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The Alkaloids of Erythrina: Clonal Evaluation and Metabolic Fate

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The Alkaloids of Erythrina: Clonal Evaluation and Metabolic Fate Louisiana State University LSU Digital Commons LSU Historical Dissertations and Theses Graduate School 1991 The Alkaloids of Erythrina: Clonal Evaluation and Metabolic Fate. Lori Denise Payne Louisiana State University and Agricultural & Mechanical College Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_disstheses Recommended Citation Payne, Lori Denise, "The Alkaloids of Erythrina: Clonal Evaluation and Metabolic Fate." (1991). LSU Historical Dissertations and Theses. 5268. https://digitalcommons.lsu.edu/gradschool_disstheses/5268 This Dissertation is brought to you for free and open access by the Graduate School at LSU Digital Commons. It has been accepted for inclusion in LSU Historical Dissertations and Theses by an authorized administrator of LSU Digital Commons. For more information, please contact [email protected]. INFORMATION TO USERS This manuscript has been reproduced from the microfilm master. UMI films the text directly from the original or copy submitted. Thus, some thesis and dissertation copies are in typewriter face, while others may be from any type of computer printer. The quality of this reproduction is dependent upon the quality of the copy submitted. Broken or indistinct print, colored or poor quality illustrations and photographs, print bleedthrough, substandard margins, and improper alignment can adversely afreet reproduction. In the unlikely event that the author did not send UMI a complete manuscript and there are missing pages, these will be noted. Also, if unauthorized copyright material had to be removed, a note will indicate the deletion. Oversize materials (e.g., maps, drawings, charts) are reproduced by sectioning the original, beginning at the upper left-hand corner and continuing from left to right in equal sections with small overlaps. Each original is also photographed in one exposure and is included in reduced form at the back of the book. Photographs included in the original manuscript have been reproduced xerographically in this copy. Higher quality 6" x 9" black and white photographic prints are available for any photographs or illustrations appearing in this copy for an additional charge. Contact UMI directly to order. University Microfilms International A Ben & Howell Information Company 300 North Zeeb Road Ann Arbor Ml 48106-1346 USA 313 761-4700 800 521-0600 Order Number 0210668 The alkaloids ofErythrtnai Clonal evaluation and metabolic fate Payne, Lori Denise, Ph.D. The Louisiana State University and Agricultural and Mechanical Col., 1091 UMI 300 N. Zeeb Rd. Ann Arbor, MI 48106 THE ALKALOIDS OF ERYTHRINA: CLONAL EVALUATION AND METABOLIC FATE A Dissertation Submitted to the Graduate Faculty of the Louisiana State University and Agricultural and Mechanical College in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the Department of Chemis&y by Lon Denise Payne B.S., University of California at Davis, 1982 December 1991 ACKNOWLEDGEMENTS There are many people I would like to take this opportunity to thank for contributing to the success of this project and for making my time at LSU enjoyable. First I would like to thank my research advisor, Dr. Joe P. Foley, for allowing me to do this work and for his flexibility and support during the research. I appreciate the time my fellow group members, Skip Little, Jeff Crow, Mark Jeansonne, Rene Arenas and Eric Ahuja, took in discussing research and practical problems of the laboratory, Jeff Corkern and Roberto Wong were instrumental in the GC/MS and LC/MS work respectively. Financial support in the form of a teaching assistantship from the Department of Chemistry is acknowledged. I thank Ravi Laxman for his prodding and los muchachos at CAT1E, especially Frank Lopez and Gerardo Rodriqu6z, for informative discussions and sample handling. I also acknowledge the help of the Interlibrary Loan Service in attaining several important scientific papers. I am grateful to the members of my dissertation committee, especially Dr. Nikolaus Fischer and Dr. Barbara Shane for their constructive comments. Gifts of B-erythroidine from Dr. V. Boekelheide of the University of Oregon, erysodine and erysovine from Dr. A. H. Jackson of the University of Cardiff, and erythraline and erythratine from Dr. M. Jui-ichi of the Mukogawa Women’s University in Japan are gratefully acknowledged. And finally I would like to thank my family, particularly my husband Alejandro Dittel and my parents, Walt and Sue Payne, for their emotional and financial support and immense patience. ii TABLE OF CONTENTS C&gfi ACKNOWLEDGMENTS ....................................................................... u LIST OF TABLES .................................................................................. vi LIST OF FIGURES ................................................................................ vii LIST OF ABBREVIATIONS ................................................................. ix ABSTRACT ................................................................................................ xii CHAPTER 1 INTRODUCTION AND OBJECTIVES ........................... 1 1.1 Introduction .......................................................... 2 1.2 The Genus Erythrina and its Traditional Uses .......... 5 1.3 Erythrina as Forage .............................................. 6 1.4 Antiqualitative Agents in Erythrina ...................... 7 1.5 Objectives and Overview ...................................... 7 2 REVIEW OF LITERATURE ........................................... 9 2.1 Erythrina Alkaloids: Occurrence, Isolation and Identification ..................................... 10 2.1.1 Folkers, Unna, Majors and Koniuszy .......... 10 2.1.2 Deulofeu ................................................... 14 2.1.3 Boekelheide .............................................. 15 2.1.4 Other Studies on Structure Elucidation ........ 15 2.1.5 Occurrence of Erythrina Alkaloids .............. 16 2.1.6 Jackson, Chawla and Coworkers ............... 20 2.2 Erythrina Alkaloids: Biosynthesis ........................ 21 2.2.1 Early Studies ............................................. 21 2.2.2 Barton and Coworkers .............................. 22 2.3 Erythrina Alkaloids: Synthesis ............................. 27 2.4 Erythrina Alkaloids: Pharmacology and Toxicology .. 28 2.4.1 Research at Merck .................................... 29 2.4.2 Clinical Studies ........................................ 31 2.4.3 Other Pharmacological Studies .................. 32 2.5 Summary ................................................................. 34 iii 3 SAMPLE COLLECTION, STATISTICAL ANALYSIS AND LIQUID CHROMATOGRAPHIC TECHNIQUES .... 35 3.1 Introduction ............................................................... 36 3.2 Experimental .............................................................. 37 3.2.1 Clonal Selection ........................................... 37 3.2.2 Sample Collection and Preparation ............. 39 3.2.3 Extraction of Fresh and Frozen Material ....... 39 3.2.4 Total Nitrogen Determination ..................... 40 3.2.5 Dry Weight Determinations ........................ 41 3.2.6 Blade to Leaf Ratios ................................... 41 3.2.7 Statistical Analysis ....................................... 41 3.2.8 Thin Layer Chromatography ....................... 41 3.2.9 Reversed Phase HPLC ................................. 42 3.2.10 HPLC/MS Studies ...................................... 42 3.3 Results ........................................................................ 43 3.3.1 Statistical Analysis ...................................... 43 3.3.2 Reversed Phase HPLC .............................. 44 3.3.3 HPLC/MS ................................................... 45 3.4 Disscussion and Conclusions ..................................... 48 4 CLONAL EVALUATION OF ERYTHRINA ALKALOIDS BY GAS CHROMATOGRAPHY AND MASS SPECTROMETRY ..................................... 53 4.1 Introduction ............................................................... 54 4.2 Experimental .............................................................. 55 4.2.1 Clonal Selection and Sample Preparation ...... 55 4.2.2 Extraction of Dry and Lyophilized Plant Material 56 4.2.3 Statistical Analysis .................................... 56 4.2.4 GC/MS Analysis ................................. 56 4.2.5 Identification of Erythrina Alkaloids .......... 58 4.3 Results and Discussion ............................................ 60 4.4 Conclusions ................................................................ 79 5 POSSIBLE METABOLIC FATE OF ERYTHRINA ALKALOIDS ......................................................... 80 5.1 Introduction ............................................................... 81 5.2 Experimental .............................................................. 86 5.2.1 Feeding Study .......................................... 86 5.2.2 Milk Analysis ........................................... 86 5.2.3 Rumen Incubations .................................. 87 5.2.4 GC/MS Analysis ..................................... 88 5.2.5 Synthetic Hydrogenations ........................ 88 5.2.6 Statistical Analysis ................................... 88 5.3 Results ..................................................................... 89 5.4 Discussion ............................................................... 100 5.5 Conclusion .............................................................. 104 iv 6 SUMMARY, CONCLUSIONS AND RECOMMENDATIONS 105 6.1 Summary
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