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(+)-Pisatin Biosynthetic Pathway by Rnai and Development of a Novel Method to Elicit the Production of Plant Secondary Metabolites

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(+)-Pisatin Biosynthetic Pathway by Rnai and Development of a Novel Method to Elicit the Production of Plant Secondary Metabolites Study of the (+)-Pisatin Biosynthetic Pathway by RNAi and Development of a Novel Method to Elicit the Production of Plant Secondary Metabolites Item Type text; Electronic Dissertation Authors Kaimoyo, Evans Publisher The University of Arizona. Rights Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author. Download date 28/09/2021 15:24:36 Link to Item http://hdl.handle.net/10150/193608 STUDY OF THE (+)-PISATIN BIOSYNTHETIC PATHWAY BY RNAi AND DEVELOPMENT OF A NOVEL METHOD TO ELICIT THE PRODUCTION OF PLANT SECONDARY METABOLITES By Evans Kaimoyo Copyright © Evans Kaimoyo 2005. A Dissertation Submitted to the Faculty of the DIVISION OF PLANT PATHOLOGY AND MICROBIOLOGY In Partial Fulfillment of the Requirements For the Degree of DOCTOR OF PHILOSOPHY WITH A MAJOR IN PLANT PATHOLOGY In the Graduate College THE UNIVERSITY OF ARIZONA 2005 2 THE UNIVERSITY OF ARIZONA GRADUATE COLLEGE As members of the Dissertation Committee, we certify that we have read the dissertation prepared by Evans Kaimoyo entitled Study of the (+)-Pisatin Biosynthetic Pathway by RNAi and Development of a Novel Method to Elicit the Production of Plant Secondary Metabolites and recommend that it be accepted as fulfilling the dissertation requirement for the Degree of Doctor of Philosophy _______________________________________________________________________ Date: ___________ Dr. Hans D. VanEtten October 6, 2005 _______________________________________________________________________ Date: ____________ Dr. David R. Gang October 6, 2005 _______________________________________________________________________ Date: _____________ Dr. Leland S. Pierson October 6, 2005 _______________________________________________________________________ Date: ____________ Dr. Martha C. Hawes October 6, 2005 _______________________________________________________________________ Date: _____________ Dr. Richard A. Jorgensen October 6, 2005 Final approval and acceptance of this dissertation is contingent upon the candidate’s submission of the final copies of the dissertation to the Graduate College. I hereby certify that I have read this dissertation prepared under my direction and recommend that it be accepted as fulfilling the dissertation requirement. ________________________________________________ Date: ____________ Dissertation Director: Hans D. VanEtten October 6, 2005 3 STATEMENT BY AUTHOR This dissertation has been submitted in partial fulfillment of requirements for an advanced degree at The University of Arizona and is deposited in the University Library to be made available to borrowers under rules of the Library. Brief quotations from this dissertation are allowable without special permission, provided that accurate acknowledgment of source is made. Requests for permission for extended quotation from or reproduction of this manuscript in whole or in part may be granted by the copyright holder. SIGNED: Evans Kaimoyo 4 ACKNOWLEDGEMENTS I wish to sincerely thank my research supervisor, Professor Hans D. VanEtten, profound thinker, distinguished scientist and scholar for his ever available and generous support, patience and more so help throughout this project. I also want to thank in a special way Professors Leland S. Pierson, Martha Hawes and the Division of Plant Pathology and Microbiology for their support. Words of thanks also go to Dr. Esteban Temporini and Dr. Cathy Wasmann for the technical support. I also want to thank my lab mates Jeff, Gerard and Nela for a good working environment. To my wife Sitali and children, Ing’utu and Kakanda, thank you for your support. To my beloved sisters, Agnes, Joyce, Grace, Ms. Sikota and Ruth, my dear good friends Connie and Buddy Prince, Judy and Paul Steward, Pastor Israel and Augusta Olaore, Sonia and the whole Seventh Day Adventist Church at Sharon, thank you very much for being there daily. 5 DEDICATION This dissertation is dedicated to the late great Ms Ing’utu S. S. Kakanda, my dearest mother and friend, ever inspiring and striving for the good of others but never complaining or despising anybody. To my children Ing’utu and Kakanda, this is for you to remember this: “the race is not to the swift, nor the battle to the strong, neither yet bread to the wise, nor yet riches to men of understanding, nor yet favor to men of skill; but time and chance affect them all”. Evans Kaimoyo 6 TABLE OF CONTENTS LIST OF FIGURES ............................................................................................................ 