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Echinops Heterophyllus Family Republic of Iraq Ministry of Higher Education and Scientific Research University of Baghdad College of Pharmacy PHYTOCHEMICAL INVESTIGATION AND TESTING THE EFFECT OF IRAQI ECHINOPS HETEROPHYLLUS FAMILY COMPOSITAE ON WOUND HEALING A Thesis Submitted to the Department of Pharmacognosy and Committee of the Graduate Studies of the College of Pharmacy - University of Baghdad in A Partial Fulfillment of the Requirements for the Degree of Doctor of Philosophy in Pharmacy (Pharmacognosy) By Enas Jawad Kadhim (M.Sc. Pharmacognosy, 2001) Supervisor: Prof. Dr. Alaa A. Abdulrasool Co-supervisor: Assist Prof. Dr. Zainab J. Awad 2013 1434 بسى هللا انشحًٍ انشحٍى ﴿ٌَشفع ٱلل ه ٱن زٌ ٍَ َءا َي ُ هٕ ا ي ُ هك ى َٔ ٱن ز ٌ ٍَ أٔح هٕ ا ٱن ع ه َى َد َس َ خ ج َٔ ٱلل ه ب ًَ ا ح َع ًَ ه هٌٕ َخ ب ٍ ش ﴾ طذق هللا انعظٍى سورة المجادلة : اﻻٌة ۱۱ Certificate We certify that this thesis entitled (Phytochemical investigation and testing the effect of Iraqi Echinops heterophyllus Family Compositae on wound healing) was prepared under our supervision at the Department of Pharmacognosy, College of Pharmacy- University of Baghdad in a partial fulfillment of the requirements for the degree of Doctor of Philosophy in Pharmacy (Pharmacognosy) Signature: Supervisor: Prof. Dr. Alaa A. Abdulrasool Date: Department: Signature: Co-supervisor: Ass. Prof. Dr . Zainab J. Awad Date: Department In view of the available recommendation, I forward this thesis for debate by the Examining Committee: Signature: Name: Chairman of the Committee Graduate Studies in the College of Pharmacy Date: Certificate We, the Examining Committee after reading this thesis entitled (Phytochemical investigation and testing the effect of Iraqi Echinops heterophyllus Family Compositae on wound healing) and examining the student (Inas Jawad Kadhim ) in its content, found it adequate as a partial fulfillment of the requirements for the degree of Doctor of Philosophy in Pharmacy (Pharmacognosy). Signature: Signature: Signature: Name: Name: Name: (Member) (Chairman) (Member) Date: Date: Date: Signature: Signature: Name: Name: (Member) (Member) Date: Date: Approved for the University Committee for Graduated Studies. Signature: Name: Dr. Ahmed A. Hussein Dean of College of Pharmacy-University of Baghdad Date: Dedication TO My Parents, Husband, Sisters,Brothers,my sweet daughters "Sarah & Rand" and all my Friends with respect Enas 6 ACKNOWLEDGEMENTS Prays and thanks be to Allah and prayer and peace upon Prophet Mohammed and his Descendants. I would like to express my greatest thank to my supervisor Prof. Dr. Alaa A. Abdulrasool ( Chairman of Baghdad University) for his scientific guidance, kindness, and prompt help whenever needed. My great thanks go to my co-supervisor Ass. Prof. Dr . Zainab J. Awad, for her encouragement, endless support during the study My appreciation to Ass. Prof. Dr. Ahmed A. Hussein (Dean of College of Pharmacy- University of Baghdad) for his continuous support and facilities to the postgraduate students. I would like to express my gratitude and appreciation to Lecturer Maha Noori Hamad (Head of Pharmacognosy Department, College of Pharmacy, University of Baghdad) for her cooperation, continuous guidance, patience, and help in providing me the research materials and all possible facilities. Also, I wish to express my deepest grateful to Ass. Prof Dr. Abed AL-Jabbar Khalaf, (College of Science- Al-Mustansiriya University) and the doctors: Ass. Prof Mohammed Hasan, Lecturer Ahlam Qasear Lecturer Ammar Abed-Al-Razaq, , (College of Pharmacy-Baghdad University), Dr. Munther Faisal (Dean of College of Pharmacy Al-Mustansiriya University) for their help in explaining the NMR analysis. 7 I am also thankful to Asst. Lecturer Zena Qaragholi for her assistance throughout the work. I would like to express my sincere appreciation to Prof. Ali Al-Shammaa for his advice, supervision throughout this work I can never thank enough the staff members in the Department of Pharmacognosy College of Pharmacy-Baghdad University for their continuous praying, love, and encouragement. Special thanks are extended to my friends, Dr. Nada-Al-Shawi , Dr. Dair Arif and Dr. Nawal Ayash for their valuable advice , support and helping during my study. I wish to express my gratefulness to Mrs. Zaineb, Mr. Ali and Mr. Salah Mahdy Baker, in College of Science in Al- Mustansiriya University for their great help in running FTIR, CHN and GC-MS spectrometer. Special thanks to lecturer Salema Sultan (College of Pharmacy-Baghdad