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Savithri Galappathie Thesis Faculty of Science, Engineering & Technology Department of Chemistry & Biotechnology Investigation of antimicrobial activity and phytochemical characterisation of plant extracts Submitted in total fulfillment of the requirements for the degree of Doctor of Philosophy in Chemistry By Savithri Galappathie Department of Chemistry and Biotechnology Faculty of Science, Engineering and Technology Swinburne University of Technology October 2018 ii Abstract Traditional medicine based on plant extracts and herbal remedies has been increasingly accepted in Western countries with the modernisation of traditional medicine being a hot area of research in recent years. During 1980-2014, there were 1562 new pharmaceutical drugs developed to treat diseases with about 49% being derived from medicinal plants. There are around 500,000 plant species worldwide but only one percent of these have been used as therapeutic agent. The Sarawak Biodiversity Centre (SBC), Kuching, Malaysia, has provided chemical plant extracts from their collection of Southeast Asian plants that were screened for their antibacterial and antifungal properties. The results of this study so far have demonstrated that many of the Sarawak traditional medicinal plants have effects on microorganisms causative agents for diarrhoea, stomachache, fever, headaches, cough and inflammation. Out of fifty Asian plant extract that were screened, six were found to exhibit broad spectrum activity against several strains of bacteria and fungi and there was significant effect against both Gram-positive and Gram-negative bacteria. The use of these plant species by indigenous groups in Malaysia for the treatment of these illnesses can therefore be substantiated by our findings. In addition to this research, a study was undertaken to discover the basis of the healing abilities reported for an Australian bush medicine. One native Australian and one Bornean plant were the subject of further characterisation using an approach developed for bioguided fractionation. Solid Phase Extraction tubes were used to divide the complex mixture of the plant extract into smaller fractions that were then tested for bioactivity. This process was then repeated for the active fractions and instrumental analysis of these secondary fractions was used for identification. iii Eremophila longifolia leaf extract produced using the conventional immersion technique exhibited better antimicrobial activity compared to Accelerated Solvent Extraction, acetonitrile was found to be the most suitable extraction solvent and optimal activity was found with extracts produced using the conventional immersion technique at 21°C and 5 days There were two novel natural compounds isolated using bioguided fractionation from the leaves of the Australian plant, Eremophila longifolia, and they were chemically identified as neryl ferulate and neryl p-coumarate. Although the bioactivity was weak, their discovery has further advance knowledge of an important indigenous medicine. Asian plant Baccaurea lanceolata fruit extracts showed the most antimicrobial activity against Gram-positive and Gram-negative bacterial strains, the active compound was isolated, and it was chemically identified as tartaric acid. The overall goal of this project was to identify the compounds responsible for observed bioactivity. iv This thesis dedicated to my late father, Mr. Ranjith Perera Gunaratne, his sister Mrs. Mangala Fernando and my primary school science teacher Mrs. Jayantha Fernando, especially because of you, I love science. v Acknowledgements Firstly, I would like to express my sincere gratitude to all my supervisors Dr. Peter Mahon, Professor Enzo Palombo and Dr François Malherbe for the continuous support towards my research project. Special thanks to Peter, who gave me the necessary advice for all chromatographic analysis, separation studies and coached me to think accordingly. His words were “Savi, do the experiments systematically and it has to be consistent”. Tremendous thanks to Professor Danny Meyer for her expert advice for statistical pathways and analysis. The Sarawak Biodiversity Center is the primary provider of the Bornean plant extracts for this study and my humble appreciation to the staff who were involved in the collection of the plant from the different geological locations in the forest. To the University of Queensland, I am immensely grateful to Dr. Mark Butler and his colleagues for providing necessary instrumentation analysis to finalise this research. Also, a big thank you to senior LC-MS application specialist Mr. Alex Chen, at Thermo Fisher Sciences Australia, for providing unrestricted assistance of analysis for all my samples. I thank fellow colleagues, Mr. Ngan Nguyen and Yeannette Lizama, always with a smile on their face, Dr. Rebecca Phillips and Dr. Shanthi Joseph providing microbial advice and the cultures. Also, big thank you to Dr. Avinash Karpe, Dr. Rohan Shah, Dr. Snehal Jadhav and Dr. Yulia Alekseeva for their precious support to survive in difficult situations. Finally, I would love to thank my beloved rebellion gang, my mum Nikulas, husband Suppriya and kids, Amanda and her partner Julian, Tanya, Ruwini and her family, my physics and chemistry teacher/cousin Lalani Kadigamuwa for her support in secondary school and my beloved friend Pjrena, for their unconditional love and support including the encouragement to finish. I love you guys with all of my heart vi Declaration To the best of my knowledge, this PhD thesis does not contain any published materials including tables, figures and appendices, in whole, or in part, for the award of any other academic degree or diploma by another individual. Except where otherwise indicated, this work is my own oeuvre. Savithri Galappathie 2018 vii List of publications Journal publications • Savithri Galappathie, Enzo A. Palombo, Tiong Chia Yeo, Diana Lim Siok Ley, Chu Lee Tu, François M. Malherbe and Peter J. Mahon, Comparative antimicrobial activity of Southeast Asian plants used in Bornean folkloric medicine.Journal of Herbal Medicine, 2014, 4 (2), 96-105 • Savithri Galappathie, David J. Edwards, Alysha G. Elliott, Matthew A. Cooper, Enzo A. Palombo, Mark S. Butler and Peter J. Mahon, Antibacterial Nerol Cinnamates from the Australian Plant Eremophila longifolia. Journal of Natural Products, 2017, 80 (4), 1178–1181 viii Table of Contents Abstract ............................................................................................................................ iii Acknowledgements ........................................................................................................... vi Declaration....................................................................................................................... vii List of publications.......................................................................................................... viii Table of Contents .............................................................................................................. ix List of Figures ................................................................................................................. xiv List of Tables .................................................................................................................. xvi List of Abbreviations and Acronyms .............................................................................. xvii Chapter 1 ........................................................................................................................... 1 1.1 Aims of the thesis ..................................................................................................... 2 1.2 Outcomes of the work undertaken in the throughout the study ................................. 3 1.3 Thesis Overview ....................................................................................................... 5 Chapter 2 ........................................................................................................................... 7 2.1 Plant medicines with antimicrobial activity .............................................................. 8 2.1.1 Ethnomedicinal significance of plants.................................................................8 2.1.2 Plants used for antibacterial medicines ...............................................................9 2.1.3 Plants used for antifungal medicines ................................................................. 11 2.1.4 Medicinal plants for the treatment of neurological and psychiatric disorders ..... 11 2.1.5 Plants for malaria therapy ................................................................................. 12 2.1.6 Plant medicine and acupuncture interrelated treatments .................................... 13 2.1.7 Plant medicine for cancer therapy ..................................................................... 13 2.2 Australian native plant collected from Byrock in New South Wales, Australia ........ 20 2.2.1 Description, distribution, ethnomedicinal and phytochemical identities of ........ 20 2.3 Southeast Asian plant collection from Sarawak, Province of Malaysia .................... 26 2.3.1 Description, distribution, ethnomedicinal and phytochemical identities of Baccaurea lanceolata (Miq.) Müll.Arg ..................................................................... 26 2.3.2 Description, distribution, ethnomedicinal and phytochemical identities of Fibraurea tinctoria Lour ..........................................................................................
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