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Thesis Kehkashan Khan Chemistry i CHEMICAL AND SPECTROSCOPIC STUDIES ON CORDIA ROTHII AND RELATED MEDICINAL PLANTS Thesis submitted for the fulfilment of the degree of DOCTOR OF PHILOSOPHY by Kehkashan Khan DEPARTMENT OF CHEMISTRY, UNIVERSITY OF KARACHI, KARACHI-75270, PAKISTAN. April, 2014 ii iii Dedicated to My Parents, Family Members, and Teachers iv Acknowledgements Countless thanks to Graceful Almighty Allah Subhana-u-Taala who has given me an excellent opportunity for exploring a minor fraction of the bounty of nature and has blessed us with His last Holy Prophet (Peace be upon Him), whose guidance and teachings lead us on a path towards Almighty Allah. It is impossible to express my indebtedness to those, who remain involved directly or indirectly in giving this dissertation a final shape. I am deeply indebted to my research supervisor Prof. Dr. Sadiqa Firdous, Department of Chemistry, University of Karachi, for her invaluable guidance, constructive criticism, careful advice, constant encouragement and moral support throughout the course of this investigation. She always put her best efforts to facilitate my research work. I acknowledge with deep gratitude to my co-supervisor Dr. Munawwer Rasheed, Asst. Prof., Department of Chemistry, and now Assoc. Prof., Center of Excellence in Marine Biology, University of Karachi, for his expert opinion, dedicated and committed efforts, generous support, and keen interest that enabled me in accomplishing this gigantic task in time. My humble thanks go to Prof. Dr. Azhar Ali, Chairman, Department of Chemistry, University of Karachi, for providing necessary facilities. I am also thankful to Prof. Dr. P. J. A. Siddiqui, Director, CEMB for providing lab space to finalize my thesis write up. I wish to acknowledge Prof. Dr. M. Iqbal Choudhary H.I., S.I., T.I., Director, H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, for providing v the facilities of library, spectral analyses and for bioactivity assays under HEC scheme. I am deeply grateful to Prof. Dr. Viqar Uddin Ahmad H.I., S.I., Khawarizmi Laureate, Distinguished National Professor, H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, for his kind advice, useful insight, and generous support during this endeavor. My grateful acknowledgements are to Prof. Dr. Shaheen Faizi S.I. , H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, for her expert advice, valuable comments, and suggestions received over a period of years. I take this opportunity to express my sincere thanks and appreciation to Dr. Zulfiqar Ali, National Center for Natural Product Research, School of Pharmacy, University of Mississippi, MS-38677, USA for his helpful comments, valuable criticism and generous help extended in solving many research problems. I would like to thank Prof. Dr. Aqeel Ahmad for providing help in conducting antibacterial and antifungal assays. Heartly thanks are due to my colleagues Dr. Sadia Zikr-Ur-Rehman, Dr. Anila Naz, Dr. Samina Bano, Nida Hassan Ansari, Muhammad Nadir, Muneeba Khan, Muhammad Ibrahim Jaffery, Rajkumar Dewani, Farah Safdar, Javeria Khalid, Umme Hani, Rahma Khan, and Sana for providing me the friendly and supportive environment during my research days. Thanks are also reserved for the technical and