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Mass Spectrometric Characterization and Analysis of Anti-Oxidative

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Mass Spectrometric Characterization and Analysis of Anti-Oxidative Mass Spectrometric Characterization and Analysis of Anti-oxidative Properties of Medicinal Herbs By Xiao Suo WANG A thesis submitted for the admission to the degree of Master of Science in the Faculty of Medicine, University of New South Wales, Sydney July 2003 DECLARATION I hereby declare that this submission is my own work and to the best of my knowledge it contains no materials previous published or written by another person, nor material which to a substantial extent has been accepted for the award of any other degree or diploma at UNSW or any other educational institution, except where due acknowledgement is made in the thesis. Any contribution made to the research by others, with whom I have worked at UNSW or elsewhere, is explicitly acknowledged in the thesis. I also declare that the intellectual content of this thesis is the product of my own work, except to the extent that assistance from others in the project’s design and conception or in style, presentation and linguistic expression is acknowledged. (Signed)…………………………………………………………. ii ABSTRACT The aim of this project was to investigate a range of medicinal herbs which have radical scavenging and antioxidant activities and then apply novel mass spectrometric techniques to investigate and analyse active components responsible for their pharmaceutical actions. A sensitive electron capture negative ionization of gas chromatography-mass spectrometry (ECNI-GC-MS) method was developed to assess hydroxyl radical production, as indicated by 3.4-dihydroxyphenylacetic acid (DOPAC) production, which allows excellent evaluation of hydroxyl radical scavenging and antioxidant activity of a number of medicinal Chinese herbs. Melatonin is an effective multiple radical scavenger and antioxidant and has been used in this study for the comparison of radical scavenging activity with medicinal herbs. To analyse active compounds from herbal extracts, mass spectrometric techniques were used to separate components that suppressed hydroxyl radical production from Dimocarpus longan Lour, determine known ginsenosides from ginseng extracts as well as to identify and quantify melatonin in ten herbal extarcts. The results obtained indicated that 1) the utilization of alumina in the ECNI-GC-MS method diminished interferences from “noise” products in a Fenton-type reaction, which allows obtaining pure final hydroxyl radical product and this method demonstrated optimal sensitivity and reliability; 2) Aqueous extracts of all herbs analysed showed different levels of hydroxyl radical scavenging activity. Dimocarpus longan Lour, Chrysanthemum morifolium Ramat, Lonicera hypoglauca Miq, Ginkgo iii biloba L, Rehmannia flutinosa and Libosch Cornus officinalis Sieb all exhibited stronger inhibitory effect on hydroxyl radical production than melatonin. 3) Aqueous extract of Dimocarpus longan Lour. showed the greatest inhibitory effect on hydroxyl radical production among the other herbs tested. The active fractions of this herb eluted just after the void volume using HPLC suggesting that the active compounds responsible for radical scavenging activity are polar and water soluble. They may belong to phenol group of chemicals. 4) Herbal extracts using non-polar solvents showed no effect on hydroxyl radical production suggesting active compounds in those herbs are water soluble. 5) Different species and origins of ginseng were compared for their radical scavenging activity. Chinese fresh ginseng (Oriental ginseng) showed higher activity than Korean ginseng tablet and American ginseng. Seven known active ginsenosides were identified using HPLC-MS-MS. 6) Melatonin was found at varying concentrations in ten herbs, which may contribute to the radical scavenging activity of herbs, on the other hand, it may provide the justification of clinical use and food resources, particularly for those herbs contain high level of melatonin. iv ACKNOWLEDGMENTS For helping me directly in my attempts to complete my study during last the two years, I wish to express my sincere appreciation to the following people: • My supervisor, Associate Professor George A. Smythe, for his wise and expert guidance, encouragement, timeless effort and consistent patience throughout my entire study. I am also grateful to his concern and help for my life in Australia. His arrangement of a BMSF research scholarship which made this work possible by supplying financial assistance during my course of work. • Dr. Vimal Kapoor for being my co-supervisor and Dr. Ranjna Kapoor for their support in my study. • My great appreciation goes to Anne Poljak, for her invaluable suggestions and teachings when I analysed samples in HPLC and MALDI-TOF as well as