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Allium Ursinum and Allium Sativum

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Allium Ursinum and Allium Sativum PHARMACEUTICAL AND CHEMICAL ANALYSIS OF THE COMPONENTS CARRYING THE ANTIPLATELET ACTIVITY OF EXTRACTS FROM ALLIUM URSINUM AND ALLIUM SATIVUM Dissertation zur Erlangung des akademischen Grades Dr.rer.med. an der Medizinischen Fakultät der Universität Leipzig eingereicht von: Dina Talat Tawfiq Sabha geboren am 18.08.1979 in Amman/ Jordanien angefertigt in der Klinik für Herzchirurgie, Universität Leipzig (Direktor:Prof. Dr. Friedrich-Wilhelm Mohr) Betreuer: Prof. Dr. Stefan Dhein i Bibliographische Beschreibung: Titel: Pharmazeutische und chemische Analyse der Inhaltsstoffe von Allium ursinum und Allium sativum, die für die Thrombozytenaggregations- hemmende Wirkung verantworlich sind. (englischer Original-Titel: Pharmaceutical and chemical analysis of the components carrying the antiplatelet activity of extracts from Allium ursinum and Allium sativum) -2011. 126 Seiten. Leipzig, Medizinische Fakultät der Universität Leipzig, Klinik für Herzchirurgie, Dissertation, 2011. Autor: Sabha, Dina Talat Tawfiq 126 S., 102 Lit., 9 Tabellen, 55 Abbildungen ii Contents 1. Introduction: ...................................................................................................................... 1 1.1 Historical background.................................................................................................. 1 1.2 Antiplatelets drugs: Types and side effects ................................................................. 2 1.3 Need for new approach................................................................................................ 4 1.4 Allium sativum (common garlic) ................................................................................. 5 1.5 Allium ursinum (wild garlic) ....................................................................................... 9 1.6 Aims of the study....................................................................................................... 12 2. Materials and Methods .................................................................................................... 13 2.1 Material...................................................................................................................... 13 2.1.1. Equipment and Devices......................................................................................... 13 2.1.2 Glassware used in the work.................................................................................... 14 2.1.3 Chemicals, reference substances and other materials............................................. 15 2.1.4 Plant material.......................................................................................................... 16 2.2 Methods ..................................................................................................................... 16 2.2.1 Methods of extraction............................................................................................. 16 2.2.1.1 Extract preparation .............................................................................................. 16 2.2.1.2 Steam distillation................................................................................................. 17 2.2.2 Methods of characterization. ................................................................................ 19 2.2.2.1 Thin layer chromatography ................................................................................. 19 2.2.2.1.1 TLC of polyphenols (flavonoids and tannins).................................................. 21 2.2.2.1.2 TLC of alliins / allicins..................................................................................... 22 2.2.2.1.3 TLC of saponosides.......................................................................................... 22 2.2.2.1.4 Markers and references for TLC in our experiment......................................... 24 2.2.2.2 HPLC (High performance liquid chromatography)...................................... 25 2.2.2.2.1 Definition of the HPLC .................................................................................. 25 2.2.2.2.2 HPLC in our experiment................................................................................... 27 2.2.2.2.3 HPLC of the active compounds...................................................................... 28 2.2.3 Methods of Fractionation and Isolation.................................................................. 29 2.2.3.1 Liquid –liquid separation..................................................................................... 29 2.2.3.2 Column chromatography..................................................................................... 30 2.2.3.2.1 General Description.......................................................................................... 30 2.2.3.2.2 Column chromatography of the chloroform extract......................................... 33 2.2.3.2 .3 Column chromatography of the most active fraction (11-17) ......................... 34 2.2.3.2.3.1 Column chromatography of the most active fraction out of 11-17 (fraction number 1)......................................................................................................................... 35 2.2.4 Methods of chemical identification, nuclear magnetic resonance (NMR)............. 37 2.2.4.1 Definition........................................................................................................... 37 2.2.4.2 NMR methods ..................................................................................................... 37 2.2.4.2.1 1d 1H-NMR (one dimensional proton NMR)................................................. 38 2.2.4.2.2 2d-1H-NMR (COSY)....................................................................................... 38 2.2.4.2.3 1d-13C-NMR..................................................................................................... 39 2.2.4.2.3.1 DEPT (Distortionless Enhancement by Polarization Transfer)..................... 39 2.2.4.2.3.2 HSQC (Heteronuclear Single Quantum Coherence)................................... 39 2.2.4.2.3.3 HMBC (Heteronuclear Multible Bond Coherence) ...................................... 40 2.3 Materials and methods used in blood testing .......................................................... 41 2.3.1 Materials:.............................................................................................................. 41 2.3.1.1 Chemical materials: ............................................................................................. 41 2.3.1.2 Solutions:............................................................................................................. 41 iii 2.3.1.3 Equipment and Devices..................................................................................... 42 2.3.1.3.1 Blood centrifigation device ............................................................................ 42 2.3.1.3.2 Platelets count device ....................................................................................... 42 2.3.1.3.3 Platelets aggregation profiler............................................................................ 42 2.3.2 Methods of measuring platelets aggregation and the inhibitory activity of the extracts............................................................................................................................. 42 2.3.2.1 In-vitro examination .......................................................................................... 42 2.3.2.2 Platelet aggregation ............................................................................................. 43 3. Results ............................................................................................................................. 45 3.1.1 Effects of common Garlic on platelets aggregation and it’s mechanism of action 45 3.1.2 Testing of the aqueous and methanolic extracts (comparison of wild garlic to common garlic)................................................................................................................ 47 3.1.3 Allium ursinum effect on Platelet aggregation ....................................................... 51 3.1.4 Concentration response curve for Allium sativum and Allium ursinum ................. 53 3.2 Fractionation of the alcoholic (ethanolic) extract from wild garlic leaves................ 54 3.2.1 TLCs of the ethanolic extract of wild garlic........................................................... 54 3.2.2 The results of antiplatelets aggregation of the four ethanolic Allium ursinum extracts............................................................................................................................. 60 3.3 Separartion of the chloroform extract........................................................................ 61 3.3.1 Column chromatography for the chloroform extract of alcoholic Allium ursinum raw extract....................................................................................................................... 61 3.3.2 TLC of the most active fraction from chloroformic extract ................................... 61 3.3.3 Antiplatelets aggregatory effect for the chloroform fractions of Allium ursinum.. 63 3.4 Column chromatography for fraction 11-17.............................................................. 63 3.4.1 TLC for fractions obtained from fraction 11-17..................................................... 64 3.4.2 Antiplatelets aggregatory effects for the 11-17 subfractions.................................. 64 3.4.3 Dose response
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