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Shafiq Ahmad Tariq PHARMACOLOGICAL SCREENING, PHYTOCHEMICAL EVALUATION AND PHARMACOGNOSTIC STUDIES OF INDIGOFERA GERARDIANA AND CRATAEGUS SONGRICA Desertation Submitted to the Department of Pharmacy, University of Peshawar in partial fulfillment of the requirements for the Degree of DOCTOR OF PHILOSOPHY IN PHARMACEUTICAL SCEINCES By SHAFIQ AHMAD TARIQ DEPARTMENT OF PHARMACY UNIVERSITY OF PESHAWAR PAKISTAN 2009 Acknowledgements ACKNOWLEDGEMENTS All kinds of admiration is for Allah Almighty WHO created the universe and bequeath the mankind with knowledge and astuteness to search for his secret. The author is thankful to him who gave the impending, audacity and patience to complete this research work. I am indebted to my research supervisor Prof. Dr Mohammad Nisar Director Institute of chemistry university of Peshawar for his guidance, valuable, suggestions and stimulating discussions as well as enthusiastic support throughout the course of this investigation. I appreciatively acknowledge Dr Raza Shah HEJ Research Institute of chemistry, International centre for chemical and Biological Sciences University of Karachi for his time and expertise that was always generously available during my research stay at HEJ Karachi. The author’s thanks goes to faculty members, department of pharmacy, Prof. Dr Abdul Wadood and Prof Dr Riaz Naseem for their interest, moral support and encouragement. With deep sense of gratitute and appreciation I would like to extend my thanks to Mr. Sirtaj and Mr Ishfaq Hameed. I owe special thanks to Dr Manzoor Ahmad Malakand University to completing this assignment. Special appreciation is due to my lab fellow Mr. Obaidollah, Mr. Saleem Ullah Khan, MrInamullah khan, Mr Ihsan Ali, Mr.Waquar Ahmad Kaleem and Mr.Mugal Qaym for their generous support and encouragement during my research period. Thanks to my parents and my most profound apperception goes to my wife and kids Bilal Ahmad and Ajlal Ahmad who had been a springboard in my academic support. i DDeeddiiccaatteedd TToo MMyy GGrraanndd FFaatthheerr ((llaattee)) May their soul rest in piece (Amin) && PPaarreennttss Contents CONTENTS Entry Title Page No. ACKNOWLEDGMENT i LISTS OF TABLES LIST OF FIGURES LIST OF ABBREVIATIONS SUMMARY PART – A Pharmacognostic studies, Phytochemical Evaluation and Pharmacological Screening, of Indigofera gerardiana 1.0 Introduction 1 1.1 General Introductions 1 1.1.1 Plant as source of drug 2 1.1.2 Bioactive compounds from herbs 3 1.1.3 Role of natural products on economy 6 1.2 Genus Indigofera 7 1.2.1 Indigofera gerardiana 7 1.2.2 Natural habitat 8 1.2.3 Native distribution 8 1.2.4 Plant description 8 1.2.5 Folk medicinal use 8 1.3 Flavonoids 10 1.3.1 Introduction 10 1.3.2 Classification of Flavonoids 10 1.3.3 Structural behavior of Flavonoids 11 1.3.4 Biosynthesis of Flavonoids 15 1.3.5 General aspects of Flavonoids 15 1.3.6 Individual steps to Flavonoids classes 19 1.3.6.1. Flavanone Formation 19 1.3.6.2 Isofalovone Formation 20 1.3.6.3 Flavone Formation 21 1.3.6.4 Flavonol Formation 22 1.3.6.5 Glycosylation of Flavonoids 23 1.3.6.6 Methylation of Flavonoids 23 ii Contents Entry Title Page No. 1.3.7 Biological Properties of Flavonoids 24 1.3.8 Important Sources of Flavonoids 27 1.4 Pharmacognositc Studies 28 1.4.1 Morphology and Anatomy 29 1.4.2 Nutrition 29 1.4.3 Microchemical Test 30 1.5 Pharmacological Studies 32 1.5.1 Antibacterial Assay 32 1.5.2 Antifungal Assay 33 1.5.3 Brine Shrimp Bioassay 34 1.5.4 Insecticidal Assay 35 1.5.5 Phytotoxic Assay 36 1.5.6 Anti leishmanial Assay 36 2.0 Pharmacognostic Investigations 37 2.1 Collection and preservation 37 2.1.1 Macroscopic features 37 2.1.2 Anatomical studies 38 2.1.3 Microscopic drug study 38 2.1.4 Nutrition analysis 38 2.1.4.1 Detection of ash 38 2.1.4.2 Determination of moisture 39 2.1.4.3 Determination of protein by macrojeldahl distillation method 40 2.1.4.4 Determination of fat or ether extract 41 2.1.4.5 Determination of crude fiber by fibertec 42 2.1.4.6 Carobhydrate contents 43 2.1.5 Microchemical tests 43 2.2 Phytochemical Studies 46 2.2.1 General notes 46 2.2.2 General experimental conditions 46 2.2.2.1 Physical constants 46 2.2.2.2 Spectroscopy 46 2.2.2.3 Plant material 47 iii Contents Entry Title Page No. 2.2.2.4 Extraction, fractionation and isolation 47 2.3 Physical and spectroscopic