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Al-Farabi Kazakh National University UDC: 547.972+249.90+661.123 On Al-Farabi Kazakh National University UDC: 547.972+249.90+661.123 On manuscript rights REDA AHMED ABDEL-HAMID Investigation of chemical constituents and biological activities of some native halophytes 6D072100 − Chemical Technology of Organic Substances Dissertation submitted in fulfillment of the requirements for the degree Doctor of Philosophy (PhD) Supervisors Prof. Dr. Abilov Zh.A. Al-Farabi Kazakh National University, Kazakhstan Prof. Dr. Ross S.A. Mississippi University, USA Republic of Kazakhstan Almaty, 2014 List of contents STANDARD REFERENCES ……………………………………………...…. 5 ABBREVIATION …………………………………………………………..…. 6 INTRODUCTION …………………………………………………………...… 8 1 LITERATURE REVIEW ………………………………………………....... 12 1.1 Classification and distribution of halophytes …………………………...… 12 1.2 Cellular adaptations of the plants against salt stress Synthesis of compatible solutes (Osmolyte production) ………………………………. 13 1.3 Diversity of Halophytes ………………………………………………… 13 1.4 General characters of the genus Camphorosma …………………..…………. 14 1.5 General characters of the genus Zygophyllum ………………………..………. 16 1.6 Chemical review of halophytes …………………...………………………. 18 1.6.1 Triterpenes and saponins …………………………………………...…. 18 1.6.1.1 Isolation and characterization of saponins ……………………...… 24 1.6.1.2 Identification of triterpenes and saponins by NMR and Mass spectrometry ……………………...…………………………….... 28 1.6.2 Polyphenolic compounds …………………………………………… 31 1.6.2.1 Chromones …………………………………………………..…… 32 1.6.2.2 Flavonoids ……………………………………...…………………. 33 1.6.3 Isolation of essential oils from halophytes …………………………..... 37 1.7 Biological review of halophytes …………………………………...……. 38 1.7.1 Economic potentials of halophytes …………………………………… 39 1.7.2 Antidiabetic activity ………………………………………...………… 41 1.7.3 Antipyretic activity …………………………………………….……. 42 1.7.4 Antimicrobial activity ………………………………………….……. 42 1.7.5 Antioxidants …………………………………………...……………… 43 1.7.6 Cytotoxicity and anticancer activity ……………………………….... 44 1.7.7 Anti-inflammatory activity ……………………………………..…….. 45 1.7.8 Phytotoxicity and other activities …………………………………...… 45 2 MATERILAS AND METHODS ………………………………………..….. 46 2.1 Materials …………………………………………...…...………………… 46 2.1.1 Plant material ……………………………………………...……...…... 46 2.1.2 General laboratory chemicals ……………………………………….... 46 2.1.3 Chromatographic and UV materials ………………………………..… 46 2.1.4 Solvents ……………………………………...………………………... 47 2.2 Methods ……………………………………...……………………………. 47 2.2.1 Chromatographic methods ………………………………………….... 47 2.2.1.1 Thin layer chromatography and paper chromatography ………….. 47 2.2.1.2 Vacuum liquid chromatography (VLC) …………………………... 48 2.2.1.3 Column chromatography ………………………………...……….. 48 2.2.1.4 Flash chromatography (Biotage) ………………………………...... 49 2.2.1.5 Solid phase extraction (SPE) …………………………………...… 49 2.2.2 Structure elucidation of the isolated secondary metabolites ………….. 49 2 2.2.2.1 Mass spectrometry (MS) …………………………...……………... 49 2.2.2.2 Nuclear magnetic resonance spectroscopy (NMR) ……………….. 50 2.2.2.3 Infra red spectroscopy (IR) ………………………………….…... 50 2.2.2.4 Ultra violet spectroscopy (UV) ………………………………...…. 51 2.2.2.5 Melting point Determination …………………………………...…. 51 2.2.3 Fatty and amino acids analysis ……………………………………...... 51 2.2.4 Analysis of the lipophilic constituents ……………………………...… 51 2.2.5 Essential oil analysis ……………………………………………..…... 52 2.2.6 Preliminary phytochemical screening ……………………………….... 53 2.2.7 Biological screening ……………………………...…………………… 54 2.2.7.1 In vitro phytotoxic bioassay ………………………………...…….. 54 2.2.7.2 Evaluation of protein tyrosine phosphates1B activity ……………. 55 2.2.7.3 Anti-tumor activity …………………...…………………………… 55 2.2.7.4 Antimicrobial activity …………………………………...………... 56 3 RESLUTS AND DISCUSSION …………………………………..………… 58 3.1 Qualitative and quantitative analysis of Zygophyllum fabago and Camphorosma lessingii…………………..……………………………………... 58 3.2 Extraction and solvent partitioning of Zygophyllum fabago………………... 61 3.2.1 Chromatography of the n-hexane fraction of Zygophyllum fabago……. 62 3.2.2 Chromatography of the chloroform fraction of Zygophyllum fabago…. 62 3.2.3 Chromatography of the ethyl acetate fraction of Zygophyllum fabago.. 63 3.2.4 Chromatography of the n-butanol and aqueous fractions of Zygophyllum fabago ………..………………………………………………. 63 3.3 Extraction and solvent partitioning of Camphorosma lessingii…………..… 67 3.3.1 Chromatography of the n-hexane and chloroform fractions of Camphorosma lessingii………..…………………………………...………. 67 3.3.2 Chromatography of the ethyl acetate and aqueous fractions of Camphorosma lessingii……………………..…………………..…………. 68 3.4 Analysis of fatty and amino acid contents of Zygophyllum fabago and Camphorosma lessingii ………………………………………..……………….. 70 3.4 1 Analysis of fatty acid contents ……………………………………...