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Thesis Final 29Nov2011.Pdf UNIVERSITY OF KWAZULU-NATAL THE PHYTOCHEMISTRY AND BIOLOGICAL ACTIVITY OF SECONDARY METABOLITES FROM KENYAN VERNONIA AND VEPRIS SPECIES 2011 JOYCE JEPKORIR KIPLIMO Pa ge | ii THE PHYTOCHEMISTRY AND BIOLOGICAL ACTIVITY OF SECONDARY METABOLITES FROM KENYAN VERNONIA AND VEPRIS SPECIES JOYCE JEPKORIR KIPLIMO 2011 A thesis submitted to the school of Chemistry, Faculty of Science and Agriculture, University of KwaZulu-Natal, Westville, for the degree of Doctor of Philosophy. This Thesis has been prepared according to Format 4 as outlined in the guidelines from the Faculty of Science and Agriculture which states: This is a thesis in which chapters are written as a set of discrete research papers, with an Overall Introduction and Final Discussion. Where one (or all) of the chapters has already been published. Typically these chapters will have been published in internationally- recognized, peer- reviewed journals. As the candidate’s supervisor, I have approved this thesis for submission. Supervisor: Signed: --------------------------------Name: ------------------------- Date: -------------- Pa ge | iii ABSTRACT This work is an account of the phytochemical analysis of two genera, Vernonia and Vepris which are used as remedies for illness by the Kalenjin community of Kenya. Species of Vernonia are known to yield sesquiterpene lactones, which typify the genus whereas Vepris is rich in alkaloids and limonoids which have a wide range of biological activities. The species studied in this work were Vernonia auriculifera, Vernonia urticifolia, Vepris glomerata and Vepris uguenensis. Phytochemical studies revealed a range of compounds being present in the four species. From Vernonia , triterpenoids, a sesquiterpene amine, a carotenoid and a polyene were isolated. This was the first account of a sesquiterpene amine from a plant species and the first account of the novel polyene. The triterpenoids showed moderate antibacterial activity, with β-amyrin acetate and oleanolic acid being effective at decreasing adhesion of selected gram-negative and gram-positive bacteria. Lutein and urticifolene showed good antibacterial activity against Enterococcus feacium and Pseudomonas aeruginosa. In Vepris , a range of compounds were isolated, belonging to the furoquinoline alkaloids, coumarins, flavonoids, cinnamic acid derivatives, lignins, cinnamaldehydes, triterpenoids and limonoids. Five new compounds; a cinnamaldehyde derivative (glomeral), two flavonoids (veprisinol, uguenenprenol) and two A, D-seco -limonoids (uguenensene and uguenensone) were amongst the compounds isolated. Antibacterial studies showed that glomeral inhibited the growth of Staphylococcus aureus and Shigella dysentrieae at low concentrations (MIC of 2 µg mL -1 and 0.4 µg mL -1 respectively). Antioxidant assays of several compounds revealed that, veprisinol, haplopine-3,3’-dimethylallyl ether, uguenenprenol and 7-O-methylaromadenrin are good antioxidant agents. The limonoids isolated from Vepris uguenensis also make up an interesting biogenetic relationship. Pa ge | iv Structural elucidation was carried out by 1D and 2D NMR spectroscopy in conjuction with mass spectrometry, infrared, ultraviolet and circular dichroism analysis where applicable. Biological assays were carried out using standard methods at laboratories in the University of KwaZulu-Natal and Kenya Medical Research Institute (KEMRI-Nairobi). Pa ge | v ABBREVIATIONS ANOVA analysis of variance 1H NMR proton nuclear magnetic resonance spectroscopy 13 C NMR C-13 nuclear magnetic resonance spectroscopy COSY correlated spectroscopy DEPT distortionless enhancement by polarization transfer DPPH 2,2-diphenyl-1-picrylhydrazyl EIMS electron impact mass spectroscopy FRAP ferric reducing antioxidant potential HMBC heteronuclear multiple bond coherence HSQC heteronuclear single quantum coherence HRMS high resolution mass spectroscopy MS mass spectroscopy NOESY nuclear overhauser effect spectroscopy RSA radical scavenging activity UV ultraviolet Ac acetate br broad resonance m multiplet c concentration cc column chromatography Pa ge | vi d doublet dd double doublet Hz hertz Me methyl s singlet t triplet IR infrared Mp melting point tlc thin layer chromatography Pa ge | vii DECLARATIONS DECLARATION 1 - PLAGIARISM I, Joyce Jepkorir Kiplimo declare that 1. The research reported in this thesis, except where otherwise indicated, is my original research. 2. This thesis has not been submitted for any degree or examination at any other university. 3. This thesis does not contain other persons’ data, pictures, graphs or other information, unless specifically acknowledged as being sourced from other persons. 