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Fatimah Temitayo Ishola B CHEMICAL COMPOSITION OF THE ESSENTIAL OILS OF FIVE FRUIT TREES AND NON-VOLATILE CONSTITUENTS OF Theobroma cacao L. POD-HUSK BY FATIMAH TEMITAYO ISHOLA B. Sc., M. Sc. (Ibadan) 116570 A Thesis in the Department of Chemistry, Submitted to the Faculty of Science in partial fulfillment of the requirements of the Degree of DOCTOR OF PHILOSOPHY of the UNIVERSITY OF IBADAN AUGUST, 2016 ABSTRACT Essential Oils (EOs) are volatile secondary metabolites characterised by a strong odour and widely used for pharmacological and industrial applications. There is dearth of information on chemical compositions and bioactivities of EOs of some fruit trees in Nigeria. This study was therefore designed to extract and characterise the EOs from selected fruit trees, screen the EOs for bioactivity as well as to isolate and characterise non-volatile constituents from Theobroma cacao L. pod-husk due to its availability. The plant samples (Carica papaya L., Theobroma cacao L., Persea americana M., Ananas comosus (L) Merr and Chrysophyllum albidum G. Don) were collected in Ibadan, identified and authenticated at the Herbarium of Forest Research Institute of Nigeria, Ibadan. Essential oils were extracted from the leaves, stem-barks, root-barks, fruits, peels, pod-husk and seeds of the plants using hydro-distillation method and analysed by Gas Chromatography (Flame Ionization Detector and Mass Spectrometry) techniques. The antibacterial activity of the EOs at 20 µg/mL was assayed on two Gram-positive and four Gram-negative bacteria using Microplate Alamar Blue Assay measured in UV/Visible spectrophotometer. The antioxidant activity of the EOs at 20 µg/mL was determined by radical scavenging procedure while insecticidal activity was evaluated by contact toxicity test using three grain pests. Pure compounds were isolated from methanol extract of T. cacao pod-husk by chromatographic techniques. The chemical structures of the compounds were elucidated using Infrared, Nuclear Magnetic Resonance and Mass Spectroscopic techniques. Data were analysed using descriptive statistics. Twenty-seven EOs were obtained and their yield ranged from 0.1 to 1.2% (v/w). The major components in P. americana EOs were β-caryophyllene (12.7%; leaf), tetradecanal (31.8%; root-bark), globulol (25.4%; peel), (Z,Z)-4,15-octadecadien-1-ol acetate (21.8%; seed), tetradecanal (24.9%; stem-bark) and p-xylene (40.5%; fruit). Carica papaya EOs mainly comprised benzylisothiocyanate (89.1%; seed), octadecanol (62.5%; root), octadecanol (71.1%; stem), m-xylene (35.1%; stem-bark), heptadecanol (25.2%; fruit), phytol (21.8%; leaf), benzylisothiocyanate (71.5%; root- bark) and 9-hexadecen-1-ol (16.9%; peel). P-xylene (62.4%; fruit), p-xylene (29.9%; shoot) and tetradecanoic acid (8.6%; peel) dominated A. comosus EOs. The principal constituents in T. cacao EOs were hexadecanoic acid (78.7%; leaf), o-xylene (53.3%; ii seed), ledol (33.6%; pod-husk) and β-bisabolol (17.3%; stem-bark). The dominant compounds in C. albidum EOs were m-xylene (66.7%; seed), p-xylene (21.4%; seed- bark), ethylhexadecanoate (19.9%; leaf), hexadecanoic acid (14.7%; stem-bark), m- xylene (53.1%; root-bark) and hexadecanoic acid (14.7%; fruit-bark). The chemical constituents for twenty-one of the EOs of the fruit plants were obtained for the first time ever. Theobroma cacao leaf EO exhibited the highest inhibition against Gram- negative bacteria at 78.6%, while P. americana fruit and peel EOs showed the highest inhibition against Gram-positive bacteria at 69.9%. Persea americana fruit and seed EOs displayed the highest and lowest radical scavenging activity at 42.1 and 1.2%, respectively. The EOs showed activity between 0 to 20% in insecticidal assay. Column chromatography of the methanol extract of T. cacao pod-husk yielded three known triterpenes: 24-hydroxy-9,19-cycloanost-25-en-3-one, stigmast-5-en-3β-ol and ergosta- 5α,8α-epidioxy-6,22-dien-3β-ol. The EOs have antibacterial and antioxidant properties which is indicative of their potential as sources of pharmaceuticals. Keywords: Fruit tree, Essential oils, Antibacterial activity, Triterpenes, Theobroma cacao L. Word count: 488 iii DEDICATION This research work is dedicated to: MY LOVING DAD & MUM A MESSAGE TO MY PARENTS You are one in a billion couples; For Parents like you are hard to come by If you don’t mind my saying it, I owe everything in my life to you And nothing to myself. Your examples of hardwork, honesty, Enthusiasm in others’ progress and kindness Encourage and spur me on To hope for the really worthwhile things in life. Your love inspires me. Your guidance and support saw me through The most trying periods of my life To be factual, the greatest blessing of my life Is that I have you as Parents. iv ACKNOWLEDGEMENTS My deep and sincere