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Bioactive Alkaloids from Medicinal Plants of Lombok Surya Hadi University of Wollongong

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Bioactive Alkaloids from Medicinal Plants of Lombok Surya Hadi University of Wollongong University of Wollongong Research Online University of Wollongong Thesis Collection University of Wollongong Thesis Collections 2002 Bioactive alkaloids from medicinal plants of Lombok Surya Hadi University of Wollongong Recommended Citation Hadi, Surya, Bioactive alkaloids from medicinal plants of Lombok, Doctor of Philosophy thesis, Department of Chemistry, University of Wollongong, 2002. http://ro.uow.edu.au/theses/1117 Research Online is the open access institutional repository for the University of Wollongong. For further information contact the UOW Library: [email protected] BIOACTIVE ALKALOIDS FROM MEDICINAL PLANTS OF LOMBOK A Thesis Submitted in Fulfillment ofthe Requirements for the Award ofthe Degree of DOCTOR OF PHILOSOPHY from The University of Wollongong by SURYA HADI, Ir. M.Sc. (Hons.) Department of Chemistry October 2002 CERTIFICATION I, Surya Hadi, declare that this thesis, submitted in fulfillment of requirement for the award of Doctor of Philosophy, in the Department of Chemistry, University of Wollongong, is wholly my own work unless otherwise referenced or acknowledge. The document has not been submitted for qualifications at any other academic institution. SURYA HADI 10 October 2002 u PUBLICATIONS 1. Initial Studies on Alkaloids from Lombok Medicinal Plants (Molecules)1 2. Constituents of Medicinal Plants of Lombok: A New Antibacterial Alkaloid from Voacangafoetida (Bl.) Rolfe (Phytochernistry, in preparation) 3. New Bioactive Alkaloids from Young Trees of Alstonia scholaris R. Br. (Planta Medica, in preparation) (1) Hadi, S.; Bremner, J. B. Initial studies on alkaloids from Lombok medicinal plants. Molecules [online computer file] 2001, 6, 117-129. Ill ACKNOWLEDGEMENTS I would like to give my sincere thanks to my supervisor, Prof. John B. Bremner for his continuous guidance and support during the course of this study. Thanks are extended to Aus Aid for the scholarship and to the Institute for Biomolecular Science in providing extra funds to assist this project. My utmost thanks to the following people Who extended their kind aid in completing this work: Dr. John Korth for training me to operate the Low Resolution Chemical Ionisation/Electron Impact Mass Spectrometer; Larry Hick for his help in performing High Resolution Chemical Ionisation/Electron Impact Mass Spectrometry; the NMR people, Sandra Chapman, Ellen Manning, and Yoke Berry for their assistance in training me in using the NMR spectrometer; Dr. David Perkins, not only for his kind help in correcting my thesis but also for his warm friendship; Dr. Irawati and Mr. Made Sudana for their great contribution to facilitate the collection of medicinal plants; Mr. Taspin for his help in collecting the plants; Dr. Kirsten Benkendorff for her guidance in the antibacterial testing; Dr. Sumalee Kamchonwongpaisan for the antimalarial testing; and finally to my best friends in the Bremner research group, Susan, Collette, Waya, Siritron, Nisit, Johana, and Burak (Dr. Coban) for their uncountable help and friendship. iv TABLE OF CONTENTS Certification ii Publications iii Acknowledgements iv Table of Contents v List of Abbreviations ix Abstract xi Chapter 1 INTRODUCTION 1 1.1. General 1 1.2. Resistance to Antibacterial Agents 3 