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Phytochemical Investigation of Rhamnus Triquetra and Ziziphus Oxyphylla

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Phytochemical Investigation of Rhamnus Triquetra and Ziziphus Oxyphylla PHYTOCHEMICAL INVESTIGATION OF RHAMNUS TRIQUETRA AND ZIZIPHUS OXYPHYLLA BY FARHANA MAZHAR ROLL NO. 76-GCU-Ph.D-CHEM-2009 SESSION: 2009-2013 DEPARTMENT OF CHEMISTRY GC UNIVERSITY, LAHORE PHYTOCHEMICAL INVESTIGATION OF RHAMNUS TRIQUETRA AND ZIZIPHUS OXYPHYLLA Submitted to the GC University Lahore in partial fulfillment of the requirements for the award of the degree of DOCTOR OF PHILOSOPHY IN CHEMISTRY BY FARHANA MAZHAR ROLL NO. 76-GCU-Ph.D-CHEM-2009 SESSION: 2009-2013 DEPARTMENT OF CHEMISTRY GC UNIVERSITY, LAHORE In the name of Allah, The Most Compassionate, The Most Merciful RESEARCH COMPLETION CERTIFICATE Certified that the research work contained in the thesis entitled “Phytochemical Investigation of Rhamnus triquetra and Ziziphus oxyphylla” has been carried out and completed by Ms. Farhana Mazhar, Roll No. 76-GCU-PhD-CHEM-2009, under my supervision during her PhD (Chemistry) studies in the laboratories of the Department of Chemistry. The quantum and the quality of the work contained in this thesis is adequate for the award of degree of Doctor of Philosophy. Dated: --------- __________ Dr. Muhammad Jahangir Supervisor Submitted through ______________________ _____________________ Prof. Dr. Ahmad Adnan Controller of Examination Chairman. GC University, Lahore Department of Chemistry, GC University, Lahore. DECLARATION I Ms.Farhana Mazhar, Roll No. 76-GCU-PhD-CHEM-2009, student of Ph.D in the subject of Chemistry, session 2009-2013, hereby declare that the matter printed in the thesis titled “Phytochemical Investigation of Rhamnus triquetra and Ziziphus oxyphylla” is my own work and has not been printed, published and submitted as research work thesis or publication in any form in any University, Research Institute etc. in Pakistan or abroad. Dated: --------- _____________________ Signature of Deponent DEDICATION Affectionately Dedicated to my Beloved Parents, For their endless love, support and encouragement Especially my Brother Syed Kashif Mazhar for his help and patience, for every period I was away and Family due to whom Prayers and Cooperation I became able to reach this status. ACKNOWLEDGEMENT In the name of Allah Almighty, who is the most beneficent the merciful. All praise to Almighty Allah who blessed me with knowledge, courage and strength to work and to his Last and Beloved Prophet Hazrat Muhammad (May Peace be upon Him) for whom this wide and huge universe was assembled and who is the pioneer of education and research. Being his spiritual follower and believer, I tried to get educated and explore the artifacts and secrets of the universe. My deepest gratitude and thanks are extended to my supervisor Dr. Muhammad Jahangir, Assistant Professor, Department of Chemistry, GC University, Lahore,for his keen interest, proficient suggestions, sympathetic guidance and persistent encouragement, whom intelligence and experiences enabled me to learn a lot. I really acknowledge his tolerance for students diversified attitudes, understanding and experience in different research fields. His support, prayers and guidance helped me to complete this task. I feel great honour and pleasure in expressing thanks to Prof. Dr. Ahmad Adnan, Chairman, Department of Chemistry for his guidance and kind behaviour during the course of my studies. He always remains in touch with the new research activities in the world. I would also express my profound thanks to Prof. Dr. Islam Ullah Khan, Ex. Chairman and Dean of Arts and Sciences, for his proficient suggestions, sympathetic guidance and persistent encouragement. I wish to express my deep, heartfelt and sincere regards to Dr. Athar Abbasi, Associate professor, Department of Chemistry, GC University, Lahore, for his learned guidance, skilled advice, sympathetic and inspiring attitude. I am very thankful and obliged to Dr. Khalid M. Khan (HEJ Research Institute of Chemistry, University of Karachi) and Dr. Nisar Ullah (KSA) for providing all out help in spectroscopic analysis. I would particularly like to express my profound thanks to Dr. Muhammad Shahid, University of Agriculture, Faisalabad, Mrs. Saiqa Ishtiaq, University College of Pharmacy, PUNJAB University, Lahore for providing help for pharmacological activities and Mr. Muhammad Ajaib, Department of Botany GC University, Lahore, for providing me the plant material. I am highly acknowledged Higher Education Commission of Pakistan for financial support for the completion of this worthy task. The continued encouragement and prays of my loving parents,Abu and Ammi are an ever remaining treasure for me, who always appreciated and guided me to take next step in life and provided me facilities and best working environment. Whatever I