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ISOLATION and CHARACTERIZATION of NEW COMPOUNDS from Strychnos Henningsii and THEIR ANTI-MALARIAL ACTIVITIES

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ISOLATION and CHARACTERIZATION of NEW COMPOUNDS from Strychnos Henningsii and THEIR ANTI-MALARIAL ACTIVITIES i ISOLATION AND CHARACTERIZATION OF NEW COMPOUNDS FROM Strychnos henningsii AND THEIR ANTI-MALARIAL ACTIVITIES MUMINA PAUL KITHOME SC/PGC/20/06 A RESEARCH THESIS SUBMITTED AS PARTIAL FULFILLMENT FOR AWARD OF A MASTER OF SCIENCE DEGREE CERTIFICATE IN ORGANIC CHEMISTRY, DEPARTMENT OF CHEMISTRY AND BIOCHEMISTRY OF UNIVERSITY OF ELDORET, KENYA NOVEMBER, 2013 ii DECLARATION DECLARATION BY THE STUDENT I declare that the research project presented here is my original work, and has not been presented in any institution for award of any degree. Paul KithomeMumina Signature SC/PGC/20/06 Student …….…………………… DECLARATION BY THE SUPERVISORS This thesis has been submitted for examination with our approval as university supervisors Professor P. K. Ndalut Signature University of Eldoret Dept. of Chemistry and Biochemistry ……………………….. Professor P. K. Kipkemboi Signature University of Eldoret Dept. of Chemistry and Biochemistry ………………………... iii DEDICATION This piece of research is heartily dedicated to my wife, Josephine and son, Emmanuel Kithome for the strength, prayers and encouragement both have given me during this study period. This pushed me to carry on even when it was hard sometimes to go on. iv ABSTRACT Traditional medicines play an important role in the management of common fever associated with malarial symptoms, particularly in the rural Africa. However, their potential use as sources of medicines has not been fully exploited or even identified to know the active compounds. The present study was carried out to confirm the medicinal value of Strychnos henningsii in treating malaria as it has been traditionally used by the Kamba herbalist of Machakos, and Makueni and Embu Counties. The herbalists assisted in the identification, collection and use of this plant .the dried leaves were extracted with organic solvents of different polarities to yield crude extracts. The combined crude extract was subjected to chromatographic separation technique to yield pure crystalline compounds. Their structures were determined by the employment of spectroscopic technique especially proton NMR and 13C which yielded nine compounds of which seven turned out to be new and unique indole alkaloids. The other two their structures could not be determined because the amount were too small for structural determination. The crude extract was tested for larvicidal activity against mosquito larvae and bioassay against Plasmodium falciparum that showed high activity. v TABLE OF CONTENTS DECLARATION ................................................................................................. ii ACKNOWLEDGEMENT ................................................................................ viii ABSTRACT ....................................................................................................... iv TABLE OF CONTENTS ..................................................................................... v LIST OF TABLES ............................................................................................. vi CHAPTER ONE ................................................................................................ 9 INTRODUCTION ............................................................................................... 9 1.1 Background information ............................................................................. 9 1.2 Life cycle of the malaria parasite ................................................................ 3 1.3 The causes of human malaria...................................................................... 3 1.4 Background on malaria treatment ............................................................... 5 1.5Malaria treatment milestones ....................................................................... 5 1.6 The future - Synthetic drugs ..................................................................... 12 1.7 Problem statement .................................................................................... 13 1.8 Justification .............................................................................................. 14 1.9 Objectives ................................................................................................ 14 CHAPTER TWO ............................................................................................. 16 LITERATURE REVIEW .................................................................................. 16 2.1 Species description and distribution .......................................................... 16 2.2 Botanic description .............................................................................. 16 2.3 Functional uses .................................................................................... 17 2.4 Related research from close plant types ............................................... 18 CHAPTER THREE ......................................................................................... 22 MATERIALS AND METHODS ....................................................................... 22 3.1 Requirements ...................................................................................... 22 3.2 Experimental: sample collection .......................................................... 23 3.3 Preparation and extraction of plant materials ....................................... 23 3.4 Isolation of the compounds from the crude extracts ............................. 24 3.5 Column chromatography ..................................................................... 25 3.6 Elution................................................................................................. 25 3.7 In vitro anti-plasmodial assay .............................................................. 26 3.8 Reading the results using microbeta counter ........................................ 27 CHAPTER FOUR ........................................................................................... 28 RESULTS ......................................................................................................... 28 4.1 Column chromatography ..................................................................... 28 4.2 Physical properties .............................................................................. 29 4.3 In vitro anti-plasmodial activity ........................................................... 30 4.4 Structure elucidation of compounds ..................................................... 31 CHAPTER FIVE ............................................................................................. 59 DISCUSSION ................................................................................................... 59 CHAPTER SIX ................................................................................................. 60 RECOMMENDATIONS ................................................................................... 60 REFERENCES .................................................................................................. 61 vi APPENDIX I ..................................................................................................... 66 LIST OF TABLES Table 4. 1 Physical properties of the crude and pure compounds ........................ 29 Table 4. 2 Results of in vitro anti-plasmodial activity ........................................ 30 Table 4. 3 Tabulation of the carbon atoms and corresponding hydrogen atoms for compound labeled PKM 092....................................................................... 32 Table 4. 4 Comparison of tabulated carbon atoms of PKM 092 and N(a)- strychnosplendine ....................................................................................... 33 Table 4. 5 Tabulation of the carbon atoms and corresponding hydrogen atoms for compound labeled PKM 094....................................................................... 36 Table 4. 6 Comparison of tabulated carbon atoms of PKM 094 and Holstiine .... 37 Table 4. 7 Tabulation of the carbon atoms and corresponding hydrogen atoms for compound labeled PKM 096....................................................................... 40 Table 4. 8 Comparison of tabulated carbon atoms of PKM 096 and N(a)- acetylstrychnosplendine .............................................................................. 41 Table 4. 9 Tabulation of the carbon atoms and corresponding hydrogen atoms for compound labeled PKM 097....................................................................... 44 Table 4. 10 Comparison of tabulated carbon atoms of PKM 097 and Diaboline . 45 Table 4. 11 Tabulation of the carbon atoms and corresponding hydrogen atoms for compound labeled PKM 099....................................................................... 48 Table 4. 12 Comparison of tabulated carbon atoms of PKM 099 and Diaboline . 49 Table 4. 13 Tabulation of the carbon atoms and corresponding hydrogen atoms for compound labeled PKM 104....................................................................... 52 Table 4. 14 Comparison of tabulated carbon atoms of PKM 104 and N(a)- acetylstrychnosplendine .............................................................................. 53 Table 4. 15 Tabulation of the carbon atoms and corresponding hydrogen atoms for compound labeled PKM 107....................................................................... 56 Table 4. 16 Comparison of tabulated carbon atoms of PKM 107 and N(a)- acetylstrychnosplendine .............................................................................. 57 vii viii ACKNOWLEDGEMENT I am greatly indebted
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