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Fate and Transport of an Estrogen Conjugate 17ß-Estradiol-17

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Fate and Transport of an Estrogen Conjugate 17ß-Estradiol-17 FATE AND TRANSPORT OF AN ESTROGEN CONJUGATE 17ß-ESTRADIOL-17- SULFATE IN SOIL-WATER SYSTEMS A Dissertation Submitted to the Graduate Faculty of the North Dakota State University of Agriculture and Applied Science By Xuelian Bai In Partial Fulfillment for the Degree of DOCTOR OF PHILOSOPHY Major Department: Soil Science August 2013 Fargo, North Dakota North Dakota State University Graduate School Title FATE AND TRANSPORT OF AN ESTROGEN CONJUGATE 17 β- ESTRADIOL-17-SULFATE IN SOIL-WATER SYSTEMS By Xuelian Bai The Supervisory Committee certifies that this disquisition complies with North Dakota State University’s regulations and meets the accepted standards for the degree of DOCTOR OF PHILOSOPHY SUPERVISORY COMMITTEE: Francis Casey Chair Heldur Hakk Thomas DeSutter Peter Oduor Eakalak Khan Approved: 8-26-2013 Francis Casey Date Department Chair ABSTRACT The hypothesis of this study was that a sulfate conjugated estrogen, i.e. 17 β-estradiol-17- sulfate (E2-17S), could be a precursor to free estrogens detected in the environment. The objectives of were to investigate the fate and transport processes of E2-17S in various soil-water systems. Radiolabeled E2-17S was synthesized using a series of chemical for the subsequent soil batch experiments. The batch experiment results showed that E2-17S dissipated more quickly from the aqueous phase of the topsoil compared to the subsoil, demonstrating that soil organic carbon played a significant role. The aqueous dissipation of E2-17S was attributed to sorption to the soil surface and transformation to form multiple metabolites. The non-linear sorption isotherms indicated limited sorption of E2-17S, and the concentration-dependent log KOC values were 2.20 and 2.45 for the sterile topsoil and subsoil, respectively. The total radioactive residue measured in the irreversible sites was greater than the reversible sites, demonstrating that irreversible sorption was the predominant sorption process. The observed multiple metabolites suggested that E2-17S underwent complex transformation pathways. For the aqueous phase speciation, mono- and di-hydroxy-E2-17S were consistently detected under all soil conditions, which indicated that hydroxylation was the major transformation process. Also, the hydroxyl metabolites were found at higher concentrations in the topsoil than the subsoil. In the reversibly sorbed phase, free estrogens (i.e. 17 β-estradiol and estrone) were detected at relatively low levels (≤ 2% of applied dose) for all soils, demonstrating that deconjugation/hydrolysis and subsequent oxidation did occur. Furthermore, both hydroxylation and hydrolysis of E2-17S took place under the non-sterile and sterile conditions. iii Although deconjugation was not a major pathway, E2-17S could be a precursor of free estrogens in the environment. A comprehensive one-site fully kinetic model was applied to simulate the overall governing processes in the soil-water systems and to describe the distribution of multiple metabolites in the aqueous, reversibly sorbed, and irreversibly sorbed phases.. The model gave rise to a satisfactory fit for all experimental data obtained from the batch studies, and the 36 estimated parameters were derived at relatively high confidence. iv ACKNOWLEDGMENTS I would like to express my sincere appreciation to my advisor Dr. Frank Casey, for his guidance, encouragement, patience, and support during my graduate study. Under his direction, I have learned how to perform scientific research from research questions to published results. I would like to acknowledge my committee member Dr. Heldur Hakk for his guidance and mentoring on all my laboratory work in the Biosciences Research Laboratory of USDA-ARS. I also want to thank the other members of my advisory committee, Dr. Tom DeSutter, Dr. Eakalak Khan, and Dr. Peter Oduor, for their comments and advice on my research and manuscripts. I sincerely thank Mrs. Colleen Pfaff (Biosciences Research Laboratory, USDA-ARS, Fargo, ND) and Mr. Nathan Derby (Department of Soil Science, North Dakota State University, Fargo, ND) for their technical support and contribution to this research. I appreciated Dr. Jane Schuh (Department of Veterinary and Microbiological Sciences, North Dakota State University, Fargo, ND) who provided great help for the soil gamma-irradiation procedure. I want to thank the postdoctoral fellow Dr. Suman Shrestha in the Department of Soil Science for his help on the radioactive material synthesis and modeling paper. I would like to thank the Department of Soil Science for providing a pleasant work environment. This project is supported by Agriculture and Food Research Initiative Competitive Grant No. 2010-65102-20400 from the USDA National Institute of Food and Agriculture. I was fortunate to be awarded by the North Dakota Water Resources Research Institute fellowship to pursue my Ph.D. v I am grateful to my father, brother, sister-in-law, and nephew for their love, understanding, and encouragement. vi DEDICATION To my late mother Mrs. Meijun Song, for who she had been, what she had done, and all the love she had given to me. vii TABLE OF CONTENTS ABSTRACT ................................................................................................................................... iii ACKNOWLEDGMENTS ...............................................................................................................v DEDICATION .............................................................................................................................. vii LIST OF TABLES ....................................................................................................................... xiii LIST OF FIGURES ..................................................................................................................... xiv LIST OF APPENDIX TABLES .................................................................................................. xvi LIST OF APPENDIX FIGURES................................................................................................. xix GENERAL INTRODUCTION ........................................................................................................1 Organization of the Dissertation ................................................................................................2 Literature Review.......................................................................................................................2 Adverse effects to aquatic wildlife ......................................................................................2 Sources .................................................................................................................................4 Fate and transport of estrogens ............................................................................................6 Environmental detections.....................................................................................................9 Estrogen conjugates ...........................................................................................................11 Objectives of the Study ............................................................................................................13 PAPER 1. SYNTHESIS AND CHARACTERIZATION OF RADIOLABELED 17ß- ESTRADIOL CONJUGATES.......................................................................................................14 Abstract ....................................................................................................................................14 viii Introduction ..............................................................................................................................14 Experiment ...............................................................................................................................17 Materials ............................................................................................................................17 Synthesis of [4-14 C]17 β-estradiol-3-glucuronide ...............................................................20 Synthesis of [4-14 C]17 β-estradiol-17-sulfate .....................................................................20 Results and Discussion ............................................................................................................22 Synthesis of [4-14 C]17 β-estradiol-3-glucuronide ...............................................................22 Synthesis of [4-14 C]17 β-estradiol-17-sulfate .....................................................................24 Conclusions ..............................................................................................................................26 Acknowledgements ..................................................................................................................26 References ................................................................................................................................27 PAPER 2. DISSIPATION AND TRANSFORMATION OF 17ß-ESTRADIOL-17- SULFATE IN SOIL-WATER SYSTEMS ....................................................................................32 Abstract ....................................................................................................................................32 Introduction ..............................................................................................................................32 Materials and Methods .............................................................................................................35
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