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The Formation of Androstenone Conjugates in Testis Tissue of the Mature Boar

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The Formation of Androstenone Conjugates in Testis Tissue of the Mature Boar THE FORMATION OF ANDROSTENONE CONJUGATES IN TESTIS TISSUE OF THE MATURE BOAR by JILLIAN EVE DESNOYER A Thesis Presented to the University of Guelph In partial fulfillment of requirements for the degree of Master of Science in Animal and Poultry Science (Toxicology) Guelph, Ontario, Canada © Jillian E. Desnoyer, November, 2011 ABSTRACT THE FORMATION OF ANDROSTENONE CONJUGATES IN TESTIS TISSUE OF THE MATURE BOAR. Jillian Eve Desnoyer Advisor: University of Guelph, 2011 Dr. E.J. Squires The accumulation of androstenone in the fat of mature boars results in boar taint; the conjugation of androstenone would decrease this important meat quality problem by decreasing the accumulation and increasing the excretion of androstenone. Leydig cells and testis microsomes from mature boars were incubated with radiolabeled pregnenolone, and the free and conjugated metabolites were examined by HPLC. Sulfated androstenone with a mass of 367 m/z was directly identified by MS, with a novel tentative structure of 3-keto-4- sulfoxy-androstenone. Addition of enolase to the microsomal incubations increased the formation of 3-keto-4-sulfoxy-androstenone. Overexpression of SULT2A1 in HEK cells resulted in the sulfoconjugation of dehydroepiandrosterone, but not androstenone, suggesting that SULT2A1 may not be involved in sulfoconjugation of androstenone. This thesis describes the novel direct characterization of androstenone sulfate and the importance of enolase in its formation. The relevance to boar taint metabolism is discussed. ACKNOWLEDGEMENTS To Dr. Jim Squires: Thank you for your boundless breadth of knowledge, understanding and encouragement throughout the completion of this thesis. Your patience and willingness to deal with all of my self-proclaimed “stupid questions” was unparalleled to any other during my education. Delving feet first into this project would have been far more intimidating if it weren’t for you. I appreciate it more than I can possibly say. To my advisory committee Dr. Gregoy Bedecarrats and Dr. Jim Raeside – thank you for your continued support and help throughout the process of researching and writing this thesis. Without the knowledge that you were there to help, I wouldn’t have been able to proceed with the utmost confidence. Dr. Raeside, your incredible talents at pouring Percoll gradients are, well, incredible as is your amazing knowledge of everything related to reproductive endocrinology. To Yanping Lou: you are the technical superhero of our lab. Your ability to fix the HPLC when all seemed lost – on a regular basis – is incredible. Without your teaching, technical support and constantly smiling face, our lab wouldn’t function and wouldn’t be nearly as great. To Heather Christie: thank you for getting up early with me to isolate those pesky Leydig cells and for being THE woman to see for all things related to steroidal conjugates. I loved our endless talks and I look forward to continuing them for years to come. To Dr. Jim Atkinson: thank you for your teasing and reassurance throughout the process of both my undergraduate degree and this thesis. I cannot possibly say how much our chats both meant to and helped me. To my lab mates both past and present: Matt, thank you for putting up with my endless questions related to transfection and cloning and for all of my random trivia tidbits that interrupted you daily. I’m sure you’ll miss me when the lab is completely quiet. Kim, thank you for everything. I missed your presence greatly this last year and, when you’re all grown up and back from Indiana, I look forward to pestering you to play Munchkin. To Andy, thank you. I would never have made it through this without you. Thank you for sitting through constant repeats of the same presentations, listening to me wax poetic about androstenone sulfate and for getting excited with me when I found something – anything – exciting. Thank you for taking care of our little furry animals while I delved headfirst into the most trying educational triumph of my life - thus far. Also, to Ella, flint and Bailey: ruff ruff meow meow ruff barrooo. This translates roughly to “thank you for the constant cuddles and love”. To my family and friends – without your support and encouragement, this wouldn’t have been possible. Mom, your biweekly phone calls and feigned excitement over a project you barely understood was awesome. I can’t believe I finally did it and I know I couldn’t do it without you. Dad, thank you for believing in me, even when it wasn’t said aloud, I know you knew I could do it. Thank you to my friends who sat through my presentations, giving helpful and great advice. Not only has this project taught me more about endocrinology and molecular biology than I could ever have imagined, it has taught me more than that. It has taught me that my love of research is boundless and that, more importantly, I can do it. It is through the support, patience and encouragement of the above people that I can truly say I am a Mistress of Science. iii TABLE OF CONTENTS THE fORMATION Of ANDROSTENONE CONJUGATES IN TESTIS TISSUE fROM THE MATURE BOAR............................................................................................................................................................i LIST OF FIGURES....................................................................................................................................................vii LIST Of TABLES.........................................................................................................................................................x LIST Of ABBREVIATIONS...................................................................................................................................xii CHAPTER I: REVIEW Of THE LITERATURE................................................................................................. 1 1.1 Boar Taint and Pig Production.................................................................................................................... 1 1.1.1 Introduction..................................................................................................................................1 1.1.2 Current Solutions........................................................................................................................3 1.1.2.1 Carcass Measurements/On-Line Testing....................................................................3 1.1.2.2 Semen Sexing.........................................................................................................................4 1.1.2.3 Immunocastration...............................................................................................................5 1.1.2.4 Other GnRH Agonists ..........................................................................................................7 1.2. Steroidogenesis, 16-Androstene Steroids and Steroid Circulation............................................ 9 1.2.1 Location of Steroidogenesis in the Boar...........................................................................9 1.2.2 Steroidogenesis Throughout the Lifetime of the Pig ...............................................10 1.2.3 Enterohepatic Circulation of Steroids ............................................................................12 1.2.4 Binding of Steroid Hormones in the Blood and Saliva ............................................14 1.2.4.1 Steroid Hormone Movement in the Blood ...............................................................14 1.2.4.2 Steroid Binding in Boar Saliva.....................................................................................16 1.2.5 Steroids and Target Tissues Including Adipose Tissue ..........................................17 1.3 Androstenone Metabolism .........................................................................................................................19 1.3.1 Androstenone Synthesis.......................................................................................................19 1.3.2 Androstenone Degradation and Excretion...................................................................22 1.3.3 Androstenone Sulfate ............................................................................................................23 1.4 Enzymes Involved in Conjugation...........................................................................................................25 1.4.1 Sulfotransferases.....................................................................................................................25 1.4.1.1 SulFotransFerase 2A1 .......................................................................................................27 1.4.1.2 SulFotransFerase 2B1 .......................................................................................................28 1.4.2 Steroid Sulfatase ......................................................................................................................29 iv 1.4.2 Enolases.......................................................................................................................................30 1.4.3 UDP-glucuronosyl transferases.........................................................................................32 1.5 Rationale for Experiment............................................................................................................................34 CHAPTER II: HYPOTHESIS AND OBJECTIVES............................................................................................36
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