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Chemical Analysis of Medicinal and Poisonous CHEMICAL ANALYSIS OF MEDICINAL AND POISONOUS PLANTS OF FORENSIC IMPORTANCE IN SOUTH AFRICA P. A. STEENKAMP Submitted in fulfilment of the requirements for the degree PHILOSOPHIAE DOCTOR in CHEMISTRY in the FACULTY OF SCIENCE at the UNIVERSITY OF JOHANNESBURG Promotor: PROF. F.R. VAN HEERDEN Co-promotor: PROF. B-E. VAN WYK MAY 2005 Created by Neevia Personal Converter trial version http://www.neevia.com Created by Neevia Personal Converter trial version ACKNOWLEDGEMENTS I wish to express my sincere appreciation to all whose assistance and advice contributed to the creation of this thesis, and in particular the following: Professor F.R. van Heerden , my promotor, for her continued interest, advice, invaluable guidance with the chemical aspects of the project and NMR data interpretation of chapters six, seven and eight. Professor B-E. van Wyk , my co-promotor, for his enthusiasm, editorial guidance and invaluable assistance with the botanical aspects of the project. The Department of Health for their financial support and the Forensic Chemistry Laboratory for the use of their infrastructure to complete this research. Doctor L.H. Steenkamp, my wife, for her love, patience, assistance and encouragement. My children, Anton and Andries, for their patience, support and understanding. My colleagues of the Forensic Toxicology Research Unit for their support. Miss Kim Lilley of the Waters Corporation (USA) for her technical support and advice on mass spectrometry. My mother for her unwavering support and encouragement. My friends and family for their interest and encouragement. Finally, but most important, I want to express my gratitude to GOD for His grace and provision, and for the ability and opportunity to study a small part of His wonderful creation. TO GOD ALL THE GLORY ii Created by Neevia Personal Converter trial version http://www.neevia.com CONTENTS PAGE ACKNOWLEDGEMENTS ii CONTENTS iii ABBREVIATIONS ix INDEX OF TABLES xi INDEX OF FIGURES xiii SUMMARY xviii OPSOMMING xxi CHAPTER 1 Aim of study 1 CHAPTER 2 Introduction 3 2.1 Forensic science 3 2.2 Forensic technology 3 2.2.1 Deaths from drug abuse 7 2.2.2 Accidental poisoning 7 2.2.3 Suicidal poisoning 8 2.2.4 Homicidal poisoning 8 2.3 Medicinal plants 10 2.4 Analytical methods used in toxicology 13 2.4.1 Colour tests 14 2.4.2 Microdiffusion test 14 2.4.3 Immunoassays 14 2.4.4 Chromatography 14 2.4.4.1 Thin-layer chromatography 15 2.4.4.2 Gas chromatography 15 2.4.4.3 High performance liquid chromatography 16 2.4.5 Column theory 18 2.4.6 HPLC-MS systems (LC-MS) 21 2.5 Development of extraction procedures 24 2.6 Development of chromatographic screening methods 25 2.7 Screening of viscera and muti samples of forensic interest 25 2.8 Identification and confirmation of compounds 27 2.9 Selection of the medicinal and poisonous plants for the study 29 iii Created by Neevia Personal Converter trial version http://www.neevia.com CHAPTER 3 Nicotiana glauca 3.1 Botanical description 32 3.2 Origin and distribution 32 3.3 Type of toxin 33 3.4 Active components and pharmacological effects 33 3.5 Ethnopharmacological importance 33 3.6 Poisoning 3.6.1 Accidental 34 3.6.2 Deliberate 34 3.7 FCL JHB investigation 34 3.8 Experimental procedure 3.8.1 Standards and reagents 35 3.8.2 Instruments and conditions 35 3.8.3 Chemical fingerprinting of N. glauca trees 35 3.8.4 Chemical extraction and analysis of viscera and case exhibits 36 3.9 Result and discussion 3.9.1 Chromatography and detection of anabasine 36 3.9.2 Chemical fingerprinting of N. glauca trees 37 3.9.3 Evaluation of SPE extraction and analysis of viscera and exhibit 38 3.10 Forensic applicability 43 CHAPTER 4 Datura stramonium / Datura ferox 4.1 Botanical description 45 4.2 Origin and distribution 46 4.3 Type of toxin 46 4.4 Active components and pharmacological effects 46 4.5 Ethnopharmacological importance 47 4.6 Poisoning 4.6.1 Accidental 47 4.6.2 Deliberate 48 4.7 FCL JHB investigation 48 4.8 Experimental procedure 4.8.1 Standards and reagents 48 4.8.2 Instruments and conditions 49 4.8.3 Chemical fingerprinting of D. stramonium and D. ferox plants 49 4.8.4 Chemical extraction and analysis of viscera case exhibits 50 4.9 Result and discussion iv Created by Neevia Personal Converter trial version http://www.neevia.com 4.9.1 Chromatography and detection of atropine and scopolamine 50 4.9.2 Chemical fingerprinting of D. stramonium and D. ferox plants 53 4.9.3 Evaluation of SPE extraction and analysis of viscera samples 53 4.10 Forensic applicability 56 CHAPTER 5 Callilepis laureola 5.1 Botanical description 58 5.2 Origin and distribution 58 5.3 Type of toxin 58 5.4 Active components and pharmacological