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Phytochemical Investigation of Three Leguminosae Plants for Larvicidal Activity Against Aedes Aegypti

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Phytochemical Investigation of Three Leguminosae Plants for Larvicidal Activity Against Aedes Aegypti UNIVERSITY OF NAIROBI COLLEGE OF BIOLOGICAL AND PHYSICAL SCIENCES DEPARTMENT OF CHEMISTRY PHYTOCHEMICAL INVESTIGATION OF THREE LEGUMINOSAE PLANTS FOR LARVICIDAL ACTIVITY AGAINST AEDES AEGYPTI BY MARCO MAKUNGU I 56/80611/2012 A THESIS SUBMITTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE AWARD OF THE DEGREE OF MASTERS OF SCIENCE IN CHEMISTRY OF THE UNIVERSITY OF NAIROBI 2015 DECLARATION This thesis is composed of my original work, and contains no material previously published or written by another person except where due reference has been made in the text. It has not been submitted to qualify for the award of any other degree or diploma in any university or other tertiary institution. The research was carried out in the Department of Chemistry of the University of Nairobi. Marco Makungu I 56/80611/2012 This thesis has been submitted for examination with our approval as University supervisors. Prof. Abiy Yenesew Department of Chemistry University of Nairobi Kenya Dr. Solomon Derese Department of Chemistry University of Nairobi Kenya ii DEDICATION This thesis is dedicated to my wife Nakaniwa (Kekuu) and my children Jenipha Modest Makungu and Jossia Madi Makungu iii ACKNOWLEDGEMENTS I would like to express my sincere gratitude to my supervisors Prof. Abiy Yenesew and Dr. Solomon Derese who introduced me to the fascinating field of Natural Products Chemistry research. Thank you for your inspiring and supportive guidance. Your optimistic attitude and consistent enthusiasm towards research are the qualities I most wish to emulate. Dr. Albert Ndakala and Dr. Joseph J. Magadula are also warmly acknowledged for constructive comments, advice, and continuous support throughout the studies. I am greatly indebted to Dr. Matthias Heydenreich, University of Potsdam, for high resolution NMR and MS analysis. In line with this, I have been lucky to meet and work with many outstanding people. I thank the PhD students Tsegaye Deyou, Negera Abdissa, Ivan Gumula, Yoseph Atilaw, Souaibou Yaouba, and MSc students, Dennis Akampurira, Rogo Michael and George Kwesiga for academic and social support. I am also grateful to the German Academic Exchange Services (DAAD) and the Natural Products Research Network for Eastern and Central Africa (NAPRECA) for the award of scholarship. I extend my thanks to Mr. Kevin Omwomo of the School of Biological Sciences, University of Nairobi, for technichal support in the larvicidal tests, Mr. F. Mbago (Department of Botany, University of Dar es Salaam) and Mr. P. Mutiso, (School of Biological Sciences, University of Nairobi) for identification of the plants. I would also like to thank the academic and technical staff of the Department of Chemistry, University of Nairobi for their cooperation, encouragement and support during my research. Finally, I would like to thank the Prime Minister’s Office, Regional Administration and Local Government, Tanzania as well as University of Dar es Salaam for the provision of the study leave. iv LIST OF ABBREVIATIONS AND ACRONYMS ANVR African Network for Vector IFS Isoflavone Synthase Resistance IMM Integrated Mosquito Management 1D One Dimension IUCN International Union for Conservation 2D Two Dimensions of Nature br s Broad singlet J Coupling constant CC Column Chromatography LC50 Concentration causing 50% Lethality CHI Chalcone Isomerase m multiplet CHS Chalcone Synthase m/z Mass to charge ratio CoA Co-enzyme A MeOH Methanol COSY Correlation Spectroscopy MHz Mega Hertz CD Circular Dichroism NADH Nicotinamide Adenine Dinucleotide d doublet Dehydrogenase DCM Dichloromethane NaTHNac National Travel Health Network DCPP Disease Control Priorities Project and Care dd double doublet NIAID National Institute of Allergy and DHF Dengue Hemorrhagic Fever Infectious Diseases DMSO Dimethylsulphoxide NMR Nuclear Magnetic Resonance DSS Dengue Shock Syndrome NOESY Nuclear Overhauser and Exchange ED50 Effective Dose at 50% Spectroscopy EI-MS Electron Impact Ionization Mass NICD-NHLS. National Institute for Spectrometry Communicable Diseases -Division of ESI Electrospray Ionization the National Health Laboratory EtOAc Ethyl acetate Service HMBC Heteronuclear Multiple Bond SPRTTD Special Programme for Research Correlation and Training in Tropical Diseases HMQC Heteronuclear Multiple Quantum t triplet Coherence SD Standard Deviation HSQC Heteronuclear Single Quantum TDNP Tanzania Daima News Paper Correlation UNICEF United Nation Children Fund Hz Hertz UV Ultra-Violet IC50 Inhibitory Concentration at 50% ORD Optical Rotatory Dispersion v TABLE OF CONTENTS DECLARATION ...................................................................................................... ii DEDICATION......................................................................................................... iii ACKNOWLEDGEMENTS..................................................................................... iv LIST OF ABBREVIATIONS AND ACRONYMS ..................................................v LIST OF FIGURES ................................................................................................. xi LIST OF TABLES.................................................................................................. xii LIST OF SCHEMES.............................................................................................. xiii LIST OF APPENDICES........................................................................................ xiv ABSTRACT........................................................................................................... xvi CHAPTER ONE ........................................................................................................1 INTRODUCTION .....................................................................................................1 1.1 Background..................................................................................................................... 1 1.2 Problem Statement.......................................................................................................... 5 1.3 Objectives ....................................................................................................................... 6 1.3.1 Overall Objective...................................................................................................... 6 1.3.2 Specific Objectives ................................................................................................... 6 1.4 Justification of the Research ........................................................................................... 6 CHAPTER TWO .......................................................................................................8 LITERATURE REVIEW ..........................................................................................8 2.1 Mosquito-Borne Diseases ............................................................................................... 8 vi 2.1.1 Malaria .................................................................................................................... 11 2.1.2 Dengue Fever.......................................................................................................... 13 2.2 Plants as Sources of Larvicidal Agents......................................................................... 15 2.2.1 Larvicides from the Family Leguminosae .................................................................... 15 2.3 Botanical Information ................................................................................................... 16 2.3.1 The Family Leguminosae ....................................................................................... 16 2.3.1.1 The Genus Derris ............................................................................................ 17 2.3.1.1.1 Derris trifoliata ........................................................................................... 19 2.3.1.2 The Genus Millettia......................................................................................... 20 2.3.1.2.1 Millettia micans........................................................................................... 22 2.3.1.2.2 Millettia oblata............................................................................................ 22 2.4 Ethno-Medical and Pharmacological Information of the Genera Millettia and Derris 23 2.4.1 Ethno-Botanical Uses of the Genus Millettia ......................................................... 23 2.4.2 Ethno-Botanical Uses of the Genus Derris............................................................. 25 2.5 Phytochemistry of the Family Leguminosae ................................................................ 26 2.5.1 Flavonoids............................................................................................................... 27 2.5.2 Isoflavonoids........................................................................................................... 30 2.5.3 Some Compounds of the Genus Millettia............................................................... 32 2.5.3.1 Flavanones....................................................................................................... 33 2.5.3.2 Isoflavones....................................................................................................... 35 vii 2.5.3.3 Rotenoids......................................................................................................... 38 2.5.3.4 Pterocarpanoids ..............................................................................................
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