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University of Khartoum Graduate College Medical and Health Studies Board University of Khartoum Graduate College Medical and Health Studies Board Isolation and Structure Elucidation of Leishmanicidal Alkaloids from Argemone mexicana L. and Nauclea latifolia Smith. By Omima Mekki Khider Mekki B. Sc. (1999), M. Sc. (2005) (U of K) A thesis submitted in fulfillment of the requirement for the award of the degree of Doctor of Philosophy in Pharmaceutical Chemistry of University of Khartoum Supervisor Prof. Sami Ahmed Khalid B. Pharm., M. Pharm., PhD. 2016 DEDICATION This thesis is dedicated to my lovely family, To my Parents for their lifelong devotion, patient and prayers To my dearest Brothers and Sisters for their kind help and prayers To my respectful supervisor prof. Sami for his kind support Omima TABLE OF CONTENTS Contents Page No TABLE OF CONTENTS i ACKNOWLEDGMENTS v ABBREVIATIONS vii ENGLISH ABSTRACT ix ARABIC ABSTRACT xi LIST OF FIGURES xii LIST OF TABLES xiii 1. INTRODUCTION 1 1.1 Background information 1 1.2 Problem statement 2 1.3 Aim and Objectives 3 1. 4 Justifications 3 2. LITERATURE REVIEW 5 2.1 Neglected Tropical Diseases (NTDs) caused by protozoan 5 parasites 2.1.1 Contribution of Medicinal Plants to NTDs 6 2.1.2 Ethnopharmacology of Sudanese medicinal plants with special 7 emphasis on NTDs 2.2 Leishmaniasis 8 2.2.1 Leishmanial chemotherapy 12 2.2.2 Medicinal plants reported to exhibited antileishmanial activity 13 i 2.2.3 Alkaloids from medicinal plants reported to exhibited 27 antileishmanial activity 2.3 Plants investigated in the present study 88 2.3.1 Argemone mexicana L. (Papaveraceae) 88 2.3.1.1 The botanical description of A. mexicana L. 88 2.3.1.2 Ethnopharmacological importance of A. mexicana L. 50 2.3.1.3 Phytochemistry of A. mexicana L. 53 2.3.1.4 Biosynthesis of benzophenanthridine alkaloids 58 2.3.1.5 Pharmacological activity of protoberberine and protopine 66 alkaloids 2.3.2 Nauclea latifolia Smith. (Rubiaceae) 63 2.3.2.1 The botanical description of N. latifolia Smith. 63 2.3.2.2 Ethnopharmacological importance of N. latifolia Smith. 63 2.3.2.3 Phytochemistry of N. latifolia Smith. 66 2.3.2.4 Biosynthesis of monoterpene indole alkaloid Strictosamide 44 66 2.3.2.5 Pharmacological activity of β-carboline alkaloids 68 3. MATERIALS AND METHODS 07 3.1 General experimental conditions 76 3.1.1 Organic solvents, glassware, chemicals and reagents 76 3.1.2 Spectroscopic techniques 76 3.1.3 Chromatography 71 3.1.4 Detection method on TLC by spraying reagents 72 3.2 Plant Materials 72 3.2.1 Extraction and fractionation of plant materials 72 ii 3.3 Phytochemical screening 73 3.3.1 Isolation of compounds from Argemone mexicana L. 73 3.3.1.1 Isolation of compounds from petroleum ether fraction 73 3.3.1.2 Isolation of compounds from ethyl acetate fraction 74 3.3.2 Isolation of compounds from Nauclea latifolia Smith. 76 3.3.2.1 Isolation of compounds from petroleum ether fraction 76 3.3.2.2 Isolation of compounds from chloroform fraction 76 3.3.2.3 Isolation of compounds from ethyl acetate fraction 78 3.4 BIOLOGICAL ASSAYS 08 3.4.1 Materials 78 3.4.2 Antileishmanial assay 77 3.4.2.1 Maintenance of Parasites 79 3.4.2.1.1 Preparation of Biphasic medium (NNN medium) 79 3.4.2.1.2 Preparation of complete RPMI 1640 medium 79 3.4.2.1.3 Subculture of parasites 86 3.4.2.2 Preparation of sample 80 3.4.2.3 In vitro assay by colorimetric method 80 3.4.2.3.1 In vitro assay against extracellular promastigote 80 3.4.2.4 In vitro assay by macrophage method 81 3.4.2.4.1 Procedure for harvesting macrophages from the mice 81 3.4.2.4.2 In vitro assay against intracellular amastigotes 81 iii 3.4.3 Cytotoxicity assay 82 3.4.3.1 Cell-line 82 3.4.3.2 Method 82 4. RESULTS AND DISCUSSION 84 4.1 Secondary metabolites isolated from Argemone mexicana L. 84 4.1.1 Characterization of AM/1 as Sitost-4-en-3-one (β-Sitostenone) 84 113 4.1.2 Characterization of AM/2 as norchelerythrine 85 87 4.1.3 Characterization of AM/3 as berberine 10 87 4.2 Secondary metabolites isolated from Nauclea latifolia Smith. 71 4.2.1 Characterization of NL/1 as β-Sitosterol 114 71 4.2.2 Characterization of NL/2 as naucleficine 115 74 4.2.3 Characterization of NL/3 as strictosamide 44 78 4. 