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Phytochemical and Antiplasmodial Investigation of Rhamnus Prinoides

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Phytochemical and Antiplasmodial Investigation of Rhamnus Prinoides PHYTOCHEMICAL AND ANTIPLASMODIAL INVESTIGATION OF RHAMNUS AND KNIPHOFIA FOLIOSA BY MERON GEBRU A THESIS SUBMITED IN PARTIAL FULFILMENT OF THE DEGREE OF MASTER OF SCIENCE IN CHEMISTRY OF THE UNIVERSITY OF NAIROBI 2010 University of N A IR O B I Library DECLARATION This thesis is my original work and has never been presented for a degree in any university. .1 Meron Gebru This thesis has been submitted for examination w ith our approval as supervisors SUPERVISORS PROF ABIY YENESEW Department of Chemistry University of Nairobi Dr MARTIN MBUGUA Department of Chemistry University of Nairobi Department of Chemistry University of Nairobi ii DEDICATION THIS THESIS IS DEDICATED TO AFEWORKI ABRAHAM AND HIS FAMILY THEIR ADVICE, LOVE AND SUPPORT MADE ME WHO I AM TODAY YOU WILL ALWAYS BE IN MY HEART MERON iii ACKNOWLEDGEMENT My deepest gratitude goes to my supervisors Prof. Abiy Yenesew, Dr. Martin Mbugua and Dr. Solomon Derese for their continuous guidance, encouragement and support throughout the research and write-up of the thesis. I sincerely thank the German Academic Exchange Service (DAAD) for giving me the scholarship through NAPRECA. I am sincerely grateful to Prof. Martin G. Peter and Dr. Matthias Heydenreich, University of Potsdam, and for Prof. Gerhard Bringmann and Michael Knauer of the University of Wurzburg for analyzing samples on high resolution NMR and MS. 1 would also like to appreciate Mr Hosea Akala of the United States Army Medical Research Unit- Kenya for performing the antiplasmodial tests. I am grateful for the academic and technical staff of the Department of Chemistry, University of Nairobi for their assistance and support. I am also thankful to the former and current members of the Natural product research group, University of Nairobi, for their support and assistance during the course of my study. I am highly indebted to my beloved parents, siblings, family, friends and Biniam for their endless encouragement, support and love. IV LIST OF ABBREVIATIONS AND SYMBOLS mJz Mass to Charge ratio HMQC Heteronuclear multiple quantum coherence ( 1 Jen) HMBC Hetronuclear multiple bond correlation (2Jcn, 3J c h ) COSY Correlated spectroscopy HRMS High resolution mass spectroscopy NOESY Nuclear overhauser and exchange spectroscopy NMR Nuclear magnetic resonance ID One dimension analysis 2D Two dimension analysis MS Mass spectroscopy UV Ultra violet ^-max Maximum wavelength of absorption nm Nanometer MHz Mega hertz Hz Hertz J Coupling constant s Singlet d Doublet cId Double of a doublet ddd Doublet of a doublet of a doublet t Triplet TLC Thin layer chromatography PTLC Preparative thin layer chromatography IC50 Concentration of 50% inhibition TABLE OF CONTENTS DEDICATION.....................................................................................................................................Ill ACKNOW LEDGEMENT................................................................................................................ IV LIST OF ABBREVIATIONS AND SYMBOLS............................................................................V TABLE OF CO NTEN TS................................................................................................................. VI ABSTRACT........................................................................................................................................XII CHAPTER 1 ......................................................................................................................................... 1 INTRODUCTION................................................................................................................................1 1.0 GENERAL.................................................................................................................................... 1 1.1 PROBLEM STATEMENT.......................................................................................................... 4 1.2 JUSTIFICATION.........................................................................................................................4 1.3 OBJECTIVES...............................................................................................................................5 1.3.1 GENERAL OBJECTIVE.....................................................................................................5 1.3.2 SPECIFIC OBJECTIVES.....................................................................................................5 CHAPTER 2 ...........................................................................................................................................7 LITERATURE R EV IE W ...................................................................................................................7 2.1 BACKGROUND ON MALARIA...............................................................................................7 2.1.1 LIFE CYCLE OF MALARIA............................................................................................10 2.1.2 CHEMOTHERAPY OF MALARIA................................................................................. 12 2.1.2.1 QUININE AND ITS DERIVATIVES........................................................................13 2.1.2.2. ANTIFOLATE COMBINATION DRUGS.............................................................. 15 2.1.2.3 ANTIBIOTICS.............................................................................................................16 2.1.2.4 ARTEMISININ AND DERIVATIVES.....................................................................17 2.1.2.5 MISCELLANEOUS COMPOUNDS.........................................................................18 2.1.3 VACCINE DEVELOPMENT............................................................................................19 2.1.4 DRUG RESISTANCE........................................................................................................ 20 2.2 BOTANICAL INFORMATION.............................................................................................. 22 2.2.1 THE FAMILY RHAMNACEAE......................................................................................22 2.1.1.1 THE GENUS RHAMNUS........................................................................................... 23 2.2.1.2 RHAMNUS PRINOIDES............................................................................................ 23 2.2.2 THE FAMILY ASPHODELACEAE............................................................................... 24 2.2.2.1 THE GENUS KNIPHOF1A........................................................................................25 2.2.2.2 KNIPHOFIA FOLIOSA.............................................................................................. 26 2.3 ETHNOMEDICINAL USES OF THE GENUS RHAMNUS.................................................27 2.4 ETHNOMEDICINAL USES OF THE GENUS KNIPHOFIA...............................................31 vi 2.5 BIOLOGICAL ACTIVITY OF THE GENUS 32 2.6 BIOLOGICAL INFORMATION ON KN1PHOF1A SPECIES.............................................. 33 2.7 PHYTOCHEMISTRY OF THE RHAMNACEAE AND ASPHODELACEAE..................34 2.7.1 PHYTOCHEMICAL INFORMATION ON SPECIES..............................36 2.7.2 PHYTOCHEMICAL INFORMATION ON KNIPHOFIA SPECIES...........................42 CHAPTER 3........................................................................................................................................ 49 RESULTS AND DISCUSSION....................................................................................................... 49 3.1 PRELIMINARY TEST............................................................................................................. 49 3.2 CHARACTERIZATION OF COMPOUNDS........................................................................ 50 3.2.1 CHARACTERIZATION OF COMPOUNDS ISOLATED FROM RHAMNUS PRINOIDES..................................................................................................................................50 3.2.1.1 ANTHRAQUINONES................................................................................................50 3.2.1.1.1 CHRYSOPHANOI. < I >....................................................................................... 50 3.2.1.1.2 PHYSCION (2).....................................................................................................51 3.2.1.1.3 EMODIN (3)......................................................................................................... 52 3.2.1.2 FLAVONOL................................................................................................................ 54 3.2.1.2.1 RHAMNAZIN (4 )................................................................................................54 3.2.1.3 NAPHTHALENIC DERIVATIVES......................................................................... 56 3.2.1.3.1 /J-SORIGENIN (5)................................................................................................56 3.2.1.3.2 GESHOIDIN (6) ...................................................................................................58 3.2.2 CHARACTERIZATION OF COMPOUNDS ISOLATED FROM KNIPHOFIA FOLIOSA.......................................................................................................................................60 3.2.2.1 MONOMERIC ANTHRAQUINONES.................................................................... 60 3.2.2.1.1 CHRYSOPHANOL (1 ).......................................................................................60 3.2.2.1.2
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