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The Islamia University of Bahawalpur Pakistan Phytochemical and Biological Studies of Calligonum polygonoides and Crateva adansonii A thesis submitted to the Department of Pharmacy In Partial Fulfillment of the Requirements for the Degree Of DOCTOR OF PHILOSOPHY (PHARMACEUTICAL CHEMISTRY) BY IRFAN PERVAIZ (Pharm.D, MPhil) Faculty of Pharmacy & Alternative Medicine The Islamia University of Bahawalpur Pakistan STUDENT’S DECLARATION I, Irfan Pervaiz, PhD Scholar (Pharmaceutical chemistry) of the Department of Pharmacy, The Islamia University of Bahawalpur, hereby declare that the research work entitled “Phytochemical and Biological Studies of Calligonum polygonoides and Crateva adansonii” is done by me. I also certify that this thesis does not incorporate any material without acknowledgment; and to the best of my knowledge and belief that it does not contain any material previously published where due reference is not made in the text. Irfan Pervaiz SUPERVISOR’S DECLARATION It is hereby certified that work presented by Irfan Pervaiz in the thesis titled, “Phytochemical and Biological Studies of Calligonum polygonoides and Crateva adansonii” is based on the research study conducted by candidate under my supervision. It is certified that no material has been used in this thesis which is not his own work, except where due acknowledgement has been made. Plagiarism as checked by Turnitin Software is 15% which is in the limit as described by Higher Education Commission. He has fulfilled all the requirements and is qualified to submit this thesis in partial fulfillment for the degree of Doctor of Philosophy (PhD) in the Department of Pharmacy. Prof. Dr. Saeed Ahmad Supervisor List of contents Acknowledgement i Abstract ii List of Tables v List of Figures vii Chapter 1 Introduction 1.1 General Introduction of Natural Products 1 1.1.1. Natural products as antimicrobial agents 2 1.1.2. Natural Products as Anticancer agents 8 Plant introduction/previous phytochemical Part A investigations on Calligonum Polygonoides 17 Chapter 2 Literature Review 17 2.1 Plant Introduction 18 2.1.1. Plant Classification 18 2.2. Family Polygonaceae 19 2.3. Genus Calligonum 19 2.3.1 Calligonum polygonoides 19 Bioactive constituents reported from the Family 2.4. Polygonaceae 20 2.4.1. Calligonum genus 20 2.4.1.1. Calligonum polygonoides 20 2.4.1.2. Calligonum leucocladum 20 2.4.2. Polygonum genus 22 2.4.2.1. Polygonum minus 22 2.4.2.2. Polygonum sachalinensis 22 2.4.2.3. Polygonum multiflorum 24 2.4.4.4. Polygonum chinense 24 2.4.4.5. Polygonum barbatum 26 2.4.3. Oxygonum genus 26 2.4.3.1. Oxygonum sinuata 26 2.4.4. Rumex genus 26 2.4.4.1. Rumex nepalensis 26 2.4.4.2. Rumex crispus 27 2.4.4.3. Rumex japonicus 27 2.4.4.4. Rumex aquaticus 27 2.4.4.5. Rumex patientia 28 2.4.4.6. Rumex dentatus 28 2.4.4.7. Rumex gmelini 29 2.4.4.8. Rumex bucephalophorus 30 Chapter 3 Phytochemical and Biological Profiling of aerial parts of Calligonum Polygonoides 32 Biological Evaluation of different fractions of 3.1. Calligonum polygonoides 33 3.1.1. DPPH Free Radical Scavenging Activity 33 3.1.2. α-glucosidase inhibition assay 34 3.1.3. Carbonic anhydrase inhibition assay 34 3.1.4. Urease Inhibition assay 35 3.1.5. Xanthine oxidase inhibition assay 35 3.1.6. Tyrosinase Inhibition Assay 36 GC-MS analysis of n-hexane fraction of Calligonum 3.2. Polygonoides 37 LC-MS Evaluation of Crude Methanolic Extract of 3.3. Calligonum Polygonoides 38 Structure Elucidation of Compounds Isolated from n- 3.4. hexane fraction (CpC-N) 48 3.4.1. Cycloartenol (145) 48 3.4.2. Beta-Amyrin (146) 49 3.4.3. Stigmasterol (147) 52 Structure Elucidation of Compounds Isolated from 3.5. Butanolic fraction (CpC-B) 54 3.5.1. Rhododendrin (148) 54 3.5.2. Glucogallin (149) 56 3.5.3. Hypolaetin-8-glucoside (150) 58 3.5.4. Isoetin-4’-O-glucuronide (151) 60 3.5.5. Medicarpin 3-O-glucoside-6'-O-malonate (152) 63 3.5.6. Melanoxetin (153) 65 3.5.7. Dihydrorobinetin (154) 66 3.6. Biological Evaluation of phytochemicals isolated from Calligonum polygonoides 68 3.6.1. Urease Inhibition assay 69 3.6.2. Xanthine oxidase inhibition assay 70 3.6.3. Carbonic Anhydrase Inhibition Assay 71 3.6.4. α-glucosidase inhibition assay 71 Chapter 4 Experimental 73 4.1. General Experimental Conditions 74 4.1.1. 