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Master Document Template Copyright by Isagani Damasco Padolina 2002 The Dissertation Committee for Isagani Damasco Padolina Certifies that this is the approved version of the following dissertation: Chitin-Induced Biosynthesis of Phytoalexin 4´- Deoxyaurone In Cell Suspension Cultures of “Old Man” Cactus, Cephalocereus senilis Committee: Tom J. Mabry: Supervisor Stanley J. Roux, Jr. Alan M. Lloyd Billie L. Turner Ben A. Shoulders Chitin-Induced Biosynthesis of Phytoalexin 4´- Deoxyaurone In Cell Suspension Cultures of “Old Man” Cactus, Cephalocereus senilis by Isagani Damasco Padolina, B.S. Dissertation Presented to the Faculty of the Graduate School of The University of Texas at Austin in Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy The University of Texas at Austin May, 2002 Dedication Para kay Nanay at Tatay, sa aking mga kapatid- kay Ibarra at Linglingay, at para sa minamahal kong Anneke Acknowledgements I thank my supervising professor, Dr. Tom J. Mabry, for his patience, guidance and support. I cannot think of anything better than the training he has given me as his teaching assistant and graduate student. His no-nonsense approach to the politics and nuances of research in graduate school will always be remembered. It is both an honor and privilege to work with the “Father of Phytochemistry”. Without Dr. Mabry, there would not be a dissertation, only a good idea. I am grateful to Dr. Richard Dixon and Dr. Suzanne Rasmussen of the Samuel Roberts Noble Foundation and Dr. Paul Paré of Texas Tech for their ideas on the hypotheses that I am testing and for helping me design my pulse-chase experiments. My special thanks go to Dr. Delia Brownson for helping me get started in Dr. Mabry’s Phytochemistry lab. Her initial guidance saved me a lot of time in finding where things are and how things work. I would like to thank the other members of my dissertation committee: Drs. Stanley Roux Jr., Alan Lloyd, Ben Shoulders and Billie Turner for reviewing this dissertation as well as for their guidance during my graduate program. My dissertation project was supported financially through Dr. Mabry’s F-0130 grant from the Robert A. Welch Foundation. I am grateful for the travel grants v and research fellowships awarded to me by the Molecular Cell and Developmental Biology Department and the Plant Biology graduate program. I am privileged to spend my many summers in the Mabry lab working with some of the best phytochemists in world. I thank Drs. Nabil El-Sayed, Ahmed Ahmed, Eman Haggag and Mahmound Nasser for helping me learn the biochemical techniques of extraction, isolation and characterization of natural products. Much of my time in graduate school is spent in the lab and I would like to thank my fellow graduate students in the Mabry group- Schalk van Rooyen, Malgorzata Wojcinska, and Jeff Williams, for the sharing of ideas and for the company of helping each other. Thanks to the laboratories and graduate students of Drs. Bob Jansen, Stan Roux, Su Dharmawardhane, Malcolm Brown, James Mauseth and Jerry Brand for letting me use their equipment and for lending me some of the chemicals that I needed. I thank Dr. Greg Clark for the exchange of great ideas in doing good science. The support staff of the Plant Biology program has been a great help in weaving through the intricate logistics and bureaucracy of graduate school. I would like to thank the staff of the former Botany department- Cathy Prescott, John Lucio, Theresa Barnes, and Bill Baker, and the new Molecular Cell and Developmental Biology staff, Tamra Rogers, Maureen Meko, Al Alvarado, Melody Villareal, vi Francisco Valledares and Adam Polanco. My special thanks go to Scott Schulz for his assistance in doing my illustrations and figures. My main source of support throughout my graduate career is my teaching assistantship. My special thanks to Susan Cook of the School of Biological Sciences for all her help in my TA assignments every semester. My roommates through all these years in the Eiler house, Brian vanden Heuvel, Jan Barber, Amy Bystrom and Mandi Vaughn have made living in Austin more fun. I thank them for the dinners, the hikes, the rows and for their fantastic company. It makes me sad to see them go. The Beckman-Coulter HPLC team was instrumental (no pun intended) in helping me set up my HPLC system for my experiments. Thanks to Leiko Dahlgren for helping me with intricacies of the 171A radiodetector, to Marcia Witt for troubleshooting software and to Don Tjernlund for all the plumbing lessons. I wish to thank the numerous outstanding undergraduate students who did research in the Mabry labs and have helped me so well in dealing with the technical difficulties involved in my experiments. My special thanks go to the students who showed up and went the extra