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Identification of Antimalarial and Larvicidal Compounds

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Identification of Antimalarial and Larvicidal Compounds IDENTIFICATION OF ANTIMALARIAL AND LARVICIDAL COMPOUNDS FROM Trichilia megalantha HARMS AND Trichilia welwitschii C.D.C. (MELIACEAE) BY DORCAS ADENIKE FADARE (MATRIC NO. 58575) B.Sc. (Hons) Chem, MSc. (InOrg. Chem.), M.Phil. Pharmacogosy (UI) A thesis in the Department of Pharmacognosy Submitted to the Faculty of Pharmacy, University of Ibadan in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY (Ph.D) OF THE UNIVERSITY OF IBADAN, IBADAN March, 2017 i ABSTRACT Malaria is the second leading cause of death from infectious diseases in Africa. The global burden of malaria is increasing due to drug-resistant parasites and insecticide- resistant mosquitoes. Meliaceae has been known to possess antimalarial, larvicidal and other properties but many Nigerian Trichilia species have not been investigated. Thus there is dearth of information on the antimalarial and larvicidal activities of Trichilia megalantha (TM) and Trichilia welwitschii (TW). Therefore, this study investigated the antimalarial and larvicidal activities of both plants. Leaf, stem bark and root of TM (FHI 109556) and TW (FHI 109557) were extracted by maceration in methanol. The extracts (100-800 mg/kg) were subjected to in vivo mouse- model 4-day suppressive antimalarial evaluation using Plasmodium berghei ANKA strain. Toxicity was determined in vivo in mice and in vitro using 3-(4, 5-dimethylthiazol- 2-yl)-2, 5-diphenyltetrazolium bromide (MTT) and brine shrimp lethality (BSL) assays. The larvicidal activities of extracts and compounds were evaluated on Anopheles gambiae larvae. Antioxidant activity was also investigated with 1, 1- diphenyl-2- picrylhydrazyl radical. Chloroquine, N, N-diethyl-3-methylbenzamide (DEET), gallic acid, doxorubicin and etopoxide were used as positive controls in the antimalarial, larvicidal, antioxidant, cytoxicity and BSL assays, respectively. Isolation of compounds was done using repeated column chromatography and high performance liquid chromatography. Structures of compounds were elucidated by spectroscopy (IR, UV, NMR and MS). Linear regression was used to determine 50% lethality concentration ii (LC50), 50% inhibitory concentration (IC50) and 50% cytotoxic concentration (CC50). Data were analysed using ANOVA and Student’s t-test at p = 0.05. The stem bark extract of TM had the highest chemo-suppression (100%) at 200 mg/kg in the antimalarial assay of the extracts tested against P. berghei berghei. The leaf of TW had 93.4% compared to chloroquine, which had 98.0%. In the larvicidal assay, the stem bark extract of TM was the most toxic, with an LC50 of 74.0 µg/mL, while DEET had 120.2 µg/mL. In the BSL assay, all the extracts were found to be non-toxic with LC50 > 1000 µg/mL as compared to etopoxide (7.46 µg/mL). The ethyl acetate fraction of TM stem bark showed antioxidant activity with IC50 of 25.37±1.46 µg/mL, while gallic acid had 23.44 ± 0.43 µg/mL. Both plant extracts did not produce any significant changes in haematological, biochemical, and histological parameters of animals used. Seven compounds were isolated from active extracts namely; Ursolic acid (1), lupeol (2), scopoletin (3), β- sitosterol (4), stigmasterol (5) and stigmastenone (6) from TM and 3,3′,4-tri-O- methyl ellagic acid (7) from TW. Ursolic acid, lupeol and scopoletin had chemo-suppression of 93.4%, 88.3% and 58.5%, respectively against P. berghei, while 3,3′,4-tri-O- methyl ellagic acid from TW had 75.8% chemosuppression. Lupeol from TM had the highest larvicidal activity on An. gambiae larvae with LC50 of 6.20 µg/mL. Ursolic acid from Trichilia megalantha and 3,3′,4-tri-O-methyl ellagic acid from Trichilia welwitschii exhibited antimalarial activity. Lupeol with larvicidal activity was obtained from Trichilia megalantha. These plants could provide lead for antimalarial drug discovery and development. iii Keywords: Malaria, Larvicidal compounds, Trichilia megalantha, Trichilia welwitschii. Word count: 483 iv CERTIFICATION I certify that this project was carried out by Fadare Dorcas Adenike in the Department of Pharmacognosy, Faculty of Pharmacy, University of Ibadan; under my supervision. Edith O. Ajaiyeoba, FAS B.Sc. (Hons) Chem, MSc. (Org. Chem.), PhD (Synthetic and Natural Product Chemistry) Professor Department of Pharmacognosy Faculty of Pharmacy University of Ibadan Ibadan v DEDICATION This thesis is dedicated to my beloved husband Dr. David Abimbola Fadare and to the memory of my mother Mrs. Bernice Monisola Oteyola vi ACKNOWLEDGEMENTS Firstly, I like to acknowledge the Lord Almighty for His faithfulness and the good health I enjoyed throughout the period of this research. These few lines are too short to express my deep appreciation to my supervisor, Prof. Edith O. Ajaiyeoba. She