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Isolation of Bioactive Secondary Metabolites and Pharmacological Studies of Viola Serpens Wall

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Isolation of Bioactive Secondary Metabolites and Pharmacological Studies of Viola Serpens Wall ISOLATION OF BIOACTIVE SECONDARY METABOLITES AND PHARMACOLOGICAL STUDIES OF VIOLA SERPENS WALL By RUKHSANA Ph.D DEPARTMENT OF PHARMACY UNIVERSITY OF PESHAWAR 2017 ISOLATION OF BIOACTIVE SECONDARY METABOLITES AND PHARMACOLOGICAL STUDIES OF VIOLA SERPENS WALL Thesis submitted to the Department of Pharmacy, University of Peshawar, Peshawar, Pakistan in partial fulfillment for the Degree of DOCTOR OF PHILOSOPHY IN PHARMACEUTICAL SCIENCES FEBRUARY, 2017 DEPARTMENT OF PHARMACY UNIVERSITY OF PESHAWAR APPROVAL SHEET A Thesis presented by Rukhsana entitled “Isolation of Bioactive Secondary Metabolites and Pharmacological Studies of Viola Serpens Wall” to the Department of Pharmacy, University of Peshawar in partial fulfillment for the award of the Degree of Ph.D in Pharmaceutical Sciences. We, the undersigned have examined this thesis and do hereby approve it for the award of Ph.D Degree. External Examiner: _________________________________ Supervisor: ______________________________ PROF. DR. MUHAMMAD SAEED Chairman, Department of Pharmacy, University of Peshawar. Co-supervisor: ______________________________ DR. MANZOOR AHMAD Associate Professor, Department of Chemistry, University of Malakand. I Dedicated my this humble effort to my beloved Parents & Family ACKNOWLEDGEMENT In the name of Almighty Allah, the most merciful and beneficent, Who gave me the courage and ability for the better understanding and completion of my PhD project. I bow my head before Allah for His greatness, Who provided me strength and courage to accomplish a useful and beneficial work for the benefit of mankind. With great honor and extreme happy feelings I pay my homage and debt to my research supervisor, Prof. Dr. Muhammad Saeed, Chairman, Department of Pharmacy, University of Peshawar. His broad vision, advice, encouragement and co- operation helped and guided me for the completion of my Ph.D programme and dissertation. I am also extremely indebted to my co-supervisor Dr. Manzoor Ahmad, Associate Professor, Department of Chemistry, University of Malakand. His sincere help, guidance, provision of required resources for the accomplishment of the major part of my research work. I would like to thank Prof. Dr. Zafar Iqbal, Meritorious professor, Tamgh-e- Imtiaz, Department of Pharmacy, University of Peshawar and Prof. Dr. Fazal Subhan for their support and encouragement throughout my work. I am also grateful to all the teaching faculty of the department for their support and cooperation. I am very thankful to Professor, Prof. Dr. Haroon Khan, Abdul Wali Khan University Mardan, for his sincerity, guidance, co-operation and encouragement at every stage of my PhD work. I also acknowledge the guidance and support of Mr. Ikran Illahi, Assistant Professor and Chairman, Department of Zoology University of Malakand. i I am very grateful to Mr. Atta-ur-Rehman, Institute for Natural Product Discovery, Universiti Teknologi, MARA Puncak Alam Selangor