University) for her help in computer application. My greatfulness to lecturer Suaad H. Moslem and Miss.Muna K. Shaker (College of Pharmacy-Baghdad University) for their help in the library. I'm greatly indebted to my family( specially my father , mother and my husband Dr. Yasser Al-Shammaa ) for their patience, encouragement and care. 8 Thanks are also due to all those whom I forgot and the wholeness is only for Allah. Enas 9 List of Contents No Subject Page Acknowledgements II List of contents IV List of figures VIII List of tables XIII List of abbreviations XV Abstract XVI CHAPTER ONE : INTRODUCTION Introduction 1 1.1 Asteraceae or Compositae (Aster Family) 2 1.2 The genus Echinops Linn 4 1.3 Echinops heterophyllus P.H.Davis 6 1.3.1 Classification 6 1.3.2 Description of the plant 7 1.3.3 Distribution of the plant 7 10 1.3.4 The Folkloric uses 9 11 Pharmacological activities of different species of 1.4 Echinops extracts Antibacterial activity 11 1.4.1 1.4.2 Antifungal activity: 12 1.4.3 Antileishmanial activity 14 1.4.4 Antioxidant activity 15 1.4.5 Anticancer action 15 1.4.6 Protective effects of Echinops on testosterone- 16 induced prostatic hyperplasia 1.4.7 Hepato-protective activity of Echinops 17 1.4.8 Anti-ulcerogenic activity 17 1.4.9 Anti-inflammatory action 18 1.4.10 Diuretic action of Echinops 18 1.4.11 Analgesic activity of Echinops 19 1.4.12 Effects on C.N.S 19 1.5 Phytochemical constituents of Echinops 20 1.5.1 Alkaloids of Echinops species 20 11 1.5.1.1 Echinopsine 23 1.5.1.2 Echinopsidine 24 1.5.1.3 Echinorine 24 1.5.1.4 Echinozolinone 25 1.5.2 Flavonoids 26 1.5.2.1 Reported pharmacological activities of flavonoids 28 1.5.2.1.1 Flavonoids as antioxidants 28 1.5.2.1.2 Flavonoids in the treatment of gastric ulcer 28 1.5.2.1.3 Effect of flavonoids on inflammation 29 1.5.2.1.4 Effect of flavonoids on cancer-related pathways 30 1.5.2.1.5 Antimicrobial activity of flavonoids 30 1.5.2.1.6 Flavonoids in treatment of cardiovascular diseases 32 1.5.2.1.7 Flavonoids in treatment of diabetes mellitus 32 1.5.2.1.8 Role of flavonoids in treatment of hepato-toxicity 33 1.5.2.1.9 Effect of flavonoids on depression 33 1.5.3 Terpenoids 34 1.5.3.1 Beta-sitosterol 35 1.5.3.2 Stigmasterol 36 Aim of this study 38 12 CHAPTER TWO : EXPERIMENTAL WORK 2.1 Reagents and Materials 39 2.2 Instruments 40 2.3 Plant material 41 2.4 Experimental work 41 2.4.1 Preliminary qualitative phytochemical analysis 42 2.4.2 Extraction and fractionation of different active 44 constituents 2.4.3 Isolation and purification of different active 48 constituents 2.4.3.1 Preparative HPLC 48 2.4.3.2 Preparation of preparative TLC plates 50 2.4.3.3 Isolation of flavonoids glycosides by (CC) 51 2.4.4 Identification and characterization of the isolated 52 compounds 2.4.4.1 Thin layer chromatography (TLC) 52 2.4.4.2 Melting point(M.P.) 52 2.4.4.3 Ultra violet (UV) spectrum analysis 52 2.4.4.4 Fourier transforms infrared(FT-IR) spectra 52 2.4.4.5 Elemental microanalysis (CHN) 53 13 2.4.4.6 One proton and thirteen carbon nuclear magnetic 53 resonance spectroscopy1H and 13C (NMR) analysis 2.4.4.7 Qualitative and quantitative estimation of isolated 53 compounds by HPLC 2.4.5 Investigation of some pharmacological activity of 54 the different isolated fractions CHAPTER THREE : RESULTS and DISCUSSION 3.1 Preliminary qualitative phytochemical analysis 57 3.2 Extraction and fractionation of different active 58 constituents 3.3 Preliminary identification of different Echinops parts 60 by TLC 3.4 Isolation and purification of different active 78 constituents 3.4.1 Isolation and purification of alkaloids 78 3.4.1a Isolation and purification of alkaloids by preparative 78 HPLC 3.4.1b Isolation and purification of alkaloids by preparative 80 TLC 3.4.1.2 Characterization and identification of the isolated 82 alkaloids (E1, E2 and E3) 3.4.1.2.1 M. P. 82 14 3.4.1.2.2 U.V. spectra 82 3.4.1.2.3 3.4.1.2.3- FT.IR spectra 84 3.4.1.2.4 CHN 88 3.4.1.2.5 1H &13C NMR analysis 88 3.4.2.1 Isolation and purification of flavonoids glycoside by 93 column chromatography (CC) 3.4.2.2 Characterization and identification of the isolated 95 flavonoids glycoside (EJ1 and EJ2) 3.4.2.2.1 M. P. 95 3.4.2.2.2 U.V. spectra 95 3.4.2.2.3 FT.IR spectra 96 3.4.2.2.4 CHN 100 3.4.2.2.5 1H &13C NMR analysis 100 3.4.3.1 Isolation and purification of flavonoids as (aglycon) 109 by preparative TLC 3.4.3.2 Characterization and identification of the isolated 110 myricetin, quercetin and kaempferol 3.4.3.2.1 TLC 110 3.4.3.2.2 M. P. 110 3.4.3.2.3 U.V.
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