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Characterization of Sanguinarine Reductases from Papaver Somniferum (Unpublished Master's Thesis)

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Characterization of Sanguinarine Reductases from Papaver Somniferum (Unpublished Master's Thesis) University of Calgary PRISM: University of Calgary's Digital Repository Graduate Studies The Vault: Electronic Theses and Dissertations 2015-05-20 Characterization of sanguinarine reductases from Papaver somniferum Bross, Crystal Bross, C. (2015). Characterization of sanguinarine reductases from Papaver somniferum (Unpublished master's thesis). University of Calgary, Calgary, AB. doi:10.11575/PRISM/25290 http://hdl.handle.net/11023/2260 master 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 Characterization of sanguinarine reductases from Papaver somniferum by Crystal Dawn Bross A THESIS SUBMITTED TO THE FACULTY OF GRADUATE STUDIES IN PARTIAL FULFILMENT OF THE REQUIREMENTS FOR THE DEGREE OF MASTER OF SCIENCE DEPARTMENT OF BIOLOGICAL SCIENCES CALGARY, ALBERTA MAY, 2015 © Crystal Dawn Bross 2015 Abstract Papaver somniferum (opium poppy) produces several pharmacologically relevant benzylisoquinoline alkaloids, such as the analgesics codeine and morphine, the muscle relaxant papaverine, the potential anti-cancer drug noscapine, and the antimicrobial agent sanguinarine. Sanguinarine is a highly cytotoxic benzophenanthridine alkaloid synthesized by the plant to defend against herbivory and pathogens. However, sanguinarine can bind DNA, induce apoptosis, and will inhibit the growth of plant cell cultures that do not synthesize benzophenanthridine alkaloids. Therefore, it is proposed that sanguinarine reductase (SanR) exists in plants that synthesize benzophenanthridine alkaloids to facilitate the detoxification of sanguinarine through its reduction to dihydrosanguinarine. Three transcripts encoding SanRs were identified in opium poppy transcriptome databases and were characterized biochemically and physiologically using enzyme assays, virus-induced gene silencing, and immunolocalization to gain insight into the role of SanR as an enzyme of detoxification. ii Acknowledgements I would like to thank those who supported me during the completion of my thesis. Thank you to my lab members, especially Guillaume Beaudoin, Thu-Thuy Dang, Scott Farrow, Donald Dinsmore, Xue Chen, Eun-Jeong Lee, and Jeremy Morris, for their guidance and assistance, and willingness to help in any way. And thank you to my friends, Ramya Singh and Bonnie McNeil, for keeping me grounded, and offering an outside perspective on my research. I would also like to thank my committee, Dr. Doug Muench and Dr. Marcus Samuel, for their guidance. And thank you to Dr. Ed Yeung, Dr. Christoph Sensen, and Ye Zhang for their expertise in botany and phylogeny. Lastly, a special thank you to my parents for their unconditional love, support, and encouragement. You were always there when I needed you, and I am forever grateful. iii Table of Contents Abstract .............................................................................................................................. ii Acknowledgements .......................................................................................................... iii Table of Contents ............................................................................................................. iv List of Tables ................................................................................................................... vii List of Figures and Illustrations ................................................................................... viii List of Symbols, Abbreviations, and Nomenclatures ..................................................... x 1 INTRODUCTION....................................................................................................... 1 1.1 Alkaloids .............................................................................................................. 1 1.2 Benzylisoquinoline alkaloid biosynthesis ............................................................ 2 1.3 Epimerization of reticuline and morphine biosynthesis ....................................... 5 1.4 Sanguinarine biosynthesis .................................................................................... 7 1.5 Sanguinarine is a cytotoxic compound ................................................................ 9 1.6 Localization of alkaloids and biosynthetic enzymes in planta .......................... 11 1.7 Objectives .......................................................................................................... 13 2 MATERIALS AND METHODS ............................................................................. 14 2.1 Media ................................................................................................................. 14 2.1.1 Lysogeny broth (LB) media .................................................................. 14 2.1.2 Antibiotics ............................................................................................. 14 2.1.3 Blue/white selection .............................................................................. 14 2.1.4 Agrobacterium tumefaciens induction medium .................................... 15 2.1.5 Agrobacterium tumefaciens infiltration solution ................................... 15 2.2 Buffers................................................................................................................ 15 2.2.1 Plasmid DNA isolation buffers ............................................................. 15 2.2.2 2X CTAB RNA extraction buffer ......................................................... 15 2.2.3 2X SDS-PAGE sample buffer ............................................................... 16 2.2.4 10X SDS-PAGE electrode buffer ......................................................... 16 2.2.5 10X Western blot transfer buffer .......................................................... 16 2.2.6 1X Transfer buffer for Western blotting ............................................... 16 2.2.7 10X Tris-buffered saline (TBS) buffer .................................................. 16 2.2.8 1X TBS-Tween ..................................................................................... 16 2.2.9 Plant protein extraction buffer ............................................................... 16 2.2.10 Sodium phosphate buffer, pH 7.6 (100 mM) ...................................... 16 2.2.11 Coomassie stain ................................................................................... 17 2.2.12 Solvent A mass spectrometry running buffer ...................................... 17 2.3 Gel electrophoresis............................................................................................. 17 2.3.1 50X TAE buffer .................................................................................... 17 2.3.2 30% Acrylamide solution ...................................................................... 17 2.3.3 Separating gel (12%) ............................................................................. 17 2.3.4 Resolving gel (4%) ................................................................................ 18 iv 2.4 Organisms .......................................................................................................... 18 2.4.1 Bacteria .................................................................................................. 18 2.4.2 Plants ..................................................................................................... 18 2.5 Plasmids ............................................................................................................. 19 2.5.1 Subcloning plasmid ............................................................................... 19 2.5.2 Recombinant protein expression plasmid ............................................. 20 2.5.3 Virus-induced gene silencing (VIGS) plasmids .................................... 20 2.6 Cloning and Transformations ............................................................................ 22 2.6.1 Sequence identification and primer design ........................................... 22 2.6.2 PCR amplification of DNA and ligation ............................................... 33 2.6.3 Bacterial transformation ........................................................................ 34 2.6.4 Plant transformation .............................................................................. 35 2.7 Escherichia coli protein induction, purification, and detection ......................... 36 2.8 Plant protein purification, and detection ............................................................ 38 2.9 Alkaloids ............................................................................................................ 38 2.9.1 Isolation of benzophenanthridine alkaloids ........................................... 39 2.10 Enzyme assays ................................................................................................. 40 2.11 Antibody production ........................................................................................ 40 2.11.1 Dot blots .............................................................................................. 41 2.12 Immunolocalization ......................................................................................... 41 2.12.1
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