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Expanding the Role of Oxidoreductases in Benzylisoquinoline Alkaloid Metabolism in Opium Poppy

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Expanding the Role of Oxidoreductases in Benzylisoquinoline Alkaloid Metabolism in Opium Poppy University of Calgary PRISM: University of Calgary's Digital Repository Graduate Studies The Vault: Electronic Theses and Dissertations 2015-11-19 Expanding the Role of Oxidoreductases in Benzylisoquinoline Alkaloid Metabolism in Opium Poppy Farrow, Scott Cameron Farrow, S. C. (2015). Expanding the Role of Oxidoreductases in Benzylisoquinoline Alkaloid Metabolism in Opium Poppy (Unpublished doctoral thesis). University of Calgary, Calgary, AB. doi:10.11575/PRISM/26041 http://hdl.handle.net/11023/2648 doctoral thesis University of Calgary graduate students retain copyright ownership and moral rights for their thesis. You may use this material in any way that is permitted by the Copyright Act or through licensing that has been assigned to the document. For uses that are not allowable under copyright legislation or licensing, you are required to seek permission. Downloaded from PRISM: https://prism.ucalgary.ca UNIVERSITY OF CALGARY Expanding the Role of Oxidoreductases in Benzylisoquinoline Alkaloid Metabolism in Opium Poppy by Scott Cameron Farrow A THESIS SUBMITTED TO THE FACULTY OF GRADUATE STUDIES IN PARTIAL FULFILMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY GRADUATE PROGRAM IN BIOLOGICAL SCIENCES CALGARY, ALBERTA November, 2015 © Scott Cameron Farrow 2015 Abstract Benzylisoquinoline alkaloids (BIAs) are a large and structurally diverse group of plant specialized metabolites with several possessing pharmacological properties including the analgesic morphine, the cough suppressant codeine, and the vasodilator papaverine. In opium poppy, the antepenultimate and final steps in morphine biosynthesis are catalyzed by oxidoreductases belonging to the 2-oxoglutarate/Fe(II)-dependent dioxygenase gene family, namely thebaine 6-O-demethylase (T6ODM) and codeine O-demethylase (CODM). When assayed with a wider range of BIAs, CODM, T6ODM, and the functionally unassigned paralogs DIOX2 and DIOX7, renamed protopine O-dealkylase (PODA) and papaverine 7-O-demethylase (P7ODM), respectively, showed novel and efficient O-dealkylation activities, including regio­ and substrate-specific O-demethylation and O,O-demethylenation. Preferred substrates for O,O­ demethylenation by CODM and PODA were protopine alkaloids that serve as intermediates in the biosynthesis of benzo[c]phenanthridine and rhoeadine derivatives. Virus-induced gene silencing (VIGS) used to suppress the abundance of CODM and/or T6ODM transcripts indicated a direct physiological role for these enzymes in the metabolism of protopine alkaloids, and revealed their indirect involvement in the formation of the antimicrobial benzo[c]phenanthridine sanguinarine and certain rhoeadine alkaloids in opium poppy. Furthermore, the efficient substrate- and regio-specific 7-O-demethylation of papaverine by P7ODM yielding pacodine suggests an unexpected biosynthetic route to pacodine. In addition to these findings, my thesis investigated oxidoreductases from the cytochromes P450 (CYP) and aldo-keto reductase (AKR) gene families. Using the functionally characterized codeinone reductase (COR) AKR translated nucleotide sequence as a query, we identified a COR paralogue from an opium poppy transcriptome database that was fused and in frame with a CYP. The resulting protein fusion ii catalyzed the S-to-R epimerization of reticuline via 1,2-dehydroreticuline. The fusion protein, renamed reticuline epimerase (REPI), was detected in opium poppy and in Papaver bracteatum, which accumulates the morphinan alkaloid thebaine. In contrast, orthologs encoding independent CYP and AKR enzymes catalyzing the respective synthesis and reduction of 1,2­ dehydroreticuline were isolated from Papaver rhoeas, which does not accumulate morphinan alkaloids. Suppression of REPI transcripts using VIGS in opium poppy reduced levels of (R)­ reticuline and morphinan alkaloids and increased the overall abundance of (S)-reticuline and its O-methylated derivatives. Discovery of REPI completes the isolation of genes responsible for known steps of morphine biosynthesis. iii Acknowledgements There are several people that helped me during the past six years of my PhD, and without them this thesis would not have been possible. First and foremost, I would like to thank my supervisor Dr. Peter Facchini for providing me with the opportunity to work on these exciting projects. Your guidance and support have been invaluable over the duration of my PhD. I would like to thank my supervisory committee and several faculty members for their support and encouragement throughout my studies. These include: Dr. Dae-Kyun Ro, Dr. Marcus Samuel, Dr. Doug Muench and Dr. C.C. Chinnappa. I would also like to