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Ph.D Thesis by FARMAN ULLAH KHAN Ph.D Scholar INSTITUTE OF

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Ph.D Thesis by FARMAN ULLAH KHAN Ph.D Scholar INSTITUTE OF “Isolation and Structural Studies on the Bioactive Constituents of Bergenia ciliata and Synthesis, Spectral Characterization and Antibacterial Study of a Schiff Base Metal Complexes” Ph.D Thesis BY FARMAN ULLAH KHAN Ph.D Scholar INSTITUTE OF CHEMICAL SCIENCES GOMAL UNIVERSITY, DERA ISMAIL KHAN, PAKISTAN 2016 “Isolation and Structural Studies on the Bioactive Constituents of Bergenia ciliata and Synthesis, Spectral Characterization and Antibacterial Study of a Schiff Base Metal Complexes” Thesis Submitted For the Fulfillment of the Degree Of DOCTOR OF PHILOSOPHY BY FARMAN ULLAH KHAN INSTITUTE OF CHEMICAL SCIENCES GOMAL UNIVERSITY, DERA ISMAIL KHAN, PAKISTAN 2016 DEDICATION Every challenging work need self-effort as well as guidance elders especially those who are very close to our heart. My humble effort I dedicate to my sweat and loving Mother Whose affection, love, encouragement and prays of day And night made me able to get such success and honor, Along With all hard-working and respected Teachers TABLE OF CONTENTS Chapter Title Page No. List of Tables ........................................................................................ i i List of Figures ...................................................................................... ii Acknowledgments ................................................................................ iii Summary .............................................................................................. iv PART A Chapter-1: Introduction ........................................................................................ 1 1.1 Bioactive Compounds .............................................................. 1 1.2 Natural Products “The Bioactive Compounds” ....................... 2 1.3 Family Saxifragaceae ............................................................... 4 1.4 Genus Bergenia ........................................................................ 5 1.5 Medicinal Importance of Genus Bergenia ............................... 18 1.6 Bergenia ciliate ........................................................................ 20 1.7 Biological Activities ................................................................. 22 1.8 Scientific Classification ............................................................ 23 1.9 Pharmacological Significance of B. ciliate .............................. 23 1.10 Primary Metabolites ................................................................. 24 1.11 Secondary Metabolites ............................................................. 24 1.12 Biosynthesis of Flavonoids ...................................................... 26 Chapter-2: Results and Discussion ....................................................................... 33 2.1 Bioactive Constituents from Bergenia ciliate .......................... 33 2.2 Extraction and Isolation ........................................................... 34 2.3 Biological Activities of the Isolated Compounds .................... 36 2.4 Antimicrobial Activity ............................................................. 36 2.5 Materials and Methods ............................................................. 37 2.6 Plant Collections and Identification ......................................... 37 2.7 Microorganisms ........................................................................ 37 2.8 Screening for Antibacterial Activity ........................................ 38 2.9 Determination of Minimum Bactericidal Concentration (MBC) ...................................................................................... 40 2.10 Screening for Antifungal Activity ............................................ 40 2.11 Results ...................................................................................... 40 2.12 Discussion ................................................................................ 45 Chapter-3: Experimental ....................................................................................... 46 3.1 Reagents and Chemicals ........................................................... 46 3.2 Chromatographic Techniques .................................................. 46 3.3 Processing of Plant Materials ................................................... 48 3.4 Isolation of the Compounds from Ethyl Acetate Soluble Fraction .................................................................................... 49 3.5 Biological Activities ................................................................. 57 References ........................................................................................... 59 PART B: Synthesis, Spectral Characterization and Antibacterial Study of Schiff Base Metal Complexes Chapter-1: Introduction ....................................................................................... 67 1.1 Sulfonamides ............................................................................ 67 1.2 Sulfonames as Anti-Viral Agents ............................................. 68 1.3 Sulfonamides as Anticancer Agents ......................................... 69 1.4 Sulfonamides as Antibacterial Agents ..................................... 69 Chapter-2: Literature Review ............................................................................... 71 Chapter-3: Results and Discussion ....................................................................... 78 3.1 Synthesis of a Schiff Base Metal Complexes Derived from N-[(E)-(5-Chloro-2-Hydroxyphenyl) Methylidene]-4- Nitrobenzenesulfonamide ......................................................... 78 3.2 Synthesis of a Schiff Base Metal Complexes Derived From 4-Bromo-N-[(E)-(5-Chloro-2-Hydroxyphenyl) Methylidene]Benzenesulfonamide ........................................... 85 3.3 Conclusion ................................................................................ 92 Chapter-4: Experimental ....................................................................................... 93 4.1 Material and Method ................................................................ 92 References ........................................................................................... 99 List of Publications ............................................................................. 104 LIST OF TABLES Table No. Title Page No. Table 1.1: Compounds Isolated from Bergenia Species .......................................... 6 Table 2.1: Zone of Inhibitions of reference antibiotics ............................................ 39 Table 2.2: Inhibition zones of Afzelechin (173) to Damascenone (177) ................ 41 Table 2.3: MIC and MBC Bergenia ciliata of Afzelechin (173) ............................. 42 Table 2.4: Antifungal activities of compounds Afzelechin (173) to Damascenone (177) ........................................................................................................ 44 Table 3.1: Inhibition zones of Afzelechin (173) to Damascenone (177) ................. 58 Table 3.2: MIC and MBC Bergenia ciliata of Afzelechin (173) ............................. 58 Table 3.1a: Physical characteristics of Schiff base ligand (L1) and its metal complexes ............................................................................................... 80 Table 3.2a: Micro-analytical data of Schiff base ligand (L1) and its metal complexes ............................................................................................... 80 Table 3.3a: IR spectra cm-1 of Schiff base ligand (L1) and its metal complexes ...... 82 Table 3.4a: NMR data of Ligand (L1) and its Complexes......................................... 83 Table 3.5a: Antibacterial activity of ligand (L1) and its complexes (inhibition zone mm) ................................................................................................ 84 Table 3.1b: Physical Characteristics of Schiff Base ligand (L2) and its Metal Complexes ............................................................................................... 87 Table 3.2b: Micro-Analytical Data of Schiff Base Schiff Base ligand (L2) and its Metal Complexes .................................................................................... 87 Table 3.3b: IR spectra cm-1 of Schiff base ligand (L2) and its Metal Complexes ..... 89 Table 3.4b: NMR data of ligand (L2) and its Metal Complexes................................ 90 Table 3.5b: Antibacterial Activity of ligand (L2) and its Metal Complexes (Inhibition Zone mm) .............................................................................. 91 i LIST OF FIGURES Figure No. Title Page No. Fig. 1.1: Images of Bergenia ciliate .......................................................................... 21 Fig. 2.1: Structures of compounds 173 to 177 .......................................................... 35 Fig. 2.2: Inhibition zone of compounds 173 to 177 .................................................. 43 Fig. 2.3: MIC MBC Bergenia ciliata of Afzelechin (173) ....................................... 43 Fig. 2.4: Antifungal activities of compounds (173) to (177) .................................... 44 Fig. 3.1: Structures of compounds 173 to 177 .......................................................... 50 Fig. 3.1a: Synthesis of ligand (L1) ............................................................................. 78 Fig. 3.2a: Proposed structure of metal complexes ...................................................... 79 Fig. 3.1b: Synthesis of ligand (L2) ............................................................................
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