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Phytochemical Investigation of Aloe Turkanensis for Anticancer Activity

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Phytochemical Investigation of Aloe Turkanensis for Anticancer Activity UNIVERSITY OF NAIROBI COLLEGE OF BIOLOGICAL AND PHYSICAL SCIENCES DEPARTMENT OF CHEMISTRY PHYTOCHEMICAL INVESTIGATION OF ALOE TURKANENSIS FOR ANTICANCER ACTIVITY BY FOZIA ALI ADEM RESEARCH THESIS SUBMITED IN PARTIAL FULFILMENT FOR THE REQUIREMENTS FOR THE AWARD OF DEGREE OF MASTER OF SCIENCE IN CHEMISTRY OF THE UNIVERSITY OF NAIROBI MAY 2014 i ABSTRACT Cancer cases are on the increase all over the world including Sub-Saharan countries. In the search for new anticancer drugs, nature remains an excellent source of lead compounds. Among various classes of natural compounds quinones are well known for their anticancer activities some being drugs (e.g. daunomycin and doxorubicin). The genus Aloe including Aloe turkanensis is a rich source of quinones. The dried and ground rhizomes and leaves of Aloe turkanensis were exhaustively extracted with dichloromethane/methanol (1:1) by cold percolation. The crude extracts exerted cytotoxic activity against human extra hepatic bile duct cancer cell line (TFK-1) by showing significant reduction in cell viability. The crude extracts were then subjected to chromatographic separations on silica gel, Sephadex LH-20 and preparative TLC, which resulted in the isolation of twelve compounds. The structures of the isolated compounds were determined using spectroscopic methods including UV, 1H and 13C NMR, COSY, NOESY, HMBC and HSQC. These compounds were two naphthoquinones [3,5,8-trihydroxy-2-methylnaphthalene-1,4-dione (1) and 5,8-dihydroxy-3-methoxy-2-methylnaphthalene-1,4-dione (2)], seven anthraquinones [chrysophanol (3), aloesaponarin I (4), aloesaponarin II (5), laccaic acid D methyl ester (6) helminthosporin (8) aloe-emodin (10) and α-L-11-O-rhamnopyranosylaloe-emodin (11)], a preanthraquinone [aloesaponol I (7)] a pyrone derivative [feralolide (9)] and a benzoic acid derivative [3,4-dihydroxybenzoic acid (12)]. The naphthoquinones [3,5,8-trihydroxy-2- methylnaphthalene-1,4-dione (1) and 5,8-dihydroxy-2-methoxy-2-methylnaphthalene-1,4-dione (2)] is here reported for the second time from the genus Aloe. Furthermore, 3,5,8-trihydroxy-2- methylnaphthalene-1,4-dione (1) is reported here for the first time from the family Asphodelaceae. The in-vitro anticancer activities of the isolated compounds were conducted against the human extra hepatic bile duct carcinoma (TFK-1) and liver (HuH7) cancer cell lines. Based on the 3- [4,5-dimethylthiazol-2-yl]-2-,5-diphenyltetrazolium bromide (MTT) assay, the anthraquinone aloe-emodin (10) and the naphthoquinone 5,8-dihydroxy-3-methoxy-2-methylnaphthalene-1,4- dione (2) exhibited high inhibition against TFK-1 cell lines with IC50 values of 6.0 and 15.0 µg/mL (in TFK-1 cells) and 31 and 20 µg/mL (in HuH7 cell line), respectively. The pre- anthraquinone aloesaponol I (7) inhibited the growth of TFK-1 cells with IC50 values of 10.0 µg/mL, and with 88.0 µg/mL against the HuH7 cells. The aloe-emodin glycoside, α-L-11-O- rhamnopyranosylaloe-emodin (11) and the anthraquinone aloesaponarin II (4) inhibited viability of TKF-1 cell line with IC50 values of 23.0 µg/mL and 34.0 µg/mL, respectively; and with IC50 values of 47.0 µg/mL and 55.0 µg/mL in HuH7 cell lines, respectively. Helminthosporin (8) also significantly inhibited the growth of TFK-1 cells with IC50 values of 46.0 µg/mL but did not inhibit the HuH7 cells at the tested concentrations. This is the first report on the anticancer activity of the isolated compounds against extra hepatic bile duct (TFK-1) and liver (HuH7) cancer cell lines. Further investigation on normal cell lines and their mechanism of action has to be estsblished before the potential of these compounds as anticancer drugs can be established. ii OH O O CH3 OH O OR H3CO CH 3 HO OH OH O 7 1 R = H 2 R = CH 3 R2 O R1 R6 R5 R4 R3 O 1 2 4 3 5 6 1 2 3 4 5 6 3 R = R = OH, R = CH3, R = R = R = H 8 R = R = R = OH, R = CH3, R = R = H R1 = R5 = OH, R2 = CH , R3 = R4 = R6 = H 1 2 3 5 6 4 4 3 10 R = R = OH, R = R = R = H, R = CH2OH 1 5 2 3 4 6 5 R = R = OH, R = CH3, R = R = H, R = COOCH3 1 2 3 5 6 4 11 R = R = OH, R = R = R = H, R = CH2ORham 1 4 5 2 3 6 6 R = R = R = OH, R = CH3, R = H, R = COOCH3 O OH O CH3 OH OH OO HO HO OH OH 12 9 iii DEDICATION This thesis is dedicated to my brother, Kedir Ali Adem. I also dedicate this thesis to my memory at Saarland University, Germany. vii ACKNOWLEDGEMENTS In the name of Allah, the most gracious, benevolent and merciful who gave me the courage, good health and potency with his handful blessing to complete this thesis. I am so grateful to German Academic Exchange Service (DAAD) through the Natural Products Research Network for Eastern and Central Africa (NAPRECA) for the scholarship which enabled me to undertake MSc studies at the University of Nairobi