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I ANTIPLASMODIAL COMPOUNDS from GHANAIAN MEDICINAL PLANTS a Thesis Submitted in Fulfilment of the Requirements for the Degree Of

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I ANTIPLASMODIAL COMPOUNDS from GHANAIAN MEDICINAL PLANTS a Thesis Submitted in Fulfilment of the Requirements for the Degree Of ANTIPLASMODIAL COMPOUNDS FROM GHANAIAN MEDICINAL PLANTS A Thesis submitted in fulfilment of the requirements for the degree of DOCTOR OF PHILOSOPHY (Pharmacognosy) The Department of Pharmacognosy, Faculty of Pharmacy and Pharmaceutical Sciences Kwame Nkrumah University of Science and Technology, Kumasi, Ghana By GUSTAV KOMLAGA [B. Pharm (Hons); M.Pharm (Pharmacognosy)] December 2015 i DECLARATION I hereby declare that this submission is my own work towards the PhD and that, to the best of my knowledge, it contains no material previously published by another person or material which has been accepted for the award of any other degree of the university, except where due acknowledgement has been made in the text. Gustav Komlaga ….……………… ……………….. (PG 6958611) Signature Date Certified by: Dr. (Mrs) Rita A. Dickson …………………… …..………………… (Supervisor, KNUST) Signature Date Certified by: Professor Philippe M. Loiseau 20 nov. 2015 (Thesis Director, Université Paris Sud) Signature Date Certified by: Professor MLK Mensah ……………………… ……………………….. (Supervisor, KNUST) Signature Date Professor A. Y Mensah …………………… …………………… (Head of Dept, Pharmacognosy, KNUST) Signature Date ii DEDICATION To my Lord, my Counsellor and my closest friend, Jesus Christ, the author and finisher of my faith whose grace and mercies saw me through this study. To my loving wife and friend, Mrs Grace Yayra Komlaga and my children, Eyram Jessica Kpodua Komlaga and Elikem Gustav Komlaga. To my dear sister, Joyce Komlaga, and my mother, Madam Adeline Komlaga of blessed memory. iii ABSTRACT IN ENGLISH Malaria is a major public health challenge in Ghana, and many indigenes employ medicinal plants, beside orthodox medicines, to treat the disease. An ethnobotanical survey was performed in the Bosomtwi and Sekyere East Districts of Ghana to identify plants used locally to manage malaria. This was done in comparison with the plant ingredients in marketed herbal antimalarial remedies in the Kumasi metropolis. The survey inventoried ninety-eight (98) plant species; twelve (12; 12.2%) reported for the first time globally, and twenty (20; 20.4%) others for the first time in Ghana for the treatment of malaria. Twenty-three (23) locally available finished, often multi/polyherbal antimalarial products examined contained aerial or underground parts of twenty-nine (29) of the plants cited in the survey as ingredients. Twenty-two (22) of these products were registered by the Ghana Food and Drugs Authority; four (4) were included in the Ghana Health Service recommended herbal medicine list for treating malaria in Ghana. The aqueous as well as serially extracted organic solvents (petroleum ether, ethyl acetate, and methanol) extracts of five plants parts, selected based on their importance in the traditional treatment of malaria and lack of the appropriate data in the literature, were studied against the chloroquine-sensitive 3D7 and chloroquine-resistant W2 P. falciparum parasite in vitro. The plant materials included the whole of Phyllanthus fraternus, leaves of Tectona grandis, Terminalia ivorensis and Bambusa vulgaris, and root of Senna siamea. All the aqueous extracts showed notable antiplasmodial activity (IC50 < 10 µg/mL), except that of S. siamea, against 3D7 P. falciparum. Only T. ivorensis and S. siamea extracts showed activity against W2 P. falciparum (IC50 < 50 µg/mL). The extracts demonstrated high selectivity index (SI) for 3D7 P. falciparum (SI > 3.5) but very low SI for W2 P. falciparum. Resistance index (RI) was largely under 20. The organic fractions were equally active (IC50 < 50 µg/mL; 3D7 P. falciparum). The methanol extracts of the two most potent plant materials, the whole of P. fraternus and leaf of B. vulgaris, were subjected to phytochemical study to isolate and elucidate the chemical constituents, which were then assayed for antiplasmodial activity. The phytochemical study of the iv methanol extract of P. fraternus yielded six compounds; Pf 1 to Pf 6 identified as the lignan, phyllanthin, and five securinega alkaloids namely nirurine, ent-norsecurinine, allo-norsecurinine, bubbialine and epibubbialine. This is the first isolation of allo - norsecurinine from a natural source and bubbialine from the Phyllanthus genus. The compounds displayed significant antiplasmodial activity against both 3D7 and W2 P. falciparum (1.14 ± 0.32 µM ≤ IC50 ≤ 59.00 ± 5.43 µM); ent-norsecurinine being the most active (IC50=1.14± 0.32 µM) and against the W2 P. falciparum. Only Pf2 (nirurine) and Pf1 (phyllanthin) displayed cytotoxicity (CC50 < 100 μM; HUVECs). This is the first report of the antiplasmodial activity of these