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Phytochemical Constituents and Some Biological

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Phytochemical Constituents and Some Biological KWAME NKRUMAH UNIVERSITY OF SCIENCE AND TECHNOLOGY COLLEGE OF HEALTH SCIENCES FACULTY OF PHARMACY AND PHARMACEUTICAL SCIENCES DEPARTMENT OF PHARMACOGNOSY PHYTOCHEMICAL CONSTITUENTS AND SOME BIOLOGICAL ACTIVITIES OF SELECTED MEDICINAL PLANTS FROM GHANA BY EVELYN AFUA MIREKU SEPTEMBER 2016 PHYTOCHEMICAL CONSTITUENTS AND SOME BIOLOGICAL ACTIVITIES OF SELECTED MEDICINAL PLANTS FROM GHANA A Thesis Submitted in fulfilment of the requirement for the degree of DOCTOR OF PHILOSOPHY To the Department of Pharmacognosy Faculty of Pharmacy and Pharmaceutical Sciences College of Health Sciences Kwame Nkrumah University of Science and Technology By EVELYN AFUA MIREKU September 2016 DECLARATION I declare that this thesis is my own work. I further declare that to the best of my knowledge, this thesis does not contain any material previously published by any person or any material which has been accepted for the award of any degree of a university, except where due acknowledgement has been made in the text. ………………………….. ………………………… Evelyn Afua Mireku (PhD Candidate PG7865512) Date .......................................... ………………………… Professor Abraham Yeboah Mensah Date (Supervisor) ………………………… ……………………….. Professor Merlin L. K. Mensah Date (Supervisor) .......................................... ………………………... (Head of Department) Date ii ABSTRACT In this study, three Ghanaian medicinal plants namely, Anopyxis klaineana (Pierre) Engl. (Rhizophoraceae), Hexalobus monopetalus (A. Rich.) Engl. & Diels (Annonaceae) and Landolphia heudelotti A. DC. (Apocynaceae), were investigated for some of their biological activities and phytochemical constituents. The methanol and ethyl acetate fractions of A. klaineana stem bark at 300 mg/kg inhibited peak inflammatory responses and total paw oedema by 62.40 ± 6.32 % and 49.10 ± 10.31 % respectively in the carrageenan induced paw oedema assay. The total phenolic content and antioxidant capacity of the crude methanol extract were determined to be 110.21 ± 10.15 mg/g (tannic acid equivalent) and 110.6 ± 11.15 mg/g (ascorbic acid equivalent) respectively. The extract also scavenged DPPH free radicals with IC50 of 2.71 ± 0.21 µg/mL. The ethyl acetate fraction showed antimicrobial activity against Staphylococcus aureus and Streptococcus pyogens with MIC of 312 µg/mL. The ethyl acetate fraction of H. monopetalus exhibited antimicrobial activity against S. pyogens and Bacillus subtilis with MIC of 312 µg/mL. The crude methanol extract was found to have a total phenolic content of 66.19 ± 21.15 mg/g (tannic acid equivalent) and scavenged DPPH free radicals with IC50 of 10.1 ± 1.26 µg/mL. The total antioxidant capacity was determined to be 77.1 ± 14.15 mg/g (ascorbic acid equivalent). The methanol fraction of L. heudelotti roots exhibited antimicrobial activity against S. pyogens and B. subtilis at 312 µg/mL. The total phenolic content and antioxidant capacity of the methanol extract were determined to be 98.14 ± 14.70 mg/g (tannic acid equivalent) and 108.8 ± 14.52 mg/g (ascorbic acid equivalent) respectively. The crude extract scavenged DPPH radicals with IC50 of 6.95 ± 0.81 µg/mL. Phytochemical investigation of A. klaineana stem bark led to the isolation and characterization of six limonoids, five tirucallane triterpenes and one protolimonoid. iii Methyl angolensate and 3,23-dioxotirucalla-7,24-diene-21-oic acid exhibited significant competitive PGE2 binding inhibition with IC50s of 10.23 μM and 3.63 μM respectively. Most of the isolated compounds also demonstrated significant DPPH free radical scavenging property. From the stem bark of H. monopetalus, seven novel and two known prenylated indole alkaloids were isolated. These compounds are useful chemotaxonomic markers for the genus Hexalobus and closely related genera. From the roots of L. heudelotti, fourteen known compounds including neolignans, lignan, sesquilignans, an aromadendrane and a coumarin were isolated. The compounds showed DPPH radical scavenging and antimicrobial activity at concentration range between 12.5 and 100 µg/mL. The findings of this study have given some scientific justification to the uses of the selected medicinal plants in traditional medicine. iv DEDICATION I dedicate this thesis to my father, Dr. Emmanuel Kwasi Mireku and mother, Mrs. Philomina Mireku for their unfailing love, prayers and support throughout my PhD study. v ACKNOWLEDGEMENT Praise be to God Almighty for his gifts of life and purpose. I would like to express my deepest gratitude to my supervisors Prof. Abraham Yeboah Mensah (Department of Pharmacognosy, FPPS, KNUST) and Prof. Merlin L. K. Mensah (Department of Herbal Medicine, FPPS, KNUST) for their suggestions, critical reviews, fatherly advice and continuous support during