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The Pharmaceutical Potential of Compounds from Tasmanian Clematis Species

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The Pharmaceutical Potential of Compounds from Tasmanian Clematis species by Fangming Jin Bachelor in Pharmacology of Chinese Medicine (from Nanjing University of Traditional Chinese Medicine, China) Master of Pharmaceutical Science (from University of Tasmania, Australia) Submitted in fulfilment of the requirement for the Degree of Doctor of Philosophy School of Pharmacy University of Tasmania May 2012 The Pharmaceutical Potential of Compounds from Tasmanian Clematis species DEDICATION To My loving parents and husband, and My beloved supervisors, Dr. Christian Narkowicz and Dr. Glenn A Jacobson, For their on-going support and sacrifices, I dedicate my research to you. i The Pharmaceutical Potential of Compounds from Tasmanian Clematis species DECLARATION OF ORIGINALITY This thesis contains no material that has been accepted for the award of any other degree or diploma in any other tertiary institution. To the best of my knowledge and belief, this thesis contains no material previously published or written by any other person except where due reference is made in the text of the thesis. Fangming Jin May 7, 2012 ii The Pharmaceutical Potential of Compounds from Tasmanian Clematis species AUTHORITY OF ACCESS This thesis may be available for loan and limited copying in accordance with the Copyright Act 1968. Fangming Jin May 7, 2012 iii The Pharmaceutical Potential of Compounds from Tasmanian Clematis species ABSTRACT Aims The aim of the study was to investigate the antitumour, antibacterial and anti- inflammatory activities of some Tasmanian native Clematis spp. and to isolate and identify the potential pharmaceutical constituents. Methods The antitumour activities, antibacterial activities and anti-inflammatory effects of leaf material of Clematis spp. were screened by P388 cytotoxic assay, minimum inhibition concentrations (MICs) and inhibitory NO production by lipopolysaccharides (LPS) stimulated Raw 264.7 cells, respectively. The bioactive- guided fractionation methodologies, including cartridge fractionation, HPLC columns fractionation and Sephadex LH-20 column purification, were employed to isolate active constituents. The chemical profiles of active constituents were determined by ELSD, UV, LC-MS and GC-MS. Scanning electron microscopy (SEM), Gram stain, antibiotic interaction with chequerboard, deoxycholate-induced lysis and the antibiotic resistant mechanism study of P. aeruginosa were employed to study the antibacterial mechanism of the active constituent. The anti-inflammatory activity was also investigated by basal (unstimulated) and LPS- and phytohaemagglutinin A (PHA)-stimulated cytokine release from peripheral blood mononuclear cells (PBMC). iv The Pharmaceutical Potential of Compounds from Tasmanian Clematis species Some novel compounds in Tasmanian native Clematis spp. were determined by HPLC, LC-MS and LTQ-Orbitrap-MS. Results and discussion Ten out of eleven investigated Clematis spp. showed cytotoxic activities against P388 cells with different IC50 values (0.084-3.106 mg/ml). Ranunculin and its isomer were determined as the antitumour constituents. These compounds could be hydrolysed by the cell medium to produce protoanemonin. The antitumour study determined that ranunculin was a pro-cytotoxin with the antitumour activity derived from protoanemonin. Eight investigated Clematis spp. showed different antibacterial effects against E. coli (MIC=0.39-3.13 mg/ml) and P. aeruginosa (MIC=0.31-6.25 mg/ml). Ranunculin, the antibacterial constituent in Clematis spp., was selective against Gram negative bacteria. In particular, it had a stronger antibacterial effect than gentamicin against clinically isolated multi-drug resistant P. aeruginosa. The change in ranunculin treated sensitive P. aeruginosa was elongation and cell lysis in multi-drug resistant P. aeruginosa observed by SEM and obtained by deoxycholate- induced lysis study. These results imply that the antibacterial mechanism of ranunculin against sensitive and multi-drug resistance P. aeruginosa may be different. The antibacterial effect of ranunculin might be still contributed to by protoanemonin. v The Pharmaceutical Potential of Compounds from Tasmanian Clematis species Eleven investigated Clematis spp. showed varied inhibition of NO production. Ranunculin and its isomers were determined as one of the anti-inflammatory constituents in Tasmanian Clematis spp. For the cytokine study, in the presence of LPS and PHA, C. aristata-L leaf at 10 μg/ml significantly decreased the release of IL-1 (P<0.01) and TNF- (P<0.05) compared with LPS and PHA alone. These results provide experimental data of the anti-inflammatory activities of Tasmanian Clematis spp. Flavonoids and hydroxycinnamate esters were obtained in these investigated Clematis spp. The