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Proquest Dissertations Drug lead discovery through plant bioprospecting in Latin America Item Type text; Dissertation-Reproduction (electronic) Authors Khera, Smriti Publisher The University of Arizona. Rights Copyright © is held by the author. Digital access to this material is made possible by the University Libraries, University of Arizona. Further transmission, reproduction or presentation (such as public display or performance) of protected items is prohibited except with permission of the author. Download date 28/09/2021 20:25:54 Link to Item http://hdl.handle.net/10150/282898 DRUG LEAD DISCOVERY THROUGH PLANT BIOPROSPECTING IN LATIN AMERICA by Smriti Khera A Dissertation Submitted to the Faculty of the DEPARTMENT OF PHARMACEUTICAL SCIENCES In Partial Fulfillment of the Requirements For the degree of DOCTOR OF PHILOSOPHY In the Graduate College THE UNIVERSITY OF ARIZONA 2005 UMI Number: 3177540 INFORMATION TO USERS 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 bleed-through, substandard margins, and improper alignment can adversely affect reproduction. In the unlikely event that the author did not send 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. UMI UMI Microform 3177540 Copyright 2005 by ProQuest Information and Learning Company. All rights reserved. This microform edition is protected against unauthorized copying under Title 17, United States Code. ProQuest Information and Learning Company 300 North Zeeb Road P.O. Box 1346 Ann Arbor, Ml 48106-1346 The University of Arizona fKj Graduate College As members of the Final Examination Committee, we certify that we have read the dissertation prepared by Smritl Khera entitled Drug Lead Discovery through Plant Bloprospecting in Latin America and recommend that it be accepted as fulfilling the dissertation requirement for the Degree of Doctor of Philosophy Karl H.Schram, Ph.D. date 'A 11' s. Moore, Ph.D. ie Gunatilaka, Ph.D. date Robert B. Bates, Ph.D. f ( I I ^ Barbara N. Timmermann, Ph.D. date Final approval and acceptance of this dissertation is contingent upon the candidate's submission of the final copies of the dissertation to the Graduate College. I hereby certify that I have read this disseitation prepared under my direction and recommend that it be accepted as fulfilling the dissertation requirement. Q I | j ^ |J. 00-^ Dissertation Director; Barbara N.Timmermann, Ph.D. date 3 STATEMENT BY AUTHOR This dissertation has been submitted in partial fulfillment of requirements for an advanced degree at The University of Arizona and is deposited in the University Library to be made available to borrowers under rules of the Library. Brief quotations from this thesis are allowable without special permission, provided that accurate acknowledgment of source is made. Requests for permission for extended quotation from or reproduction of this manuscript in whole or in part may be granted by the head of the major department or the Dean of the Graduate College when in his or her judgment the proposed use of the material is in the interests of scholarship. In all other instances, however, permission must be obtained from the author. SIGNED: 4 ACKNOWLEDGEMENTS I would like to thank my dissertation advisor Dr. Barbara Timmermann for her support and encouragement throughout the course of this research. I thank her for always standing by my side through my accomplishments and failures alike. She believed in me even at times when I was unsure of myself. She has been an enormous source of strength, encouragement, scientific insight, and emotional support for me throughout the duration of this research. I would like to thank Dr. Brad Moore for his scientific vigilance and commitment to my success. His suggestions, advice and help have been invaluable to this research. I would also like to thank Dr. Moore for being extremely accessible and approachable even on matters unrelated to research. Discussions with him have been invaluable in terms of career planning and personal growth. I would also like to thank Drs. Karl Schram, Leslie Gunatilaka, and Robert Bates for their generous help, advice and consultations that have been critical to this work. I thank them for being extremely accessible and for sharing their expertise for the benefit of this research. I would like to thank Dr. Neil Jacobsen and Dr. Michael Carducci for teaching me everything I know about NMR spectroscopy and X-ray crystallography respectively. Over the years I have spent and enormous amount of time with them and without their support, advice and training this research would not have been possible. I would also like to thank Dr. Arpad Samyogyi for extremely helpful consultations about mass spectrometry and for being an excellent resource throughout this study. I would also like to thank past and present members of Dr. Timmermann's laboratory, particulary, Drs. Girma Woldemichael, Shivanand Jolad, Jianqiao Gu, Aniko Solyom, along with Veronica Rodriguez and Katy Prudic