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Identification and Characterization of Antioxidant and Cytotoxic Activities of Selected Medicinal Plants of Gallyat Region, Pakistan

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Identification and Characterization of Antioxidant and Cytotoxic Activities of Selected Medicinal Plants of Gallyat Region, Pakistan IDENTIFICATION AND CHARACTERIZATION OF ANTIOXIDANT AND CYTOTOXIC ACTIVITIES OF SELECTED MEDICINAL PLANTS OF GALLYAT REGION, PAKISTAN MUHAMMAD ISHAQUE 02-arid-270 Department of Botany Faculty of Sciences PirMehr Ali Shah Arid Agriculture University Rawalpindi, Pakistan 2018 i IDENTIFICATION AND CHARACTERIZATION OF ANTIOXIDANT AND CYTOTOXIC ACTIVITIES OF SELECTED MEDICINAL PLANTS OF GALLYAT REGION, PAKISTAN by MUHAMMAD ISHAQUE (02-arid-270) A thesis submitted in partial fulfillment of the requirements of the degree of Doctor of Philosophy in Botany Department of Botany Faculty of Sciences PirMehr Ali Shah Arid Agriculture University Rawalpindi, Pakistan 2018 ii iii iv v iii iv THIS DISSERTATION IS DEDICATED TOMy Beloved Parents For their endless love and support and To My Worthy Teachers For their guidance, encouragement and support v CONTENTS Page List of Tables xiii List of Figures xvi List of Abbreviations xxiv Acknowledgement xxvii Abstract xxix 1 INTRODUCTION 1 1.1 BIOACTIVE NATURAL COMPOUNDS 1 1.2 ANTIOXIDANT AND CYTOTOXIC BIOACTIVE 3 COMPOUNDS 1.3 DETECTION OF ANTIOXIDANT AND CYTOTOXIC 3 BIOACTIVE COMPOUNDS 1.3.1 Brine Shrimp Lethality Test (BSLT) 5 1.3.2 Potato Disc Anti-tumor Assay 5 1.3.3 DPPH Free Radical Scavenging Bioassay 6 1.4 ISOLATION AND IDENTIFICATION OF BIOACTIVE 7 NATURAL PRODUCTS 1.4.1 Chromatography 8 1.4.1.1 Column chromatography 8 1.4.1.2 Thin layer chromatography (TLC) 9 vi 1.4.1.3 Preparative thin layer chromatography (PTLC) 9 1.4.1.4 Medium pressure liquid chromatography (MPLC) 11 1.4.1.5 High performance liquid chromatography(HPLC) 11 1.4.2 Spectroscopy 12 1.4.2.1 UV-Vis spectroscopy 12 1.4.2.2 Mass spectroscopy 13 1.4.2.3 Nuclear magnetic resonance spectroscopy (NMR) 13 1.5 STUDY AREA 13 1.6 SELECTION OF MEDICINAL PLANT SPECIES FOR 15 PRESENT STUDY 1.6.1 Dryopteris ramosa (Hope) C. Chr. 16 1.6.2 Quercus leucotricophora A. Camus ex Bahadur 16 1.6.3 Arisaema flavum (Forssk.) Schott 17 1.6.4 Bidens biternata(Lour.) Merr. &Sherff 18 1.6.5 Rosa brunonii Lindl 19 1.7 OBJECTIVES OF PRESENT STUDY 18 2 REVIEW OF LITERATURE 24 3 MATERIALS AND METHODS 33 3.1 SELECTION OF PLANT SPECIES 33 3.2 COLLECTION OF PLANT MATERIAL 33 3.3 PROCESSING, DRYING AND EXTRACTION 33 vii 3.4 BIOACTIVITIES OF CRUDE METHANOLIC 34 EXTRACTS 3.4.1 Antioxidant Activities 34 3.4.1.1 Preparation of DPPH solution 34 3.4.1.2 Preparation of extract samples 34 3.4.1.3 Bioassay (DPPH) 35 3.4.2 Cytotoxic Potential of Crude Methanolic Extracts 35 3.4.2.1 Hatching of brine shrimps 36 3.4.2.2 Bioassay (BSLT) 36 3.4.3 Antitumor Potential of Crude Extracts 37 3.4.3.1 Preparing Agrobacterium tumefaciens culture 37 3.4.3.2 Viability test of A. tumefaciens 38 3.4.3.3 Procedure of bioassay 38 3.5 FRACTIONATION OF CRUDE EXTRACTS 39 3.5.1 Bioactivities of Fractions 42 3.6 PRELIMINARY TESTS FOR PHYTOCHEMICALS 42 3.7 ESTIMATION OF PHENOLIC