1.3. Resistance to Antimalarial Agents 5 1.4. The Importance of Alkaloids in Drug Discovery 6 1.4.1. Alkaloids in Plants 7 1.4.2. Contribution of Alkaloids to Humankind 8 1.4.3. Alkaloids and Drug Discovery 9 1.5. Lombok and Natural Products Development 11 1.6. The Aims ofthe Study 12 Chapter 2 SELECTION OF PLANT MATERIALS 14 2.1. General 14 2.2. Approaches to Plant Selection 15 2.3. Medicinal Plant Use in Lombok 16 v 2.4. Alkaloid Screening 17 2.5. Collection of Lombok Medicinal Plants 18 2.6. Previous Work and Geographical Distribution of Alkaloid Positive Species 25 2.7. Plants Selected for Further Study 36 Chapter 3 ALKALOIDS FROM Voacangafoetida (Bl.) Rolfe 38 3.1. Introduction 38 3.2. Indole Alkaloids: Biosynthesis and Classification 39 3.3. Alkaloids from the Genus Voacanga 47 3.4. Isolation and Structural Elucidation of Alkaloids from Voacangafoetida (Bl.) Rolfe 50 3.4.1. Lombine 50 3.4.2. Voacangine 57 3.4.3. Coronaridine 58 3.4.3. Voacristine 61 Chapter 4 ALKALOIDS FROM Psychotria malayana Jack 66 4.1. Introduction 66 4.2. Alkaloids from the Genus Psychotria 67 4.3. Biosynthesis of Calycanthine Type Alkaloids 76 4.4. Isolation and Structure Elucidation of Alkaloids from Psychotria malayana Jack.78 4.4.1. Hodgkinsine 79 4.4.2. MesoChimonanthine and /.yo-Calycanthine 81 4.4.3. The Alkaloid LPM-574 83 4.4.4. The Alkaloid LPM-186 85 vi Chapter 5 ALKALOIDS FROM Alstonia scholaris R. Br 87 5.1. Introduction 87 5.2. Alkaloids from the Genus Alstonia 88 5.3. Antiplasmodial Activity of Alstonia Alkaloids 95 5.4. Isolation and Structure Elucidation of Alkaloids from A. scholaris R. Br 101 5.4.1. Mataranine A and B 101 5.4.2. Alstonamine (Angustilobine B) 106 5.4.3. (15S* io^-Losbanine 109 5.4.4. Kotarajine 113 5.4.5. (£AAkuammidine 115 Chapter 6 ALKALOIDS FROM Clerodendron calamitosum L. and Clerodendron paniculatum L.118 6.1. Introduction 118 6.2. Alkaloids from the Family Verbenaceae 119 6.3. Isolation and Structure Elucidation of Alkaloids from C. calamitosum L. and C. paniculatum L 124 6.3.1. Alkaloids from C. calamitosum L 124 4.3.2. Alkaloids from C. paniculatum L 130 Chapter 7 ANTIMICROBIAL TESTING 133 7.1. Introduction 133 7.2. Assays for Detecting Antibacterial Activity 134 7.3. Assays for Detecting Antimalarial Activity 137 7.4. Results of Antibacterial Testing 140 7.4.1. Voacangafoetida (Bl.) Rolfe 140 7.4.2. Psychotria malayana Jack 143 7.4.3. Clerodendron calamitosum L. and Clerodendron paniculatum L 144 7.5. Results of Antimalarial Testing 145 vu Chapter 8 CONCLUSIONS AND FUTURE WORK 147 8.1. Conclusions 147 8.2. Future Work 152 Chapter 9 EXPERIMENTAL SECTION 153 9.1. General 153 9.2. Plant Collection 154 9.3. Alkaloid Screening 155 9.4. Alkaloid Isolation Procedure 156 9.4.1. Isolation and Purification of Alkaloids from Voacangafoetida (Bl.) Rolf. 159 9.4.2. Isolation and Purification of Alkaloids from Psychotria malayana Jack.... 164 9.4.3. Isolation and Purification of Alkaloids from Alstonia scholaris R. Br 168 9.4.4. Isolation and Purification of Alkaloids from Clerodendron calamitosum L. and C. paniculatum L 173 9.5. Antibacterial Assay 178 9.5.1. Sample Preparation 178 9.5.2. Antibacterial Test Procedure 178 9.6. Antimalarial Assay 179 9.6.1. Sample Preparation 179 9.6.2. Procedure of Antimalarial Activity Testing 179 REFERENCES 181 APPENDICES 209 vm LIST OF ABBREVIATIONS [oc]D Specific Optical Rotation 13C-NMR Carbon Nuclear Magnetic Resonance 'H-NMR Proton Nuclear Magnetic Resonance CH3C02H Acetic Acid CL Central Lombok COSY Correlation Spectroscopy DCM/CH2C12 