thank Dr. Chris Schofield and Dr. Justin MacCallum for participating in my defence. Much of my success during my PhD would not have been possible without the assistance of many colleagues. In particular, Dr. Darcy Burns for his assistance with NMR, Dr. Isabel Desgané-Penix for her discussions about plant physiology, Dr. Jill Hagel for her tutelage on dioxygenases and biochemical techniques, Gina Ro for her guidance with yeast work, Dr. Andrew Stopford for his assistance with mass spectrometry, and Dr. Shaobo Wu for his assistance with molecular biology techniques. I would also like to thank all of my labmates for their comraderie and teamwork. This included Dr. G. Beaudoin, Crystal Bross, Dr. T. Dang, Donald Dinsmore, Ryan Groves, Jeremy Morris, A.K. Onoyovwi and Dr. C. Wijekoon. I am also grateful for the support I received from Alberta Innovates Technology Futures and the Natural Sciences and Engineering Research Council of Canada. I am honoured to have such great friends who have helped to keep me grounded and motivated throughout my PhD. In particular, I owe a big thank you to Dr. Glen Uhrig, Dr. Neil iv Emery, Donald Dinsmore, Dave Bak, Bill Cocks, Dr. Tom Fudalewski, Dr. Moonhyuk Kwon, Dr. Matthew White, Adam Bendall, and Dwayne Scott. Of course, none of this would have been possible without my family. Grandma Jessie, Grandma Audrey, Grandpa Jack, Grandpa Wilf, Mom Jan, Dad Kent, Mom Mary, Dad Terry, sister Erin, brother Cory, sister Melanie, sister Kelly, sister Marcia, nephew Jake, niece Keira, nephew Wynton, nephew Ruben, nephew Bowen, uncle Wilson, uncle Big Jeff, uncle Little Jeff, Aunts, Uncles…Thank you for your endless support and encouragement. Most importantly, to my wife Gillian, I could not have done any of this without you. Your support, encouragement and unshakable foundation are the source of my strength. You got me through the tough times and celebrated with me through the great times. Our team approach to accomplishing goals is one of our biggest strengths. I look forward to what the future holds for our growing family. v Dedication To Gillian and Leona vi Table of Contents Abstract ............................................................................................................................... ii Acknowledgements ............................................................................................................ iv Dedication .......................................................................................................................... vi Table of Contents .............................................................................................................. vii List of Tables ..................................................................................................................... xi List of Figures and Illustrations ........................................................................................ xii Publications and Patents ....................................................................................................xv List of Symbols, Abbreviations and Nomenclature ........................................................ xvii Epigraph ........................................................................................................................... xix CHAPTER ONE: INTRODUCTION ..................................................................................1 1.1 Opium Poppy .............................................................................................................1 1.2 Benzylisoquinoline Alkaloids ....................................................................................2 1.2.1 Occurrence, Function and Medicinal Relevance of BIAs .................................2 1.2.2 BIAs of Opium Poppy .......................................................................................4 1.3 Biosynthesis of Benzylisoquinoline Alkaloids ..........................................................4 1.4 Aldo-Keto Reductases ...............................................................................................7 1.4.1 General Features of AKRs .................................................................................7 1.4.2 AKRs in Plant Metabolism ................................................................................8 1.4.3 AKRs in BIA Metabolism .................................................................................8 1.5 Cytochromes P450 Monoxygenases ........................................................................10 1.5.1 General Features of CYPs ...............................................................................10 1.5.2 CYPs in Plant Metabolism ..............................................................................13 1.5.3 CYPs in Secondary Metabolism ......................................................................15 1.5.4 CYPs in BIA Metabolism
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