gratitude goes to my supervisors; Professor O. Ekundayo and Dr. Sherifat A. Aboaba for their thorough supervision, understanding and support that propelled the success of this work. I am very grateful to the Head of Department, Prof. A. A. Adesomoju and the entire staff of Chemistry Department for the knowledge imparted to me and for allowing me to use the facilities in the department during the course of my studies. I appreciate Dr. I. O. Oladosu and Dr. O. Adewuyi for their assistance and advise at every stage of this work. With a deep sense of gratitude, I acknowledge the Third World Academy of Science (TWAS) for the fellowship award which afforded me the opportunity to use spectroscopic instruments in laboratories at the International Centre for Chemical and Biological Sciences (ICCBS), University of Karachi, Karachi, Pakistan. Professor Iqbal Choudhary (my host supervisor) is greatly acknowledged, for granting me bench space in his laboratory for my doctoral research bench work. I also wish to acknowledge Professors Atta-Ur-Rahman and Nezhun Gören, Drs. Attiyah-tul-Wahab, Sammer Yousuf and Adhikari for their support during my research work in ICCBS. I also appreciate the period spent working together with Rida, Sheeba Wajid, Farah Ayaz, Hafsha, Seitimova, Mujeeb-ur-Rehman, Zehra, Saima, Mariam, Mr. Eltayeb, Hira, Osas, Joseph, Farah Mukhtar, Mr. Seun and Habiba of ICCBS. I pray for outstanding success in your research career. To my lab-mates in Organic Chemistry, Ini Ante, Kemi Alade, Yahaya Shokunbi, Sola Akande, Dupe Akoro, Odunayo Odule and Josiah Nkop, I appreciate the harmonious working relationship. The words of encouragement by Mrs. Victoria Aderionokun are also appreciated. My sincere appreciation goes to my parents, Mr. and Mrs. J. A. Ishola for building my academic career right from the beginning up to this level. You are jewel of inestimable value and I will cherish you all my life. To my sisters and brother; Mutma‘inah (my baby mama), Rodiyah and Muhammad Addy, thanks for sharing in my moment of joy and challenges, I love you all. I am greatly indebted to my friend, brother and husband; Olamedey. Thank you for all your support and understanding which made this dream come true. Your support, v advice and love were sources of inspiration that catalysed the success of this research. To our precious gift, Far‘ah, thank you for all the sacrifices which involve time I denied you in order to complete this work. I love you. I am most indebted to Almighty Allah for sparing my life to see the end of this programme and for His favour on me in years past and years to come To others that I did not mention, and have contributed one way or the other to the success of this work, I want to say a big thank you. Fatimah Temitayo ISHOLA August, 2016 vi CERTIFICATION We certify that this work was carried out under our supervision by FATIMAH TEMITAYO ISHOLA in the Department of Chemistry, Faculty of Science, University of Ibadan, Ibadan, Nigeria. ………………………………………………………………. Supervisor Professor Olusegun Ekundayo B.Sc. (Lagos), Ph.D. (London), FAS Professor of Organic Chemistry Department of Chemistry, University of Ibadan, Ibadan, Nigeria. ……………………………………………………………....... Co-Supervisor Dr. Sherifat A. Aboaba B.Sc., M.Sc., Ph.D (Ibadan) Department of Chemistry, University of Ibadan, Ibadan, Nigeria. vii TABLE OF CONTENTS CONTENT PAGES Title page i Abstract ii Dedication iv Acknowledgment vi Certification vii Table of contents viii List of Tables xii List of Figures xiv List of Schemes xvi CHAPTER ONE: INTRODUCTION 1 1.1 Fruits as nutraceuticals 1 1.2 Justification of the research 2 1.3 Research objectives 5 CHAPTER TWO: LITERATURE REVIEW 6 2.1 Chemical Constituents of Plants 6 2.2 Plant Secondary Metabolites 6 2.2.1 Alkaloids 7 2.2.2 Phenolic Compounds 8 2.2.3 Terpenoids 8 2.2.3.1 Biosynthesis of terpenoids 13 2.2.3.2 Pharmacological relevance of terpenoids 15 2.2.3 Steroids 19 2.2.4 Saponins 19 2.3 Extraction of Secondary Metabolites 21 2.3.1 Cold Method 21 2.3.1.1 Percolation 21 2.3.1.2 Maceration 21 2.3.2 Hot Method 22 2.4 Essential Oils 23 2.4.1 Extraction of Essential Oils 26 viii 2.4.1.1 Distillation 26 2.4.1.2 Hydro or water distillation 27 2.4.1.3 Steam Distillation 27 2.4.1.4 Direct steam distillation 29 2.4.1.5 Hydro diffusion 29 2.4.1.6 Liquid Carbon Dioxide Extraction Method 29 2.4.1.7 Expression 30 2.4.1.8 Solvent Extraction 30 2.4.1.9 Florasols Extraction 31 2.4.2 Analysis of Essential Oils 31 2.4.3 Identification of Essential Oil Components 32 2.4.3.1 Retention Time 32 2.4.3.2 Retention Indices 32 2.5 Isolation of Secondary Metabolites by Chromatographic Techniques 33 2.5.1 Thin Layer Chromatography 33 2.5.2 Column Chromatography 34 2.5.3 Gas Chromatography 34 2.5.4 High Performance Liquid Chromatography 35 2.6 Spectroscopic
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