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Chemical Studies of Panax Notoginseng and Related Species, and Evaluation of Potential Antiplatelet and Anticoagulant Effects La View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by ScholarBank@NUS CHEMICAL STUDIES OF PANAX NOTOGINSENG AND RELATED SPECIES, AND EVALUATION OF POTENTIAL ANTIPLATELET AND ANTICOAGULANT EFFECTS LAU AIK JIANG NATIONAL UNIVERSITY OF SINGAPORE 2006 CHEMICAL STUDIES OF PANAX NOTOGINSENG AND RELATED SPECIES, AND EVALUATION OF POTENTIAL ANTIPLATELET AND ANTICOAGULANT EFFECTS LAU AIK JIANG (B. Sc. (Pharm.) (Hons.), NUS) A THESIS SUBMITTED FOR THE DEGREE OF DOCTOR OF PHILOSOPHY DEPARTMENT OF PHARMACY NATIONAL UNIVERSITY OF SINGAPORE 2006 ACKNOWLEDGEMENTS I would like to express my heartfelt gratitude to my thesis supervisor, Dr Koh Hwee Ling, for her patient guidance, suggestions and advice throughout the whole course of this project and thesis write-up. I would also like to extend my sincere gratitude to my co-supervisor, Dr Woo Soo On, for his helpful guidance and advice throughout this project. Under the guidance of my supervisors, I’ve learnt a lot about academic research. I am also grateful to the financial support from National University of Singapore research scholarship. The technical assistance from the laboratory officers in the Department of Pharmacy and staff from Waters Asia Ltd, is greatly appreciated too. I also wish to thank everyone in the department who have helped me in one way or another, especially my laboratory mates (namely, Huansong, Tung Kian, Yun Keng, Zou Peng and Peiling) for their help and enjoyable times in the laboratory. Special thanks also go to all my fellow friends in the department, especially Huey Ying, Yong Koy and Siok Lam, for their moral support, helpful discussions, and for sharing all the woes and wonderful times together during my postgraduate years. Last but not least, I would like to thank my family for their understanding and unwavering support. ii LIST OF PUBLICATIONS AND CONFERENCE PRESENTATIONS Publications 1. Lau AJ, Koh HL. Quality control of herbs: principles and procedures, using Panax as an example. In: Leung PC, Fong H, Xue CCL, eds. Annals of Traditional Chinese Medicine, Current review of Chinese medicine—quality control of herbs and herbal materials, vol. 2. Singapore: World Scientific Publishing Co.; 2006: Chapter 6, 87-115. 2. Hong DY, Lau AJ, Yeo CL, Liu XK, Yang CR, Koh HL, Hong Y. Genetic diversity and variation of saponin contents in Panax notoginseng roots from a single farm. J. Agric. Food Chem. 2005; 53: 8460-8467. 3. Koh HL, Lau AJ, Chan ECY. Hydrophilic interaction liquid chromatography with tandem mass spectrometry for the determination of underivatized dencichine (β-N-oxalyl-L-α,β-diaminopropionic acid) in Panax medicinal plant species. Rapid Commun. Mass Spectrom. 2005; 19: 1237-1244. 4. Lau AJ, Seo BH, Woo SO, Koh HL. High-performance liquid chromatographic method with quantitative comparisons of whole chromatograms of raw and steamed Panax notoginseng. J. Chromatogr. A 2004; 1057: 141-149. 5. Lau AJ, Woo SO, Koh HL. Analysis of saponins in raw and steamed Panax notoginseng using high performance liquid chromatography with diode array detection. J. Chromatogr. A 2003; 1011: 77-87. 