D.E., Malaysia for the spectroscopic studies of the isolated compounds. I am also very thankful to the staff of PCSIR Laboratories especially Ms. Farah Gul and Mr. Yaqoob for their co- operation and guidance in conducting anti-inflammatory activity of V. serpens. Thanks to Dr. Nuzhat Sultana from Khyber Medical College Peshawar and Mr. Mohammad Shahid, PhD scholar, for their help regarding the interpretation of histo- pathological slides. I am also very thankful to Dr. Umer Sadique Khattak, Chairman, Department of Animal Health Sciences, Agriculture University Peshawar and Mr. Sajjad Ali Shah, research assistant and PhD scholar Department of Animal Health Sciences, Agriculture University Peshawar for their facilitations and guidance in preparing the histopathological slides and taking photographs by using camera fitted microscope in the hepatoprotective and nephroprotective activities. I wish to pay my sincere appreciation to my lab fellows Ms. Attiqa Naz, Miss Samreen Pervez, Miss Noor-ul-Aain, Mr. Naveed and Mr. Asif Jan for their help, support and collective team work. At the end I pay my regards and duly acknowledge the co-operation, guidance and support of my parents, husband, sisters-in-law, brothers and sisters who encouraged and enabled me to fulfill this task . Rukhsana ii TABLE OF CONTENTS S.No. Topic Page No. Acknowledgement i List of Figures vii List of Tables ix Abbreviations xi Abstract xiii Chapter – 1 1. INTRODUCTION 1 1.1 General Introduction 1 1.2 Traditionally Used Medicinal Plants in Pakistan 3 1.3 Importance of Herbal Medicines in Different Traditions 4 1.3.1 Chinese Traditional Medicine 4 1.3.2 Japanese Traditional Medicine 5 1.3.3 Indian Traditional Medicine 5 1.4 Violaceae Family 5 1.5 Literature Survey of Genus Viola 6 1.6 Plant Introduction 12 1.6.1 Viola serpens Wall 12 1.6.2 Local Names 12 1.6.3 Morphology 12 1.6.4 Classification (Taxonomical position of V.serpens) 13 1.6.5 Geographical Distribution of V.serpens 13 1.6.5.1 World Wide Distribution 13 1.6.5.2 Distribution In Pakistan 14 1.7 Plant Distribution 15 1.8 Ethno medicinal Uses 16 1.9 Phytochemical Investigations 16 1.9.1 Nutritive Values 16 1.9.2 Essential and Fixed Oils 16 1.10 Isolated Compounds from Genus Viola 17 1.11 Pharmacological Studies 17 1.11.1 In vivo Biological Activities 17 1.11.1.1 Antibacterial Activity 17 1.11.1.2 Anti-fungal Activity 19 1.11.1.3 Antiprotozoal Activity 20 iii S.No. Topic Page No. 1.11.1.4 Cytotoxic Activity 20 1.11.1.5 Haemolytic Activity 20 1.11.1.6 Antiplasmodial Activity 20 1.11.1.7 Anti-malarial Activity 21 1.11.1.8 Anthelmintic activity 21 1.11.1.9 Antioxidant Activity 22 1.11.1.10 Anti-T.B Activity 22 1.11.1.11 Treatment of Jaundice 23 1.11.1.12 Urease Inhibitory Activity 23 1.11.1.13 Anti-HIV Effect 23 1.11.1.14 Insecticidal Activity 24 1.11.2 In vitro Biological Activities 24 1.11.2.1 Acute Toxicity 24 1.11.2.2 Antinociceptive Activity 24 1.11.2.3 Anti-Inflammatory Activity 25 1.11.2.4 Antipyratic Activity 25 1.11.2.5 Gastrointestinal Motility 26 1.11.2.6 Laxative Effect 26 1.11.2.7 Hepatoprotective Activity 27 1.11.2.8 Diuretic Activity 27 1.11.2.9 Anxiolytic Activity 27 1.11.2.10 Muscle Relaxant 28 1.11.2.11 Sedative-Hypnotic Effect 28 1.11.2.12 Anesthetic Effect 28 1.11.2.13 