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Phytochemical and Biological Study of Some Rumex Species (Rumex Vesicarius) Family Polygonaceae

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Phytochemical and Biological Study of Some Rumex Species (Rumex Vesicarius) Family Polygonaceae Phytochemical and Biological Study of some Rumex Species (Rumex vesicarius) Family Polygonaceae Thesis submitted for fulfillment of the requirement of the master degree of the pharmaceutical science in pharmacognosy by Marwa Yehia El Harriry National Organization of Drug Control and Research (NODCAR) Under the Supervision of Dr. Seham El Hawary Dr. kamilia Fouly Taha Professor of Pharmacognosy Professor of Pharmacognosy Faculty of Pharmacy Applied research center for Cairo university medicinal plants NODCAR Dr. Nadia Sokkar Associate Professor of Pharmacognosy Faculty of Pharmacy Cairo university Pharmacognosy department Faculty of Pharmacy Cairo University 2012 Acknowledgement I’m grateful to God by the grace of whom this work was accomplished. I would like to express my deep appreciation and sincere gratitude to Prof. Dr. Seham Salah El-Din El-Hawary, Professor of Pharmacognosy, Faculty of pharmacy, Cairo University for her super way of supervision, valuable scientific guidance and her useful efforts throughout this work. I would like to express my deep appreciation and sincere gratitude to Prof. Dr. Kamilia Foluy Taha, Professor of Pharmacognosy, Applied Research Center for Medicinal Plants, National Organization for Drug control and Research, for her supervision and useful efforts throughout this work. I would like to express my sincere everlasting gratitude to Dr. Nadia H. Sokkar, Associate Professor of Pharmacognosy, Faculty of Pharmacy, Cairo University for her kind and patient supervision, stainless support and unlimited help throughout the course of this work. My deepest thanks to Dr.ZeinabYousef, Assistant Professor of Biochemistry Department, National Organization for Drug control and Research for her kind help in carrying out the pharmacological and toxicological testing of the plant extracts. Finally, my deepest thanks to my parents, my family, my colleagues and friends who play a very special part in my life. Marwa Yehia El Harriry Contents Subject Page Introduction 1 Review of literature 3 Taxonomy 18 Material, apparatus and techniques 21 Part One: DNA profiling of Rumex vesicarius. 32 Part Two: Phytochemical investigation of Rumex vesicarius Chapter I: Prelimenary phytochemical screening and proximate 37 analysis Chapter II: investigation of volatile constitueunts of rumex 41 vesicarius. Chapter III: Investigation of lipoidal conistituents of Rumex 46 vesicarius. Chapter IV: Quantitative estimation of total phenolic and 55 flavonoid content in leaves of Rumex vesicarius Chapter V: Qualitative and quatitative investigation of flavonoids in Rumex vesicarius 60 Chapter VI: Quantitative estimation of anthraquinones in Rumex vesicarius 97 Chapter VII: Study of the vitamin content of Rumex vesicarius. 102 Part Three: Biological study on different organs of Rumex 106 vesicarius A- Serum biochemical analysis 109 I- Assessment of liver function 109 II- Assessment of antioxidant activities and lipid peroxidation 113 III- Assessment of liver fibrosis 120 IV- Assessment of the permeability of hepatic lysosomal 121 membrane B- Histopathological studies in liver 129 Summary 133 Recommendations 139 References 140 List of Figures Figure Page Some selected photographs of Rumex vesicarius L Figure (1) 20 wildly grown in Egypt Figure (2) RAPD analysis of the well known Rumex cultivated in 35 Egypt using five different primers Figure (3) TIC for GC/MS chart of volatile oil prepared from 42 Rumex vesicarius L Figure (4) Total Ion Chromatogram (TIC) of GC/MS chart of the 48 unsaponifiable matter of leaves of Rumex vesicarius L Figure (5) Total Ion Chromatogram (TIC) of GC/MS chart of the 52 fatty acid methyl esters of Rumex vesicarius L. Figure (6) Standard calibration curve of Gallic acid 57 Figure (7) Standard calibration curve of Quercetin 58 Figure (8) Structure of compound F1 65 Figure (9) Full mass spectrum of compound F1 66 Figure (10) Mass fragmentation of compound F1 67 Figure (11) HNMR spectrum of compound F1 68 Figure (12) Structure of compound F2 70 Figure (13) Full mass spectrum of compound F2 71 Figure (14) Mass fragmentation of compound F2 72 Figure (15) HNMR spectrum of compound F2 73 Chromatogram of ethyl acetate fraction using S5, (A) LC/PDA chromatogram and (B) LC/MS, 1;vitexin, Figure (16) 2;orientin, 3;hexosyl-quercetin, 4;rutin, 5; 7-O-rhamno- 76 hexosyl-diosmetin, 6; 7-O-rhamno-acetyl hexosyl- diosmetin LC/MS/MS chromatogram of n-butanol fraction using S6, (A) LC/PDA chromatogram and (B) LC/MS,7;catechin, 8;epicatechin, 9;feruloyl hexoside, Figure (17) 77 10;naringenin 6-C- glucoside, 11;epigallocatechin gallate, 12; catechin 6-C- glucoside and epicatechin gallate (A)Hexose