6. Lau AJ, Holmes MJ, Woo SO, Koh HL. Analysis of adulterants in a traditional herbal medicinal product using LC-MS-MS. J. Pharm. Biomed. Anal. 2003; 31: 401-406. Conference presentations 1. Lau AJ, Yeo CL, Hong DYQ, Liu XK, Yang CR, Hong Y, Koh HL. A study on the saponin contents and genetic diversity in individual Panax notoginseng roots from a good agricultural practice farm. Poster presentation at: 18th Singapore Pharmacy Congress; July 1-2, 2006; Singapore. 2. Lau AJ, Chan EC, Koh HL. Analysis of dencichine, a haemostatic agent, in Panax species using hydrophilic interaction chromatography-tandem mass spectrometry. Oral and poster presentations at: Inaugural AAPS-NUS Student Chapter Symposium; September 16, 2005; Singapore. (Best presenter award) 3. Lau AJ, Chan EC, Koh HL. Liquid chromatography-tandem mass spectrometry for the determination of dencichine, a haemostatic agent in Panax medicinal plant iii species. Oral presentation at: Inaugural Inter-varsity Symposium, 17th Singapore Pharmacy Congress; July 1-3, 2005; Singapore. (Best presenter award) 4. Lau AJ, Tanaka N, Chan EC, Koh HL. Determination of dencichine in Panax species using liquid chromatography-tandem mass spectrometry. Poster presentation at: Inaugural International Congress on Complementary and Alternative Medicines (ICCAM); February 26-28, 2005; Singapore. 5. Lau AJ, Seo BH, Woo SO, Koh HL. Chromatographic pattern matching of raw and steamed Panax notoginseng. Poster presentation at: 15th International Symposium on Pharmaceutical and Biomedical Analysis; May 2-6, 2004; Florence, Italy. 6. Lau AJ, Seo BH, Woo SO, Koh HL. Chromatographic pattern matching of Panax notoginseng, a Chinese herbal medicine. Poster presentation at: 16th Singapore Pharmacy Congress; November 22-23, 2003; Singapore. (Best poster award-1st prize) 7. Lau AJ, Woo SO, Koh HL. Analysis of raw and steamed Panax notoginseng using HPLC-DAD. Poster presentation at: AAPS Annual Meeting and Exposition; November 10-14, 2002; Toronto, Canada. Provisional patent 1. Koh HL, Lau AJ. Anti-thrombotic activities of extracts and components from raw and steamed Panax notoginseng, US Provisional Patent, No. 60/828,078, 4th Oct 2006. iv TABLE OF CONTENTS Title page i Acknowledgements ii List of publications and conference presentations iii Table of contents v Summary ix List of tables xi List of figures xiii List of abbreviations xvi Chapter 1. Introduction 1.1 Herbal medicines 1.1.1 Importance of herbal medicines 1 1.1.2 Safety of herbal medicines 1.1.2.1 Incidences of adverse effects 3 1.1.2.2 Intrinsic adverse effects 3 1.1.2.3 Extrinsic adverse effects 4 1.1.3 Efficacy of herbal medicines 6 1.1.4 Quality of herbal medicines 8 1.1.4.1 Factors affecting quality 8 1.1.4.2 Good Practices for total quality assurance 9 1.1.4.3 Detection of contamination and identification of herbal 11 medicines by chemical analyses 1.1.4.4 DNA fingerprinting 12 1.1.4.5 Standardisation 13 1.1.4.6 Chemical fingerprinting 15 1.2 Importance of antithrombotic and haemostatic therapies 1.2.1 Antithrombotic therapies 17 1.2.2 Haemostatic therapies 20 1.3 Medicinal plants as potential sources of novel therapeutic drugs 22 1.4 Panax species 1.4.1 Species of Panax 23 1.4.2 Panax notoginseng (Burk.) F. H. Chen 1.4.2.1 Introduction 25 1.4.2.2 Processing of P. notoginseng 26 1.4.2.3 Chemical constituents of P. notoginseng 27 1.4.2.4 Pharmacological studies of P. notoginseng 31 1.4.2.5 Quality control of P. notoginseng and its related 35 species v Chapter 