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DIOSPYROS LOTUS by ABDUR RAUF PHYTOCHEMICAL INVESTIGATION AND BIOACTIVITES OF PISTACIA INTEGERRIMA AND DIOSPYROS LOTUS By ABDUR RAUF Dissertation submitted to the University of Peshawar in partial fulfillment of the requirements for the Degree of Doctor of Philosophy in Chemistry INSTITUTE OF CHEMICAL SCIENCES i UNIVERSITY OF PESHAWAR, PESHAWAR PAKISTAN (DECEMBER, 2014) PHYTOCHEMICAL INVESTIGATION AND BIOACTIVITES OF PISTACIA INTEGERRIMA AND DIOSPYROS LOTUS By ABDUL RAUF DISSERTATION SUBMITTED TO THE UNIVERSITY OF PESHAWAR IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY IN CHEMISTRY ii INSTITUTE OF CHEMICAL SCIENCES UNIVERSITY OF PESHAWAR, PAKISTAN DECEMBER, 2014 DECLARATIONS This is to certify that this dissertation prepared by Mr. Abdur Rauf entitled “Phytochemical Investigation and Bioactivities of Pistacia integerrima and Diospyros lotus” is accepted in the present form by the Institute of Chemical Sciences, University of Peshawar as fulfilling this part of the requirements for the degree of DOCTOR OF PHILOSOPHY IN CHEMISTRY ________________________ ________________________ SUPERVISOR CO-SUPERVISOR Prof. Dr. Ghias Uddin Prof. Dr. Bina S. Siddiqui Institute of Chemical Science, HEJ Research Institute of Chemistry, University of Peshawar, Peshawar, University of Karachi, Karachi, Pakistan Pakistan ________________________ ________________________ iii EXTERNAL EXAMINER Prof. Dr. Yousaf Iqbal Director, Institute of Chemical Sciences, University of Peshawar, Peshawar Pakistan iv THIS THESIS IS DEDICATED TO MY FATHER AND MOTHER (An Eternal Source of Guidance) v Table of Contents Contents ................................................................................................................................................ i Acknowledgments .............................................................................................................................. x List of Figures ................................................................................................................................. xvii List of Tables .................................................................................................................................... xix List of Schemes ................................................................................................................................ xvi Abstract............................................................................................................................................ xvii List of Abbreviations .................................................................................................................... xxiv Chapter 1 Part-A GENERAL INTRODUCTION ........................................................................................................ 1 Chapter 2 INTRODUCTION (Part-A) .............................................................................................................. 3 2.1. Family Ebenaceae ..................................................................................................................... 3 2.2. Genus Diospyros ....................................................................................................................... 3 2.3. Diospyros lotus .......................................................................................................................... 5 2.4. Pharmacological studies of Diospyros..................................................................................... 7 2.4.1. Acute toxicity ..................................................................................................................... 7 2.4.2. Analgesic activity ............................................................................................................... 7 2.4.3. Antipyretic activity............................................................................................................. 7 2.4.4. Anti-inflammatory.............................................................................................................. 7 2.4.5. Hepatoprotective effect ...................................................................................................... 8 2.4.6. Antioxidant activity............................................................................................................ 8 2.4.7. Antibacterial effect ............................................................................................................. 8 2.4.8. Cytotoxic activity ............................................................................................................... 9 2.4.9. Anthelmintic activity.......................................................................................................... 9 2.4.10. Tyrosinase inhibiting activity ........................................................................................ 10 2.4.11. Xanthine oxidase inhibitory activity ............................................................................. 10 2.4.12. Collagenase inhibitory effect......................................................................................... 10 2.4.13. Lipoxygenase inhibitor effect ........................................................................................ 10 2.4.14. Protein tyrosine phosphatase 1B ................................................................................... 10 2.4.15. Cosmaceutical effect ...................................................................................................... 10 vi 2.4.16. Antihypertensive effect .................................................................................................. 11 2.4.17. Effect on rat skeletal muscles ........................................................................................ 11 2.4.18. Antidiabetic effect .......................................................................................................... 11 2.4.19. Neuropharmacological activities ................................................................................... 11 2. 5. Chemical constituents ............................................................................................................ 13 Chapter 3 RESULTS AND DISCUSSION (Part-A) ..................................................................................... 34 3.1. Preliminary phytochemical analysis of D. lotus ................................................................... 34 3.1.1. Phytochemical analysis of hard wood of D. lotus ......................................................... 34 3.1.2. Phytochemical analysis of leaves of D. lotus................................................................. 35 3.1.3. Phytochemical analysis of bark of D. lotus.................................................................... 35 3.1.4. Phytochemical analysis of roots of D. lotus ................................................................... 36 3.2. Chemical structures of isolated constituents from D. lotus roots ........................................ 38 3.2.1. New chemical constituents .............................................................................................. 38 3.2.2. Hitherto unreported chemical constituents ..................................................................... 40 3.2.1.1. Di-naphthodiospyrol A (1) ........................................................................................... 43 3.2.1.2. Di-naphthodiospyrol B ( 2) .......................................................................................... 45 3.2.1.3. Di-naphthodiospyrol C (3) ........................................................................................... 47 3.2.1.4. Di-naphthodiospyrol D ( 4) .......................................................................................... 49 3.2.1.5. Di-naphthodiospyrol E ( 5) ........................................................................................... 53 3.2.2.1. Lupeol (6) ...................................................................................................................... 56 3.2.2.2. β-Sitosterol (7)............................................................................................................... 58 3.2.2.3. Stigmasterol (8) ............................................................................................................. 60 3.2.2.4. Diospyrin (9) ................................................................................................................. 62 3.2.2.5. 8-Hydroxyisodiospyrin (10) ......................................................................................... 64 3.2.2.6. 7-Methyljuglone (11) .................................................................................................... 66 3.2.2.7. Oleanolic acid (12) ........................................................................................................ 68 3.2.2.8. Ursolic acid (13) ............................................................................................................ 70 3.2.2.9. Betulinic acid (14) ......................................................................................................... 72 3.3. Chemical composition of fixed oil from D. lotus ................................................................. 74 3.4. Biological profile of D. lotus .................................................................................................. 78 vii 3.4.1. In vitro screening .............................................................................................................
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