1H-NMR, 13C-NMR & MS 74 4.1.2. LC-MS 74 4.1.2.1. HPLC System 74 4.1.2.2. Q-TOF high resolution mass spectrometry 75 4.1.3. GC-MS Analysis 75 4.1.3.1. GC Conditions 75 4.1.3.2. GC oven temperature programme 75 4.1.3.3. GC oven temperature programme 75 4.1.3.4. Full Scan Data acquisition 76 4.1.4. Chromatographic Separation 76 4.2. Materials and Methods 76 4.2.1. Plant collection 76 4.2.2. Extraction 76 4.2.3. Liquid-Liquid Extraction 77 LC-MS Profiling of crude methanolic fraction of 4.2.4. Calligonum Polygonoides 78 4.2.4.1. Positive Ionisation Mode 78 4.2.4.2. Negative Ionisation Mode 79 4.3. Isolation & purification of chemical constituents from n- hexane fraction CpC-N 80 4.4. Isolation & purification of chemical constituents from n- butanol fraction CpC-B 82 4.5. Characterization of constituents from Calligonum polygonoides 84 4.5.1. Cycloartenol (145) 84 4.5.2. Beta-Amyrin (146) 84 4.5.3. Stigmasterol (147) 85 4.5.4. Rhododendrin (148) 86 4.5.5. Glucogallin (149) 86 4.5.6. Hypolaetin-8-glucoside (150) 87 4.4.7. Isoetin-4’-O-glucuronide (151) 88 4.5.8. Medicarpin 3-O-glucoside-6'-O-malonate (152) 88 4.5.9. Melanoxetin (153) 89 4.5.10. Dihydrorobinetin (154) 90 4.6. Biological Evaluation of different fractions of Calligonum polygonoides and its phytochemicals 91 4.6.1. DPPH Free radical scavenging assay 91 4.6.2. α-glucosidase inhibition assay 91 4.6.3. Carbonic anhydrase inhibition assay 92 4.6.4. Urease Inhibiion assay 92 4.6.5. Xanthine oxidase inhibition assay 93 4.6.6. Tyrosinase Inhibition Assay 94 4.7. Statistical Analysis 95 Chapter 5 Conclusion 96 Plant introduction/previous phytochemical Part A investigations on Crateva adansonii 98 Chapter 5 Literature Review 99 5.1. Plant Introduction 99 6.1.1. Plant Classification 101 6.2. Family Capparaceae 101 6.3. Genus Crateva 101 6.3.1 Crateva adansonii 101 6.4. Bioactive constituents reported from Capparcaeae 101 6.4.1. Crateva genus 101 6.4.1.1. Crateva adansonii 101 6.4.1.2. Crateva nurvala 102 6.4.1.3. Crateva religiosa 102 6.4.1.4. Crateva tapia 103 6.4.2. Capparis genus 104 6.4.2.1. Capparis himalayensis 104 6.4.2.2. Capparis tenera 104 6.4.2.3. Capparis flavicans 104 6.4.2.4. Capparis spinosa 105 6.4.2.5. Capparis decidua 106 6.4.3. Cadaba Genus 107 6.4.3.1. Cadaba glandulosa/ Cadaba farinose 107 6.4.3.2. Cadaba rotundifolia 109 Phytochemical and Biological Profiling of aerial parts of Chapter 7 Crtaeva adnsonii 111 Biological Evaluation of different fractions of Crateva 7.1. adansonii 112 7.1.1. DPPH Free Radical Scavenging Activity 112 7.1.2. α-glucosidase inhibition assay 113 7.1.3. Tyrosinase inhibition assay 113 7.1.4. Carbonic anhydrase Inhibiion assay 114 7.1.5. Xanthine oxidase inhibition assay 114 7.1.6. Urease Inhibition Assay 115 7.2. GC-MS analysis of n-hexane fraction of Crateva adansonii 116 7.3. LC-MS Evaluation of Crude Methanolic Extract of Crateva adansonii 117 7.4. Structure Elucidation of Compounds Isolated from n- hexane fraction (CaC-N) 129 7.4.1. Lupeol (161) 129 7.4.2. Lupanol (201) 131 7.4.3. Lupenone (202) 133 7.5. Structure elucidation of Constituents isolated from chloroform fraction 135 7.5.1. Pheophorbide (203) 135 7.5.2. Pyropheophorbide (158) 138 7.5.3. Phytosphingosine (204) 140 7.5.4. Dehydrophytosphingosine (205) 141 7.6. Structure Elucidation of constituents isolated from butanolic fraction (CaC-B) 142 7.6.1. Cadabicine (177) 142 7.6.2. Isovitexin (206) 145 7.6.3. Isovitexin-7-O-rhamnoside (207) 147 7.7. Biological Evaluation of phytochemicals isolated from Calligonum polygonoides 149 7.7.1. Urease Inhibition assay 149 7.7.2. Tyrosinase inhibition assay 150 7.7.3. α-glucosidase Inhibition Assay 151 7.7.4. Carbonic anhydrase inhibition assay 152 7.7.5. Xanthine oxidase inhibition assay 153 Chapter 8 Experimental 154 8.1. General Experimental Conditions 155 8.1.1. 1H-NMR, 13C-NMR & MS 155 8.1.2. LC-MS 155 8.1.2.1. HPLC System 155 8.1.2.2. Q-TOF high resolution mass spectrometry 155 8.1.3. GC-MS Analysis 155 8.1.4. Chromatographic Separation 155 8.2. Materials and Methods 155 8.2.1. Plant collection 155 8.2.2. Extraction 155 8.2.3. Liquid-Liquid Extraction 156 8.2.4. LC-MS Profiling of crude methanolic fraction of Calligonum Polygonoides 156 8.2.4.1. Positive Ionisation Mode 156 8.2.4.2. Negative Ionisation Mode 157 8.3. Isolation & purification of chemical constituents from n- hexane fraction CaC-N 158 8.4. Isolation & purification of chemical constituents from chloroform fraction CaC-Cl 160 8.5. Isolation & purification of chemical constituents from chloroform fraction CaC-B 162 8.6. Characterization of constituents from Calligonum polygonoides 162 8.6.1.
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