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Chemical Characterization and Absorption of Phytochemicals

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Chemical Characterization and Absorption of Phytochemicals CHEMICAL CHARACTERIZATION AND ABSORPTION OF PHYTOCHEMICALS FROM MANGIFERA INDICA L. A Dissertation by KIMBERLY ANN KRENEK Submitted to the Office of Graduate Studies of Texas A&M University in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY Chair of Committee, Stephen T. Talcott Committee Members, Susanne U. Talcott Joesph M. Awika Nancy D. Turner Head of Department, Jimmy Keeton August 2013 Major Subject: Food Science and Technology Copyright 2013 Kimberly Ann Krenek ABSTRACT It was hypothesized that ester-linked gallic acid glycosides could be absorbed and metabolized in vivo due to the instability of an ester-linked glycosides at neutral pH. To evaluate in vivo absorption of Mangifera Indica, L. var. Keitt polyphenolics, it was first necessary to chemically characterize the compounds present using HPLC-MSn analysis. Mango pulp and extracts were also incubated with a pectinase, cellulase, pectinase with ß-glucosidase activity, and a pure ß-glucosidase to learn the extent of hydrolysis with potential application to enhancing bioavailability as a result of incubation to increase mango juice yield. After which the same extracts were assessed in differentiated Caco-2 cells to discern stability at physiological pH and to characterize metabolite formation in vitro. Finally, human urinary metabolites were characterized after 10 day consumption of 400 g in 11 individuals. Mass spectroscopic characterization and HPLC quantification of mango pulp revealed for the first time two monogalloyl glucosides (MGGs) with distinct differences in their glycoside linkages, with the ester form dominating, as well as the presence of five other phenolic acid glycosides; hydroxybenzoic acid glucoside, courmaric glucoside, ferulic acid glucoside, and sinapic acid mono and di-glucosides. Six oxygenated carotenoid derivatives were identified for the first time in a phytochemical extract, namely, a phytohormone, abscisic acid and its glycoside, two catabolism products of abscisic acid, dihydrophasic acids, and two hydroxy-dimethyl decadiene-dioic acid glucopiranosylesters. Gallotannins ranging from tetra-galloyl glucosides to nona-galloyl glucosides were also identified in the pulp, but ii not quantified. Clearzyme 200XL and Rapidase AR2000 were the most effective at increasing juice yield of mango pulp due to their pectinase action. Cz reduced the amount of ester-linked MGG by 70% after 4 hours of incubation while Rap hydrolyzed the ether linked MGG. The instability of ester-linked galloyl-glycosides at pH 7.4 was characterized by HPLC-MS and after only four hours of incubation a shift from HWM tannins (>8GG) to LMW (<8GG) occurred and resulted in 25 mg/L free gallic acid. Caco-2 cells metabolized gallic acid, MGG from a mango extract, and a gallotannin extract into O-methyl gallic acid indicating catechol-O-methyl transferase (COMT) as a major metabolizing enzyme for gallic acid. Urinary metabolites were identified by HPLC-MSn in dependant scans. O-methylgallic acid-O-sulfate was identified as the major metabolite 0-6 hours post consumption, followed by O-methylgallic acid at a lower concentration. The presence of gallic acid metabolites in the urine indicates absorption of ester-linked glycosides. Colonic metabolites were detected beginning 3-6 hours after consumption of mango, and were identified as pyrogalloyl derivatives. They are hypothesized to be the products of microbial breakdown of gallotannins. Daily consumption of mango for 10 days increased the concentration of O-methylgallic acid- O-sulfate, but was not significant. iii DEDICATION To my parents, Gerard and Theresa Krenek, for their unconditional love and support of my dreams. iv ACKNOWLEDGEMENTS I could not thank my advisor, Dr. Steve Talcott, enough for his encouragement, support, and friendship these last 6 years. His mentorship has molded me into the food scientist that I am and I will be forever grateful for the time spent in his lab, and the many “life lessons” taught along the way. I couldn’t have asked for a better advisor. I would also like to thank Dr. Susanne Talcott for her advice and support on my cell culture studies, for helping make the human pilot study possible and for prodding me every step of the way. She allowed me to take my research places I never thought possible. Thanks also go to my committee members, Dr. Joseph Awika and Dr. Nancy Turner for their advice and guidance on my projects. A big thank you goes to all friends and lab mates, especially, Paula, Shirley, Enrique, and Hyemee, for their help and encouragement. A special thank you for Sunday for waking up so early for my study days and making sure everything ran smoothly. To the “original Aggie crew,” Chris, Lisbeth, Jorge, Kim, thank you for your mentorship, friendship, and example. A BIG thank you to Ryan for his assistance on my projects over the last year; I could not have finished without his help and excitement. To the members of FSGSA, thank you for your friendship and words of advice and encouragement over the last four years. I would like to thank my “college” friends for their encouragement and prayers of support, especially my former roommates, Stephanie, Katie, and Emily. I could not have done this without their willingness to listen about another failed experiment and v their words of comfort. I would also like to thank Sr. Michela, for the many prayers, advice, and for keeping me focused on what really mattered, my relationship with God and doing His will. I would like to thank in a special way Adam for his friendship and love. His sacrifice over the last few months has helped me fall even more in love. He has been here when I needed it the most and his constant encouragement and prayers has made all the difference in getting my work completed and keeping me motivated. I owe my deepest gratitude to my parents, Gerard and Theresa Krenek. Their unconditional love and support of my dreams has meant so much; they are my biggest fans and the greatest parents. To my sisters, Amanda, Hannah, and Colleen, thank you for always being there for me. I treasure the extra time I was able to spend with each of you in college and I especially appreciate your help and making sure I always had food to eat these last couple of months. I don’t know what I would have done without you. I love you all so very much! Ad maiorem Dei gloriam vi TABLE OF CONTENTS Page ABSTRACT .......................................................................................................................ii DEDICATION .................................................................................................................. iv ACKNOWLEDGEMENTS ............................................................................................... v TABLE OF CONTENTS .................................................................................................vii LIST OF FIGURES ........................................................................................................... ix LIST OF TABLES ...........................................................................................................xii CHAPTER I INTRODUCTION ....................................................................................... 1 CHAPTER II LITERATURE REVIEW ............................................................................ 4 Mango: The King of Fruits ............................................................................................ 4 Composition and Physiology ......................................................................................... 7 Polyphenolics ............................................................................................................... 10 Tannins ......................................................................................................................... 14 Absorption and Metabolism by Caco-2 Cells .............................................................. 18 Absorption and Bioavailability of Polyphenols ........................................................... 22 CHAPTER III PHYTOCHEMICAL CHARACTERIZATION OF KEITT MANGO PULP ................................................................................................................................ 29 Introduction .................................................................................................................. 29 Materials and Methods ................................................................................................. 30 Results and Discussion ................................................................................................. 34 Conclusion .................................................................................................................... 48 CHAPTER IV PHYTOCHEMICAL CHANGES IN MANGO PULP ASSOCIATED WITH DIFFERENT ENZYME PREPARATIONS ........................................................ 50 Introduction .................................................................................................................. 50 Materials and Methods ................................................................................................. 52 Results and Discussion ................................................................................................. 54 Conclusions .................................................................................................................. 61 vii CHAPTER V IN VITRO METABOLISM, CELLULAR UPTAKE, AND STABILITY OF SELECTED MANGO POLYPHENOLICS IN CACO-2 CELLS ...........................
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