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Isolation and Structure Elucidation of Bioactive Compounds From ISOLATION AND STRUCTURE ELUCIDATION OF BIOACTIVE COMPOUNDS FROM RAUVOLFIA CAFFRA SOND BY BAFEDILE DORCAS TLHAPI, BSc(Hons) (11617811) Submitted in fulfilment of the requirements for the Degree of Master of Science (Chemistry) in the Department of Chemistry University of Venda Private Bag X 5050 Thohoyandou 0950 South Africa Supervisor: Prof. IDI. Ramaite Co-Supervisor: Prof. T. van Ree DECLARATION I, Bafedile Dorcas Tlhapi, hereby declare that the dissertation for the Master of Science (MSc) Degree in Chemistry, submitted at the University of Venda, is an original research document and has not been submitted previously for a degree at this or any other university, that it is my own work in design and in execution, and that all reference material contained therein has been duly acknowledged. ……………………..………………. ……………………………… (Signature of Candidate) Date i DEDICATIONS I would like to dedicate this dissertation to my mom (Maria Tlhapi), my dad (Molefe Moses Tlhapi) and my younger sister (Moleboheng Thabia Tlhapi), who have always been my source of inspiration through difficult times. I would also like to express my genuine gratitude to everyone who played a role in my upbringing, my undergraduate and postgraduate studies. Thank you all for your encouragement, patience and support. I hope that this research will justify that hard work, discipline, and perseverance yield good results. ii ACKNOWLEDGEMENTS First and foremost, I would like to thank God the most high for giving me the strength, health, and divine protection throughout this study. I would also like to convey my sincere gratitude to the following individuals and organizations: My supervisors, Prof. IDI. Ramaite and Prof. T. van Ree, for giving me an opportunity to explore this interesting field of natural product chemistry. Their relentless guidance has immensely contributed toward the success of this project. Dr. CP. Anokwuru for his assistance, guidance and unceasing patience. This work would have been impossible without his motivation. I am very grateful. National Research Foundation and Sasol Inzalo foundation for their generous financial support. University of Venda for their facilities. Mr. P. Pandelani of University of Venda for his assistance with NMR spectroscopy. Dr. M. Stander and Mr. MJC. Taylor of University of Stellenbosch for their assistance with High Resolution Mass Spectrometry and Ultra-performance liquid chromatography mass spectroscopy analysis. Prof. J. du Preez of North-West University for his assistance with semi-preparative HPLC. Prof. H. Hoppe of Rhodes University for his assistance with biological tests (antiplasmodial, antitrypanosomal and cytotoxicity activities). Support of this project was provided by the South African Medical Research Council (MRC) with funds from National Treasury under its Economic Competitiveness and Support Package, and Rhodes University Sandisa Imbewu. Ms. MM. Boukandou of University of Venda (Department of Microbiology) for her assistance with biological tests (phytochemical analysis, antioxidant and antimicrobial activities). The Department of Chemistry (University of Venda) for their invaluable advice and support. iii Abstract Rauvolfia caffra Sond, a species of evergreen trees and shrubs in the dogbane family, (Apocynaceae), is used as a medicinal plant among traditional communities in many countries for the treatment of malaria, diabetes, coughs, gastrointestinal disturbances, skin infections, impotence, insomnia, diarrhoea, dysentery, scabies, worm infections, and both parasitic and microbial infections. Phytochemical studies have revealed that indole alkaloids are the major constituents of the stem bark. However, there are limited studies linking the compounds with the ethnomedicinal uses. The aim of this study is to isolate and characterize bioactive compounds from Rauvolfia caffra Sond. The highest phenolic content found in a fraction was 16.06±0.125 mg GAE/g, while the highest flavonoid content measured was 9.453±0.081 mg QE/g. In the DPPH free radical scavenging activity and reducing power tests, a lowest IC50 value of 0.022±0.003 µg/mL and IC0.5 value 0.518±0.044 µg/mL, respectively, was found. Six compounds were isolated from the stem bark, including lupeol, a pentacyclic tri-terpenoid isolated for the first time from the genus Rauvolfia; raucaffricine, a rare glycoalkaloid of the monoterpenoid indole class; N- methylsarpagine, an indole alkaloid isolated for the time from R. caffra and spegatrine, an indole alkaloid isolated for the first time from R. caffra, respectively. Concerning antimicrobial activity, the highest activity of a fraction was against B. cereus with MIC values as low as 12.5 mg/mL. One fraction at the tested concentration (250 μg/mL) decreased