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Chapter 1 Introduction 1-9 1.1 Mass Spectrometric Profiling and Bioevaluation of Phenolic Constituents of Coronopus didymus By Hafiza Noreen Department of Chemistry Quaid-i-Azam University Islamabad, Pakistan. 2019 Mass Spectrometric Profiling and Bioevaluation of Phenolic Constituents of Coronopus didymus A Dissertation Submitted to the Department of Chemistry, Quaid-i-Azam University, Islamabad, Pakistan In Partial Fulfillment of the Requirement for the Degree of Doctor of Philosophy In Organic Chemistry By Hafiza Noreen Department of Chemistry Quaid-i-Azam University Islamabad, Pakistan 2019 “Who ever treads a path, seeking in that path knowledge, ALLAH will make easy for him the path to paradise” Prophet Mohammad (P.B.U.H) i List of Publications List of Publications Noreen H., Semmar N., Farman M. and McCullagh J. S. O. (2017). Measurement of total phenolic content and antioxidant activity of aerial parts of medicinal plant Coronopus didymus. Asian Pac. J. Trop. Med. 10: 792-801. Noreen H., Farman M. and McCullagh J. S. O. (2016). Bioassay-guided isolation of cytotoxic flavonoids from aerial parts of Coronopus didymus. J. Ethnopharmacol. 194: 971-980. Noreen H. and Farman M. (2016). Comparative gas chromatography-mass spectrometric analysis of biologically active volatile phytochemical constituents of aerial parts and roots of Coronopus didymus. Asian J. Chem. 28: 1007-1010. Noreen H., Semmar N., Farman M. and McCullagh J. S. O. Ultra-performance liquid chromatography-tandem mass spectrometry based differentiation, identification and quantification of bioactive methylated flavone isolated from Coronopus didymus and its regioisomer. (Submitted). Noreen H., Semmar N., Farman M. and Ihsan J. Evaluation of Antifungal and Antibacterial Activity of Aerial Parts of Coronopus didymus Against Phytopathogens. (Submitted). Noreen H., Semmar N., Farman M. and McCullagh J. S. O. Comparative phytochemical analysis of aerial parts and roots of Coronopus didymus from various extraction techniques using RP-UHPLC-ESI-MS based profiling combined with principal component analysis. (Submitted). ii List of Publications Abstracts Published and Oral & Poster Presentations: 2019 Title: “Evaluation of antifungal and antibacterial activity of aerial parts of Coronopus didymus against phytopathogens” in the 17th International Conference on Pharmaceutical Microbiology and Biotechnology, April 29-30, 2019 at London, UK. 2016 Poster Presentation Title: “In vitro antioxidant and cytotoxic activity of different extracts of Coronopus didymus” in the abstract book of 15th International and 27th National Chemistry Conference. Chemistry: Innovation and Sustainability. Page # 295. 22-25 August, at Dept. of Chemistry, University of Malakand, Khyber Pakhtunkhwa, Pakistan. 2015 Title: “Exploration of phenolic constituents of Coronopus didymus by Liquid Chromatography–Mass Spectrometry” in the abstract book of 14th International and 26th National Chemistry Conference. Chemistry: Exploring solutions in the changing World. Page # 102. 05-08 October, at Dept. of Chemistry, University of the Bahawalpur, Punjab, Pakistan. 2014 Oral Presentation Title: “Identification of Volatile Phytochemical Compounds from Coronopus didymus by Gas Chromatography-Mass Spectrometry” in the abstract book of 13th International and 25th National Chemistry Conference. Chemistry: The Vision for Emerging Sciences. 20-22 October, at Institute of Chemistry, University of the Punjab, Lahore, Pakistan. iii dedication Dedicated to my Beloved Mother for her unconditional love, support and prayers iv Acknowledgements Acknowledgements All praises to Almighty ALLAH, most gracious and most compassionate, for all the strengths and blessings in completing this thesis. First of all, I want to express my heartiest gratitude to my respected supervisor, Dr. Muhammad Farman, Associate Professor, Department of Chemistry, Quaid-i-Azam University, Islamabad, for exceptional help and encouragement in my Ph.D study. I am highly indebted for all your precious time and guidelines which proved to be milestones in my study. Without your valuable comments and observations, this dissertation could not be possible for me to complete. Your positive attitude towards my learning journey and whole study process is also treasured. I am very much thankful to Dr. James S.O. McCullagh, Mass Spectrometry Research Laboratory, Chemistry Research Laboratory, University of Oxford, UK, for all the support, advice and guidance he has given me throughout six months International Research Support Initiative Program (IRSIP) scholarship and after that. Thanks for introducing me to the cell and tissue culture world. I am highly obliged for the opportunity to work at Mass Spectrometry Research Laboratory, Chemistry Research Laboratory, University