my PhD research. My sincere appreciation goes to my German host supervisor, Prof. Dr. Dr. h. c. Michael Spiteller for granting me the opportunity to further my PhD research at the Institute of Environmental Research (INFU), Faculty of Chemistry and Chemical Biology, University of Technology, Dortmund, Germany. I am grateful for his guidance and scientific discussions which ensured an efficient output of my 2-year research stay. I thank Dr. Souvik Kusari, Dr. Sebastian Zühlke and Dr. Ferdiannd Talontsi for their guidance and excellent comments. I am also very grateful to Dr. Solomon Habtermariam (Pharmacognosy Research Laboratory, Faculty of Engineering Science, University of Greenwich, United Kingdom) for assisting in running of the NMR spectra for some of my compounds. I thank the technical staff of the Departments of Pharmacognosy, Pharmacology and Pharmaceutics, Faculty of Pharmacy and Pharmaceutical Sciences, KNUST and the technical staff of INFU, TU- Dortmund, for the assistance offered me in all experiments carried out at their respective laboratories. I also thank Mr. Clifford Kofi Asare, for his assistance in the collection of the plants for this research. I appreciate the encouragement and support of friends and colleagues throughout the period of this research. vi I gratefully acknowledge the German Academic Exchange Program (DAAD) for the ‗sandwich‘ doctoral scholarship. I express my deep thanks to my family for their unconditional support, prayers and love. God bless you. vii TABLE OF CONTENT DECLARATION ........................................................................................................... ii ABSTRACT ................................................................................................................. iii DEDICATION ............................................................................................................... v ACKNOWLEDGEMENT ............................................................................................ vi TABLE OF CONTENT ............................................................................................. viii LIST OF FIGURES ..................................................................................................... xii LIST OF TABLES ....................................................................................................... xv LIST OF EQUATIONS ............................................................................................. xvii ABBREVIATIONS ................................................................................................. xviii CHAPTER 1 .................................................................................................................. 1 INTRODUCTION ......................................................................................................... 1 1.1 Background of study: Natural products in drug discovery ...................................... 1 1.2 Problem statement .................................................................................................... 4 1.2.1 Infectious diseases and antimicrobial resistance ............................................... 4 1.2.2 Inflammatory diseases and challenges with anti-inflammatory therapy ........... 5 1.3 Research Aim ........................................................................................................... 6 1.3.1 Specific Objectives ........................................................................................... 6 1.4 Justification .............................................................................................................. 6 1.5 Scope of Work ......................................................................................................... 8 1.6 Limitation ................................................................................................................. 9 CHAPTER 2 ................................................................................................................ 10 LITERATURE REVIEW ............................................................................................ 10 2.1 Inflammation .......................................................................................................... 10 2.1.1 Oxidative stress and inflammation .................................................................. 13 2.2 Anti-inflammatory agents from plant sources ....................................................... 14 2.3 Anti-inflammatory screening methods .................................................................. 17 2.3.1 Carrageenan–induced paw oedema assay ....................................................... 18 2.3.2 Modified prostaglandin E2 (PGE2) competitive inhibition assay ................... 19 2.4 Antioxidant screening methods .............................................................................
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