3Antileishmanial and cytotoxicity assays 162 4.4 Docking of the isolated compounds against leishmania enzymes 107 5. CONCLUSIONS AND RECOMMENDATIONS 110 5.1 Conclusions 11 0 5.2 Recommendations 11 2 6. REFERENCES 114 iv ACKNOWLEDGEMENTS I would like to express my special appreciation and thanks to my supervisor Prof. Dr. Sami Ahmed Khalid. He has been a tremendous mentor for me. I would like to thank him for his precious and interesting suggestions, continuous support, patience, inspiration and immense knowledge. His guidance and encouragement helped me enormously in conducting my research and the writing up of this thesis. I am deeply indebted to Prof. Dr. Atta ur Rahman of H.E.J, International Centre for Chemical and Biological Sciences (ICCBS), University of Karachi, Pakistan, for his comments and valuable suggestions. I would like to extend my thanks to Prof. Dr. Mohammed Igbal Choudhary for his kind guidance and his enjoyable lectures in NMR spectroscopy and other topics. I would like to thank both of them for providing me the access to the laboratory and research facilities. Without their precious support it wouldn’t have been possible to conduct significant part of this research. Sincere thanks and appreciation to Prof. Dr. Souad Abd Elaziz for her prayers, continuous encouragement and follow up and for taking over all my responsibilities at the University of Science and Technology during conducting my research in Pakistan. I am so grateful and obligated to the ex- dean of the Graduate College, University of Khartoum, Prof. Dr. Mohammed Ahmed Abu Alnour for his support and understanding of all circumstances and health conditions I went through during this research. v My sincere thanks are due to Mr. Fouad Abd Aljalil, Faculty of Pharmacy, University of Khartoum, for his technical assistance in the preparation of the extracts. I am deeply indebted to Dr. Farzana Navid for her kind support and being a caring and loving sister as well as a genuine friend. Special thanks to my fellow lab mates at H.E.J, ICCBS, for the stimulating discussions and the great fun we have had during our works. In particular, I am so grateful to the PhD fellow Mujeeb ur Rahman, Dr. Shabbir Husein, PhD fellow Ismaeel and Dr. Adighari. Thanks also to all technical staff of NMR, MS, HPLC laboratories and IT staff at ICCBS for their unlimited technical support during my stay in ICCBS. I would like to extend my thanks to Dr. Sammer Yousuf, Miss. Samreen Khan and Miss. Nida Ghouri for performing the antileishmanial assay. I am also obliged to Dr. Omer Mohammed Elhaj for performing the cytotoxicity assays. I do sincerely appreciate the support of Dr. Asaad Khalid and Dr. Mohammed Ahmed Mesaik for facilitating my mission at the ICCBS. I would like to express my sincere thanks and gratitude to Prof. Dr. Moawia Mukhtar, and his lab. team, Institute of Endemic Diseases, University of Khartoum, for hosting me, providing me the access to the laboratory, and teaching me how to culture the leishmania parasite and macrophage cells. Great thanks and appreciation to University of Khartoum for offering me the scholarship and the opportunity to achieve my post graduate studies. vi ABBREVIATIONS NTDs: Neglected Tropical Diseases CL: Cutaneous leishmaniasis MCL: Mucocutaneous leishmaniasis VL: Visceral leishmaniasis TDR: The special program for research and training in tropical diseases WHO: World health organization GDP: Gross domestic product HIV: Human immunodeficiency virus HAART: Highly active antiretroviral therapy DNDi: Drug for neglected diseases initiative DCM: Dichloromethane Pro: Promastigote Ams: Amastigote N. R.: Not reported DOPA: 3,4-dihydroxyphenylalanine TDC: Tryptophan decarboxylase G10H: Geraniol 10 hydroxylase SLS: Secologanin synthase STR: Strictosidine synthase SAP: Secreted aspartic protease MTT: 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (dye) DMEM: Dulbecco's Modified Eagle's Medium vii MEM: Minimum Essential Medium eagle DMSO: Dimethyl sulfoxide EDTA: Ethylenediaminetetraacetic acid HEPES: 4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid (buffer) RPMI 1640: Roswell Park Memorial Institute medium PBS: Phosphate buffered saline FBS: Fetal bovine serum FCS: Fetal calf serum NNN medium: Novy-MacNeal-Nicolle medium rpm: Revolutions per minute PI: Percentage inhibition IC50: Inhibition concentration SD: Standard deviation viii ABSTRACT Introduction: Leishmaniasis a group of clinical diseases affecting millions of the world populations in 88 countries. Accordingly, this disease is considered as one of the Neglected Tropical Diseases (NTDs) besides malaria, sleeping sickness, mycetoma and other fifteen NTDs. Chemotherapy for leishmaniasis is still deficient and there is an urgent need to discover novel antileishmanial agents, hence most of the currently available drugs have serious limitations such as long-term administration, unaffordable cost, toxicity, and developing resistance by these parasites. The objectives of this study is to isolate and elucidate the chemical structures of new anti-leishmanial secondary metabolites against both the promastigotes and amastigotes stages with special reference to alkaloids occurring in Argemone mexicana L. and Nauclea latifolia Smith, which are commonly growing plants in Sudan. Methods: The extraction of plant materials was followed by bioactivity- guided fractionation using the promastigotes of L. donovani, L. major and L. tropica of the crude ethanolic extracts of A.
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