of Oxford, UK. Special thanks to the Chairman and Head of Organic section, Department of Chemistry, Quaid-i-Azam University, for providing necessary research facilities to carry out this research work. I would also like to thank esteemed faculty of the Department of Chemistry, QAU, especially Prof. Dr. Shahid Hameed, for aiding in NMR data interpretation. I am also thankful to all the technical staff at the QAU, Islamabad for their co-operation during my work. I would like to thank Dr. James Wickens from the Mass Spectrometry Research Laboratory (Department of Chemistry, University of Oxford, UK) for his kind help with mass spectrometric analyses and the whole of the Mass Spectrometry group for all their help throughout the six months IRSIP scholarship in using the various instruments. Thanks to Dr. Barbara Odell from the NMR Research Facility (Depertment of Chemistry, University of Oxford, UK) for running all the NMR experiments for me. I would also like to thank Dr. Robert Jacob from Department of v Acknowledgements Chemistry, University of Oxford, UK, for his kind help in providing UV-Vis. spectrophotometric facility. Thanks to Prof. Dr. Mir Ajab Khan, Department of Plant Sciences, QAU, for the identification of investigated plant. I would also like to acknowledge the efforts of Mr. Javed Ihsan, Assistant Plant Pathologist, Ayub Agricultural Research Institute (AARI), Faisalabad, in providing facilities to conduct antimicrobial activity. Bundle of thanks to Higher Education Commission (HEC) of Pakistan for providing me the funds through Indigenous (Ph.D Fellowship for 5000 Scholars- Phase II) and International Research Support Initiative Program (IRSIP) scholarship which provided me the opportunity to work in Mass Spectrometry Research Laboratory, Chemistry Research Laboratory, University of Oxford, UK for a period of six months. I feel incomplete without mentioning and pay my heartiest regards to all my lab fellows and friends, both past and present who made me laugh and gave me wonderful memories. Moreover, exceptional tribute to my family who always supported me and showed their full confidence in me. Their support has greatly helped me in achieving my goal and made my accomplishments worth celebrating. Hafiza Noreen [email protected] vi Abstract Abstract Coronopus didymus is a medicinal plant used traditionally as antipyretic, expectorant, blood purifier and for alleviating symptoms of pain, inflammations, malaria, wounds and cancer. The present study was designed with the objectives of revelation of diagnostic compounds responsible for biological activity of this plant. This work is divided into two main parts, part I includes extraction, preliminary phytochemical analysis, isolation, purification, and identification of phenolic constituents by using mass spectrometric technique. Part II comprises bioevaluation of plant for cytotoxic, antioxidant and antimicrobial activities. Total phenolic content of various solvent extracts was determined using the Folin-Ciocalteu assay. Polar and non-polar constituents of C. didymus were identified by ultra performance liquid chromatography-electrospray ionization-mass spectrometric (UPLC-ESI-MS) and gas-chromatography-mass spectrometric analysis (GC-MS), respectively. Major constituents of C. didymus were isolated by using Sephadex LH-20 column chromatography and preparative mass directed HPLC method. The phenolic content was found to be the highest in the ethanolic extract (CDA Et, 47.8 mM GAE). Eighteen phytochemicals were tentatively identified from ethanolic extract by UPLC-ESI-MS analysis. The predominant compounds of aerial parts were flavonoids while roots contained glucosinolate as the major component. Sixty-three volatile phytochemicals were identified from aerial parts and roots of C. didymus by GC-MS analyses. Mass spectrometric profiling of the C. didymus extracts, confirmed that this plant contained a plenty of compounds. The structures of isolated compounds were elucidated by UV-Vis. spectroscopy (with shift reagents), LC-ESI-MS and NMR spectral data as 5,7,4'- trihydroxy-3'-methoxyflavone-4'-O-β-D-glucoside (1'), 5,7,4'-trihydroxy-3'- methoxyflavone-4'-O-(6''-acetyl)--D-glucoside (2') and 5,7,4'-trihydroxy-3'-methoxy flavone (3'). Compound 1' was identified for the first time from the genus Coronopus. vii Abstract Extracts, fractions and isolated compounds were subjected to various bioassays in a dose dependent manner to understand their anticancer, antioxidant, antifungal and antibacterial susceptibility. Isolated compounds 1'-3' showed promising activity against HeLa cells with IC50 values of 43.50, 0.63 and 3.67 µM, respectively. Significant result was also obtained with compound 3' against LN18 cells with IC50 value of 46.63 µM. In antioxidant activity,
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