolite profiling for metabolomics.................................................................. 43 Nuclear magnetic resonance ............................................................................. 44 Mass spectrometry ............................................................................................ 45 Other analytical approaches .............................................................................. 47 Metabolomics to study PhIP metabolism ......................................................... 48 Section 1-4. Summary and Specific Aims ..................................................................... 50 v CHAPTER 2. MANUSCRIPT I: EFFECTS OF CRUCIFEROUS AND APIACEOUS VEGETABLE INTAKE ON PHIP METABOLISM AND GENOTOXICITY IN WISTAR RATS ........................................................................ 55 Introduction ............................................................................................................. 56 Materials and methods ........................................................................................... 57 Chemicals and reagents ..................................................................................... 57 Animals ............................................................................................................. 58 Experimental design.......................................................................................... 58 Study diets ......................................................................................................... 59 Analysis of total glucosinolates in cruciferous vegetables ............................... 59 Analysis of furanocoumarins in apiaceous vegetables ..................................... 60 Preparation of hepatic microsomes and cytosol................................................ 61 Measurement of protein content ....................................................................... 62 Measurement of CYP1A1 and CYP1A2 activity ............................................. 62 Measurement of SULT1A1 activity .................................................................. 63 Measurement of UGT1A1 activity ................................................................... 63 Assessment of protein expression ..................................................................... 64 LC-ESI-MS/MS analysis of urinary PhIP metabolites ..................................... 65 Methyl transferase metabolism of PhIP in human liver S9 fraction ................. 65 Measurement of DNA adducts .......................................................................... 66 Statistical analysis ............................................................................................. 68 Results ...................................................................................................................... 68 vi Effects
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