data 51 2.3.1 S-1 51 2.3.2 S-2 52 2.3.3 S-3 53 2.3.4 -Sitosterol 54 2.4 Pharmacological investigation 55 2.4.1 Antibacterial assay 55 2.4.2 Antifungal assay 56 2.4.3 Brine Shrimp Bioassay 58 2.4.4 Insecticidal Activity 59 2.4.5 Phytotoxic Assay 60 2.4.6 Anti leishmanial Assay 63 2.4.7 Anti malarial Activity 64 3.1 Pharmacognostic Study 65 3.1.1 Macroscopic features of Indigefera gerardiana 65 3.1.2 Anatomical Studies of Indigefera gerardiana 67 3.1.3 Microscopic Study of Indigefera gerardiana 68 3.1.4 Nutritional Analysis of Indigefera gerardiana 68 3.1.5 Microchemical Tests of Indigefera gerardiana 69 3.2 Phytochemical Studies 70 3.2.1 Structural elucidation of new compounds 70 3.2.1.1 Compound (S-1) 70 3.2.1.2 Compound (S-2) 73 3.2.1.3 Compound (S-3) 75 3.2.2 Structural elucidation of known compound 77 3.2.2.1 -Sitosterol 77 3.3 Pharmacological Studies 80 3.3.1 Pharmacological studies on crude extract and fractions 80 3.3.1.1 Antibacterial Assay 80 3.3.1.2 Antifungal Assay 89 3.3.1.3 Brine Shrimp Bioassay 93 iv Contents Entry Title Page No. 3.3.1.4 Insecticidal Assay 96 3.3.1.5 Phytotoxic Assay 99 3.3.1.6 Anti leishmanial Assay 102 3.3.1.7 Anti malarial assay 102 PART – B Pharmacognostic studies, Phytochemical Evaluation and Pharmacological Screening, of Crataegus songrica 4.0 Introduction 104 4.1 Genus Crataegus 104 4.1.1 Related Information 106 4.1.2 Natural habitat 106 4.1.3 Native distribution 106 4.1.4 Plant description 107 4.1.5 Medicinal uses 107 5.0 Phytochemical Studies 108 5.1 General Notes 108 5.1.1 General experimental conditions 108 5.1.1.1 Spectroscopy 108 5.1.1.2 Chromatography 109 5.1.1.3 Locating reagent 109 5.1.1.4 Collection and preservation 109 5.2 Isolation of chemical constituents 114 5.2.1 Physical and spectroscopic data of isolated compounds from 115 fruit of crataegus songrica 5.2.2 Stigmasterol 3-O--D-Glucoside (T-I) 115 5.2.3 Lupeol (T-II) 116 5.2.4 3,5, 7-Trihidroxy-6, 4-dimethoxy flavone (T-III) 117 5.2.5 5,4-Dhydroxy-3, 6, 7-trimethoxy flavone (T-IV) 117 6.1 Pahramcognostic Investigations 119 6.1.1 Macroscopic features of Crataegus songrica 119 6.1.2 Anatomical Studies of Crataegus songrica 119 6.1.3 Microscopic Study of Crataegus songrica 120 6.1.4 Nutritional Analysis of Crataegus songrica 120 6.1.5 Microchemical Tests of Crataegus songrica 121 v Contents Entry Title Page No. 6.2 Phytochemical Studies 122 6.2.1 Structural elucidation of constituents isolated from barries of 122 Crataegus sangrica 6.2.1.1 Stigmasterol 3-O--D-Glucoside (T-I) 122 6.2.1.2 Lupeol (T-II) 123 6.2.1.3 3,5, 7-Trihidroxy-6, 4-dimethoxy flavone (T-III) 124 6.2.1.4 5,4-Dhydroxy-3, 6, 7-trimethoxy flavone (T-IV) 125 6.3 Pharmacological Studies 127 6.3.1 Antibacterial Assay 127 6.3.2 Antifungal Assay 133 6.3.3 Brine Shrimp Bioassay 137 6.3.4 Insecticidal Assay 140 6.3.5 Phytotoxic Assay 141 6.3.6 Anti leishmanial Assay 145 6.3.7 Anti malarial Activity 145 Plates of Anatomical and Microscopic Studies 147 (Part – A) Plates of Anatomical and Microscopic Studies 159 (Plates – B) References (Part – A) 164 References (Part – B) 176 vi List of Tables LIST OF TABLES Entry Table # Title Page # 1. 1.1 Active principles derived from ethno pharmacological source, 4 which are clinically used 2. 1.2 Pathogenesis caused by bacteria 33 3. 1.3 Pathogenesis caused by fungi 34 4. 2.1 Physical and spectroscopic data of S-1 51 5. 2.2 Physical and spectroscopic data of S-2 52 6. 2.3 Physical and spectroscopic data of S-3 53 7. 2.4 Physical and spectroscopic data of S-4 54 8. 2.5 Criteria for determining antibacterial assay 56 9. 2.6 Sabouraud dextrose agar (SDA) 57 10. 2.7 Criteria for determining antifungal assay 58 11. 2.8 Composition of medium for Lemna bioassay 62 12. 2.9 Criteria for determining Phytotoxicity 62 13. 3.1 Macroscopic features of the root of Indigofera geradiana 66 14. 3.2 Macroscopic features of the stem of Indigofera gerardiana 66 15. 3.3 Macroscopic features of the leaf of Indigofera gerardiana 66 16. 3.4 Nutritional analysis of the whole plant of Indigofera 69 gerardiana 17. 3.5 Microchemical tests of the Indigofera gerardiana 69 18. 3.6 1H (400 MHz) and 13C NMR (100MHz) Data of (S-1) in 72 MeOD 19. 3.7 1H (400 MHz) and 13C NMR (100 MHz) Data of (S-2) in 74 MeOD 20. 3.8 1H (400 MHz) and 13C NMR (100 MHz) Data of (S-2) in 77 MeOD 21.
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