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Addis Ababa University School of Graduate Studies Department of Chemistry ADDIS ABABA UNIVERSITY SCHOOL OF GRADUATE STUDIES DEPARTMENT OF CHEMISTRY Graduate Project (Chem.774) Phytochemical Investigation On The Root of Rumex Abyssinicus (Makmako) By Bizuayehu Zinaye Advisor: Dr. Ashebir Fiseha In Partial Fulfillment of the Requirements for Master of Science Degree in Chemistry July 2008 PHYTOCHEMICAL INVESTIGATION ON THE ROOT OF RUMEX ABYSSINICUS (MAKMAKO) A GRADUATE PROJECT SUBMITTED TO THE OFFICE OF RESEARCH AND GRADUATE PROGRAMME OF ADDIS ABABA UNIVERSITY IN PARTIAL FULFILMENT OF THE REQUIREMENTS FOR THE DEGREE OF MASTER OF SCIENCE IN CHEMISTRY BY BIZUAYEHU ZINAYE JULY, 2000 ii ADDIS ABABA UNIVERSTY SCHOOL OF GRADUATE STUDIES PHYTOCHEMICAL INVESTIGATION ON THE ROOT OF RUMEX ABYSSINICUS (MAKMAKO) BY BIZUAYEHU ZINAYE DEPARTMENT OF CHEMISTRY SCIENCE FACULTY JULY, 2008 APPROVED BY THE EXAMINING BOARD: Dr. Ashebir Fiseha ___________________________ Advisor Prof. Ermias Dagne ____________________________ Examiner Prof. Wendimagegn Mammo ____________________________ Examiner Dr. Gizachew Alemayehu _______________________________ Examiner iii Acknowledgement I express my sincere gratitude and appreciation for my project advisor Dr. Ashebir Fiseha for taking immense interest and permitting me to freely interact with him for his advice and suggestions related to this project work. I would like to express my warm thanks to Prof. Wandimagegn Mammo who extends his tremendous support, encouragement and running NMR Spectroscopic data for this project work. I also owe a deep sense of gratitude to my wife Nigiste Teshome who shouldered alone the burdens of family responsibility, which enable me to concentrate on my study, and this project always it remains with me live her and our children whole hearted cooperation support and best wishes through out my study I would also like to express my deepest appreciation to my brother Tadesse Zinaye and his family for the encouragement and advice they gave me during my stay in the university. I am also grateful to all academic staff and technical assistant of chemistry department of, Addis Ababa University. iv Table of Contents Content Page ACKNOWLEDGEMENT -------------------------------------------------------------------------i TABLE OF CONTENTS---------------------------------------------------------------------------ii LIST OF TABLES ---------------------------------------------------------------------------------iv LJST OF SCHEMES --------------------------------------------------------------------------------v LIST OF FIGURES ---------------------------------------------------------------------------------v ABSTRACT------------------------------------------------------------------------------------------vi 1. INTRODUTION----------------------------------------------------------------------------------1 1.1 General-------------------------------------------------------------------------------------------1 1.2. Rumex Abyssinicus and its medicinal Use-------------------------------------------------2 2. ANTHRAQUINONES--------------------------------------------------------------------------3 2.1. Chemical Investigation-----------------------------------------------------------------------3 2.2. IDENTIFICATION OF ANTHRAQUINONES-----------------------------------------5 2.2.1. Color reactions----------------------------------------------------------------------------5 2.2.2. UV- Vis Spectra--------------------------------------------------------------------------5 2.2.3. IR-Spectra----------------------------------------------------------------------------------6 v 2.2.4. NMR Spectra-------------------------------------------------------------------------------7 2.3. BIOSYNTHESIS OF ANTHRAQUINONES---------------------------------------------8 3. RUMEX ABYSSINICUS ----------------------------------------------------------------------11 3.1. Botanical Background-----------------------------------------------------------------------11 3.2. Secondary Metabolites from Rumex Abyssinicus ---------------------------------------11 4. OBJECTIVE OF THE STUDY---------------------------------------------------------------12 5. RESULT AND DISCUSSION ---------------------------------------------------------------12 5.1. Characterization of compound (4)--------------------------------------------------------14 5.2. Characterization of compound (5)--------------------------------------------------------21 6. EXPERMENTAL -----------------------------------------------------------------------------24 6.1. General --------------------------------------------------------------------------------------24 6.2. Plant Martial---------------------------------------------------------------------------------25 6.3. Extraction and