mile- Sebastian Paige, Vaishali Trivedi, Mitch Luna, Tanya Ong, Deepa Vyas, Kaye Charpentier; and to the students of homestretch semester, Spring 2002- Bradley Eng, Manny Zapata, vii Amy Chen, Yenabi Keflemariam, Darrell Brown, Otis Tucker, Hannaise Cruz and Sarah Rodgers. My cello classes at the UT School of Music not only helped me in relieving some of the stresses in grad school but has also made my education more well-rounded. I wish to thank Professor Young for all her patience in her master classes when I play out of tune and my many, many thanks goes to her TA, Tomasz Ryzezcki, the guru of cello pedagogy, for his steady guidance and unrelenting patience for a beginner like me. My fellow graduate students, not just in the botany program but also in other fields such as chemistry and zoology have been valuable for their company and exchange of ideas, trials and tribulations and other goofy stuff- Rafe Brown, Vaughan Symonds and Jen Tate, James and Grace Javier, Joey and Ruela Pabalan, Shawn and Dylan Stricklin and Wowie Ebron. I am especially grateful to the Tropa and Ari Bautista, CB and Tasha Mamaril, and Chris and Kristy Mateo for their prayers and for their friendship. I wish to thank my all of my friends from the bottom of my heart, my new friends here in the US and old friends in the Philippines, you know who you are and you viii know me well, I’m hurrying up to finish right now so I don’t have time to put all your names. You’ve seen me complain and ponder my way through the course of my dissertation project and you’ve always managed to put a smile on my face even when the rain pours. Filipinos have big extended families they are always there for you no matter what. I am grateful for the support that they have given- Auntie Nesy and Uncle Lito, Auntie Bibing and Uncle Tante, the Casabar/Damasco clan in Fresno, Papa Bob and Mama Wency, Ninang Nancy and Tita Lina, Auntie Gertrude, and my cousin Marlo Casabar and his family. My siblings whose significant experiences I have missed by being in a faraway country. I wish to thank Ibarra and Linglingay for being there and for their quiet support. Without them I would not be here, literally, in every sense of the word. My Nanay and Tatay, aside from being my parents, met and graduated at the University of Texas. Without UT in the equation, definitely no Gani and most definitely no Ph.D. No amount of words would be able to express my thanks to them for their patience and support. I am proud of them, proud to be their son and I give them my love. ix I would like to express my deepest appreciation to Anneke. She is the love of my life and my closest friend. Her many sacrifices, understanding, patience, help and support has made this scholarly journey more wonderful than I have imagined. She has diluted the chemistry part of me with botany (not just some but lots of it), she has balanced my diet with lots of vegetables, she has opened my mind to a lot more than just science and she has filled my life with happiness. Last, but far from least, I thank the Lord, Almighty and All Knowing. I am all but human and I am very humbled by my accomplishments in the duration of this work. x Chitin-Induced Biosynthesis of Phytoalexin 4´- Deoxyaurone In Cell Suspension Cultures of “Old Man” Cactus, Cephalocereus senilis Publication No._____________ Isagani Damasco Padolina, Ph.D. The University of Texas at Austin, 2002 Supervisor: Tom J. Mabry Cell suspension cultures of Cephalocereus senilis develop red pigmentation when infected by fungus. Previous work in our laboratory has established that chitin, a fungal cell wall component, can elicit the same response. These elicited cell cultures also produce several unusual flavonoids lacking the normal 4´-hydroxyl substitution in the B-ring, including the red pigment cephalocerone, a 4´-deoxyaurone. Previous enzymological studies showed that the elicited cell suspension cultures have the necessary enzymatic activities required for the conversion of L-phenylalanine to the 4´-deoxyflavonoids. Explanations for the 4´-deoxyflavonoid biosynthesis include (1) a bypass of cinnamic acid 4- hydroxylase therefore leading to an accumulation of 4´-deoxy precursors available for the 4´-deoxyflavonoid production and (2) a dehydroxylation step within the flavonoid biosynthetic pathway. xi The current biochemical investigations into the biosynthesis of the phytoalexin cephalocerone using HPLC metabolic profiling of isotope dilution experiments established the existence of a novel 4´-dehydroxylation step instead of a 4´-hydroxyl “bypass”. Our results strongly suggest that the metabolic flux involved in the selective production of 4´-deoxyflavonoids may be controlled by a specific enzyme activity that dehydroxylates the 4´-position of the tetrahydroxychalcone B-ring.
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