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Bioassay Guided Phytochemical Studies on Resins of Some Commiphora Species

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Bioassay Guided Phytochemical Studies on Resins of Some Commiphora Species BIOASSAY GUIDED PHYTOCHEMICAL STUDIES ON RESINS OF SOME COMMIPHORA SPECIES BY WORKU DINKU AYANA OFFICE OF GRADUATE STUDIES ADAMA SCIENCE AND TECHNOLOGY UNIVERSITY NOVEMBER 2020 ADAMA, ETHIOPIA i BIOASSAY GUIDED PHYTOCHEMICAL STUDIES ON RESINS OF SOME COMMIPHORA SPECIES BY Worku Dinku Ayana Advisor: Aman Dekebo (Professor) A Dissertation Submitted to the Department of Applied Chemistry School of Applied Natural Sciences Office of Graduate Studies Adama Science and Technology University November, 2020 Adama, Ethiopia i APPROVAL SHEET Adama Science and Technology University School of Applied Natural Sciences Department of Applied Chemistry This is to certify that the thesis prepared by Worku Dinku Ayana, entitled: Bioassay Guided Phytochemical Studies on Resins of Some Commiphora Species, submitted in full fulfillment of the requirement of the degree of Doctor of Philosophy in Chemistry (Medicinal Chemistry stream) complies with the regulation of the University and meets the accepted standards with respect to originality and quality. Approved by the examining committee: Name Signature Date ________________________________ _____________ _____________ Name of Student ________________________________ _____________ _____________ Advisor ________________________________ _____________ _____________ External examiner 1 ________________________________ _____________ _____________ External examiner 2 ________________________________ _____________ _____________ Internal examiner ________________________________ _____________ _____________ Chair Person ________________________________ _____________ _____________ Head of Department ________________________________ _____________ _____________ School Dean ________________________________ _____________ _____________ Post graduate Dean ii DECLARATION I hereby, declare that the dissertation submitted for the degree of Doctor of Philosophy (PhD) in Medicinl Chemistry at Adama Science and Technology University, School of Applied Natural sciences. It is my own original work, and has not been submitted previously to any institution or higher education. All sources of materials used in this work have been accordingly, acknowledged. This work was done from March 2014 to June 2020 at the Department of Applied Chemistry, School of Applied Natural Science, Adama Science and Technology University and Korean Research Institute of Chemical and Technology, under the supervision of professor Aman Dekebo. iii TABLE OF CONTENTS DECLARATION.......................................................................................................................... iii LIST OF FIGURES ..................................................................................................................... ix LIST OF TABLES ....................................................................................................................... xi LIST OF ACRONYMS AND ABBREVIATIONS ................................................................. xiv ACKNOWLEDGEMENTS ..................................................................................................... xvii ABSTRACT .............................................................................................................................. xviii CHAPTER ONE ........................................................................................................................... 1 INTRODUCTION......................................................................................................................... 1 1.1 Statement of the research problem ........................................................................................ 3 1.2 Significance of the Study ...................................................................................................... 3 1.3 Scope of the research............................................................................................................. 4 1.4 Objective of the study ........................................................................................................... 4 1.4.1 General objective ............................................................................................................ 4 1.4.2 Specific objectives .......................................................................................................... 5 CHAPTER TWO .......................................................................................................................... 6 LITERATURE REVIEW ............................................................................................................ 6 2.1 Biological activity ................................................................................................................. 6 2.1.1 Inflammation .................................................................................................................. 6 2.1.2 Cancer ............................................................................................................................. 6 2.1.3 Influenza virus ................................................................................................................ 8 2.1.4 Dengue virus ................................................................................................................... 8 2.2 The family Burseraceae ......................................................................................................... 9 2.2.1 The genus Commiphora ................................................................................................... 10 2.2.2 Ethnobotany of Commiphora species .............................................................................. 11 iv 2.3 Chemical constituents and pharmacological activity of some Commiphora species ......... 12 2.3.1 Commiphora myrrha .................................................................................................... 13 2.3.2 Commiphora mukul (guggulu) ...................................................................................... 14 2.3.3 Commiphora erlangeriana ........................................................................................... 17 2.3.4 Commiphora kua .......................................................................................................... 18 2.3.5 Commiphora africana and C. habessinica ................................................................... 19 2.3.6 C. confusa, C. molmol, C. sphaerocarpa, C. holtziana and C. kataf............................ 20 2.4 Some Bioactive Phytosterols ............................................................................................... 25 2.5 Pharmacological activities of some triterpene acids ........................................................... 27 2.6 Biosynthesis of terpenoids, phytosterols and tricyclic triterpenoids ................................... 28 CHAPTER THREE .................................................................................................................... 31 MATERIALS AND METHODS ............................................................................................... 31 3.1 Plant collection and identification ....................................................................................... 31 3.2 Extraction and isolation ....................................................................................................... 31 3.2.1 Preparation of plant extracts and liquid-liquid partitioning .......................................... 31 3.2.2 Hydro-distillation of the resins ..................................................................................... 33 3.2.3 Chromatographic methods ............................................................................................ 33 3.2.3.1 Thin Layer Chromatography (TLC) ...................................................................... 33 3.2.3.2 Flash column chromatography (FCC) ................................................................... 33 3.2.3.3 Spray reagents used for detection .......................................................................... 35 3.3 Spectroscopic method ......................................................................................................... 35 3.3.1 Experimental Vibrational Circular Dichroism (VCD) spectra. .................................... 36 3.3.2 Computational study ..................................................................................................... 36 3.3.3 Mass spectrometry ........................................................................................................ 37 3.3.3.1 Elestrospray ionization (ESI) ................................................................................. 37 v 3.3.3.2 Clean IN-Phase multiplets for heteronuclear single quantum multiple bond correlation (CLIP-HSQMBC) ............................................................................... 38 3.3.4 GC-MS analysis ............................................................................................................ 38 3.4 Biological assays ................................................................................................................. 39 3.4.1 Anti-inflammatory assay .............................................................................................. 39 3.4.1.1 Cell culture and treatment ...................................................................................... 39 3.4.1.2 Measurement of nitric oxide (NO) production ...................................................... 39 3.4.1.3 Western blot analysis
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