cross-ring cleavages, (B) Structures of Figure (18) vitexin, orientin, 6-C- hexosyl quercetin, catechin-6-C- 79 glucoside and naringenin-6-C-glucoside Mass fragments of vitexin, orientin, 6- c- hexosyl Figure (19) quercetin, naringenin 6-c- glucoside and catechin 6-c- 82 glucoside. Figure (20) Structures of rutin, 7-O-rhamno-hexosyl-diosmetin and 83 7-O-rhamno-actyl hexosyl-diosmetin Mass fragments of 7-O-rhamno-hexosyl-diosmetin and Figure (21) 84 7-O-rhamno-acetyl hexosyl-diosmetin. Structures of catechin, epicatechin , epicatechin gallate, Figure (22) 86 epigallocatechin gallate and feruloyl hexoside. Mass fragments of catechin, epicatechin , epicatechin Figure (23) 88 gallate and epigallocatechin gallate. Standard curves of authentics, (1) naringin, (2) diosmin, Figure (24) 95 (3) catechin, (4) orientin and (5) vitexin Figure (25) Standard calibration curve of rhein 98 TLC chromatogram of, A: roots, B: leaves and C: fruits Figure (26) of Rumex vesicarius L, 1, Aloe-emodin; 2 , rhein; 3, 100 emodin; 4, chrysophanol and 5, physcione. Effect of root, leaves and fruits ethanolic extracts of Rumex vesicarius L on serum enzymes (AST, ALT, Figure (27) 112 ALP, T.B, T.P) compared to silymarin in liver damaged rats Effect of root, leaves and fruits ethanolic extracts of Figure (28) Rumex vesicarius L on (MDA, SOD, CAT, GST and 119 GSH) compared to silymarin in liver damaged rats Effect of root, leaves and fruits ethanolic extracts of Figure (29) Rumex vesicarius on Liver Index, MDA, 124 Hydroxyproline(HYP) and lysosomal enzymes (ACP, β-GAL and β-NAG) Compared to Silymarin A photomicrograph of liver sections in the normal Figure (30) control rats (A) showing cords of hepatocytes radiating 130 from the central vein CCl4-intoxicated rats showing fatty degeneration, Figure (31) necrotic areas and portal loss of architecture with mild 130 congestion of blood vessels (Haematoxylin-Eosin stain, x150) (A) rats treated with (L.E+CCl4) showing improvement in the liver, (B): rats treated with (F.E+CCl4) showing mild pathological changes as fatty degenerative Figure (32) changes, (C): rats treated with (R.E+CCl4) showing mild 131 fatty degenerative changes and (D): rats treated with (Sily+CCl4) showing more or less normal architecture of liver lobules List of Tables Table Page Distribution of active constituents in different Table (1) 7 organs of genus Rumex The RAPD analysis of the species of Rumex Table(2) dentatus L. and Rumex vesicarius L. with five 36 primers Table (3) Results of preliminary phytochemical screening of 37 different organs of Rumex vesicarius L. Table (4) Pharmacopeial constants of the leaves of Rumex 40 vesicarius L. Table (5) GC/MS of the essential oil of fruits of Rumex 43 vesicarius L Table (6) The different chemical classes of the identified 46 compounds Table (7) GC/MS of the unsaponifiable matter of leaves of 49 Rumex vesicarius L. Table (8) GC/MS of the fatty acid methyl esters of leaves of 53 Rumex vesicarius L. Table (9) The absorbance measured for different 56 concentrations of standard gallic acid solution Table (10) The absorbance measured for different 58 concentrations of standard quercetin solution Table (11) TLC screening of the n-butanol extract of the 62 leaves of Rumex vesicarius L Table (12) data of compound F1 64 Table (13) data of compound F2 69 The retention times, UV absorbance and masses of Table (14) 89 the identified compounds Table (15) Quantitative estimation of phenolics in Rumex 93 vesicarius L Table (16) The peak areas for different concentrations of the 98 standard rhein Table (17) Identified anthraquinones in roots, leaves and fruits 99 of Rumex vesicarius L by HPTLC Table (18) Anthraquinone content in roots, leaves and fruits of 101 Rumex vesicarius L Vitamin content in different organs of Rumex Table (19) 105 vesicarius L. Effect of root, leaves and fruits ethanolic extracts Table (20) of Rumex vesicarius L on serum enzymes (AST, 111 ALT, ALP, T.B, T.P) compared to silymarin in liver damaged rats. Effect of root, leaves and fruits ethanolic extracts Table (21) of Rumex vesicarius L on (MDA, SOD, CAT, 118 GST and GSH) compared to silymarin in liver damaged rats Effect of root, leaves and fruits ethanolic extracts Table (22) of Rumex vesicarius L on Liver Index, Liver MDA, 123 Hydroxyproline and Lysosomal Enzymes (ACP, β-GAL and β-NAG) Compared to Silymarin List of abbreviations: a P: Probability < 0.05 b P: Probability < 0.01 c P: Probability < 0.001 ALP: Alkaline phosphatase ALT: Alanin amino transeferase AST: Aspartate amino transeferase ACP: Acid phosphatase β -GAL: β- galactosidase β-NAG: N- acetyl-β –glucosaminsidase CAT: Catalase CDNB: 1- Chloro dinitrobenzene CTAB: N-cetyl-N,N,N-tri methyl ammonium bromide CYP2E: Cytochrome P 450 system DNA: Deoxyribonucleic acid DMSO: Dimethyl sulfoxide EEF: Ethanolic extract of fruits EEL: Ethanolic extract of leaves EER: Ethanolic extract of roots ESI:
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