amounts of nine hydroxycinnamate esters were varied in each Clematis leaf material. This would be the first time to discover these hydroxycinnamte esters in Tasmanian Clematis spp. Conclusion The study demonstrated the antitumour, antibacterial and anti-inflammatory activities of Tasmanian native Clematis spp. Ranunculin was discovered to be a pro-cytotoxin of protoanemonin, which was one of the active constituents. This study was the first to investigate the therapeutic value of Tasmanian native Clematis spp. and discover the antibacterial value of protoanemonin in multi-drug resistant P. aeruginosa and its complicated antibacterial mechanism against sensitive and multidrug resistant P. aeruginosa. The anti-inflammatory activities may be the most distinguishing therapeutic value of Tasmanian Clematis spp. Furthermore, study of the chemical constituents suggested that Tasmanian Clematis spp. contained vi The Pharmaceutical Potential of Compounds from Tasmanian Clematis species phenolic compounds. Although this study only provided the basic and preliminary experimental data on the biological, potential pharmaceutical constituents and some novel compounds of Tasmanian Clematis spp., further investigation into usage and identification of effective pharmaceutical constituents would be worthy. vii The Pharmaceutical Potential of Compounds from Tasmanian Clematis species ACKNOWLEDGEMENTS First and above all I would like to thank the School of Pharmacy, University of Tasmania (UTAS) who provided scholarship to fund my PhD candidature. I express my sincere gratitude, and heartfelt thanks to my beloved supervisor Dr. Christian Narkowicz and Glenn A. Jacobson for finding this interesting research project for me. Their knowledge, support and guidance, timely words of encouragement have helped this project to reach full bloom. I am always obliged to them. I would also like to extend my sincere gratitude to School of Pharmacy technical staff: Dr. Peter Traill (Laboratory Manager), Mr Tony Whitty and Mrs Heather Galloway for their invaluable services. To Mr David Loveridge, thank you for your support on installing useful software in my computer and your friendly help when my laptop collapsed. I convey my heart felt gratefulness to the people in the Central Science Laboratory, UTAS: Associate Professor Noel Davies for sparing me his valuable time and knowledge in analysing compounds. I would like to extend my sincere thanks to Dr Karsten Goemann for carrying out scanning electron microscopy and Mr Edwin Lowe and Mr Richard Wilson for LTQ-Oribitrap-MS analysis. viii The Pharmaceutical Potential of Compounds from Tasmanian Clematis species I would like to express my upmost gratitude to Dr. Silvana Bettiol and Dr Richard Bradbury (School of Medicine, UTAS). Thank you for providing bacteria for my study, your patience in teaching me knowledge and laboratory techniques in microbiology. Thank you for providing valuable discussion and supporting information with regard to the questions I encountered in the study. To Miss Karla Mettrick (School of Medicine, UTAS), thank you for your help in the bacterial membrane permeability study and confocal microscopy. To Mr Roger Latham (Menzies Research Institute, UTAS), thank you for sharing your excellent experience with me on the laboratory techniques of microbiology. I would like to express my thanks to Associate Professor Gregory Woods (Immunology Member, Menzies Research Institute, UTAS) who provided P388 cells and Raw 264.7 cells and thank you for your teaching me the cell techniques and providing advice. To Miss Gabby Brown, thank you for your assistance in my laboratory work performed at Menzies. Thank you to Associate Professor Dominic Geraghty (School of Human Life Science, UTAS) for the cytokine study of my sample. Within the of School of Pharmacy, I would like to express my greatful thanks to Professor Stuart McLean, Mr. Adam Pirie and Dr. Kwang Choon Yee for suggestions regarding my study. ix The Pharmaceutical Potential of Compounds from Tasmanian Clematis species I would also like to acknowledge the following people: Mr Tom Wright (School of Management, UTAS) for providing plant species and for setting up facilities for growing my investigated plants in the courtyard of the School of Pharmacy; Dr. Yuji Mortia (Department of Microbiology, School of Pharmacy, Aichi Gakuin University, Japan) for studying the antibiotic resistant mechanism of Pseudomonas aeruginosa. And finally, I am grateful to the individuals over the years in School of Pharmacy for being a warm group to study amongst. x The Pharmaceutical Potential of Compounds from Tasmanian Clematis species TABLE OF CONTENT Chapter 1 Introduction to the medicinal properties of Clematis species...................... 1 1.1 Background.............................................................................................................................
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