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Louisiana State University LSU Digital Commons LSU Historical Dissertations and Theses Graduate School 1998 Antimycobacterial Natural Products From Higher Plants. Charles Lowell Cantrell Louisiana State University and Agricultural & Mechanical College Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_disstheses Recommended Citation Cantrell, Charles Lowell, "Antimycobacterial Natural Products From Higher Plants." (1998). LSU Historical Dissertations and Theses. 6660. https://digitalcommons.lsu.edu/gradschool_disstheses/6660 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. 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Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. ANTIMYCOBACTERIAL NATURAL PRODUCTS FROM HIGHER PLANTS 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 Chemistry by Charles L. Cantrell B. S., Louisiana State University, 1994 May 1998 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. UMI Number: 9836860 UMI Microform 9836860 Copyright 1998, by UMI Company. All rights reserved. This microform edition is protected against unauthorized copying under Title 17, United States Code. UMI 300 North Zeeb Road Ann Arbor, MI 48103 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. ACKNOWLEDGMENTS I wish to express my sincere appreciation to my major professor, Dr. Nikolaus H. Fischer, for his scientific as well as personal guidance, for being a wonderful professor and mentor, and a great friend. I also wish to thank Mrs. Helga Fischer for her assistance on numerous research projects and for being a true friend. I am also thankful for the support and encouragement provided to me by Dr. Scott Franzblau of the G.W.L. Hansen’s Disease Center at LSU School of Veterinary Medicine. Additionally, I wish to thank Anita N. Biswas and Ken E. White for technical support which they provided to me in performing radiorespirometric bioassays. Financial support from the National Institute of Allergy and Infectious Diseases, National Institutes of Health under contract No. Y02-AI-30123 is gratefully acknowledged. I would like to acknowledge Dale Traleaven and Marcus Nauman for their patient assistance in operating the NMR instruments. I am grateful to Dr. Frank Fronczek for providing X-ray structures of numerous compounds presented in this dissertation. I thank Dr. Lowell Urbatsch for his assistance in plant identifications and collections. Thanks to my research group, the faculty, and fellow graduate students for their support and friendship. I wish to especially thank Dr. Tiansheng Lu for his patient assistance and guidance as I began my graduate career. Lastly, I would like to thank my wife, Julie Cantrell, for her patient support and understanding throughout these years. She has been a constant source of encouragement and an inspiration to me. ii Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. TABLE OF CONTENTS ACKNOWLEDGMENTS ............................................... LIST OF TABLES ........................................................... LIST OF FIGURES ..................................................................................... ABSTRACT ................................................................................................. CHAPTER 1. INTRODUCTION AND REVIEW .................................. 1.1 Epidemiology of Tuberculosis ...................... 1.2 Current Treatment Methodology ...................... 1.3 Review of Antituberculosis Terpenoids .......... 1.3.1 Monoterpenes .................................. 1.3.2 Sesquiterpenes .................................. 1.3.3 Diterpenes ............................................... 1.3.4 Triterpenes ............................................... 1.3.5 Phytol, derivatives, and analogs .......... 1.4 Conclusions ........................................................... 1.5 References ........................................................... 2. ANTIMYCOBACTERIAL CRUDE PLANT EXTRACTS FROM SOUTH, CENTRAL, AND NORTH AMERICA 2.1 Introduction ........................................................... 2.2 Experimental ........................................................... 2.3 Results ........................................................... 2.4 Discussion ........................................................... 2.5 References ........................................................... 3. ANTIMYCOBACTERIAL CYCLOARTANES FROM BORRICHIA FRUTESCENS................................................ 3.1 Introduction ........................................................... 3.2 Results and Discussion .................................. 3.3 Experimental ........................................................... 3.4 References ........................................................... 4. ANTIMYCOBACTER1AL ACTIVITIES OF DEHYDROCOSTUS LACTONE AND ITS OXIDATION PRODUCTS ......................................................................... 4.1 Introduction ............................................................ 4.2 Results and Discussion .................................. 4.3 Experimental ............................................................ 4.4 References ............................................................ iii Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. 5. ANTIMYCOBACTERIAL SESQUITERPENE LACTONES FROM INULA HELENIUM AND RUDBECKIA SUBTOMENTOSA ............................................................ 112 5.1 Introduction ............................................................. 113 5.2 Results and Discussion ..................................... 113 5.3 Experimental ............................................................. 116 5.4 References ............................................................. 137 6. TWO NEW ANTIMYCOBACTERIAL TRITERPENES FROM MELIA VOLKENSII ................................................ 139 6.1 Introduction ............................................................. 140 6.2 Results and Discussion .................................... 141 6.3 Experimental ............................................................. 144 6.4 References ............................................................. 163 7. SUMMARY AND CONCLUSIONS..................................... 165 APPENDIX: LETTERS OF PERMISSION ............................................... 171 VITA ........................................................................................................... 173 IV Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. LIST OF TABLES 1.1 Estimated Global TB Incidence and Mortality in 1992 .......... 2 1.2 Terpenoid Minimum Inhibitory Concentrations (MICs) Against M. tuberculosis (H37R.V) 7 2.1 Antimycobacterial Activity of Various Crude Plant Extracts 36 3.1 Inhibitory Activity of Borrichia frutescens Fractions (Flowers, CH2CI2 Extract) Against Mycobacterium tuberculosis (H37R.V) 64 3.2 'H-NMR

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