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Ph.D. Thesis by IRFAN ULLAH MOLECULAR PROFILING OF BIOACTIVE CONSTITUENTS FROM MONOTHECA BUXIFOLIA (FALC.) FRUIT Ph.D. Thesis By IRFAN ULLAH DEPARTMENT OF PHARMACY UNIVERSITY OF PESHAWAR, PESHAWAR, PAKISTAN 2016 MOLECULAR PROFILING OF BIOACTIVE CONSTITUENTS FROM MONOTHECA BUXIFOLIA (FALC.) FRUIT IRFAN ULLAH A THESIS SUBMITTED TO THE DEPARTMENT OF PHARMACY, UNIVERSITY OF PESHAWAR IN PARTIAL FULFILLMENT FOR THE DEGREE OF DOCTOR OF PHILOSOPHY IN PHARMACEUTICAL SCIENCES DEPARTMENT OF PHARMACY UNIVERSITY OF PESHAWAR, PESHAWAR, PAKISTAN 2016 This thesis, entitled, “MOLECULAR PROFILING OF BIOACTIVE CONSTITUENTS FROM MONOTHECA BUXIFOLIA (FALC.) FRUIT” submitted by Mr. Irfan Ullah is hereby approved and recommended as partial fulfilment for the award of Degree of Doctor of Philosophy in Pharmaceutical Sciences”. Prof. Dr. Jamshaid Ali Khan __________________________ Research Supervisor, Department of Pharmacy, University of Peshawar. Professor Dr. Muhammad Saeed __________________________ Chairman, Department of Pharmacy, University of Peshawar. External Examiner _________________________ DEPARTMENT OF PHARMACY UNIVERSITY OF PESHAWAR, PESHAWAR, PAKISTAN 2016 Dedication Dedicated To My Dear Parents Acknowledgements Acknowledgements I am thankful to Almighty Allah, Who made me sanctified with patience, understanding, countless blessing of health, and wellbeing to complete my Ph.D. project successfully, which is certainly a landmark in my life. I would like to gratefully and sincerely thank Prof. Dr. Jamshaid Ali Khan for his guidance, understanding, patience, and most importantly, his friendship during my studies. His mentorship was paramount in providing a well-rounded experience consistent with my long-term career goals. He encouraged me to not only grow as an experimentalist but also as an instructor and an independent thinker. I am not sure many graduate students are given the opportunity to develop their own individuality and self-sufficiency by being allowed to work with such independence. For everything you’ve done for me, Sir, I thank you. I am using this opportunity to express my gratitude to Meritorious Professor. Dr. Zafar Iqbal (T.I), who supported me throughout the course of this Ph.D. project. I am sincerely grateful to him for sharing his fruitful and illuminating views on a number of issues related to the project. I am also thankful to Prof. Dr. Muhammad Saeed, Chairman, Department of Pharmacy, University of Peshawar, for the continuous support and encouragement throughout my research studies. I am also thankful to Prof. Dr. Fazal Subhan and Prof. Dr. Muhammad Ismail for their aspiring guidance and providing the required facilities during the project work. I would also like to appreciate the cooperation of all the teaching and non-teaching staff of department. Acknowledgements It is my privilege to acknowledge the admirable facilitation, expert opinion and cooperation by Prof. Dr. Muhammad Iqbal Choudhary, Dr. Achyut Adhikari, Prof. Dr. Khalid Mohammed Khan, Dr. Muhammad Ateeq, Dr. Ajmal Khan, Mr. Shahid Ali Khan, Mr. Zafar Ali Shah, and Dr. Naveed Iqbal, International Centre for Chemical and Biological Sciences (ICCBS), H.E.J Research Institute of Chemistry, University of Karachi during this long course of research venture. I am grateful to all my research seniors especially Dr. Abad Khan, Mr. Salar Muhammad, Mr. Imran Ullah, Dr. Muhammad Imran, Dr. Muzaffar Abbas, Dr. Waqar Ahmad Kaleem, Dr. Naveed Muhammad and Dr. Lateef Ahmad for enlightening me the first glance of research. Indeed I would also like to thank all my fellow lab-mates especially, Mr. Safiullah, Mr. Peer Abdul Hannan, Mr. Muhammad Shahid, Mr. Javaid Alam, Mr. Ismail, Mr. Muhammad Hassan, Dr. Muhammad Shafiq, Ms. Mehreen Rehman, Mr. Waheed Ur Rehman, Dr. Zia Ul Haq, Mr. Fawad Ahmed and Mr. Qasim Khan for the fruitful discussions, kind support, positive criticism and for all the fun we have had in the last four years. Infact I am also thankful to the Department of Pharmacy, and University of Peshawar for providing me such a great opportunity of higher studies. Last but not the least; I would like to thank my parents, brothers, sisters, my uncle Mr. Muhammad Hayat (Advocate), my grandmother and all relatives for supporting me spiritually throughout my studies and my life in general, your support and prayers really made me too much confident. Irfan Ullah Peshawar, 2016 Table of Contents Summary…..………………………………………………………………………….i-ii List of Abbreviations………..…………….……………………………………......iii-vi 1. INTRODUCTION ................................................................................................... 1 1.1. General Introduction ...................................................................................... 1 1.1.1. History of plants as a source of drugs ....................................................... 