2. Hypotheses and Objectives 42 Chapter 3. High performance liquid chromatographic analyses of Panax notoginseng and related species 3.1 Chemical fingerprinting and analysis of saponins 3.1.1 Introduction 46 3.1.2 Experimental 3.1.2.1 Materials 48 3.1.2.2 Sample preparation 52 3.1.2.3 Steaming of samples 52 3.1.2.4 Standards preparation 53 3.1.2.5 HPLC method for qualitative and quantitative analysis 53 3.1.2.6 Method validation 54 3.1.2.7 LC-MS 55 3.1.2.8 Data analysis and hierarchical clustering analysis 55 3.1.3 Results and Discussion 3.1.3.1 Method development 56 3.1.3.2 Identification of saponins 60 3.1.3.3 Method validation 60 3.1.3.4 Qualitative and quantitative comparisons of different 62 Panax samples 3.1.3.5 Qualitative and quantitative comparisons of different 67 raw P. notoginseng samples 3.1.3.6 Qualitative and quantitative comparisons of raw and 75 steamed P. notoginseng samples 3.2 Pattern matching of extracts of P. notoginseng 3.2.1 Introduction 85 3.2.2 Experimental 3.2.2.1 Materials 90 3.2.2.2 Sample preparation 90 3.2.2.3 HPLC with chromatographic pattern matching 91 analysis 3.2.3 Results and Discussion 3.2.3.1 Optimisation of pattern match processing method 92 3.2.3.2 Chromatographic pattern matching results of raw and 94 steamed P. notoginseng roots 3.2.3.3 Chromatographic pattern matching of raw and steamed 99 P. notoginseng products 3.3 Conclusion 101 Chapter 4. Isolation and identification of chemical components from steamed Panax notoginseng 4.1 Introduction 102 4.2 Experimental 4.2.1 Materials 103 4.2.2 Extraction and separation of fractions 104 4.2.3 Purification and isolation of pure components 105 4.2.4 Identification 106 vi 4.3 Results and Discussion 106 4.4 Conclusion 119 Chapter 5. Liquid chromatography-tandem mass spectrometric analysis of dencichine in Panax notoginseng and related species 5.1 Introduction 120 5.2 Experimental 5.2.1 Materials 124 5.2.2 Sample and standard preparation 125 5.2.3 HILIC/ESI-MS/MS 125 5.2.4 Method validation 126 5.3 Results and Discussion 5.3.1 Optimisation of MS/MS conditions 127 5.3.2 Optimisation of LC conditions 129 5.3.3 Optimisation of sample preparation 133 5.3.4 Method validation 134 5.3.5 Quantification of dencichine 135 5.4 Conclusion 143 Chapter 6. Platelet aggregation and blood coagulation inhibitory activities of Panax notoginseng, its related species and its chemical components 6.1 Introduction 144 6.2 In vitro platelet aggregation and blood coagulation studies 6.2.1 Experimental 6.2.1.1 Materials 148 6.2.1.2 Sample preparation 150 6.2.1.3 Animals for blood collection 150 6.2.1.4 Blood collection 151 6.2.1.5 In vitro platelet aggregation assays 151 6.2.1.6 In vitro blood coagulation assays 152 6.2.1.7 Statistical analysis 154 6.2.2 Results and Discussion 6.2.2.1 In vitro platelet aggregation assays 155 6.2.2.2 In vitro blood coagulation assays 166 6.3 In vivo and ex vivo studies 6.3.1 Experimental 6.3.1.1 Materials 177 6.3.1.2 Animals 177 6.3.1.3 Sample preparation 177 6.3.1.4 In vivo bleeding model 178 6.3.1.5 Ex vivo platelet aggregation assays 178 6.3.1.6 Ex vivo blood coagulation assays 179 6.3.1.7 Statistical analysis 179 6.3.2 Results and Discussion 6.3.2.1 Bleeding time assays 180 6.3.2.2 Ex vivo platelet aggregation assays 184 vii 6.3.2.3 Ex vivo blood coagulation assays 186 6.4 Conclusion 188 Chapter 7.
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