… 70 3.4.2 Analysis of amino acid contents …………………………………….... 73 3.5 Analysis of lipophilic contents of Zygophyllum fabago and Camphorosma lessingii ………………………………………………..…..…………………….. 76 3.6 Investigation of the essential oil constituents of Camphorosma lessingii … 78 3.7 Identification of triterpenes and sterols …………………………...………. 81 3.8 Identification of polyphenolic compounds ……………………………...... 115 3.9 Biological screening …………………………...………………………….. 124 3.9.1 Antimicrobial activity of Zygophyllum fabago and Camphorosma lessingii ………………………………………...…………………………………………. 124 3.9.2 Anti-leishmanial activity of Zygophyllum fabago……………………..…. 125 3.9.3 In vitro phytotoxic activity of Camphorosma lessingii………………..… 125 3.9.4 Antidiabetic activity of Zygophyllum fabago and Camphorosma lessingii……………………………………………………………………………………. 126 3 3.9.5 Anti-tumor activity of Zygophyllum fabago and Camphorosma lessingii……………………………………………………………………………………. 127 CONCLUSIONS ……………………………...…………………….…………... 131 REFERENCES ………………………………………………….…...…………. 133 4 STANDARD REFERENCES In the present dissertation used the following standards: GOST 2237-75 Raw medicinal plant. Flowers, leaves and grass. Part 1 (Collection) - Moscow-Pubi standards, 1994, 159 p. GOST 24027. 1-80 Raw medicinal plant. Methods of determining the authenticity, storage pests’ infestation, grinding and impurity content. GOST 24027.2-80 Raw medicinal plant. Methods for determination of moisture content, ash content, extractives and tannins, essential oil. GOST 4564-79 Raw medicinal plant. Smoke tree leaf. GOST 4517-87 Reagents. Methods of preparation of auxiliary reagents and solutions used in the analysis. GOST 6709-72 Distilled water. GOST 23932-90 Е Glassware and equipment, laboratory glass. GOST 25336-82 Glassware and equipment, laboratory glass. Types, basic parameters and dimensions. GOST (ТU) 258- Mercury glass laboratory thermometers. 2021-003-88 5 ABBREVIATIONS arab Arabinose ATCC American Type Culture Collection br.s. broad singlet BAW Butanol-acetic acid-water CA Candida albicans CC Column chromatography CCl4 Carbon tetrachloride CDCl3 deuterated chloroform COSY Homonuclear correlation spectroscopy d doublet dd double doublet DEPT Distortionless Enhancement by Polarization Transfer DMSO-d6 deuterated dimethyl sulfoxide EAs essential amino acids EI-MS Electron Impact Mass Spectroscopy ESI electrospray ionization EtOAc Ethyl acetate GLC Gas Liquid Chromatography GC gas chromatography HCT-116 Colon carcinoma cells GC/MS Gas Chromatography-Mass Spectroscopy Hep G2 Human hepatocarcinoma cell line 1H-NMR Proton nuclear magnetic resonance HMBC Heteronuclear Multiple Bond Correlation spectroscopy HMQC Heteronuclear Multiple-Quantum Correlation spectroscopy HPLC High performance liquid chromatography HR-MS High resolution mass spectrometry HR-ESI-MS High resolution Electron spray ionization mass spectrometry Hz. Hertz hr Hour hrs Hours IC50 The half maximal inhibitory concentration IR Infra-Red J Coupling constant Kg Kilogram L Length LB Luria-Bertani µ micron m multiplet MCF-7 breast adenocarcinoma cells MS Mass spectroscopy m.p. melting point m.m.p. mixed melting point 6 MHz Mega Hertz mm millimeter mM Millimolar m/z Mass/charge units MUFA Monounsaturated fatty acid NCC nitrogen-containing compounds NEAs Non-essential amino acids NMR Nuclear Magnetic Resonance PC Paper chromatography PUFA Polyunsaturated fatty acid ppm Part per million PTP1B protein tyrosine phosphates1B q quartet R.A. Relative amount rel. int. Relative intensity Rf Retention factor rha. Rhamnose RP-18 Reversed Phase Rt Retention time s singlet SA Staphylococcus aureus SDA Sabaurauds agar SPME solid-phase micro-extraction SIM selected-ion-monitoring SPE Solid phase extraction t triplet TLC Thin Layer Chromatography TMS Tetra Methyl Silane TSF Total saturated fatty acid UV Ultra violet xyl. Xylose 7 INTRODUCTION General characteristics of the work: This work is dedicated to the investigation of the chemical composition and biological activity of some native halophytic plants Camphorosma lessingii and Zygophyllum fabago belonging to the family Chenopodiaceae and Zygophyllaceae in order to establish new sources for biologically active substances to be used in medicine, agriculture and industrial processes. Urgency of the work: Many plants such as halophytes have not yet received much attention as sources of bioactive molecules due to limited popularity or lack of commercial applications. Halophytes and their derivatives have properties that make them safer and alternatives to commercial drugs in many countries. These plants are not only available at an affordable cost, but are widely distributed and can be propagated by the local population. It is known that a significant part of land in Asia and Africa affected by salinization,
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