Dichloromethane DDQ 2,3-Dichloro-5,6-dicyano-l,4-benzoquinone DEPT Distortionless Enhancement by Polarisation Transfer DMAPP Dimethylallyl diphosphate DNA Deoxyribonucleic Acid EL East Lombok FDA Fluorescein Diacetate GABA Garama-Aminobutyric Acid HGPRT Hypoxanthine Guanine Phosphoribosyl Transferase HIV Human Immunodeficiency Virus HMBC Heteronuclear Multiple Bond Correlation HRCLMS High Resolution Chemical Ionisation Mass Spectrometry HREIMS High Resolution Electron Impact Mass Spectrometry HSQC Heteronuclear Single Quantum Coherence ix HTS High-Throughput Screening IMPDH Inosine Monophosphate Dehydrogenase IPP Isopentenyl Diphosphate IR Infrared K2HgL Potassium tetraiodomercurate LRCIMS Low Resolution Chemical Ionisation Spectrometry LREIMS Low Resolution Electron Impact Spectrometry MeOH Methanol MIC Minimum Inhibitory Concentration MRSA Methicillin-Resistant Staphylococcus aureus Na2C03 Sodium carbonate NMR Nuclear Magnetic Resonance NOE Nuclear Overhauser Effect NOESY ID Nuclear Overhauser Exchange Spectroscopy One Dimension rRNA ribosome Ribonucleic Acid UTIs Urinary Tract Infections UV Ultraviolet WL West Lombok 5 Chemical shift (ppm) x ABSTRACT The aims of this project were to: 1) assess the efficacy of a combined chemo- and bio- rational approach involving alkaloid occurrence with antimicrobial medicinal plant use, focussing on plants from Lombok island. Lombok has a large population while herbal medicines are widely used with a diverse range of plant species. 2) Investigate the alkaloid constituents of selected plants including isolation, purification, and characterisation, and structure elucidation. 3) Evaluate antibacterial and antimalarial activities of crude alkaloid extracts and major alkaloid compounds isolated from the plants. 4) Identify compounds as possible new drug leads. A combined chemo- and bio-rational strategy based on alkaloid content and traditional medicinal plant use was demonstrated to be an effective and efficient approach to finding new biologically active compounds in nature. Several new alkaloids were isolated with some potential for development as antibacterial and antimalarial agents. Some previously known alkaloids were also isolated, and in some cases NMR features not previously reported in the literature are presented. A new optically active indole alkaloid, lombine (major), and the known alkaloid voacangine (minor), were identified from the bark of Voacanga foetida (Bl.) Rolfe, used ethnomedically for the treatment of wounds, itches, and swellings. The fruits of the plant produced three known alkaloid compounds, coronaridine (major), voacangine, and xi voacristine, together with the new indole alkaloids mataranine A and B, which were also isolated from Alstonia scholaris R. Br. in this study. Voacristine was found as a major alkaloid together with the minor alkaloid voacangine from the leaves of V. foetida (Bl.) Rolfe. A structural revision for voacristine was also completed. Initial antibacterial testing of the crude alkaloid extract from V. foetida (Bl.) Rolfe (bark and fruits) showed activity against both Gram-positive bacteria [Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli). The new alkaloids lombine (bark) and mataranine A and B (fruits) also exhibited antibacterial activity. Bactericidal activity was observed for lombine at a concentration of 0.5 mg/ml against S. aureus and E. coli. At the lower concentration of 0.05 mg/l, it partially inhibited the growth of both S.
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