9 LIST OF TABLES............................................................................................................ 11 ABSTRACT...................................................................................................................... 12 CHAPTER 1: INTRODUCTION..................................................................................... 14 Phytoalexins as Plant Disease Resistance Compounds.......................................... 14 Status of the (+)-Pisatin Biosynthetic Pathway ...................................................... 22 From the Phenylpropanoid and Acetate-Polymalonate Pathways to Formononetin ...................................................................................... 22 From Formononetin to (+)-Pisatin .......................................................................... 27 The Origin of 6a-OH in (+)-Pisatin ......................................................................... 31 The Late Steps of (+)-Pisatin Biosynthesis ............................................................. 32 Hairy Root Cultures as a Model System to Analyze the Biosynthesis of Plant Secondary Metabolites.............................................................................................. 40 Analysis of Gene Function in Plant Secondary Metabolic Pathways by RNAi .................................................................................................... 42 Elicitation of Plant Secondary Metabolites ............................................................ 45 Objectives of the Dissertation .................................................................................. 49 CHAPTER 2: INACTIVATION BY RNAI OF PEA GENES SUPPORTS THE INVOLVEMENT OF INTERMEDIATES WITH (-)-OPTICAL ACTIVITY AND A BI- FUNCTION O-METHYLTRANSFERASE IN THE (+)-PISATIN BIOSYNTHETIC PATHWAY....................................................................................................................... 51 Abstract...................................................................................................................... 51 Introduction............................................................................................................... 53 Materials and Methods............................................................................................. 59 Bacteria and Plasmid Vectors...................................................................... 59 Reagents and Secondary Metabolites.......................................................... 60 Construction of RNAi Binary Vectors for HMM, IFR and SOR Gene Silencing ...................................................................................... 60 Triparental Matings...................................................................................... 62 Transformation of Pea Stem Tissue ............................................................ 63 Elicitation, Extraction and Analyses of (+)-Pisatin and Other Secondary Metabolites.................................................................................. 64 Results ........................................................................................................................ 67 Analysis of (+)-Pisatin and other Isoflavonoids in Non-Transgenic Pea Hairy Root Cultures .............................................................................. 67 Analysis of Transgenic Hairy Root Cultures Expressing the RNAi Construct of the HMM Gene....................................................... 73 Analysis of Transgenic Hairy Root Cultures Expressing the RNAi Construct of the IFR Gene.......................................................... 77 Analysis of Transgenic Hairy Root Cultures Expressing the RNAi Construct of the SOR Gene......................................................... 78 Discussion................................................................................................................... 79 7 TABLE OF CONTENTS - Continued RNAi and Hairy Root Cultures as Tools for Studying the Biosynthesis of Plant Secondary Metabolites ................................................................... 79 Analysis of Hairy Root Cultures Blocked at the HMM Enzymatic Step.............................................................................................. 80 Involvement of Intermediates With (-)-Optical Activity in (+)-Pisatin Biosynthesis ................................................................................ 86 Sophorol Reductase as a Branch Point in (+)-Pisatin and (-)-Maackiain Biosynthesis in Pea........................................................................................ 87 CHAPTER 3: IN VITRO METABOLISM OF (-)-7,2'-DIHYDROXY-4',5'- METHYLENEDIOXYISOFLAVANOL TO INTERMEDIATES POSSIBLY INVOLVED IN (+)-PISATIN BIOSYNTHESIS AND DEMONSTRATION OF (-)- DMDI
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