effects 59 5.5 Ethnopharmacological importance 59 5.6 Poisoning 5.6.1 Accidental 59 5.6.2 Deliberate 59 5.7 FCL JHB investigation 60 5.8 Experimental procedure 5.8.1 Standards and reagents 60 5.8.2 Instruments and conditions 5.8.2.1 LC – MS conditions 61 5.8.2.2 Flow-injection analysis 63 5.8.2.3 Evaluation of the analytical procedure 63 5.8.3 Extraction of C. laureola tubers and unknown powdered samples 63 5.8.4 Chemical extraction and analysis of viscera and case exhibits 64 5.9 Result and discussion 5.9.1 Chromatography and detection of atractyloside 64 5.9.2 Evaluation of the analytical method 66 5.9.3 SPE of ATR, C. laureola tuber and powdered herbal samples 67 5.9.4 Analysis of C. laureola tuber and unknown powdered samples 67 5.9.5 Solid phase extraction and analysis of viscera samples 68 5.9.6 Optimisation of mass spectral conditions for trace analysis 73 5.10 Forensic applicability 77 CHAPTER 6 Boophone disticha 6.1 Botanical description 78 6.2 Origin and distribution 78 6.3 Type of toxin 79 6.4 Active components and pharmacological effects 80 6.5 Ethnopharmacological importance 80 v Created by Neevia Personal Converter trial version http://www.neevia.com 6.6 Poisoning 6.6.1 Accidental 80 6.6.2 Deliberate 82 6.7 FCL JHB investigation 82 6.8 Experimental procedure 6.8.1 Standards and reagents 82 6.8.2 Instruments and conditions 83 6.8.3 Chemical extraction of B. disticha bulb and Ammocharis coranica scales 84 6.8.4 Isolation of the alkaloids from the bulb of B. disticha 85 6.8.5 Chemical extraction and analysis of viscera and case exhibits 87 6.9 Result and discussion 6.9.1 Chromatography and detection of Amaryllidaceae alkaloids 87 6.9.2 Chemical extraction and purification of B. disticha bulb compounds 90 6.9.3 Chromatographic fingerprinting of B. disticha and A. coranica 93 6.9.4 Analysis of case exhibits and viscera samples 96 6.10 Forensic applicability 103 CHAPTER 7 Abrus precatorius 7.1 Botanical description 105 7.2 Origin and distribution 105 7.3 Type of toxin 106 7.4 Active components and pharmacological effects 107 7.5 Ethnopharmacological importance 107 7.6 Poisoning 7.6.1 Accidental 107 7.6.2 Deliberate 107 7.7 FCL JHB investigation 108 7.8 Experimental procedure 7.8.1 Standards and reagents 108 7.8.2 Instruments and conditions 108 7.8.3 Chemical extraction of A. precatorius seeds 109 7.8.4 Isolation of abrine and hypaphorine from A. precatorius seeds 112 7.9 Result and discussion 7.9.1 Chromatography and detection of abrine and hypaphorine 113 7.9.2 Chemical extraction of A. precatorius seeds 118 7.9.3 Purification of abrine and hypaphorine 118 7.10 Forensic applicability 119 vi Created by Neevia Personal Converter trial version http://www.neevia.com CHAPTER 8 Ricinus communis 8.1 Botanical description 123 8.2 Origin and distribution 123 8.3 Type of toxin 124 8.4 Active components and pharmacological effects 124 8.5 Ethnopharmacological importance 125 8.6 Poisoning 8.6.1 Accidental 125 8.6.2 Deliberate 125 8.7 FCL JHB investigation 126 8.8 Experimental procedure 8.8.1 Standards and reagents 126 8.8.2 Instruments and conditions 127 8.8.3 Chemical extraction of R. communis seeds 128 8.8.4 Isolation of ricinine from R. communis seeds 128 8.9 Result and discussion 8.9.1 Chemical extraction of R. communis seeds 129 8.9.2 Chromatography and detection of ricinine 130 8.9.3 Purification of ricinine 134 8.10 Forensic applicability 136 CHAPTER 9 Nerium oleander / Thevetia peruviana 9.1 Botanical description 137 9.2 Origin and distribution 138 9.3 Type of toxin 139 9.4 Active components and pharmacological effects 139 9.5 Ethnopharmacological importance 140 9.6 Poisoning 9.6.1 Accidental 140 9.6.2 Deliberate 141 9.7 FCL JHB investigation 141 9.8 Experimental procedure 9.8.1 Standards and reagents 142 9.8.2 Instruments and conditions 143 9.8.3 Chemical extraction of N. oleander and T. peruviana leaves 145 9.8.4 Chemical extraction and analysis of viscera and case exhibits 146 9.9 Result and discussion 9.9.1 Chromatography and detection of cardiac glycosides 146 vii Created by Neevia Personal Converter trial version http://www.neevia.com 9.9.2 Chemical extraction of N. oleander and T. peruviana leaves 154 9.9.3 Chemical extraction and analysis of viscera and case exhibits 157 9.10 Forensic applicability 163 CHAPTER 10 Bowiea volubilis 10.1 Botanical description 166 10.2 Origin and distribution 166 10.3 Type of toxin 167 10.4 Active components and pharmacological effects 167 10.5 Ethnopharmacological importance 167 10.6 Poisoning 10.6.1 Accidental 168 10.6.2 Deliberate 168 10.7 FCL JHB investigation 168 10.8 Experimental procedure 10.8.1 Standards and reagents 169 10.8.2 Instruments and conditions 169 10.8.3 Chemical extraction of B.
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