compounds. Similar study of the methanol extract of B. vulgaris yielded 6 compounds, Bv1 to Bv6, identified as p-coumaric acid [(E)-3-(4-hydroxyphenyl) acrylic acid], cinnamic acid, dehydrovomifoliol [(E)-4-hydroxy-3,5,5-trimethyl-4-(3-oxobut-1-en-1-yl)cyclohex- 2-en-1-one], 3-oxo-α-ionol [9-hydroxy megastigma-4, 7-dien-3-one], loliolide [6- hydroxy-4, 4, 7a-trimethyl-5, 6, 7, 7a-tetrahydrobenzofuran-2(4H)-one] and tricin [5,7,4’-trihydroxy-3’,5’-dimethoxyflavone]. The six compounds are the first ever- reported isolations from B. vulgaris. All the compounds from B. vulgaris displayed significant activity against 3D7 (IC50 < 5 μΜ and W2 strains of P. falciparum (IC50 < 7 μM). Bv1 (p-coumaric acid) was the most active against 3D7 P. falciparum (IC50: 0.84 ± 0.90 μM) and Bv2 (cinnamic acid) the most active against W2 P. falciparum (IC50: 1.41 ± 0.38 μM). The compounds displayed no cytotoxicity (CC50 > 100 μM; HUVECs). This is the first report of the antiplasmodial activity of the six compounds. These twelve (12) compounds with remarkable antiplasmodial activity add to the library of natural compounds with antiplasmodial activity. This study has illustrated the potentials of Ghanaian medicinal plants as source of natural antiplasmodial compounds, and has justified the use of the plants in traditional treatment of malaria. v ACKNOWLEDGMENTS I give thanks, praise, glory, honour, and adoration to God Almighty for his enabling grace that saw me through this study. I am very grateful to the French Embassy in Ghana for the scholarship, to Misses Soleansky Stéphanie and Nina Amah of the embassy for facilitating my trips to and from Paris. Special thanks to the staff of Campus France for their support while in France. I am very thankful to KNUST for granting me the study leave. I am indebted to the Vice Chancellor of KNUST, Professor William Otoo Ellis, the Provost of the College of Health Sciences, Professor Tsri Agbenyega, the Dean of the Faculty of Pharmacy and Pharmaceutical Sciences, Professor Charles Ansah, for their special support. I am profoundly grateful to my thesis director at Université Paris Sud, Professor Philippe M. Loiseau, for his help especially for finding a pharmacognosy laboratory and pharmacognosy supervisor in France for me. My heartfelt appreciation to Professor Pierre Champy, my pharmacognosy supervisor at the Université Paris Sud for ensuring my work at his laboratory was without hitches and for his helpful criticisms and insightful suggestions, which greatly contributed to this work. I am grateful to Dr Sandrine Cojean of Paris Sud, for the supervision of the antiplasmodial study and her personal involvement in the experiments. I also thank my supervisors at KNUST, Kumasi, Ghana; Dr Rita A. Dickson for her valuable guidance throughout this study and Professor Merlin L.K. Mensah for his time, patience, helpful criticisms, and suggestions, which greatly contributed to the accomplishment of this study. I acknowledge Professor Bruno Figadère, the Head of BioSCIS research unit, Paris Sud, for his cordiality during the study. Thanks to Mr Sylvain Connan formerly of Maison Francaise, KNUST for linking me to Philippe for the collaboration. To Dr Ahmed- Mehdi Beniddir, I am highly indebted for his indispensable assistance. My vi appreciations to Karine Leblanc and Jean-Christophe Jullian for running the spectroscopies of the isolated compounds. I acknowledge Dr Joel Dade of Université Félix Houphouët Boigny, Côte d’Ivoire for his help in the structural elucidation of the isolated compounds. I want to make a special mention of Drs Lauran Evano, Lauran Ferrie of Laboratoire Chemie naturelle substance therapeutique (BioSCIS) and Sebastien Pomel and Vanessa Le Moal of the Antiparasitic Chemotherapy Laboratory (BioSCIS) not forgetting Adams, David, Long, Aminata, Soulaf Suyyagh-Albouz and indeed all colleagues in the BioSCIS unit for always being at hand to help. I am very thankful to Dr Christian Agyare with whom this project topic was initiated. Thanks to Mrs Helena Owusu-Ansah of the Department of Pharmacogonsy for her help. To all my friends who kept on encouraging me throughout this study, I am grateful. Finally, I am so grateful to my wife, Mrs Grace Yayra Komlaga and my children, Eyram Jessica Kpodua Komlaga and Elikem Gustav Komlaga for their support, not forgetting my sister Joyce Komlaga in Germany for her constant financial support throughout this study. vii TABLE OF CONTENTS DECLARATION ......................................................................................................... ii DEDICATION ............................................................................................................ iii ABSTRACT IN ENGLISH ........................................................................................ iv ACKNOWLEDGMENTS .......................................................................................... vi TABLE OF CONTENTS
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