am that is because of the countless prayers of my parents, who instilled in me a charm for education and value of being organized. I am greatly indebted to my sister Noreen Mazhar, Ambreen Mazhar and my elder brother Syed Atif Mazhar and my bhabi Sammina Kashif for their divine love, prayers, constant care, encouragement and continuous support throughout my studies. My sincere appreciations are also extended to my friends and colleagues Dr. Tayyaba Shahzadi, Raisa Khanum, Saima Idrees, Farah Khalid, Afza Malik, Ume Farwa, Ammar Yasir and Hafiz M. Faizan Haider and all others for providing me valuable assistance, moral supports and smiling moments during my stay in GCU. I acknowledge all technical and non technical staff of Chemistry Department for their co-operation and nice behaviour. Farhana Mazhar CONTENTS ACKNOWLEDGEMENT SUMMARY CONTENTS LIST OF TABLES LIST OF FIGURES LIST OF SCHEMES Chapter- 1 INTRODUCTION 1.1 Natural Products 01 1.1.1 Importance of Natural Product as Medicines 01 1.2 Phytochemicals 02 1.2.1 Bioactive Phytochemicals present in Medicinal Plants 02 1.2.2 Classification of Phytochemicals 03-06 1.3 Family Rhamnaceae 06 1.3.1 Genus Rhamnus 07 1.3.2 Rhamnus triquetra 07 1.3.3 Genus Ziziphus 09 1.3.4 Ziziphus oxyphylla 10 1.4 Antioxidant Activity 11- 13 1.5 Antimicrobial Activity 13- 14 1.6 Enzyme Inhibition/ Inhibitory Activities 14- 15 1.7 Hemolytic Activity 16 1.8 Anti- inflammatory and Analgesic Activity 16 1.9 Hepatoprotective Activity 17- 19 Chapter- 2 LITERATURE REVIEW 2.1 Literature review of Rhamnus triquetra 20-19 2.2 Literature review of Ziziphus oxyphylla 28- 40 Chapter- 3 EXPERIMENTAL WORK 3.1 General Experimental Conditions 41 3.1.2 Chromatographic Techniques 41 3.1.3 Detection of Compounds 41 3.2 Rhamnus triquetra 3.2.1 Plant Material 42 3.2.2 Extraction and Fractionation of plant material 42 3.2.3 Isolation and Purification of Compounds of Rhamnus triquetra 44 3.2.4 Characterization of Chemical Constituents of Rhamnus triquetra 46 3.2.4.1 Characterization of Physcion 46 3.2.4.2 Characterization of Madagascin 46 3.3 Ziziphus oxyphylla 3.3.1 Collection and Identification of plant material 47 3.3.2 Extraction and Fractionation 3.3.3 Isolation and Purification of Compounds of Ziziphus oxyphylla 49 3.3.4 Characterization of Chemical Constituents of Ziziphus oxyphylla 51 3.3.4.1 Characterization of ß- Sitosterol 51 3.3.4.2 Characterization of Betulinic Acid 51 3.3.5 Extraction of Essential Oil through Water Distillation 52 3.3.5.1 GC-MS Analysis 52 3.4 Fluorescence Analysis 52 3.5 Physicochemical Studies 53 3.5.1 Loss on drying 53 3.5.2 Total Ash 53 3.5.3 Water soluble Ash 53 3.5.4 Acid Insoluble Ash 54 3.5.5 Determination of n- hexane soluble Extractive value 54 3.5.6 Determination of chloroform soluble Extractive value 54 3.5.7 Determination of ethanol soluble Extractive value 54 3.6 Phytochemical Screening 55 3.6.1 Test for Alkaloids 55 3.6.2 Test for Flavonoids 55 3.6.3 Test for Tannins 55 3.6.4 Test for reducing sugar 56 3.6.5 Test for Terpenoids 56 3.6.6 Test for Saponins 56 3.6.7 Test for Phenolics 56 3.6.8 Test for Cardiac Glycosides 56 3.7 Determination of Antioxidant Activities 57 3.7.1 Chemical and Standards of Antioxidant Activities 57 3.7.2 DPPH Radical Scavenging Activity 57 3.7.3 Total Antioxidant Activity by Phosphomolybdenum method 58 3.7.4 Ferric Reducing Antioxidant Power Assay 58 3.7.5 Total Phenolic Contents 59 3.7.6 Ferric Thiocyanate Assay 60 3.8 Enzyme Inhibition Study 61 3.8.1 In- vitro Acetylcholine esterase Inhibition Assay 61 3.8.2 Protease Inhibition Assay 62 3.9 Antibacterial Activity 63 3.9.1 Strains Used for Antibacterial Activity 63 3.9.2 Agar Well Diffusion method 63 3.10 Hemolytic Activity 63 3.11 Pharmacological Activities 64 3.11.1 Animals 64 3.11.2 Anti-inflammatory Activity 64 3.11.2.1 Carregeenan Induced Rat Paw Edema 65 3.11.2.2 Formalin Mice Paw Edema 65 3.11.3 Analgesic Activity 66 3.11.3.1 Hot Plate method 66 3.11.3.2 Tail Flick method 66 3.11.3.3 Acetic acid Induced writhing method 67 3.11.4 Hepatoprotective Activity 67 3.11.4.1 Chemical and Standards 68 3.11.4.2 Experimental Protocol 68 3.11.4.3 Interval of Dose 68 3.11.4.4 Blood Sampling 68 a) Estimation of Aspartate aminotransferase activity 69 b) Estimation of Alanine aminotransferase activity 69 c) Estimation of Alkaline phosphatase activity 71 d) Estimation of Bilirubin activity 72 3.11.4.5 Histopathology of Liver 73 3.11.5 Statistical Analysis 73 Chapter- 4 RESULTS AND DISCUSSION 4.1 Structure Elucidation of Chemical Constituents of Rhamnus triquetra 4.1.1 New Source Compounds of Rhamnus triquetra 74 4.1.1.1 Structure Elucidation of Physcion 74 4.1.1.2 Structure Elucidation of Madagascin 75 4.1.2 GC- MS Analysis of Chloroform fraction of Rhamnus triquetra 77 4.2 Structure Elucidation of Chemical Constituents of Ziziphus oxyphylla 4.2.1 New Source Compounds from Ziziphus oxyphylla 78
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