CONSTITUENTS OF 44 EXTRACTS 3.8 ESTIMATION OF TOTAL FLAVONOID 44 CONSTITUENTS 3.9 ISOLATION OF COMPOUNDS 45 viii 3.9.1 Column Chromatography 45 3.9.1.1 Normal phase 45 3.9.1.2 Reverse phase 46 3.9.1.3 Sephadex LH20 46 3.9.3 Thin Layer Chromatography (TLC) 46 3.9.3 High Performance Liquid Chromatography(HPLC) 47 3.9.4 Medium Pressure Liquid Chromatography(MPLC) 47 3.9.5 Preparative Thin Layer Chromatography (PTLC) 47 3.10 IDENTIFICATION of ISOLATED COMPOUND 48 3.10.1 Melting Point of Isolated Compounds 48 3.10.2 TLC Spraying Reagents 48 3.10.3 UV-Absorption Spectr0scopy 48 3.10.4 Mass Spectrometry 49 3.10.5 Fourier Transform Infrared Radiation (FT-IR) 49 Spectroscopy 3.10.6 Nuclear Magnetic Resonance (NMR) Spectroscopy 49 3.11 STATISTICAL ANALYSIS 50 4 RESULTS 51 4.1 BIOACTIVITIES OF CRUDE EXTRACTS 51 4.1.1 Antioxidant Potential of Crude Extracts 51 4.1.2 Cytotoxic Potential of Crude Extracts 52 ix 4.1.3 Potato Disc Anti-tumor Assay on Crude Methanol Extracts 56 of Selected Plants 4.2 FRACTIONATION AND BIOACTIVITIES OF 59 FRACTIONS 4.2.1 Antioxidant Potential of Fractions 59 4.2.2 Cytotoxic Potential of Fractions 59 4.2.3 Antitumor Potential of Fractions 60 4.3 PRELIMINARY PHYTOCHEMICALS ANALYSIS 60 4.3.1 Determination of Total Phenolic and Total Flavonoid 71 Contents 4.4 ISOLATION AND STRUCTURE ELUCIDATION OF 72 COMPOUNDS 4.4.1 Isolation of Pure Compound From Aqueous Fraction of D. 72 ramosa 4.4.1.1 Column chromatography of group 2 78 4.4.1.2 Isolation of compounds from group 3 80 4.4.2 Structural Elucidation of Isolated Compound From 83 Aqueous Fraction of D. Ramosa 4.4.2.1 Identification and structural elucidation of isolated 83 compound DAF-MI-01 4.4.2.2 Identification and structural elucidation of isolated 87 compound DAF-MI-02.1 4.4.2.3 Identification and structural elucidation of isolated 98 x compound DAF-MI-02.2 4.4.3 Isolation of Compounds From Ethyl Acetate Fraction of D. 119 ramosa 4.4.3.1 Identification of isolated compound (DEF-4MP1910) 120 4.4.4 Isolation of Pure Compound From Ethyl Acetate Fraction 134 of R. brunonii 4.4.4.1 Isolation of compounds from sub group 5 (Ethyl acetate 135 fraction of R. brunonii): 4.4.4.2 Isolation of Compounds From sub Group 4 (Ethyl acetate 135 fraction of R. brunonii). 4.4.4.3 Identification of Isolated Compound REF-5s5: 137 4.4.4.4 Identification of Isolated Compound REF-5s67 141 4.4.4.5 Identification of Isolated Compound REF-Mi-01-49 154 4.5 BIOACTIVITIES OF ISOLATED COMPOUNDS 173 4.5.1 Free Radical Scavenging Potential of Isolated Pure 173 Compounds. 4.5.2 Cytotoxic Potential of Isolated Compound Against Brine 174 Shrimps (BSLT). 5 DISCUSSION 181 5.1 BIOLOGICAL ASSAYS ON CRUDE METHANOL 181 EXTRACT (CME) 5.2 BIOACTIVITIES OF FRACTIONS 185 5.3 QUALITATIVE AND QUANTITATIVE ESTIMATION 187 xi OF PHYTOCHEMICALS 5.4 IDENTIFICATION OF ISOLATED COMPOUNDS 189 FROM AQUEOUS FRACTION OF D. RAMOSA. 5.5 IDENTIFICATION OF ISOLATED COMPOUNDS 196 FROM ETHYL ACETATE FRACTION OF D. RAMOSA. 5.6 IDENTIFICATION OF ISOLATED COMPOUNDS 198 FROM ETHYL ACETATE FRACTION OF R. brunonii. 