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Josefine BICKEL Josefine BICKEL Phytochemische Analyse der Alge Dasycladus vermicularis DIPLOMARBEIT eingereicht an der LEOPOLD-FRANZENS-UNIVERSITÄT INNSBRUCK INSTITUT FÜR PHARMAZIE/PHARMAKOGNOSIE Zur Erlangung des akademischen Grades MAGISTRA DER PHARMAZIE Innsbruck, März 2018 Inhaltsverzeichnis 1 Inhaltsverzeichnis 1 Inhaltsverzeichnis ............................................................................................................... 2 2 Einleitung ............................................................................................................................ 5 3 Abstract ............................................................................................................................... 7 4 Zusammenfassung ............................................................................................................... 8 5 Allgemeiner Teil ................................................................................................................. 9 5.1 Dasycladus vermicularis (Scropoli) Krasser .............................................................. 9 5.1.1 Klassifikation ......................................................................................................... 9 5.1.2 Nähere Beschreibung von Dasycladus vermicularis ........................................... 10 5.1.3 Cumarine .............................................................................................................. 11 5.1.4 Einteilung der Cumarine ...................................................................................... 11 5.1.5 Biosynthese der Cumarine ................................................................................... 12 5.1.6 Cumarine in der Alge Dasycladus vermicularis .................................................. 14 5.2 Phenolische Carbonsäuren ....................................................................................... 15 5.2.1 Biosynthese .......................................................................................................... 15 5.2.2 Sulfatierte Phenolcarbonsäuren ............................................................................ 15 5.3 Chromatografie ......................................................................................................... 17 5.3.1 Klassische Säulenchromatografie......................................................................... 18 5.3.2 Gelpermeationschromatografie ............................................................................ 19 5.3.3 HPLC .................................................................................................................... 20 5.3.4 Flash-Chromatografie ........................................................................................... 24 5.3.5 Präparative HPLC ................................................................................................ 25 5.4 NMR Spektroskopie ................................................................................................. 25 6 Spezieller Teil ................................................................................................................... 26 6.1 Herstellung des Wasser-Methanol-Extrakts ............................................................. 26 6.2 Dünnschichtchromatografische Vorversuche .......................................................... 26 6.2.1 Trennung des Wasser-Methanol Rohextraktes mittels Flash-Chromatografie .... 26 2 Inhaltsverzeichnis 6.2.2 HPLC Analysen der Fraktionen ........................................................................... 29 6.2.3 DasyA-W1 ............................................................................................................ 29 6.2.3.1 Fraktionen DasyA-W1-Rev8 und DasyA-W1-Rev9 .................................... 30 6.2.3.2 Fraktionen DasyA-W1-Rev10 und DasyA-W1-Rev11 ................................ 31 6.2.3.3 Fraktionen DasyA-W1-Rev12, DasyA-W1-Rev13 und DasyA-W1-Rev14 31 6.2.4 DasyA-W2 ............................................................................................................ 35 6.2.4.1 Fraktionen DasyA-W2-Rev6, DasyA-W2-Rev7 und DasyA-W2-Rev8 ...... 35 6.2.5 DasyA-W-4 .......................................................................................................... 37 6.2.5.1 Fraktionen DasyA-W4-Rev25, DasyA-W4-Rev31 und DaysA-W4-Rev32 38 6.2.5.2 Fraktion DasyA-W4-Rev45 ......................................................................... 39 6.3 Herstellung des Methanolextraktes .......................................................................... 40 6.3.1 Fraktion DasyA-M1-Se5 ...................................................................................... 41 6.3.2 Fraktion DasyA-M1-Se7 ...................................................................................... 43 6.4 Zuordnung der isolierten Substanzen ....................................................................... 44 6.5 Synthese der Cumarine ............................................................................................. 46 6.5.1 Synthese von 3,7-Dihydroxycumarin und 3,6-Dihydroxycumarin ...................... 46 6.5.2 Synthese von 3,6,7 Trihydroxycumarin ............................................................... 47 6.6 Sulfatierung .............................................................................................................. 51 6.6.1 Sulfatierung des 3,6,7-Trihydroxycumarins ......................................................... 51 6.6.2 Sulfatierung der 4-OH-Zimtsäure ........................................................................ 53 7 Zusammenfassung ............................................................................................................. 55 8 Experimenteller Teil ......................................................................................................... 57 8.1 Herkunft des Algenmaterials .................................................................................... 57 8.2 Durchführung der einzelnen Arbeitsschritte ............................................................ 57 8.2.1 Herstellung des Methanol-Wasser-Extrakts ......................................................... 57 8.2.2 Herstellung des Methanol Extrakts ...................................................................... 57 8.2.3 Dünnschichtchromatografie ................................................................................. 58 8.2.4 Flash-Chromatografie ........................................................................................... 58 3 Inhaltsverzeichnis 8.2.4.1 Auftrennung des Methanol- Wasser Extraktes ............................................. 58 8.2.4.2 Auftrennung der Fraktionen DasyA-W2-Rev6, DasyA-W2-Rev7 und DasyA- W2-Rev8 62 8.2.4.3 Auftrennung der Fraktionen DasyA-W4-Rev25, DasyA-W4-Rev31 und DasyA-W4-Rev32 ......................................................................................................... 62 8.2.4.4 Auftrennung der Fraktion DasyA-W4-Rev45 .............................................. 63 8.2.5 Gelpermeationschromatografie ............................................................................ 64 8.2.5.1 Auftrennung der Fraktionen DasyA-W1-Rev8 und DasyA-W1-Rev9 ........ 64 8.2.5.2 Auftrennung der Fraktionen DasyA-W1-Rev10 und DasyA-W1-Rev11 .... 65 8.2.5.3 Auftrennung der Fraktionen DasyA-W1-Rev13, DasyA-W1-Rev14 und DasyA-W1-Rev15 ......................................................................................................... 65 8.2.5.4 Methanol Extrakt .......................................................................................... 66 8.2.5.5 Aufreinigung des synthetisierten 3,6,7-Trihydroxycumarins ...................... 67 8.2.5.6 Aufreinigung des synthetisierten 6,7-Dihydroxycumarin-3-sulfats ............. 68 8.2.6 Analytische HPLC ................................................................................................ 69 8.2.7 Präparative HPLC ................................................................................................ 71 8.2.7.1 Fraktion DasyA-W9-Se4 .............................................................................. 71 8.2.7.2 Fraktion DasyA-M1-Se5 .............................................................................. 71 8.2.7.3 Fraktion DasyA-M1-Se7 .............................................................................. 72 8.2.8 Durchführung der Synthesen ................................................................................ 73 8.2.8.1 Aufbau der Reaktionsapparaturen ................................................................ 73 8.2.8.2 Herstellung der Reagenzien für die Synthesen............................................. 73 8.2.9 Chemikalienverzeichnis ....................................................................................... 74 8.3 Sonstiges ................................................................................................................... 75 9 Abkürzungsverzeichnis ..................................................................................................... 76 10 Lebenslauf ..................................................................................................................... 78 11 Danksagung ................................................................................................................... 79 12 References ..................................................................................................................... 80 4 Einleitung 2 Einleitung Zum Schutz vor Umweltschäden, vor
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