Isolation-------------------------------------------------------------------25 6.4. Spectral data -------------------------------------------------------------------------------27 7. CONCLUSION--------------------------------------------------------------------------------28 vi 8. REFERANCES--------------------------------------------------------------------------------29 9. APPENDIX------------------------------------------------------------------------------------32 LIST OF TABLES Table 1: Carbonyl absorption frequency of hydroxylanthraquinone -------------------------6 Table 2: Peak multiplicity pattern of anthraquinone---------------------------------------------8 Table 3: Anthraquinones extracted from Rumex abyssinicus--------------------------------11 1 Table 4: Comparison of the observed H NMR (400 MHz, CDCl3) spectral data of Compound (4) with the reported value of Chrysophanol --------------------------15 Table 5: Proton decupled 13C NMR and DEPT (400MHZ, CDCl3) spectral data of Compound (4)----------------------------------------------------------------------------16 Table 6: 13C NMR (DEPT) and HSQC spectral data of compound (4) ---------------18 Table 7: Observed correlation in HMBC spectral data of Compoundp(4)----------18 Table 8: Comparison of the observed 1H NMR spectral data of Compound (5) with the reported value of Emodin ---------------------------------------------------------------22 Table 9: Comparison of the observed 13C NMR spectral data (400MHZ, DMSO- d6) Compound (5) and Emodin -------------------------------------------------23 vii LIST OF SCHEMES Scheme 1: Biosynthesis of anthraquinone via acetate path way------------------------10 Scheme 2: Method of extraction of the plant material------------------------------------13 LIST OF FIGURES Figure 1: Partial structure of ring A of compound (4)-------------------------------------15 Figure 2: Partial structure of ring C of compound (4)-------------------------------------19 Figure 3: HMBC correlation of compound (4)---------------------------------------------20 Figure 4: Structure of Chrysophanol (4)----------------------------------------------------21 Figure 5: Structure of Emodin (5)------------------------------------------------------------22 viii ABSTRACT PHYTOCHEMICAL INVESTIGATION ON THE ROOT OF RUMEX ABYSSINICUS By: Bizuayehu Zinaye Advisor.Dr. Ashebir Fiseha The n-hexane: ethylacetate (7:3) extract of Rumex abyssinicus afforded two known anthraquinone, chrysophanol and Emodin. The root of rumex abyssinicus is traditionally used for the treatment of sexually transmitted disease such as gonorrhea, Lung-TB and leporsy. Structural determination was accomplished by means of IR, UV, 1D and 2D NMR. ix 1. INTRODUCTION 1.1. General Phytochemical studies of plants, animals and microorganisms helps in order to have deeper understanding of the factor underlying for the growth, development and differentiation of their chemistry out comes[1]. Plant and animals produce a very large numbers of chemicals. These chemical products can be classified in to primary and secondary metabolites. Primary metabolites are those, which are common to all species and can be subdivided in to proteins, carbohydrates, lipids and nucleic acids. Primary metabolites are essentially ubiquitous and certainly essential for life and they function in cycle [2]. The secondary metabolite are often referred to as ‘’natural products’’ secondary metabolites can be subdivided in to trepenoids, alkaloids, steroids, shikimates and polyketides. The classification is based on the means buy which the materials were made. In principle, secondary metabolites are non- essential to life but they definitely contribute to the species fitness of survival. Different plant and animal species can employ different biosynthetic route to produce the same metabolites [3, 4]. Natural product as the name implies, are those chemical compounds derived from living organisms, plants, animals, insects and the study of natural product accounts in the investigation of their structure, formation, use and purpose in the organisms [5] .Natural products isolated from plants and arid microorganism have been providing noble, clinically active drugs. The key to the success of discovering naturally occurring therapeutic agents rests on bioassay guided fractionation and purification procedures [6]. Individual secondary metabolites may be common to a number of species or may be produced by only one organism. Relative species often have related patterns of secondary metabolite production, according to the secondary metabolite they produce species can be subdivided in to different parts. Such classification is known as chemotaxonomy. Tow plant may be found to have identical physical make up which botanists use for classification, but differ in the secondary metabolites
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