careful reading of this thesis. • Dr. Ross Grant, for being freely given of his time and expert to help me in every aspect of the work. My special and earnest thanks also go to his great encouragement, inspiration and steady help. • Martin Bucknall, for teaching me to use HPLC-MS and sharing his vast knowledge on mass spectrometry with me. I also wish to acknowledge his counsel and support for my whole study. • I wish to express a sincere vote of thanks to Dr. Mark Raftery, for his kind helps whenever I encountered difficulties. • Anne Tucker, for her continual care and assistance during the last two years. • Every member in BMSF from past and present are valued friends, for their generosity and friendship which gave me a great time in Australia. Particularly v for the friendship and assistance from Alison Maxwell, Eve Jary, Rona Francisco, Amin Malik Shah Abdul Majid and Silverraji Samiveloo. • Finally, I would like to extend my thanks to my family for their support and love. My special friend, Barbara Brook, of whose eternal friendship, constant inspiration and wise thoughts. My hearty thanks go to my friends Edward Lee, Rita Gao, Yiguang Lin, Lijuan Xie, Huiwen Chen, Yunxia Zuo, Gerard Holland, Jenny Zheng and Jianwei Lin for their friendship and help whenever I need. vi Table of Contents Title………………………………………………………………………...i Declaration………………………………………………………………..ⅱ Abstract…………………………………………………………………...ⅲ Acknowledgments…………………………………………………………v Table of contents…………………………………………………………ⅶ List of publications…………………………………………………….....ⅸ List of abbreviations………………………………………………………ⅹ List of figures and tables………………………………………………….xii CHAPTER 1 General Introduction………………………………………………..1 Summary…………………………………………………………......2 1.1 Introduction………………………………………………......4 1.2 Properties of medicinal herbs………………………………...8 1.3 Extraction, identification and mass spectrometric analysis of active principles from medicin herbs……………………19 1.4 Aims and scope of the current work………………………...37 CHAPTER 2 General Methods…………………………………………………...39 Summary…………………………………………………………...40 2.1 Materials and chemicals………………………………….....41 2.2 Extraction methods………………………………………….42 2.3 Instrumentation……………………………………………...50 2.4 Assessment of hydroxyl radical generation………………....61 2.5 Evaluation of radical scavenging activity of herbal extracts……………………………………………………...63 2.6 Analysis of components from herbal extracts……………....64 2.7 Statistical analysis………………………………………......68 CHAPTER 3 GC - MS Analysis of Hydroxyl Radical and DOPAC Production……………………………………………………….....69 Summary…………………………………………………………...70 3.1 Introduction…………………………………………………71 3.2 Materials and methods……………………………………...72 3.3 Results and discussion……………………………………...72 3.4 Conclusions………………………………………………....82 vii CHAPTER 4 Evaluation of Radical Scavenging Activity of Herbal Extracts Using GC-MS....................................................................................83 Summary…………………………………………………………...84 4.1 Introduction………………………………………………....85 4.2 Materials and methods……………………………………...86 4.3 Results and discussion……………………………………...86 4.4 Conclusions…………………………………………………95 CHAPTER 5 Analysis of Active Components from Herbal Extracts………….97 Summary…………………………………………………………...98 5.1 Analysis of Active Components from Ginseng Using HPLC- MS…………………………………………………………...99 5.1.1 Introduction………………………………………………….99 5.1.2 Materials and methods……………………………………...102 5.1.3 Results and discussion……………………………………...102 5.1.4 Conclusions………………………………………………...113 5.2 Analysis of Active Components from Dimocarpus Longan Lour ……………………………………………………………….114 5.2.1 Introduction………………………………………………....114 5.2.2 Materials and methods……………………………………...114 5.2.3 Results………………………………………………………115 5.2.4 Discussion…………………………………………………..122 5.2.5 Conclusions…………………………………………………124 5.3 Analysis of Melatonin in Herbal Extracts……………….125 5.3.1 Introduction…………………………………………………125 5.3.2 Materials and methods……………………………………...126 5.3.3 Results………………………………………………………126 5.3.4 Discussion…………………………………………………..137 5.3.5 Conclusions…………………………………………………138 CHAPTER 6 Conclusions and Future Directions………………...……………140 REFERENCES……………………………………………………..145 viii LIST OF PUBLICATIONS PUBLICATIONS ARISING FROM THIS THESIS 1. XiaoSuo Wang, Vimal Kapoor, George A. Smythe, Extraction and Chromatography-Mass Spectrometric Analysis of the Active Principles from Selected Chinese Herbs and Other Medicinal Plants. The American Journal of Chinese Medicine, 2003. In press. 2. XiaoSuo Wang and George A. Smythe, Assessment of hydroxyl radical generation and radical scavenging activity of Chinese medicinal herbs using GC-MS. Submitted to Redox Report, 2003. In press. ABSTRACT 1. XiaoSuo Wang and George A. Smythe, Assessment of hydroxyl radical generation and production of DOPAC using GC-MS. Proceedings of the Scientific Meeting of the Society for Free Radical Research, Wollongong,
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