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Untersuchungen Zur Bildung Von Hydroxyzimtsäureestern in Ocimum Basilicum, Cichorium Intybus Und Actaea Racemosa

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Untersuchungen Zur Bildung Von Hydroxyzimtsäureestern in Ocimum Basilicum, Cichorium Intybus Und Actaea Racemosa Untersuchungen zur Bildung von Hydroxyzimtsäureestern in Ocimum basilicum, Cichorium intybus und Actaea racemosa Dissertation zur Erlangung des Doktorgrades der Naturwissenschaften (Dr. rer. nat.) dem Fachbereich Pharmazie der Philipps-Universität Marburg vorgelegt von Victoria Ingeburg Maria Werner aus Saalfeld/Saale Marburg/Lahn 2018 Dem Fachbereich Pharmazie der Philipps-Universität Marburg als Dissertation eingereicht am: 06.11.2018 Erstgutachter: Prof. Dr. Maike Petersen Zweitgutachter: Prof. Dr. Andreas Heine Tag der mündlichen Prüfung: 20.12.2018 Hochschulkennziffer: 1180 Originaldokument gespeichert auf dem Publikationsserver der Philipps-Universität Marburg http://archiv.ub.uni-marburg.de Dieses Werk bzw. Inhalt steht unter einer Creative Commons Namensnennung Keine kommerzielle Nutzung Weitergabe unter gleichen Bedingungen 3.0 Deutschland Lizenz. Die vollständige Lizenz finden Sie unter: http://creativecommons.org/licenses/by-nc-sa/3.0/de/ Das erste, das der Mensch im Leben vorfindet, das letzte, wonach er die Hand ausstreckt, das kostbarste, was er im Leben besitzt, ist die Familie. Adolph Kolping Für meine Familie Inhaltsverzeichnis Inhaltsverzeichnis 1 Einleitung ..................................................................................................................... 5 1.1Wegwarte - Cichorium intybus L. ................................................................................... 5 1.1.1 Botanik ..................................................................................................................... 5 1.1.2 Pharmazeutische und allgemeine Bedeutung .......................................................... 5 1.1.3 Inhaltsstoffe .............................................................................................................. 6 1.2Basilikum - Ocimum basilicum L. ................................................................................... 7 1.2.1 Botanik ..................................................................................................................... 7 1.2.2 Pharmazeutische und allgemeine Bedeutung .......................................................... 7 1.2.3 Inhaltsstoffe .............................................................................................................. 8 1.3Zichoriensäure ............................................................................................................... 9 1.4Traubensilberkerze - Actaea racemosa L. ................................................................... 10 1.4.1 Botanik ................................................................................................................... 10 1.4.2 Pharmazeutische Bedeutung ................................................................................. 10 1.4.3 Inhaltsstoffe ............................................................................................................ 11 1.5Cimicifugasäuren ......................................................................................................... 13 1.5.1 Allgemeines ............................................................................................................ 13 1.5.2 Biosynthese ............................................................................................................ 15 1.5.3 Vorkommen ............................................................................................................ 15 1.5.4 Piscidin- und Fukinsäure ........................................................................................ 17 1.6Acyltransferasen .......................................................................................................... 19 1.6.1 Serin Carboxypeptidase-artige Acyltransferasen (SCPL) ...................................... 19 1.6.2 BAHD-Acyltransferasen ......................................................................................... 19 1.7Ziele der Arbeit ............................................................................................................ 24 1.7.1 Aufklärung der Biosynthese der Zichoriensäure .................................................... 24 1.7.2 Aufklärung der Biosynthese der Cimicifugasäuren ................................................ 24 2 Material und Methoden .............................................................................................. 25 2.1Chemikalien und Geräte .............................................................................................. 25 2.1.1 Chemikalien ............................................................................................................ 25 2.1.2 Verwendete Kits ..................................................................................................... 28 2.1.3 Molekularbiologische Reagenzien und Enzyme ..................................................... 28 2.1.4 Antikörper für Westernblot-Analyse ........................................................................ 28 2.1.5 Größenmarker ........................................................................................................ 29 2.1.6 Samen und Pflanzen, Extrakte ............................................................................... 29 2.1.7 Bakterienstämme ................................................................................................... 29 2.1.8 Vektoren ................................................................................................................. 30 2.1.9 Analytische Materialien .......................................................................................... 30 2.1.10Primer ..................................................................................................................... 30 2.1.11Geräte .................................................................................................................... 31 2.1.12Verwendete Software ............................................................................................. 32 I Inhaltsverzeichnis 2.2Puffer, Lösungen und Medien ..................................................................................... 33 2.2.1 Allgemeine Puffer ................................................................................................... 33 2.2.2 Nährmedien für Bakterienkulturen .......................................................................... 33 2.2.3 Medien für die Pflanzenzellkultur ........................................................................... 34 2.2.4 Puffer für die DNA-Extraktion ................................................................................. 36 2.2.5 Puffer für die Nukleinsäure-Gelelektrophorese ...................................................... 36 2.2.6 Puffer und Lösungen zur Proteinaufreinigung und -konzentrationsbestimmung .... 37 2.2.7 Puffer und Lösungen für die SDS-PAGE ............................................................... 38 2.2.8 Puffer und Lösungen für den Westernblot .............................................................. 39 2.3Allgemeine Methoden .................................................................................................. 40 2.3.1 Herstellung steriler Kalluskulturen .......................................................................... 40 2.3.2 Überimpfen von Zellkulturen .................................................................................. 41 2.3.3 Elicitierung von Suspensionskulturen ..................................................................... 41 2.3.4 Zugabe von Substraten zu den Zellkulturen ........................................................... 42 2.3.5 Proteinstruktur-Modelling ....................................................................................... 42 2.3.6 Phylogenetische Untersuchungen .......................................................................... 42 2.4Analytisch-chemische Methoden ................................................................................. 43 2.4.1 Dünnschichtchromatographie (DC) ........................................................................ 43 2.4.2 Hochleistungsflüssigchromatographie (HPLC) ....................................................... 43 2.4.3 Massenspektrometrie ............................................................................................. 44 2.4.4 Herstellung von CoA-Estern ................................................................................... 45 2.4.5 Isolierung von Piscidinsäure ................................................................................... 49 2.4.6 Isolierung von Fukinsäure ...................................................................................... 49 2.4.7 Photometrische Konzentrationsbestimmung .......................................................... 51 2.4.8 Isolierung von phenolischen Inhaltsstoffen ............................................................ 51 2.4.9 Gehaltsbestimmung mittels HPLC ......................................................................... 51 2.4.10Bestimmung des Gesamtphenolgehaltes ............................................................... 52 2.5Molekularbiologische Methoden .................................................................................. 53 2.5.1 RNA-Extraktion ....................................................................................................... 53 2.5.2 DNase-Verdau ........................................................................................................ 53 2.5.3 cDNA-Synthese .....................................................................................................
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