non-technical staff of the Department of Chemistry, and ICCBS, University of Karachi. The monetary assistance of HEC for Instrumental access and for conducting bioactivity assays is gratefully acknowledged that vi immensely facilitated this research endeavor. Words cannot express the extensive support extended to me by my parents and family members. Their love, patience, endless care, co- operation, and prayers encouraged and strengthened me to complete this dissertation task during a very difficult stage of my life. I thank them all with the core of my heart. Kehkashan Khan April 2014 vii PAGE SECTION CONTENT No. ABSTRACT 1 INTRODUCTION 1.1 General Introduction 5 1.2 Family Boraginaceae 7 1.3 Genus Cordia 8 1.4 Cordia rothii Roem. & Schult 8 1.5 Identification of Metabolites from Genus Cordia Exploiting GC/GC-MS 76 BIOSYNTHESES 2.1 Biosyntheses 77 2.2 Biosynthesis of Saturated Fatty Acids 78 2.3 Biosynthesis of Unsaturated Fatty Acids 80 2.4 Biosynthesis of Cerebrosides 82 2.5 Biosynthesis of Terpenes 83 2.6 Glycosylation Reactions 91 RESULTS AND DISCUSSION 3.1 Characterization of Isolated and Purified Compounds 97 3.1.1 Structure Elucidation of 2′′ -Butoxyethyl 3-[3 ′,5 ′-di( tert -butyl)-4′- 99 hydroxyphenyl]-propanoate, Mairajinol (30 ) ― A New Compound 3.1.2 Characterization of Stigmast-5-en-3β-ol (β-Sitosterol) ( 26) 106 3.1.3 Characterization of (24 S)-Stigmast-5, 22-dien-3β-ol (Stigmasterol) ( 27) 107 3.1.4 Characterization of Octacosan-1-ol ( 74 ) 108 3.1.5 Characterization of Stigmast-5-en-3-O-β-D-glucoside ( β-Sitosterol 109 glucoside) ( 79 ) 3.1.6 Characterization of (2 S) Methyl 2-hydroxy-3-(4 ′-hydroxyphenyl)- 110 propanoate (Latifolicinin C) ( 62 ) viii 3.1.7 Characterization of 1-O-β-D-Glucopyranosyl-(2 S,3 S,4 R,8 Z)-2-[(2 ′R)-2′- 112 hydroxytetracosanoyl amino]-1,3,4-octadecanetriol-8-ene ( 80 ) 3.1.8 Characterization of (2 R) 2-Hydroxy-3-(4 ′-hydroxyphenyl) propanoic acid 114 [(2 R) ( p-hydroxyphenyl) lactic acid] ( 81 ) 3.1.9 Characterization of Syringaresinol mono-β-D-glucoside ( 82 ) 115 3.1.10 Characterization of 6-Hydroxy-3-oxo-α-ionol 9-O-β-D-glucopyranoside 116 (Roseoside) ( 83 ) 3.1.11 Characterization of 3,5-Dihydroxy-megastigma-6,7-dien-9-one-3-O-β-D- 118 glucopyranoside (Staphylionoside D) (84 ) 3.1.12 Characterization of (2 E)3-(3 ′,5 ′-Dimethoxy-4′-O-β-D-glucopyranosyl- 120 phenyl)-prop-2-en-1-ol (Syringin) ( 85 ) 3.2 Studies on Non-polar to Moderately Polar Fractions of Root, Stem and 122 Leaves Exploiting Gas Chromatography - Flame Ionization Detection (GC-FID) and Gas Chromatography - Mass Spectrometry (GC-MS) 3.2.1 Methodology 122 3.2.2 Results 123 3.2.3 Discussion 135 3.2.4 Structure Elucidation Using GC-EI-MS 158 3.3 Bioactivities 167 3.3.1 Sample Preparation for Bioactivity 168 3.3.2 Bioassays 168 3.3.2.1 Antimicrobial Activity 168 3.3.2.2 Toxicity Studies 170 3.3.2.3 Antioxidant and Immunomodulating Activity 171 3.3.2.4 Insecticidal Activity 174 3.3.2.5 Antiglycation Studies 174 EXPERIMENTAL 4.1 General Experimental 175 4.2 Extraction, Fractionation, Isolation, and Identification Schemes 177 4.2.1 Schemes of work for Root of C. rothii 177 ix 4.2.2 Schemes of work for Stem of C. rothii 183 4.2.3 Schemes of work for leaves of C. rothii 187 4.3 Characterization of Isolated Compounds 193 4.3.1 Characterization of 2′′ -Butoxyethyl 3-[3 ′,5 ′-di( tert -butyl)-4′- 193 hydroxyphenyl]-propanoate, Mairajinol (30 ) ― A New Compound 4.3.2 Characterization of Stigmast-5-en-3β-ol ( β-sitosterol) ( 26) 194 4.3.3 Characterization of (24 S)-Stigmast-5, 22-dien-3β-ol (Stigmasterol) ( 27) 195 4.3.4 Characterization of (2 S-) Methyl 2-hydroxy-3-(4 ′-hydroxyphenyl)- 196 propanoate (Latifolicinin C) ( 62 ) 4.3.5 Characterization of Octacosan-1-ol ( 74 ) 197 4.3.6 Characterization of Stigmast-5-en-3-O-β-D-glucoside ( β-Sitosterol 198 glucoside) (79 ) 4.3.7 Characterization of 1-O-β-D-Glucopyranosyl-(2 S,3 S,4 R,8 Z)-2-[(2 ′R)-2′- 199 hydroxytetracosanoyl amino]-1,3,4-octadecanetriol-8-ene ( 80 ) 4.3.8 Characterization of (2 R) 2-Hydroxy-3-(4 ′-hydroxyphenyl)-propanoic acid 200 [(2 R) ( p-hydroxyphenyl) lactic acid] (81 ) 4.3.9 Characterization of Syringaresinol mono-β-D-glucoside ( 82 ) 201 4.3.10 Characterization of 6-Hydroxy-3-oxo-α-ionol 9-O-β-D-glucopyranoside 202 (Roseoside) (83 ) 4.3.11 Characterization of Staphylionoside D (84 ) 203 4.3.12 Characterization of (2 E) 3-(3 ′,5 ′-Dimethoxy-4′-O-β-D-glucopyranosyl- 204 phenyl)-prop-2-en-1-ol (Syringin) ( 85 ) 4.4 Identification of Natural Compounds using GC-MS Analyses 204 4.4.1 Gas Chromatographic Data 204 4.4.1.1 Gas Chromatographic Data of C. rothii Roots 204 4.4.1.2 Gas Chromatographic Data of C. rothii Stem 216 4.4.1.3 Gas Chromatographic Data of C. rothii Leaves 226 4.4.2 Gas Chromatographic Electron Impact Mass Spectral (GC-EIMS) Data 232 4.4.2.1 GC-EIMS Data of Identified Constituents 232 4.4.2.2 GC-EIMS Data of Un-identified Constituents 238 x 4.5 Bioactivities 243 4.5.1 Sample Preparation of Extracts from Root, Stem, and Leaves for 243 Bioactivities 4.5.2 Bioassays 243 4.5.2.1 Antimicrobial activity 243 4.5.2.2 Toxicity studies 251 4.5.2.3 Antioxidant & Immunomodulatory activities 254 4.5.2.4 Insecticidal activity 260 4.5.2.5 In Vitro Glycation 261 REFERENCES 262 APPENDICES xi xii xiii Abstract Chapter 1 of the dissertation discusses the medicinal and pharmacological importance and phytochemistry of Cordia rothii Roem. & Schult and thus the plant was selected for further studies. Chapter 2 summarizes the biosynthesis of selected phytochemicals of this plant. Chapter 3 and 4 covers the current studies on root, stem and leaves of C. rothii . Altogether 88 phytochemicals are being reported here. 12 were isolated, purified and characterized while 79 were identified using GC-MS studies. 3 metabolites ( 26 , 27 and 62 ) were isolated as well as were also identified in the GC-MS study. Isolated compounds included stigmast-5-en-3β-ol (26 ), (24 S) stigmasta-5,22-dien-3β-ol ( 27 ) 2′′ -butoxyethyl 3-[3 ′, 5 ′-di( tert -butyl)-4′-hydroxy- phenyl]-propanoate (30 ), (2 S) methyl 2-hydroxy-3-(4 ′-hydroxyphenyl)-propanoate (62 ), octacosan-1-ol ( 74 ), stigmast-5-en-3-O-β-D-glucoside (79 ), (2 S,1 ′S,2 ′S,3′R,7 ′Z)-N-1′-(O-β-D- glucopyranosyl)methyl-2′,3 ′-dihydroxy-heptadec-7′-enyl-2-hydroxytetracosaneamide ( 80 ), (2 R) 2-hydroxy-3-(4′-hydroxyphenyl)-propanoic acid (81 ), syringaresinol mono-β-D- glucoside ( 82 ), 6-hydroxy-3-oxo-α-ionol 9-O-β-D-glucopyranoside (83 ), 3,5-dihydroxy- megastigma-6,7-dien-9-one-3-O-β-D-glucopyranoside (84 ), and 3-(3 ′,5 ′-dimethoxy-4′-O-β-D- glucopyranosyl-phenyl)-prop-2E-en-1-ol (85 ).
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