and also research visit to the University of Saarland, Germany. I would like to express my gratitude to my supervisors, Professor Abiy Yenesew, Dr. John M. Wanjohi and Dr. Amir O. Yusuf of the Department of Chemistry, University of Nairobi for their advice, guidance and encouragement. Special thank goes to Professor Abiy Yenesew for his insightful guidance and supervision throughout my research. I would also like to thank Prof. Alexandra K. Kiemer, Saarland University, Germany, for hosting me for research visits to conduct part of my research in her laboratory. I also thank Dr. Sonja Kessler and Dr. Joseph Zapp for their advice during my stay in Germany. I also appreciate Dr. Matthias Heydenreich, University of Potsdam, Germany for high resolution NMR analyses. I do hereby thank fellow students, labmates and the staff at Department of Chemistry, University of Nairobi, for their assistance and support in many ways. In particular, I am grateful to Dr. Solomon Deresse and Dr. Albert Ndakala for their help in my research and for shaping my academic career. Finally, my special thanks goes to my parents, my brothers, my sisters and Seid for their consistent support and encouragement that helped me to complete my studies. I love you all! viii TABLE OF CONTENTS ABSTRACT ............................................................................................................................... i ACKNOWLEDGEMENTS..................................................................................................... viii LIST OF TABLES ................................................................................................................... xii LIST OF APPENDICES ......................................................................................................... xiii LIST OF ABBREVIATIONS...................................................................................................xiv CHAPTER ONE .........................................................................................................................1 INTRODUCTION ......................................................................................................................1 1.1. Background of the study ...............................................................................................1 1.2. Statement of the Problem ..............................................................................................4 1.3. General objective ..........................................................................................................5 1.4. Specific objectives ........................................................................................................5 1.5. Justification ...................................................................................................................5 CHAPTER TWO ........................................................................................................................6 LITERATURE REVIEW ............................................................................................................6 2.1. The Cancer Problem......................................................................................................6 2.1.1. Hepatocellular cancer (HCC) .................................................................................6 2.1.2. Extra hepatic bile duct cancer (EBDC) ..................................................................8 2.2. Cancer Treatment ........................................................................................................ 10 2.2.1. Cancer chemotherapy ........................................................................................... 10 2.2.1.1. Anticancer drugs from higher plants .................................................................... 11 2.3. Botanical Information on the Genus Aloe .................................................................... 15 2.3.2. The subfamily Alooideae ..................................................................................... 16 2.3.3. The genus Aloe .................................................................................................... 16 2.3.4. Aloe turkanensis................................................................................................... 17 2.4. Uses of Aloe ................................................................................................................ 18 2.5. Phytochemical Information on Aloe Species ................................................................ 19 2.5.1. Anthraquinones of Aloe .............................................................................................. 19 2.5.2. Pre-anthraquinones of Aloe ..................................................................................... 21 2.5.3. Anthrones of Aloe ...................................................................................................
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