for their training, help and guidance. At a personal level, I would also like to acknowledge my grandparents- Vidya Rani and Thakar Das Kalra, late Rattan Kumari and late Tilak Raj Khera for their vision and values that have helped shape my life. Their support and encouragement was invaluable throughout my graduate career. I would also like to thank Abhishek Gupta, who has been a home away from home for me for the past several years. His support and friendship have been very critical to the successful completion of this work. Finally, I would like to thank my wonderful parents Manmohan Krishna and Manju Khera for supporting me every step of the way through graduate school. If not for their encouragement, and love it would not have been possible to pursue my education so far away from home and accomplish my goals. DEDICATION To my mom, Manju, for her many sacrifices in raising me, and her tireless strength, love, patience and wisdom that has always guided me through the most challenging of times. And to my papa, Manmohan Krishna, for his belief in me that has always bolstered my own belief in myself. 6 TABLE OF CONTENTS Page LIST OF FIGURES 12 LIST OF TABLES 18 ABSTRACT 20 CHAPTER I - INTRODUCTION 22 1.1 Natural Products in the Post-Genomic Era 22 1.2 Plants as a Source of Pharmaceuticals and Lead Compounds 25 1.3 The International Cooperative Biodiversity Group (ICBG) Program 29 1.4 Collection and Investigation Stragies 31 1.5 Ahead 34 CHAPTER II- A NEW ANTIBACTERIAL TRITERPENE AND A NEW IRIDOID FROM CAIOPHORA CORONATA 36 2.1 Introduction 36 2.2 Distribution and Botanical Features 37 2.3 Systematics and Phytochemistry in Loasaceae 37 2.4 Ecological Significance of Iridoids in the Loasaceae 40 2.5 Statement of Purpose 42 2.6 Bioassay Guided Fractionation 43 2.7 Structure Elucidations and Identification 47 2.7.1 Structure Elucidation of ip,3P-Dihydroxyurs-12-en-27-oic Acid (1)... .47 2.7.2 Structure Elucidation of Caiophoraenin (2) 53 7 TABLE OF CONTENTS - Continued Page 2.7.3 Identification of Isoboonein (3) 61 2.8 Antibacterial Activity 63 2.9 LC/MS Survey 65 2.10 Experimental Section 76 2.10.1 NMR Experiments 76 2.10.2 Plant Material 76 2.10.3 In Vitro Antimicrobial Activity Testing 77 2.10.4 LC/MS Instrumentation and Technique 78 Sample Preparation 78 Standard Preparaton 79 HPLC/DAD 79 2.10.5 Spectroscopic Data 79 ip,3P-Dihydroxyurs-12-en-27-oic Acid (1) 79 Caiophoraenin (2) 79 CHAPTER III - GROWTH INHIBITION OF MYCOBACTERIUM TUBERCULOSIS BY THE CONSTITUENTS 0¥ MYRCIANTHES COQUIMBENSIS 80 3.1 Introduction 80 3.2 Distribution and Botanical Features 81 3.3 Taxonomy and Nomenclature 82 8 TABLE OF CONTENTS - Continued Page 3.4 Chemical Composition of the Volatile Leaf Oil 84 3.5 Statement of Purpose 89 3.6 Bioassay Guided Fractionation 90 3.7 Structure Elucidation and Identifications 97 3.7.1 Structure Elucidation of (15,3'S',4/?)-l-Methyl-4-(l-methylethenyl)-l,3- cyclohexanediol (3p-Hydroxy-c/5-p-terpineol, 10) 97 3.7.2 Identification of Oleanolic Acid (11) 107 3.7.3 Identification of 3p-Caffeoyl-12-oleanen-28-oic Acid (12) 107 3.7.4 Idetification of Trans (+)-sobrerol (13) 109 3.7.5 Identification of Epi-catechin (14) 110 3.7.6 Identification of Catechin (15) 110 3.8 AntitubercularActivity Ill 3.9 LC/MS Survey 113 3.10 Experimental Section 129 3.10.1 NMR Experiments 129 3.10.2 Preparation of the (R)- and (5)-MTPA Derivatives of 10 129 3.10.3 Plant Material 130 3.10.4 Microplate Alamar Blue Assay 131 3.10.5 Vero Cell Cytotoxicity Assay 133 9 TABLE OF CONTENTS - Continued Page 3.10.6 GC/MS 134 3.10.7 LC/MS Instrumentation and Technique 134 Sample Preparation 134 Standard Preparation 135 HPLC/DAD 135 3.10.8 Spectroscopic Data 136 (1S,3S,4R)- 1-Methyl-4-( 1 -methylethenyl)-1,3-cyclohexanediol (10)....136 CHAPTER IV - CHLOROFORM SOLVATE OF (47?,5/?,75,85,95)-7-HYDROXY-8- HYDROXYMETHYL-4-METHYLPERHYDROCYCLOPENTA[C]PYRAN-1-ONE FROM VALERIANA LAXIFLORA 137 4.1 Introduction 137 4.2 Results and Discussion 139 4.3 Experimental Section 145 4.3.1 Plant Material 145 4.3.2 Isolation 145 4.3.3 Refinement 146 CHAPTER V - (3/?,55,9/?,105,135,145,17/?,18/?,21/?)-(-)-FERN-7-EN-3a-OLFROM SEBASTIANIA BRASILIENSIS 148 5.1 Introduction 148 5.2 Results and Discussion 150 10 TABLE OF CONTENTS - Continued Page 5.3 Experimental Section 151 5.3.1 Plant Material 151 5.3.2 Isolation 157 5.3.3 Preparation of the {R)- and (5)-MTPA Derivatives of 30 157 5.3.4 Refinement 158 CHAPTER VI - SUMMARY AND CONCLUSIONS 160 6.1 Summary 160 6.2 Antitubercular Triterpenoids 162 6.3 Structure-Activity Relationships in Antitubercular Triterpenoids 164 6.3.1 The Oleananes 164 6.3.2 TheUrsanes 169 6.3.3 The Lupanes 172 6.3.4 The Hopanes and a Femane 175 6.3.5 The Steroids 178 CHAPTER VII - GENERAL EXPERIMENTAL 183 7.1 General Instrumentation 183 7.2 HPLC/DAD/MS/MS 184 7.3 X-ray Crystallography Data Collection 184 APPENDIX A 185 11 TABLE OF CONTENTS - Continued Page APPENDIX B 189 REFERENCES 205 12 LIST OF FIGURES Page Figure 2.1.
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