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The Glucosinolate/Myrosinase System: Variation in Glucosinolates, Hydrolysis Products, Transcript Abundance, and Quinone Reductase Bioactivity in Brassica Sp

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The Glucosinolate/Myrosinase System: Variation in Glucosinolates, Hydrolysis Products, Transcript Abundance, and Quinone Reductase Bioactivity in Brassica Sp TITLE PAGE THE GLUCOSINOLATE/MYROSINASE SYSTEM: VARIATION IN GLUCOSINOLATES, HYDROLYSIS PRODUCTS, TRANSCRIPT ABUNDANCE, AND QUINONE REDUCTASE BIOACTIVITY IN BRASSICA SP. CROPS BY TALON M. BECKER DISSERTATION Submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Crop Sciences in the Graduate College of the University of Illinois at Urbana-Champaign, 2015 Urbana, Illinois Doctoral Committee: Professor John A. Juvik, Chair Professor Elizabeth H. Jeffery Professor Steven C. Huber Professor Donald P. Briskin Abstract Glucosinolates, and more specifically their hydrolysis products, are secondary metabolites present in Brassica crops that are important for plant defense from insects and pathogens. In addition, these compounds have long been associated with anti-cancer activity in mammals through the induction of phase II detoxification enzymes, among other mechanisms. For this reason, the improvement of anti-cancer activity through selective breeding of edible plants that produce glucosinolates, such as the Brassica, has gained in popularity as a breeding objective. In this research we survey variation in glucosinolate and glucosinolate hydrolysis product profiles as well as anti-cancer activity in a range of Brassica crops in an attempt to identify differences, if any, in the underlying agents of anti-cancer activity in these crops. Also, we have investigated how environmental effects and interactions between the environment and genetic background of the plant influence glucosinolates, their hydrolysis products, and anti-cancer activity in an attempt to better understand the feasibility of breeding for anti-cancer activity. It was found that environmental effects on anti-cancer activity may be too great to allow for direct breeding for this trait. However, the data suggest that breeding for individual GSs and GSHPs known to influence anti-cancer activity is feasible. With this is in mind, predictive models were built using gene transcript abundance data for genes associated with the glucosinolate/myrosinase system in an attempt to predict final phytochemical phenotypes in broccoli. It was found that models built using gene transcript abundance as predictors delivered satisfactory predictive ability for phytochemical phenotypes collected in the same growing season as the transcript abundance data, but that ability did not hold across growing seasons, at least in the two growing seasons associated with this study. Lastly, we examined the effect of methyl jasmonate (MeJA) elicitation on the transcript levels of glucosinolate/myrosinase system genes in broccoli. MeJA ii treatment showed significant effects on transcript abundance for a number of the surveyed genes, although varietal and environmental effects also influenced transcriptional response to MeJA. Also, many genes showed positive and negative dosage responses in transcript abundance to increasing concentrations of MeJA within the cultivar Green Magic grown in 2010. iii Acknowledgements I would like to acknowledge and thank my committee members for their help throughout my PhD dissertation research. In particular, I would like to thank my advisor, Dr. John A. Juvik, for his mentorship and insight in the planning and completion of my research. It was in his class that my interest in manipulating phytochemical profiles through breeding was first sparked. Also, I would like to express my gratitude to Dr. Elizabeth H. Jeffery for allowing the use of her laboratory facilities in the completion of my research and for her guidance and direction. She has always pushed me to better understand the underlying mechanisms of phytochemical bioactivity, making me a better multi-disciplinary scientist. I would also like to express my thanks to Drs. Steven C. Huber and Donald P. Briskin for their service on my committee and helpful and constructive suggestions. I would like to also thank Dr. Mosbah M. Kushad. Even though he was not able to serve on my final defense committee, he was instrumental in my studies and PhD research. Thank you to the members of the Juvik and Jeffery labs for their help and friendship. Many people have been helpful in the completion of my research through their mentorship, assistance, and willingness for discussion. Thank you to Drs. Hyoung Seok Kim and Kang Mo Ku for introducing me to Brassica research, particularly the glucosinolate/myrosinase plant defense system. In particular, Dr. Kang Mo Ku was a great help in teaching me the analytical chemistry skills needed to complete my research, and Molly Black, of the Jeffery lab, was a great help in facilitating my research through her lab management. Also, my lab members Dr. Won Byoung Chae, Dr. Justin Gifford, Alicia Gardner, Laura Chatham, and Michael Paulsmeyer, as well as the many undergraduate workers that have passed through our lab, were very helpful in their willingness to discuss research topics and help with anything I might need. Lastly, I would like iv to thank a visiting researcher in our lab, Dr. Mario Lee, for his mentorship and advice. Even though I was not one of his students, he treated me as though I was. Thank you to AgroFresh and the Department of Crop Sciences for the financial support necessary to complete this research, and thank you to Monsanto for the Fellowship that allowed me to pursue a higher education. Finally, thank you to all of my family and friends outside of UIUC. Your love and support was greatly appreciated, and the completion of this project and degree would not have been possible without it. v Table of Contents Chapter 1. Literature Review ........................................................................................................................ 1 1.1 Rationale ....................................................................................................................................... 1 1.2 Glucosinolates ............................................................................................................................... 2 1.2.1 Biosynthesis ................................................................................................................................. 3 1.2.2 Hydrolysis and aglycone rearrangement ..................................................................................... 7 1.3 Cancer and chemoprotection ..................................................................................................... 11 1.3.1 The influence of diet on cancer development ........................................................................... 12 1.3.2 Glucosinolate hydrolysis products and their chemopreventive and anti-proliferative bioactivity ............................................................................................................................................................ 15 1.3.3 Nrf2/Keap1/ARE signaling cascade ............................................................................................ 20 1.3.4 Quantifying chemopreventive bioactivity.................................................................................. 21 1.4 Jasmonates .................................................................................................................................. 21 1.4.1 Jasmonic acid biosynthesis ........................................................................................................ 22 1.4.2 Conversion of JA into methyl jasmonate and other jasmonates ............................................... 23 1.4.3 Jasmonate signal perception ..................................................................................................... 24 1.4.4 Methyl jasmonate response in Brassica and Arabidopsis.......................................................... 26 1.5 Tables and Figures................................................................................................................................. 29 Chapter 2. Survey of variation in chemopreventive bioactivity, glucosinolate, and glucosinolate hydrolysis product profiles in common Brassica crop species ................................................................... 39 2.1 Abstract ............................................................................................................................................. 39 2.2 Introduction ...................................................................................................................................... 39 2.3 Materials and methods ..................................................................................................................... 42 2.3.1 Cultivation of plant material ...................................................................................................... 42 2.3.2 Determination of GS content ..................................................................................................... 44 2.3.3 Determination of glucosinolate hydrolysis product profiles ..................................................... 45 2.3.4 Determination of percent nitrile formation............................................................................... 46 2.3.5 Quinone reductase induction potential (QRIP) assay ................................................................ 48 2.3.6 Statistical analysis ...................................................................................................................... 49 2.4 Results ..............................................................................................................................................
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