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Phytochemistry and Biological Activity of the Root Extract of Millettia

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Phytochemistry and Biological Activity of the Root Extract of Millettia PHYTOCHEMISTRY AND BIOLOGICAL ACTIVITY OF THE ROOT EXTRACT OF MILLETTIA OBLATA JOCELYN WAMBUI KAMAU MASTER OF SCIENCE (Medicinal chemistry) JOMO KENYATTA UNIVERSITY OF AGRICULTURE AND TECHNOLOGY 2012 Phytochemistry and biological activity of the root extract of millettia oblata Jocelyn Wambui Kamau A thesis submitted in partial fulfilment for the degree of Master Science in Medicinal Chemistry in the Jomo Kenyatta University of Agriculture and Technology 2012 DECLARATION This thesis is my original work and has not been presented for a degree in any other University Signature ……………………………… Date……………………. Jocelyn Wambui Kamau This thesis has been submitted for examination with our approval as University supervisors: Signature…………................ Date……………………. Dr. Solomon Derese UON, Kenya Signature............................… Date………….....……… Dr. Joseph Gikunju JKUAT, Kenya Signature………………….... Date……………………. Dr. Geoffrey Rukunga KEMRI, Kenya ii DEDICATION This thesis is dedicated to my beloved children Kamau and Njeri whose outstanding support, LOVE and encouragement steers me through my darkest moments. iii ACKNOWLEDGEMENTS Glory, praise, thanks and honour to the Almighty God whose promises and blessings endure forever. I sincerely thank my supervisors Dr S. Derese, Dr J. Gikunju and Dr G. Rukunga for their wisdom, knowledge and wise counsel throughout my work. Special thanks to Prof. Abiy Yenesew, University of Nairobi, Chiromo campus, for his support, encouragement and Nuclear Magnetic Resonance (NMR) analysis of samples. I am also indebted to my collegues and co-researchers from the University of Nairobi (Chiromo), the Kenya Medical Research Institute (KEMRI) and Jomo Kenyatta University of Agriculture and Technology (JKUAT) for their support and informed guidance in various technical aspects of the project. I thank my parents profoundly for their love; endless support and timely advice, which have shielded and cushioned me from major obstacles and challenges throughout my life. Lastly, my deepest gratitude to all family members for their prayers, encouragement and invariable reminder of my obligation to accomplish my work expeditiously. iv TABLE OF CONTENTS DECLARATION…………………………………………………………………...ii DEDICATION …………………………………………………………………….iii ACKNOWLEDGEMENTS……………………………………………………….iv TABLE OF CONTENTS………………………………………………………......v LIST OF TABLES………………………………………………………………….x LIST OF FIGURES………………………………………………………………xii LIST OF APPENDICES………………………………………………………….xii ABBREVIATIONS AND SYMBOLS…………………………………………..xiv ABSTRACT……………………………………………………………………...xvii CHAPTER ONE……………………………………………………………….......1 1.0 INTRODUCTION………………………………………………………....1 1.1 BACKGROUND INFORMATION…………………………………….......1 1.2 PROBLEM STATEMENT……………… ............................... ……………9 1.3 JUSTIFICATION................ ……………………………………………….10 1.4 ALTERNATE HYPOTHESIS .... …………………………………………11 1.5 RESEARCH QUESTIONS………………………………………………..12 1.6 STUDY OBJECTIVES ........ ………………………………………………11 1.6.1 General objective………………………………………………………...12 1.6.2 Specific objectives. ………………………………………………………11 CHAPTER TWO………………………………………………………………….12 2.0 LITERATURE REVIEW………………………………………………...12 v 2.1 BACKGROUND INFORMATION……………………………………….12 2.1.1 Malaria…………. ………………………………………………………12 2.1.2 History of malaria................................................................................... 13 2.1.3 Malaria burden and economic impact ..................................................... 13 2.1.4 Malaria prevalence ................................................................................. 14 2.2 STRUCTURAL CLASSIFICATION OF ANTI-MALARIALS ................ 14 2.3 RESISTANCE TO ANTI-MALARIAL DRUGS ...................................... 18 2.4 BACTERIAL AND FUNGAL INFECTIONS ........................................... 18 2.5 BOTANICAL INFORMATION OF MILLETTIA OBLATA....................... 20 2.5.1 Taxonomy of Millettia oblata ................................................................. 20 2.5.2 Millettia oblata ....................................................................................... 21 2.6 ETHNO-MEDICAL INFORMATION ...................................................... 23 2.6.1 Ethno-medical uses of Leguminoceae family .......................................... 23 2.6.2 Ethno-medical uses of genus Millettia .................................................... 24 2.7 PHYTOCHEMISTRY OF FABACEAE ................................................... 26 2.7.1 Phytochemical information of flavonoids ............................................... 26 2.7.2 Compounds isolated from Millettia......................................................... 