5.7 ANTIOXIDANT AND CYTOTOXIC PROPERTIES OF 206 ISOLATED COMPOUNDS FUTURE RECOMMENDATIONS 208 SUMMARY 209 LITERATURE CITED 211 APPENDICES 240 xii List of Tables Table No. Page 1.1 Plants derived bioactive compounds and their uses in human 4 health care. 1.2 Taxonomic classification of selected plant species 21 3.1 Crude methanolic extract yield of selected plant species. 40 3.2 Amount of fractions obtained after solvent-solvent 40 fractionation of crude extracts. 4.1 Antioxidant potential of crude extracts of selected 53 plants in terms of IC50. 4.2a Mean percentage lethality of crude extracts against Brine 55 shrimp (BSLT). 4.2b Mean percentage lethality of Nicotine (standard) 55 against Brine shrimp (BSLT). 4.3 Determination of LD50 for crude extracts in BSLT. 57 4.4 Antitumor potential of crude extracts of selected plants. 61 4.5 Mean percentage scavenging and IC50 of fractions obtained 61 from crude extracts of D. ramosa, Q. leucotricophora and R.brunonii 4.6 Mean percentage death (lethality) of different fractions of 64 selected plants against brine shrimps. 4.7 Calculation of LD50 of fractions of selected plants. 69 xiii 4.8 Mean percentage tumor inhibition and IC50 of 69 fractionsobtained from CME of D. ramosa and R. brunonii. 4.9 Preliminary phytochemical analysis of crude extracts. 73 4.10 Qualitative phytochemical analysis of fractions obtained 74 from CME of D. ramosa, Q. leucotricophora and R. brunonii 4.11 Total phenolic contents of crude extracts of selected plants. 75 4.12 Total flavonoid contents of crude extracts of selected plants. 76 4.13 Solvent mixture used as mobile phase in MPLC and number 79 of fractions obtained during purification of sub group 2a (D. ramosa aqueous fraction) 4.14 NMR (1H &13C) chemical shift values and DEPT analysis 90 ofisolated compound DAF-MI-01. 4.15 NMR (1H &13C) chemical shift values and DEPT analysis 101 of isolated compound DAF-MI-02.1. 4.16 NMR (1H &13C) chemical shift values and DEPT 112 analysisofisolated compound DAF-MI-02.2. 4.17 Mobile phase used during column chromatography of ethyl 121 acetate fraction of D. ramosa. 4.18 NMR (1H &13C) chemical shift values and DEPT analysis 128 ofisolated compound DEF-MP1910. 4.19 Mobile phase used during column chromatography of ethyl 142 acetate fraction of R. brunonii. 4.20 NMR (1H &13C) chemical shift values and DEPT analysis 146 xiv ofisolated compound REF-5s5. 4.21 NMR (1H &13C) chemical shift values and DEPT analysis 157 ofisolated compound REF-5s67. 4.22 NMR (1H &13C) chemical shift values and DEPT analysis 166 ofisolated compound REF-MI-01-49. 4.23 Mean percentage scavenging potential and IC50 of isolated 176 pure compounds. 4.24 Mean percentage lethality and LD50of isolated compounds 178 inBrine Shrimp Lethality Test (BSLT). xv List of Figures Page Figure No. 1.1 Mechanism of DPPH free radical scavenging bioassay 10 1.2 Instruments a) MPLC and b) HPLC instrument 10 1.3 Map of Pakistan highlighting study area (Galyat region) 22 and collection sites of medicinal plants for the present study. 1.4 Selected medicinal plant species of Gallyat region, 23 Pakistan 3.1 Fractionation scheme of crude methanolic extract 41 4.1 Dose dependent free radical scavenging potential of 53 crudemethanolic extracts of selected plants 4.2 Free radical scavenging potential of selected crude 54 extracts.
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