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Johnson-Ajinwophd2017.Pdf This work is protected by copyright and other intellectual property rights and duplication or sale of all or part is not permitted, except that material may be duplicated by you for research, private study, criticism/review or educational purposes. Electronic or print copies are for your own personal, non- commercial use and shall not be passed to any other individual. No quotation may be published without proper acknowledgement. For any other use, or to quote extensively from the work, permission must be obtained from the copyright holder/s. IDENTIFICATION, SEMI-SYNTHESIS AND EVALUATION OF ANTI-OVARIAN CANCER COMPOUNDS FROM PLANTS USED IN TRADITIONAL MEDICINES OKIEMUTE ROSA JOHNSON-AJINWO Thesis submitted to Keele University for the degree of Doctor of Philosophy June 2017 IDENTIFICATION, SEMI-SYNTHESIS AND EVALUATION OF ANTI-OVARIAN CANCER COMPOUNDS FROM PLANTS USED IN TRADITIONAL MEDICINES OKIEMUTE ROSA JOHNSON-AJINWO INSTITUTE OF SCIENCE AND TECHNOLOGY IN MEDICINE KEELE UNIVERSITY THESIS SUBMITTED TO KEELE UNIVERSITY FOR THE DEGREE OF DOCTOR OF PHILOSOPHY JUNE 2017 ABSTRACT Ovarian cancer is the second leading cause of death among women in the gynaecological category of cancers. The current post surgery treatment which involves the use of platinum- based therapy with its attendant adverse drug-resistance often results in the return of the cancer. This research work, explored the role of natural products as the major source of new drugs by the evaluation of the anti-ovarian cancer activities of three selected medicinal plants and the semi-synthesis of analogues of an anti-cancer agent; thymoquinone from Nigella sativa. Using a bioassay-guided approach, an investigation of the cell growth inhibition of the extracts/fractions of these plants on four human ovarian cancer cell lines, A2780, OVCAR 4, OVCAR 8, and CIS-A2780 showed that Acalypha wilkesiana, Margaritaria discoidea and Rutidea parviflora had promising anti-ovarian cancer activities. This is the first report of the anti-cancer activities of M. discoidea and R. parviflora. The bioactive compounds of the plants were isolated by HPLC, identified by mass spectrometry/NMR spectroscopy and investigated for cytotoxicity. Gallic acid, (IC50 range of 6.2±0.3 – 26.9±4.1 µM) was the active compound in A. wilkesiana. The significantly bioactive compounds of M. discoidea were securinine, (IC50 range of 2.7±0.7 – 8.7±0.1 µM), betulinic acid, (IC50 of 16.0±1.9 µM) and gallic acid. While palmatine, (IC50 range of 5.5±0.9 – 7.9±0.5 µM) was the major active compound in R. parviflora. Twenty-one thymoquinone analogues including eleven semi- synthetic ones were evaluated for cytotoxicity. A synthetic 2-dimethylamino-5-methyl-1,4- benzoquinone demonstrated optimum activity (IC50 range of 4.7±0.5 – 11.2±1.9 µM) and superior aqueous solubility. Palmatine, securinine and 2-dimethylamino-5-methyl-1,4- benzoquinone showed induction of apoptosis via increased caspase 3/7 activity. Palmatine demonstrated PAPR cleavage by western blot analysis. 2-dimethylamino-5-methyl-1,4- benzoquinone showed synergy with carboplatin and paclitaxel. These studies have provided scientific evidences for the potential treatment of ovarian cancer with these traditional medicinal plants and hit compounds for future optimization towards clinical trials. i CONTENTS ABSTRACT ............................................................................................................................. i Contents ................................................................................................................................. ii FIGURES ............................................................................................................................. vii TABLES .............................................................................................................................. xiii ABBREVIATIONS ............................................................................................................... xvi PUBLICATIONS ................................................................................................................. xviii Journal Articles ............................................................................................................................. xviii Book Chapter ................................................................................................................................ xviii Conference Abstracts .................................................................................................................. xviii POSTER AWARD .......................................................................................................................... xix APPENDICES ...................................................................................................................... xx ACKNOWLEDGEMENTS .................................................................................................... xxi Chapter One........................................................................................................................... 1 Introduction ......................................................................................................................................... 1 1.1 Cancer .......................................................................................................................................... 1 1.2 Ovarian Cancer ........................................................................................................................... 1 1.3 Medicinal Plants-A Proven Source of Cancer Drugs ............................................................ 3 1.3.1 Natural Products Derived and Platin-derived Drugs Clinically Used in the Treatment of Ovarian Cancer ...................................................................................................... 5 1.3.2 Plant natural products in Clinical Trials ............................................................................ 8 1.3.3 Natural Products Derived Drugs in Pre-Clinical Trials for the Treatment of Ovarian Cancer ........................................................................................................................................... 12 1.3.4 Recent Plant-Derived Compounds with Activities on Ovarian Cancer Cell Lines ... 15 Polyscias duplicate (Thouars ex Bail.) Lowry and G.M. Plunkett (Araliaceae) ...................... 18 1.3.5 Some Other Compounds with Anti-cancer Activities ................................................... 29 1.4 Literature Survey of the Medicinal Plants Investigated in this study ................................. 31 1.4.1 Acalypha wilkesiana- A Plant with Potential Chemotherapeutic Activities ............... 31 1.4.2 Margaritaria discoidea - An unexplored plant for Anti-cancer Activities .................... 33 ii 1.4.3 Rutidea Parviflora- An un-researched Plant with Potentials for Cancer Treatment 38 1.5 Thymoquinone - A Potential Anticancer Lead ...................................................................... 39 1.6 Research Design ...................................................................................................................... 43 1.7 Aims and Objectives ................................................................................................................. 45 Chapter Two......................................................................................................................... 48 General Materials and Methods .................................................................................................... 48 2.1 Materials ..................................................................................................................................... 48 2.1.1 Reagents ............................................................................................................................. 48 2.1.2 Plant Materials ................................................................................................................... 48 2.1.3 Cancer assay materials .................................................................................................... 48 2.1.4 The ovarian cancer cell lines ........................................................................................... 49 2.1.5 The Human Ovarian Epithelial (HOE) Cell Line ........................................................... 49 2.2 Methods ...................................................................................................................................... 50 2.2.1 Cell Growth Conditions ..................................................................................................... 50 2.2.2 Resuscitation of cryopreserved cells .............................................................................. 50 2.2.3 Trypsinization of Cells ....................................................................................................... 50 2.2.4 Cryopreservation of Cells ................................................................................................. 51 2.3 Cell Growth Assay .................................................................................................................... 51 2.3.1 Drug Combination Experiments ...................................................................................... 53 2.3.2 Trypan Blue assay ............................................................................................................. 54 2.4 Apoptosis Studies ....................................................................................................................
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