Uterotonic Effect 29 1.11.2.14 Anti-neurotensive 29 1.11.2.15 Anti-cancer Activity 29 1.11.2.16 Anti-hypertensive Effect 30 1.11.2.17 Anti-dyslipidemic Effect 30 1.11.2.18 Expectorant and Anti-tussive Effect 30 1.12 Aims and Objectives 33 Chapter – 2 2. EXPERIMENTAL 34 2.1 General Experimental Condition 34 2.2 Spectroscopic Technique 34 2.3 Physical Constants 35 2.4 Column Chromatography (CC) 35 2.5 Thin Layer Chromatography (TLC) 35 2.6 Drugs and Reagents 35 2.7 Plant Materials 37 iv S.No. Topic Page No. 2.7.1 Extraction and Fractionation 37 2.7.2 Isolation and Purification 40 2.8 Experimental Data of New Compounds from Viola serpens 42 2.8.1 Commulin-A (1) 42 2.8.2 Commulin- B (2) 42 2.8.3 Commulin- C (3) 43 2.9 Experimental Data of Known Compounds From Viola serpens 43 2.9.1 5-Hydroxy-7-methoxy flavone (tectochrysine) (4) 43 2.9.2 4́, 5-Dihydroxy-7-methoxy-6, 8-dimethylflavone (Sideroxylin)(5) 44 2.9.3 2,5-Dihydroxy-4-methoxybenzophenone (Cearoin) (6) 44 2.10 In-vivo Biological Activities 45 2.10.1 Experimental Animals 45 2.10.2 Acute Toxicity 45 2.10.3 Analgesic Activity 46 2.10.3.1 Acetic Acid Induced Writhing 46 2.10.3.2 Formalin Test 46 2.10.4 Anti-inflammatory Activity 47 2.10.4.1 Carrageenan Induced Paw Edema 47 2.10.4.2 Histamine Induced Paw Oedema 48 2.10.4.3 Xylene Induced Ear Edema 48 2.10.5 Larvicidal Bioassay 49 2.10.6 Nephroprotective and Hepatoprotective Activities 50 2.10.6.1 Animals Used 50 2.10.6.2 Animals Grouping and Dosing 50 2.10.6.3 Chemicals Used 51 2.10.6.4 Histopathology 51 2.10.6.5 Hematological and Serological profile of infected Rabbits 54 2.10.6.6 Statistical analysis 56 2.10.6.7 Collection and analysis of urine 56 2.11 In-vitro Biological Activities 58 2.11.1 Anti-oxidant Activity 58 2.11.1.1 Superoxide Anion Radical Scavenging Assay 58 2.11.1.2 DPPH Radical Scavenging Activity 58 2.11.2 Antibacterial Assay 59 2.12 Enzyme Inhibition 60 2.12.1 Chemicals Required for Anticholine Esterase 60 2.12.2 Acetylcholinesterase Inhibition 60 v S.No. Topic Page No. Chapter – 3 3. RESULTS AND DISCUSSION 61 3.1 Biological Activities 61 3.1.1 In-vitro Biological Activities 61 3.1.1.1 Antimicrobial Activity 61 3.1.2 Effect of Crude extract/Fraction of V.serpens in DPPH free Radical 66 3.1.3 Effect of Crude Extract/ Fractions of V.serpens in Larvicidal Effect 68 3.1.4 Effect of Crude Extract/ Fractions of V.serpens in Acetyl Cholinesterase Assay 70 3.2 In-vivo Biological Activities 72 3.2.1 Acute Toxicity 72 3.2.2 Hepatoprtotective and Nephroprotective Effects of Crude Extract/Fractions of V. serpens 72 3.2.2.1 Hepatoprotectve Effect 72 3.2.2.2 Nephroprotective Effect of V.serpens Crude Extract and its Subsequent Fraction 77 3.2.2.3 Antinociceptive Activity 84 3.2.2.4 Anti-inflammatory Activity 94 3.3 Isolated Compounds 112 3.3.1 New Compound From Viola serpens 112 3.3.1.1 Commulin-A (1) 112 3.3.1.2 Commulin-B (2) 114 3.3.1.3 Commulin-C (3) 117 3.3.2 Known Compounds from Viola serpens 120 3.3.2.1 5-Hydroxy-7-methoxy flavone (tectochrysine) (4) 120 3.3.2.2 4́, 5-Dihydroxy-7-methoxy-6, 8-dimethylflavone (Sideroxylin) (5) 121 3.3.2.3 2, 5-Dihydroxy-4-methoxybenzophenone (Cearoin) (6) 122 CONCLUSION 124 REFERENCES 126 vi LIST OF TABLES S.No.
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