1 1.1.2. Medicinal importance of plants ................................................................ 2 1.1.3. Modern day drugs from medicinal plants ................................................. 2 1.1.4. Some dietary supplements as preventive medicine .................................. 4 1.1.5. Market value of natural products in the world .......................................... 5 1.1.6. Research on medicinal plants; a basic need of the day ............................. 6 1.1.7. History of herbal products during 19th and 20th centuries ......................... 8 1.1.8. Bioassay-guided isolation from natural products ..................................... 9 1.1.9. Medicinal plants as best sources of important drugs .............................. 10 1.1.10. Secondary metabolites ............................................................................ 18 1.1.10.1. Major classes of plant specialized compounds…………………… .19 1.1.11. Status of medicinal plants in the world ................................................... 21 1.1.12. Medicinal plants status in Pakistan ......................................................... 22 1.1.13. Family Sapotaceae .................................................................................. 24 1.1.14. Status of family Sapotaceae in medicinal plants ..................................... 25 1.1.15. Biological activities of family Sapotaceae .............................................. 25 1.1.16. The genus Monotheca ............................................................................. 31 1.2. Plant Introduction ............................................................................................... 32 1.2.1. Monotheca buxifolia ............................................................................... 32 1.2.2. Synonyms ................................................................................................ 32 1.2.3. Morphology............................................................................................. 34 1.2.4. Fruit ......................................................................................................... 34 1.2.5. Distribution ............................................................................................. 34 1.2.6. Ethnobotanical uses ................................................................................ 34 1.2.7. Previously reported activities of Monotheca buxifolia fruit ................... 35 1.3. Aim and Objectives ............................................................................................ 36 2. MATERIAL AND METHODS ............................................................................. 37 2.1. General Experimental Requirements .................................................................. 37 2.1.1. Experimental Conditions ........................................................................ 40 2.1.1.1 Physical Constants….……………………………………………… .40 2.1.2. Spectroscopy ........................................................................................... 40 2.1.2.1 UV Spectra……………………………………………………… …..40 2.1.2.2 IR Spectra…………..…………………………………………… ….40 2.1.2.3 Nuclear Magnetic Resonance (NMR) ………….……………… ..…41 2.1.3. Spectrometry…………………………………………………………...42 2.1.3.1. Mass Spectra………………………………………………....… …42 2.1.3.2. Gas Chromatography-Mass Spectrometry (GC-MS)………..…… 42 2.2. Isolation and Purification of Compounds ........................................................... 42 2.2.1. Column Chromatography (CC)............................................................... 42 2.2.2. Thin-layer Chromatography (TLC) ........................................................ 43 2.2.3. Visualizing Compounds Spot on Developed TLC.................................. 43 2.2.4. Ceric Sulphate Solution .......................................................................... 43 2.2.5. Dragendorff’s Solution ........................................................................... 43 2.2.6. Iodine solution ........................................................................................ 44 2.2.7. Preparative HPLC (Recycling HPLC) .................................................... 44 2.3. Plant Materials .................................................................................................... 44 2.3.1. Collection ................................................................................................ 44 2.3.2. Extraction ................................................................................................ 45 2.3.3. Fractionation ........................................................................................... 45 2.4. Animals Used ....................................................................................................
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