picked me up from the dung hill where I was abandoned and believed that I can make it when some felt I did not have the capability of a research work. I wish to thank her for her unflattering trust and constant encouragements which have been essential to my success throughout the period of the study. I am grateful for her patience, financial contributions, prayers, motivation, enthusiasm, her effort in understanding a student’s personality and her immense knowledge in the field of natural products chemistry. My pursuit into the world of science would not have been the same without Prof. Ajaiyeoba. It has been a distinct privilege for me to work with her. I am deeply indebted to her. I wish to acknowledge the Department of Pharmacognosy, University of Ibadan, for the opportunity of a research work. I hereby extend my thanks to the HOD and entire staff of the Department of Pharmacognosy for their contribution to the success of this research. I appreciate the efforts of Prof. O.G. Ademowo and Prof. Grace O. Gbotosho who permitted the use of their laboratories for animal study. Mrs. Victoria Thomas and Mrs. Braimoh, I hereby acknowledge your care and technical assistance. vii A depth of gratitude to Dr. Oyindamola O. Abiodun and Dr. Omonike O. Ogbole. You both were a source of inspiration to me. You were my friends and sisters, who shared all my joy and pain throughout the course of this program. Dr Woquan Sama Luma is hereby appreciated. I want to say a big thank you to Mr. J. O. Olayemi, Dr. O. A. Osiyemi, and all the members of Phytomedicine group, Department of Pharmacognosy headed by Prof Edith O. Ajaiyeoba, you were great. I am happy to be associated with you. I am also grateful to Dr. Nwozo Sarah, an angel who brought light into my dark path. Thank you for those words of encouragement and advice all through the course of the study. Prof. & Mrs O. Oluremi are highly appreciated. I appreciate the effort of my host, Prof. Iqbal Choudary and all members of Lab 212, HEJ, ICCBS, University of Karachi where isolation and characterization of compounds were carried out. My gratitude goes to my Pastors D. O. Omiyale, K.O. Moranti, and the entire members of Deeper Life Bible Church, University of Ibadan and Goodness Estate. Dr & Dr (Mrs) T.O. Ogundiran, Prof. & Dr.(Mrs) J.O. Babayemi, Dr & Dr (Mrs) P.A. Amosun, Prof. & Dr (Mrs) C.O. Agullana, Prof. & Dr (Mrs) O. Fagbola, Mr &Mrs. M.O.Oladokun and Dr. & Mrs J.S. Ashidi are highly appreciated for your prayers and financial assistance. Special thanks to a special friend, Mrs Oluwakemi Kehinde for all you have been. “Thank you” to all who stood by me in my temptations. To Mrs Alice Omiyale (Mama) for taking care of my children during my working hours I say “Thank you, ma”. viii My love and gratitude go to my brothers and sister; Mrs. Sola Ogunjobi, Mrs. Taiwo Ajetumobi, Mr. Kehinde Oteyola, Mr Gboyega Oteyola, Revd. (Dr.) Tope Oteyola and Mr. Lekan Oteyola for their support, prayers and encouragement. God will satisfy you all with good things. My heartfelt appreciation goes to my late parents; Mr J. A. Oteyola, for the foundation laid in my academic career and Mrs Monisola Oteyola, though not western educated, you always put our education as first priority in life. My unreserved appreciation goes to my loving husband, Dr. David Abimbola Fadare for your unconditional love, support and encouragement. You were patient to hear my frustrations, always believing that everything will soon be alright and that I could make it. Thank you for making everything I needed available. I also acknowledge my children, IniOluwa, EriOluwa and OgoOluwa, you are really blessings from the Lord. Obviously, I would not be sitting here typing these acknowledgements without the love and mercies of the Almighty God. You made all things possible at your own appointed time. There is no one like YOU. ix TABLE OF CONTENTS ABSTRACT ........................................................................................................................ ii CERTIFICATION .............................................................................................................. v DEDICATION ................................................................................................................... vi ACKNOWLEDGEMENTS .............................................................................................. vii TABLE OF CONTENTS .................................................................................................... x LIST OF FIGURES .......................................................................................................... xx LIST OF TABLES ......................................................................................................... xxiii ABBREVIATIONS .......................................................................................................
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