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Phytochemical Investigation of Three Leguminosae Plants for Cancer Chemopreventive Agents

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Phytochemical Investigation of Three Leguminosae Plants for Cancer Chemopreventive Agents UNIVERSITY OF NAIROBI COLLEGE OF BIOLOGICAL AND PHYSICAL SCIENCES DEPARTMENT OF CHEMISTRY PHYTOCHEMICAL INVESTIGATION OF THREE LEGUMINOSAE PLANTS FOR CANCER CHEMOPREVENTIVE AGENTS BY IVAN GUMULA A THESIS SUBMITTED IN FULFILLMENT OF THE REQUIREMENTS FOR THE AWARD OF THE DEGREE OF DOCTOR OF PHILOSOPHY (PhD) IN CHEMISTRY OF THE UNIVERSITY OF NAIROBI 2014 ii DEDICATION This work is dedicated to my family iii ACKNOWLEDGEMENTS First of all, I would like to thank the University of Nairobi for admitting me as a Doctoral student. I wish to extend my heartfelt gratitude to my supervisors; Prof. Abiy Yenesew, Dr. Solomon Derese and Prof. Isaiah O. Ndiege whose close supervision coupled with resourceful guidance/advice enriched me with the knowledge, skills and attitude resulting in the success of this research. I am grateful to the German Academic Exchange Services (DAAD) and the Natural Products Research Network for Eastern and Central Africa (NAPRECA) for financial support during my studies. I appreciate the help extended to me by Dr. Matthias Heydenreich of the University of Potsdam in spectroscopic/spectrometric analyses of some of the compounds reported in this thesis. Special thanks go to the Swedish Institute for sponsoring my research visit to the University of Gothenburg. I am indebted to my host supervisor, Prof. Máté Erdélyi, and the Halogen Bond Research Group of the Department of Chemistry and Molecular Biology, at the University of Gothenburg for his unwavering support and guidance in isolation and spectroscopic techniques and analysis. My sincere gratitude is extended to Dr. John P. Alao and Prof. Per Sunnerhagen of the Department of Chemistry and Molecular Biology at the University of Gothenburg for carrying out cytotoxicity assays. I acknowledge Mr Simon G. Mathenge of the East African Herbarium, Nairobi, for the identification of the plant species studied. I wish to thank my fellow postgraduate students in the research group at the Department of Chemistry, University of Nairobi: Dr. Milkyas Endale, Dr. Francis Machumi, Dr. Hannington Twinomuhwezi, Ms. Martha Induli, Mr. Denis Akampurira, Mr. Robert Masinde and Mr. Daniel Buyinza for their cooperation and moral support. Last but not least, I wish to appreciate my beloved wife Prossy and children Elizabeth, Nathan and Dorcus, for the support they accorded to me throughout the study period. Glory is to the Almighty God-the alpha and the omega. iv ABSTRACT Cancer is one of the largest single and common causes of death in humans around the world. It is estimated to have claimed up to 8.2 million lives in the year 2012 and with an incidence of 14.1 million new cases. Plant metabolites such as flavonoids have been reported to display cancer chemopreventive properties such as anti-oxidant, anti-estrogenic effects and cytotoxicity. Three Leguminosae plants, Platycelphium voёnse, Millettia usaramensis subsp. usaramensis and Flemingia grahamiana, were phytochemically investigated to give a range of flavonoid derivatives, two triterpenoids and an anthraquinone. Twenty three of the isolated compounds are new and their structures were established using a combination of techniques including NMR, UV, CD and MS. From the stem bark of Platycelphium voёnse twelve compounds, including seven isoflavanones, one isoflavone, two 3-methoxyflavones and two triterpenes, were isolated and identified. Five of the isoflavanones including platyisoflavanones A (163) and C (166) are new. Similar investigation of the root bark of Millettia usaramensis subsp. usaramensis resulted in the isolation of thirteen compounds including two new flavanone derivatives: (2R,3R)-4'-O-geranyl-7-hydroxyflavanonol (179) and (S)-4'-O-geranyl-7-hydroxyflavanone (180) in addition to seven known 12a-hydroxyrotenoids, two isoflavones, one chalcone and a cinnamoyl alcohol derivative. From the roots of Flemingia grahamiana, seven isoflavones and five prenylated flavanones, including a new flavanone derivative, 5,3',4'-trihydroxy-8- ,-dimethylallyl-2'',2''-dimethylpyrano-[5'',6'':6,7]-flavanone (191), along with a chromone and a gallocatechin derivative were obtained. Exposure of 8-(,-dimethylallyl)-2'',2''- dimethylpyrano-[5'',6'':6,7]-flavanones to deuterated dimethylsulfoxide led to isomerization of the flavones yielding the corresponding 6-,-dimethylallyl-2''',2'''-dimethylpyrano- [5''',6''':8,7]-flavanone isomers. This is the first report of such rearrangement. From the leaves of F. grahamiana, a range of flavonoids were isolated and identified. These included the known chalcone, flemingin A (196) and eleven new chalcones [including flemingin G (197)], two new flavanones and two new Z-aurones [such as flemingiaurone A (211)]. Five rotenoids, one triterpene, one isoflavanone and two chalcones were active against the MCF-7 human breast cancer cell line. Compounds 163 and 196 were cytotoxic against Vero cells and both were active against Mycobacterium tuberculosis. Compound 196 and four other chalcones exhibited strong radical scavenging activity against DPPH. Attempt to synthesize 2,5,2′-trihydroxy-4′,5′-dimethoxychalcone from 2-hydroxy-4,5- dimethoxyacetophenone and 2,5-diallyloxybenzaldehyde in the presence of KOH/methanol led to the formation of 2,5-diallyloxy-2′-hydroxy-4′,5′-dimethoxychalcone. Deprotection of the allyl groups using Pd(PPh3)4, prepared in-situ, in the presence of K2CO3/methanol, yielded a partially deprotected, 5-allyloxy-2,2′-dihydroxy-4′,5′-dimethoxychalcone. v HO O OH OCH3 O OH O OCH3 OH O OH 163 196 OH OH OH OH HO O O O OH O OH O OH OCH3 166 197 O H OH HO O OH R O O H O 179: R = OH 180: R = H OH O HO 191 OH H3CO O H3CO O 211 vi TABLE OF CONTENTS DECLARATION ------------------------------------------------------------------------------------- ii DEDICATION --------------------------------------------------------------------------------------- iii ACKNOWLEDGEMENTS ------------------------------------------------------------------------ iv ABSTRACT ------------------------------------------------------------------------------------------ v LIST OF TABLES ----------------------------------------------------------------------------------- xii LIST OF SCHEMES -------------------------------------------------------------------------------- xiv LIST OF ABBREVIATIONS AND SYMBOLS ----------------------------------------------- xv CHAPTER ONE: INTRODUCTION --------------------------------------------------------- 1 1.1 General -------------------------------------------------------------------------------------- 1 1.2 Problem Statement -------------------------------------------------------------------------- 2 1.3 Objectives ------------------------------------------------------------------------------------ 2 1.3.1 General objective --------------------------------------------------------------------------- 2 1.3.2 Specific objectives -------------------------------------------------------------------------- 2 1.4 Justification of the Study ------------------------------------------------------------------ 3 CHAPTER TWO: LITERATURE REVIEW ----------------------------------------------- 4 2.1 Causes of Cancer --------------------------------------------------------------------------- 4 2.1.1 Internal factors ------------------------------------------------------------------------------ 4 2.1.2 External (Environmental) factors ------------------------------------------------------- 4 2.1.2.1 Chronic infections ------------------------------------------------------- 4 2.1.2.2 Chemicals in the environment ----------------------------------------- 5 2.1.2.3 Radiations and free radicals -------------------------------------------- 7 2.1.3 Hereditary factors --------------------------------------------------------------------------- 8 2.2 Mechanism of Carcinogenesis ------------------------------------------------------------ 8 2.2.1 Role of enzymes in cancinogenesis ------------------------------------------------------ 10 2.2.2 Estrogens, phytoestrogens and carcinogenesis ------------------------------------------ 12 2.3 Natural Product-Based Anticancer Agents ---------------------------------------------- 14 2.4 Cancer Preventive Measures -------------------------------------------------------------- 17 2.5 Natural Products in Cancer Chemoprevention ------------------------------------------ 18 2.6 The Family Leguminosae ------------------------------------------------------------------ 22 2.6.1 The Sub-family Papilionoideae ----------------------------------------------------------- 22 2.6.2 Botanical information on the plants under study ---------------------------------------- 23 2.6.2.1 Botanical information on Platycelphium voënse ---------------------- 23 2.6.2.2 Botanical information on Millettia ------------------------------------ 24 2.6.2.3 Botanical information on Flemingia grahamiana ------------------ 24 2.6.3 Ethnobotanical uses of Leguminosae --------------------------------------------------- 25 2.6.3.1 Ethnopharmacological uses of Millettia ------------------------------ 26 2.6.3.2 Ethnopharmacological uses of Flemingia ---------------------------- 26 2.6.4 Phytochemistry of Leguminosae -------------------------------------------------------- 27 vii 2.6.4.1 Phytochemistry of Platycelphium voënse ------------------------------ 28 2.6.4.2 Phytochemistry of Millettia ---------------------------------------------- 28 2.6.4.2.1 Isoflavones from Millettia --------------------------------------- 29 2.6.4.2.2 Rotenoids from Millettia ---------------------------------------- 31 2.6.4.2.3 Flavones,
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