the viability of Plasmodium falciparum (4.149±6.979 %) with an IC50 value of 6.533 μg/mL. The crude extract and some fractions affected the viability of the Trypanosomes at the tested concentration (250 μg/mL), giving -0.133 ± 0.206 %, 11.334 ± 2.692 %, 1.026 ± 0.143 % and 20.769 ± 9.054 % with IC50 values of 18.50 μg/mL, 14.15 μg/mL, 15.58 μg/mL and 34.71 μg/mL, respectively. Furthermore, the fractions did not show significant cytotoxic effects at a concentration of 50 μg/mL. Key words: bioactive compounds, polyphenolic content, Rauvolfia caffra Sond, antioxidant, antimicrobial, antiplasmodial, antitrypanosomal and cytotoxic activities. iv Table of Contents DECLARATION……………………………………………………………………………...i DEDICATIONS……………………………………………………………………………...ii ACKNOWLEDGEMENTS………………………………………………………………...iii Abstract………………………………………………………………………………………iv List of Symbols and Abbreviations…………………………………………………………ix List of Figures……………………………………………………………………………..…xi List of Tables…………………………………………………………………………..…...xiii List of Schemes……………………………………………………………………………..xiv Chapter 1: General introduction……………………………………………………………1 1.1. Background……………………………………………………………………………...1 1.2. Problem Statement……………………………………………………………………...2 1.3. Aim……………………………………………………………………………………….3 1.4. Objectives…………………………………………....…………………………………..3 1.5. Dissertation Outline…………………………………………………………………….4 Chapter 2: Literature Review……………………...……………………………………….5 2.1. Medicinal plants for pharmacological purposes………………………………………5 2.2. Oxidative stress and antioxidant activity………………………………………………5 2.3. The use of medicinal plants as antibacterial agents…………………………………...6 2.4. Cytotoxic activity……………….………………………………………………………..7 2.5. Medicinal plants as antimalarial agents………………………………………………..8 2.6. Antitrypanosomal activity of medicinal plants…………………………...……………8 2.7. Phytochemical constituents……………………………………………………………..9 2.7.1. Glycosides……………………………………………………………………………10 2.7.2. Flavonoids…………………………………………………………………………...10 2.7.3. Tannins………………………………………………………………………………13 2.7.4. Alkaloids……………………………………………………………………………..13 2.7.5. Terpenes……………………………………………………………………………..15 v 2.7.6. Phenolics……………………………………………………………………………..17 2.8. The subject of this study: Rauvolfia caffra……………………………………………18 2.8.1. The genus Rauvolfia………………………………………………………………...19 2.8.1.1. Rauvolfia serpentine………………………………………………………………...19 2.8.1.2. Rauvolfia vomitoria…………………………………………………………………20 2.8.1.3. Rauvolfia stricta…………………………………………………………………….20 2.8.2. Taxonomy……………………………………………………………………………21 2.8.3. Ecology and physiology………………………………………………..……………21 2.8.4. Ethnomedicinal uses…………………………………………...……………………22 2.8.5. Phytochemistry of the genus Rauvolfia…………………………………………....23 2.9. Pharmacological activities……………………………………………………………..27 2.9.1. Antibacterial activity………………………………………………………………..27 2.9.2. Antioxidant activity…………………………………………………………………28 Chapter 3: Materials and Methods………………………………………….……………29 3.1. Plant collection and preparation………………………………………………………29 3.2. Extraction of plant materials (bioactive compounds) from the stem bark of R. caffra……………………………………………………………………………………..29 3.3. Isolation of fractions using column chromatography…………..……………………31 3.4. Purification of isolated compounds…………………………………………………...32 3.5. Structure elucidation of isolated compounds………………………………………...33 3.5.1. General experimental procedure………………………………………………….34 3.5.2. Spectroscopic data…………………………………………………………………..35 3.5.2.1. 3β-Lup-20(29)-en-3-ol (59)………………………………………………………...35 3.5.2.2. (16S,17R,19E)-21α-(β-D-glucopyranosyloxy)-1,2-didehydro-2,7-dihydro-7β,17- cyclosarpagan-17-yl acetate (61)…………………………………………………...36 3.5.2.3. 10,17-dihydroxy-1,4-dimethylsarpaganium (63)…….…………………………. 37 3.5.2.4. (15α,19E)-10,17-dihydroxy-4-methylsarpagan-4-ium (64)……………………...38 3.6. Bioactivities of Rauvolfia caffra……………………………………………………….39 3.6.1. Determination of the content of polyphenol compounds…………………………39 3.6.1.1. Total phenolic content (TPC)……………………………………………………...39 3.6.1.2. Total flavonoid content (TFC)…………………………………………………….39 3.6.2. Antioxidant activities……………………………………………………………….40 3.6.2.1. Free radical scavenging assay (DPPH)……………………………………………40 vi 3.6.2.2. Reducing power…………………………………………………………………….41 3.6.3. Antimicrobial activity………………………………………………………………42 3.6.3.1. Test microorganisms……………………………………………………………….42 3.6.3.2. Determination of the minimal inhibitory concentration (MIC)…………………42 3.6.4. Cytotoxic activity….…………………………………...……………………………43 3.6.5. Antiplasmodial activity……………………………………………………………..43 3.6.6. Antitrypanosomal activity………………………………………………………….44 3.6.7. Single concentration screening……………………………………………………..44 3.6.8. Dose-response relationships………………………………………………………..44 3.6.9. Statistical analysis…………………..………………………………………………45 Chapter 4: Results and Discussion……………………………………………………….46 4.1.
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