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A Search for Biologically Active Phytochemicals from Endemic Plants of the Southeastern United States

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A Search for Biologically Active Phytochemicals from Endemic Plants of the Southeastern United States Louisiana State University LSU Digital Commons LSU Historical Dissertations and Theses Graduate School 1997 A Search for Biologically Active Phytochemicals From Endemic Plants of the Southeastern United States. Steven Lynn Robbs Louisiana State University and Agricultural & Mechanical College Follow this and additional works at: https://digitalcommons.lsu.edu/gradschool_disstheses Recommended Citation Robbs, Steven Lynn, "A Search for Biologically Active Phytochemicals From Endemic Plants of the Southeastern United States." (1997). LSU Historical Dissertations and Theses. 6402. https://digitalcommons.lsu.edu/gradschool_disstheses/6402 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 m icrofilm master. U M I 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. Hie 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 affect 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 wifi indicate the deletion. Oversize materials (e.g., maps, drawings, charts) are reproduced by sectioning the original, beginning at the upper left-hand comer 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. A Bell & Howell Information Company 300 North Zeeb Road. Ann Arbor. Ml 48106-1346 USA 313/761-4700 800/521-0600 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. A SEARCH FOR BIOLOGICALLY ACTIVE PHYTOCHEMICALS FROM ENDEMIC PLANTS OF THE SOUTHEASTERN UNITED STATES 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 Chemistiy by Steven L. Robbs B.S., University of Arizona 1983 M.S., University of Arizona 1989 May, 1997 Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. UMI Number: 9735997 UMI Microform 9735997 Copyright 1997, 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 would like to express my appreciation for the Fischer's maintenance of one of the last vestiges of phytochemical research in Louisiana at the "Fischer Fytochemical Farm". Dr. Nikolaus H. Fischer's guidance, encouragement and patience have been deeply valued during my time spent in the Deep South. Mrs. Fischer's maternal support has also been greatly appreciated and her sumptuous birthday treats will be always be fondly remembered. The ecological studies of the Florida scrub and the statistical analysis of data would not have been possible without the assistance of the following individuals: Dr. Bruce Williamson, Helga Fischer, Dr. Andrew Baldwin and Lori Grelen. My training in the use of the NMR was facilitated by Marcus Nauman and Dr. Dale Treleaven. Special thanks to Dr. Guido Pauli and Dr. Tian-Sheng Lu, who provided invaluable assistance in the interpretation of spectra and in the methods of phytochemical analysis. I would like to express my gratitude to Dr. Tracy McCarly, for managing the Mass Spectrometry facilities and to Dr. Frank Fronczek and his graduate students for determining the X-ray structures presented in this manuscript. Special thanks to Dr. Scott Franzblau and his staff at the Hansen’s disease Laboratory for performing the anti- mycobacterial assays. The identification of plant specimens by the botanists, Dr. Lowell Urbatsch and Dr. Tom Wendt, is greatly appreciated. Thanks to Dr. Dale Thomas for providing me with the first material ofEuthamia leptocephela and his assistance in collecting plant material. Lastly, I would like to express my appreciation of all the members of our group and friends in Baton Rouge who have made living here a memorable experience. ii Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. TABLE OF CONTENTS ACKNOWLEDGMENTS ...................................................................................... ii LIST OF TABLES .................................................................................................. iv LIST OF FIGURES .................................................................................................. v ABSTRACT ............................................................................................................... viii CHAPTER 1. INTRODUCTION ......................................................................... 1 Phytochemicals ......................................................................... 2 Terpenoids ...................................................................................... 3 Polyacetylenes ......................................................................... 14 Phenolics ...................................................................................... 14 2. INVESTIGATIONS OF BIOLOGICALLY ACTIVE PHYTOCHEMICALS FROM THE FLORIDA SCRUB ...................... 18 Introduction ...................................................................................... 19 Results and Discussion ............................................................ 23 Experimental ...................................................................................... 27 3. ISOLATION AND STRUCTURAL ELUCIDATION OF NATURAL PRODUCTS FROM EUTHAMIA SPECIES ................................... 52 Introduction ...................................................................................... 53 Results and Discussion ............................................................ 59 Experimental ...................................................................................... 68 4. BIOLOGICAL ACTIVITIES OF PLANT EXTRACTS AND ISOLOATED COMPOUNDS AGAINST MYCOBACTERIUM TUBERCULOSIS AND MYCOBACTERIUM AVIUM ............................................................ 101 Introduction ...................................................................................... 102 Results and Discussion ............................................................ 103 Experimental 105 5. CONCLUSIONS ...................................................................................... 108 REFERENCES .................................................................................................. I ll VITA 118 iii Reproduced with permission of the copyright owner. Further reproduction prohibited without permission. LIST OF TABLES 1.1. Major classes of secondary plant compounds 3 2.1. Germination of four test species in response to cyclic monoterpenes 30 2.2. Germination of four test species in response to famesol and geraniol ........................................................................................................ 31 2.3. Germination of four test species in response to depsides ............................ 31 2.4. Radicle elongation of four test species in response to cyclic monoterpenes .................................................................................................. 32 2.5. Radicle elongation of four test species in response to famesol and geraniol .................................................................................................. 33 2.6. Radicle elongation of four test species in response to depsides .......... 33 2.7. 13C and lH NMR spectral data of atranorin ................................................ 43 2.8. Fractional atomic coordinates and equivalent isotropic thermal parameters of atranorin .................................................................................................. 44 3.1. Volatile terpenoid compounds in Euthamia leptocephala and E. tenuifolia detected by GC/MS ...................................................................................... 60 3.2. 13C NMR spectral data of compounds 1,2, and 3 73 3.3. NMR spectral data of compounds 1,2, and 3 73 3.4. Fractional atomic coordinates and equivalent isottopic thermal parameters of limonidilactone ...................................................................................... 74 3.5. Fractional atomic coordinates and equivalent isotropic thermal parameters of 6-B-hydroxylimonidilactone ........................................................................
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