4. This thesis does not contain other persons' writing, unless specifically acknowledged as being sourced from other researchers. Where other written sources have been quoted, then: a. Their words have been re-written but the general information attributed to them has been referenced b. Where their exact words have been used, then their writing has been placed in italics and inside quotation marks, and referenced. 5. This thesis does not contain text, graphics or tables copied and pasted from the Internet, unless specifically acknowledged, and the source being detailed in the thesis and in the References sections. Signed ………………………………………………………… Pa ge | viii DECLARATION 2-PUBLICATIONS DETAILS OF CONTRIBUTION TO PUBLICATIONS that form part and/or include research presented in this thesis (include publications in preparation, submitted, in press and published and give details of the contributions of each author to the experimental work and writing of each publication) Publication 1 Kiplimo, J. J., Chenia, H., Koorbanally N. A. 2011 . Triterpenoids from Vernonia auriculifera Hiern exhibit antimicrobial activity, African Journal of Pharmacy and Pharmacology , 5 (8), 1150 – 1156. Publication 2 Kiplimo, J. J., Everia, C. A. and Koorbanally, N. A. 2011 . A Novel polyene from Vernonia Urticifolia (Asteraceae), Journal of Medicinal Plants Research , 5 (17), 4202-4211. Publication 3 Kiplimo, J. J., Islam, Md. S., Koorbanally, N. A. Novel flavonoid and furoquinoline alkaloids from Vepris glomerata and their antioxidant activity, Natural Products Communication accepted for publication on 4 th October, 2011 . Publication 4 Kiplimo, J. J. and Koorbanally, N. A. Antibacterial activity of an epoxidised prenylated cinnamaldehdye derivative from Vepris glomerata, manuscript submitted to Phytochemistry Letters . Publication 5 Kiplimo, J. J., Islam, Md. S., Koorbanally, N. A. Ring A, D-seco Limonoids and Flavonoid from the Kenyan Vepris uguenensis Engl. and their antioxidant activity, manuscript submitted to Journal of Natural Products in November 2011. Pa ge | ix From all the above publications, my role included carrying out all the experimental work and writing of the publications. The co-authors contribution was that of an editorial nature and checking on the scientific content and my correct interpretation. Signed: ………………………………….. Pa ge | x ACKNOWLEDGEMENTS I would like to thank my supervisor, Dr Neil Anthony Koorbanally. Thank for your support and encouragement throughout my three years of study. Your passion and humility has always encouraged me to give my best to my studies. These three years in your dynamic Natural Products Research Group (NPRG) have afforded me with a wealth of learning experience and I want to thank you for your input into my academic career. My thanks also go to Dr Shahidul Islam for guiding me through the antioxidant assays and for helping with statistical analyses of my data. Dr Hafizah Chenia is also acknowledged for guiding me through the antibacterial and antibiofilm assays. I would also like to thank my colleagues in the Natural Products Group Dr Nizam Shaik, Dr Habila, Adele, Aliyu, Amaya, Asif, Damien, Dorothy, Edith, Erick, Hamisu, Kaalin, Shiksha, Sunayna, Thrineshen and Victoria for the good working relationship in the lab. My special thanks goes to my friend Mrs Roshila Moodley who has been very close to me here in UKZN. I am grateful to Mr Dilip Jagjivan for guiding me in NMR analyses, Mathew Sibonelo for HREIMS analysis, Neal Broomhead and Anita Naidoo for GC-MS analysis and Dr Brand of the University of the Stellenbosch for CD analyses. My thanks also go out to all the academic and technical staff in the School of Chemistry. My special thanks goes to the Kenyan community here at the University of KwaZulu-Natal, especially ‘Nduguzangu’ my brothers in the Analytical and Catalysis lab. They have been my family here in Durban ‘Asante Sana’. To my Patient Husband Mr Philip Bett I would like to say “you are the Best” you have kept me going. Thank you for your support, understanding and encouragement during my study Pa ge | xi period. To my children Kimutai, Jebii and Kiprotich you have motivated me to work harder to achieve my dream. Mostly, I want to acknowledge God for His abundance of love and blessings that He has showered upon me. I would like to acknowledge the Organization for Women in Science for the Developing World (OWSDW) for their financial support and the University of KwaZulu-Natal for the adequate facilities in the research lab. Last but not least I would like to acknowledge the Teachers Service Commission (TSC)- Kenya for the study leave. Pa ge | xii TABLE OF CONTENTS ABSTRACT .............................................................................................................. iii ABBREVIATIONS ................................................................................................... v
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