27 2.7.2.1 Isoflavones from Millettia................................................................. 27 2.8 FLAVONES AND ANTHOCYANINS OF MILLETTIA ........................... 44 2.8.1 Flavanones of Millettia ........................................................................... 50 2.8.2 Flavanonols from Millettia ..................................................................... 54 2.8.3 Chalcones of Millettia ............................................................................ 55 2.8.4 Rotenoids of Millettia ............................................................................. 59 vi 2.8.5 Minor compounds from the genus Milletti .............................................. 66 2.9 BIOLOGICAL ACTIVITY OF FABACEAE FAMILY ............................ 75 2.9.1 Anti-microbial isoflavonoids from Fabaceae .......................................... 75 2.9.2 Anti-plasmodial activity of Fabaceae ...................................................... 77 2.10 BIOLOGICAL ACTIVITY OF MILLETTIA ............................................. 79 2.11 ANTI-BACTERIAL AND ANTI-FUNGAL BIOASSAYS ....................... 81 2.11.1 Agar diffusion assays ............................................................................. 81 2.11.2 Critical inhibitory concentration (CIC) ................................................... 81 2.11.3 Minimum inhibitory concentration (MIC)............................................... 82 2.12 ANTI-PLASMODIAL ACTIVITY ........................................................... 82 CHAPTER THREE………………………………………………………………84 3.0 MATERIALS AND METHODS………………………………………...84 3.1 STUDY DESIGN AND SITE ................................................................... 84 3.2 CLEANING AND STERILIZING GLASSWARE .................................... 84 3.3 EXTRACTION AND ISOLATION OF COMPOUNDS FROM THE MILLETTIA OBLATA ROOT EXTRACT ............................................................. 85 3.3.1 General procedures ................................................................................. 85 3.3.2 Solvents………………………………………………………………… . 85 3.3.3 Plant materials ........................................................................................ 85 3.4 BIOLOGICAL ACTIVITY ASSAYS ....................................................... 87 3.4.1 Anti-plasmodial activity assay ................................................................ 87 3.4.1.1 Plasmodial parasites ......................................................................... 87 3.4.1.2 In-vitro anti-plasmodial activity assay procedure .............................. 88 vii 3.5 ANTI-BACTERIAL AND ANTI-FUNGAL ACTIVITY .......................... 90 3.5.1 Preparation of the medium ...................................................................... 90 3.5.2 Anti-bacterial and anti-fungal test micro-organism strains ...................... 90 3.5.3 Standardisation of the inocula suspension ............................................... 90 3.5.4 Anti-bacterial activity assay.................................................................... 91 3.5.5 Assay for anti-fungal activity.................................................................. 92 3.5.6 Determination of the Minimum Inhibitory Concentration (MIC) ............ 92 CHAPTER FOUR………………………………………………………………..94 4.0 RESULTS AND DISCUSSION………………………………………….94 4.1 PHYTOCHEMICAL PROFILES .............................................................. 94 4.2 CHARACTERIZATION THE COMPOUNDS ISOLATED FROM MILLETTIA OBLATA ROOT EXTRACT ............................................................. 94 4.2.1 Isoerythrin A 4’-(3-methylbut-2-enyl) ether (1) ...................................... 94 4.2.2 Calopogonium isoflavone B (2) .............................................................. 97 4.2.3 4-Hydroxylonchocarpin (3) .................................................................... 99 4.2.4 7, 2’-Dimethoxy-4’, 5’- methylenedioxyisoflavone (4) ......................... 101 4.2.5 Lupeol (5) ............................................................................................ 104 4.3 BIOLOGICAL ACTIVITIES .................................................................. 105 4.3.1 In vitro anti-plasmodial activity ............................................................ 105 4.3.1.1 In-vitro anti-plasmodial activity of crude extracts ........................... 105 4.3.1.3 Influence of the hydrocarbon proportion on anti-plasmodial activity107 4.3.2 Anti-bacterial activity ........................................................................... 108 4.3.2.1 Pre-liminary anti-bacterial activity evaluation ................................. 108 viii 4.3.2.3 Definitive anti-bacterial activity evaluation ..................................... 112 4.3.3 In-vitro anti-fungal activity evaluation .................................................. 115 4.3.4 Minimum Inhibitory Concentration
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