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Table of Contents TABLE OF CONTENTS Title page, illustration from Van Wyk, 2001 Declaration………………………………………………………………………………..II Acknowledgements………………………………………………………………………III Abstract…………………………………………………………………………………..IV Table of Contents………………………………………………………………………..VII List of Figures.…………….……………………………………………………………..IX List of Tables…………………………………………………………………………….XII List of Abbreviations…………………………………………………………………...XIV 1 Introduction 1.1 Tuberculosis .........................................................................................................1 1.2 The organism........................................................................................................2 1.3 Symptoms and diagnosis......................................................................................3 1.4 Treatment of tuberculosis .....................................................................................4 1.5 Anti-tuberculosis drugs ........................................................................................4 1.6 Drug-resistant tuberculosis...................................................................................5 1.7 Traditional medicine in South Africa...................................................................7 1.8 Drugs derived from natural products ...................................................................8 1.9 Plants with antimycobacterial activity.................................................................9 1.10 Tuberculosis drug development .........................................................................14 1.11 Project objectives ...............................................................................................17 2 Plant selection and crude extract preparation 2.1 Introduction........................................................................................................18 2.2 Materials and methods .......................................................................................18 2.3 Results ................................................................................................................20 2.4 Discussion..........................................................................................................29 3 Antimicrobial testing of crude extracts 3.1 Introduction........................................................................................................32 3.2 Materials and methods .......................................................................................32 3.3 Results ................................................................................................................34 3.4 Discussion..........................................................................................................40 4 Antimycobacterial testing of crude extracts 4.1 Introduction........................................................................................................46 4.2 Materials and methods .......................................................................................47 4.3 Results ................................................................................................................49 4.4 Discussion..........................................................................................................51 5 The isolation and characterization of anacardic acids from Ozoroa paniculosa 5.1 Introduction........................................................................................................53 5.2 Materials and methods .......................................................................................55 5.3 Results ................................................................................................................59 5.4 Discussion ..........................................................................................................69 6 The antimicrobial and antimycobacterial activity of anacardic acids 6.1 Introduction........................................................................................................72 6.2 Materials and methods .......................................................................................72 6.3 Results: Compound 1 .........................................................................................72 6.4 Results: HPLC Fractions ....................................................................................85 6.5 Discussion..........................................................................................................90 7 The cytotoxicity testing of anacardic acids 7.1 Introduction........................................................................................................93 7.2 Materials and methods .......................................................................................93 VII TABLE OF CONTENTS 7.3 Results ................................................................................................................95 7.4 Discussion..........................................................................................................96 8 Conclusion………………………………………………………………………..97 9 Future work……………………………………………………………………...100 10 Presentations…………………………………………………………………….101 11 References……………………………………………………………………….102 12 Appendix: Nuclear Magnetic Resonance: 2-Dimensional Data ..…….………...114 VIII LIST OF FIGURES AND SCHEMES Figure 1.1: The estimated geographical distribution of tuberculosis cases in 2003 (WHO, 2005) .................................................................................................1 Figure 1.2: A model of the mycobacterial cell wall, proposed by Minnikin, showing the primary constituents of lipids, mycolates, arabinogalactan and peptidoglycan. The funnel-shaped structure in the centre represents a porin, responsible for the movement of molecules across the cell wall (Hong and Hopfinger, 2004). ...............................................................................................2 Figure 1.3: The structures of RIF, INH, PYR and EMB......................................................5 Figure 1.4: Prevalence of MDR-TB among new TB cases between 1994 and 2002 (WHO, 2004a)……………………………………………………………………….6 Figure 1.5: The chemical structures of some antimycobacterial natural products……….11 Figure 2.1: A diagramatic representation of the experimental processes followed in this project………………………………………………………………………………..19 Figure 2.2: Pictures of selected medicinal plants used in this study. (A) Siphonochilus aethiopicus; (B) Mentha longifolia; (C) Salvia africana-lutea; (D) Tetradenia riparia; (E) Helichrysum odoratissimum; (F) and (G) Eriocephalus africanus; (H) Agathosma betulina; (I) Ozoroa paniculosa ..............................................30 Figure 3.1: Examples of the disc diffusion method. Plate ‘A’ shows the activity of the acetone extract of H. odoratissimum (45) and C. scabrida acetone and methanol extracts (47 and 63 respectively) against B. cereus. Plate ‘B’ shows the activity of the acetone extracts of T. riparia (35), S. cordatum bark (42) and H. odoratissimum (45) against S. aureus………………………………………………………………………….35 Figure 3.2: An example of the broth micro-dilution method for the determination of MIC’s of extracts against E. faecalis. The wells from left to right contain the negative control, culture control, solvent control, antibiotic control and in duplicate, the acetone extracts of A. robusta, C. scabrida, D. stramonium and O. paniculosa……..….35 Figure 4.1: The BACTEC 460 apparatus (A) with racks containing the inoculated vials ready to be tested and the individual 12B vials containing the radiolabelled carbon substrate (B). ..........................................................................................................47 Figure 5.1: Selected plant extracts exhibiting the greatest antimicrobial and antimycobacterial activity………………………………………………………………...55 Figure 5.2: The zones containing the active principles on TLC viewed under UV 365nm (A) and agar overlay bio-autography plates of fractions 2 (B) and 3 (C) after column chromatography of the crude extract of O. paniculosa showing the zones of inhibition of M. aurum growth…………………………………………………………...60 Figure 5.3: The HPLC profile of the eluted fractions HPLC1, 2 and 3 using a semi-preparative C-18 column and visualizing at 300nm on a Shimadzu LC10AS at the University of Cape Town…………………………….…………………………….61 Figure 5.4: LC-MS results of active fraction 3 of O. paniculosa performed at the University of Stellenbosch………………………………………………………………..61 Figure 5.5: High resolution mass spectrum of compound 1 ..............................................62 Figure 5.6: The 13C spectrum of compound 1....................................................................62 IX LIST OF FIGURES AND SCHEMES Figure 5.7: The 1H spectrum of compound 1.....................................................................63 Figure 5.8: The structure of 6-[8(z)-pentadecenyl]salicylic acid isolated from Ozoroa paniculosa……………………………………………………………………….65 Figure 5.9: Mass spectrometry indicating the isotopic distribution of the tailing edge of fraction HPLC3…………………………………………………………………..66 Figure 5.10: The 13C spectrum of HPLC3..........................................................................67 Figure 5.11: The 1H spectrum of HPLC3...........................................................................67 Figure 5.12: The structure of 6-pentadecylsalicyclic acid with the saturated side chain isolated from fraction HPLC3 of O. paniculosa………………………..………….69 Figure 5.13: The structures of the saturated (structure
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