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Mining Sudanese Medicinal Plants for Natural Compounds Against Malaria and Neglected Tropical Diseases

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Mining Sudanese Medicinal Plants for Natural Compounds Against Malaria and Neglected Tropical Diseases Mining Sudanese Medicinal Plants for Natural Compounds against Malaria and Neglected Tropical Diseases INAUGURALDISSERTATION zur Erlangung der Würde eines Doktors der Philosophie vorgelegt der Philosophisch-Naturwissenschaftlichen Fakultät der Universität Basel von Abdelhalim Babiker Mohamed Mahmoud aus dem Sudan Basel, 2020 Originaldokument gespeichert auf dem Dokumentenserver der Universität Basel edoc.unibas.ch Genehmigt von der Philosophisch-Naturwissenschaftlichen Fakultät auf Antrag von Prof. Dr. Pascal Mӓser Prof. Dr. Thomas J. Schmidt Basel, den 23.06.2020 Prof. Dr. Martin Spiess Dekan To my father Who taught me that perseverance and hard work always pays off. May your inspiring soul rest in peace. Table of Contents Acknowledgment ...................................................................................................................................................... I Abbreviations .......................................................................................................................................................... III Summary .................................................................................................................................................................... V 1. INTRODUCTION: Neglected Tropical Diseases, Drug Discovery, and the Sudan .................... 1 1.1 Neglected Tropical Diseases ............................................................................................................................ 3 1.1.1 NTDs and Sudan .......................................................................................................................................... 4 1.2 Drug Discovery for NTDs: ................................................................................................................................. 6 1.2.1 Challenges and Gaps .................................................................................................................................. 6 1.2.2 Drug Development Strategies for NTDs: ........................................................................................... 7 1.3 Ethnomedicine in Sudan and Biodiversity .............................................................................................. 12 1.4 Objectives .............................................................................................................................................................. 14 1.5 References ............................................................................................................................................................. 16 2. Mining Sudanese Medicinal Plants for Antiprotozoal Agents .................................................... 23 2.1 Abstract .................................................................................................................................................................. 25 2.2 Introduction ......................................................................................................................................................... 27 2.3 Results..................................................................................................................................................................... 29 2.3.1 Review of medicinal plants from Sudan .......................................................................................... 29 2.3.2 Testing for antiparasitic activity ........................................................................................................ 32 2.3.3 Two-way clustering of the bioactivity data ................................................................................... 33 2.3.4 Testing for cytotoxicity .......................................................................................................................... 35 2.3.5 Extracts with selective anti-trypanosomal activity .................................................................... 36 2.3.6 Extracts of selective antiplasmodial activity ................................................................................. 36 2.3.7 HPLC-based activity profiling .............................................................................................................. 37 2.3.8 Dereplication of active principles ...................................................................................................... 38 2.4 Discussion ............................................................................................................................................................. 42 2.5 Material and Methods ....................................................................................................................................... 45 2.6 References ............................................................................................................................................................. 50 2.7 Supporting Information: ................................................................................................................................. 58 3. HPLC-Based Activity Profiling for Antiprotozoal Compounds in Croton gratissimus and Cuscuta hyalina ........................................................................................................................................... 69 3.1 Abstract .................................................................................................................................................................. 71 3.2 Introduction ......................................................................................................................................................... 72 3.3 Results and Discussion..................................................................................................................................... 74 3.3.1 Extraction and HPLC-based Activity Profiling .............................................................................. 74 3.3.2 Compound Isolation and Structure Elucidation .......................................................................... 75 3.3.3 Activity against Leishmania donovani Axenic and Intracellular Amastigotes ................. 77 3.3.4 Activity against Trypanosoma brucei rhodesiense ....................................................................... 78 3.3.5 Activity against Plasmodium falciparum ......................................................................................... 79 3.3.6 Correlation between Chemical Structure of Isolated Flavonoids and Antiprotozoal Activity…………….…………………………………………………………………………………………………79 3.4 Materials and Methods..................................................................................................................................... 81 3.5 References ............................................................................................................................................................. 91 3.6 Supporting Information ................................................................................................................................... 95 4. Lignans, Amides, and Saponins from Haplophyllum tuberculatum and their Antiprotozoal Activity ............................................................................................................................ 113 4.1 Abstract ............................................................................................................................................................... 115 4.2 Introduction ...................................................................................................................................................... 116 4.3 Results and Discussion.................................................................................................................................. 117 4.3.1 Extraction and HPLC-based Activity Profiling ........................................................................... 117 4.3.2 Compound Isolation and Structure Elucidation ....................................................................... 118 4.3.3 Comparison to previously reported compounds ..................................................................... 121 4.3.4 Biological testing .................................................................................................................................... 122 4.3.5 Activity against Leishmania donovani axenic amastigotes ................................................... 123 4.3.6 Activity against Plasmodium falciparum ...................................................................................... 123 4.3.7 Activity against Trypanosoma brucei rhodesiense .................................................................... 124 4.4 Materials and Methods.................................................................................................................................. 125 4.5 References .......................................................................................................................................................... 134 4.6 Supporting Information: .............................................................................................................................. 139 5. Natural Products Against Madurella mycetomatis ....................................................................... 151 5.1 Abstract ............................................................................................................................................................... 153 5.2 Introduction .....................................................................................................................................................
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