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Phytochemische Und Pharmakologische in Vitro Untersuchungen Zu Hypericum Empetrifolium WILLD

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Phytochemische Und Pharmakologische in Vitro Untersuchungen Zu Hypericum Empetrifolium WILLD Phytochemische und pharmakologische in vitro Untersuchungen zu Hypericum empetrifolium WILLD. Dissertation zur Erlangung des Doktorgrades der Naturwissenschaften (Dr. rer. nat.) der Fakultät für Chemie und Pharmazie der Universität Regensburg vorgelegt von Apotheker Sebastian Schmidt aus Bamberg 2013 Diese Arbeit wurde im Zeitraum von September 2009 bis September 2013 unter der Anleitung von Herrn Prof. Dr. Jörg Heilmann am Lehrstuhl für Pharmazeutische Biologie der Universität Regensburg angefertigt. Das Promotionsgesuch wurde eingereicht am: 19. September 2013 Tag der mündlichen Prüfung: 08. November 2013 Prüfungsausschuss: Prof. Dr. Gerhard Franz (Vorsitzender) Prof. Dr. Jörg Heilmann (Erstgutachter) Prof. Dr. Adolf Nahrstedt (Zweitgutachter) Prof. Dr. Joachim Wegener (Dritter Prüfer) Danksagung Zuallererst möchte ich mich bei Prof. Dr. Jörg Heilmann für die Möglichkeit bedanken, in seinem Arbeitskreis zu arbeiten und eine Dissertation zu einem interessanten Thema anzufertigen. Vielen Dank, lieber Jörg, für Deine stets herzliche und freundschaftliche Art, mir in allen fachlichen Fragen, aber auch in privaten Dingen mit Rat und Tat zur Seite zu stehen. Meinem Freund Dr. Guido Jürgenliemk, der mir durch seine Erfahrung in phytochemischen, botanischen, zwischenmenschlichen und vor allem kulinarischen Problemen eine große Hilfe war, möchte ich ganz besonders danken. Lieber Guido, Du warst immer da! Dr. Birgit Kraus sei herzlich gedankt für Ihre Unterstützung im Umgang mit den Mikroskopen und den vielen guten Anregungen und Tipps rund um die Zellkultur. Bei Gabi Brunner und Anne Grashuber möchte ich mich and dieser Stelle ausdrücklich und von Herzen für die wertvolle Hilfe in allen praktischen Dingen bedanken. Unserer Sekretärin Hedwig Ohli wünsche ich Alles Gute und hoffe, dass sie ganz bald schon wieder die unterhaltsame erste Ansprechpartnerin im Sekretariat des Lehrstuhls sein wird. Den Mitarbeitern der Zentralen Analytik, Annette Schramm, Georgine Stühler, Fritz Kastner, Josef Kiermaier und Wolfgang Söllner möchte ich für die Messungen der NMR- und MS- Spektren meinen Dank aussprechen. Herrn PD Dr. Axel Dürkop danke ich für die Hilfe bei der Aufnahme der CD-Spektren, sowie Herrn Prof. Dr. Thomas Schmidt aus Münster für die Simulation der ECD-Spektren. Frau Prof. Dr. Eleni Skaltsa und ihrem Arbeitskreis in Athen bin ich für das Sammeln und Extrahieren des Pflanzenmaterials sehr zu Dank verpflichtet. Meinen lieben Laborkollegen danke ich von Herzen für die Unterstützung und die Aufheiterung, die fachlichen Diskussionen und lustigen Stunden im Labor, welche das Arbeiten im Arbeitskreis zu einem unvergesslich schönen Abschnitt in meinem Leben gemacht haben: Ich danke Susanne Knuth, die mich erst auf die Idee brachte, zu promovieren und darüber hinaus den weltbesten Grünkohl kocht, Kathi Zenger und Beata Kling, die mich immer zum Sport animiert haben – manchmal sogar mit Erfolg, Rosi Scherübl für ihre stets fröhliche Art und ihr unvergleichliches Lachen, Moni Untergehrer für die angenehmen Stunden im „Glaskasten“, meinem fränkischen Freund und Kupferstecher Markus Löhr, meinem persönlichen Literaturpapst und Freund in allen Lebenslagen Marcel Flemming, Daniel Bücherl als Inbegriff der Redseligkeit und Freund der belanglosen Unterhaltung, dem tschechischen Sprachgenie Petr Jirasek, meinem Sonnenschein Edna Makule und meinem stets korrekten, grundehrlichen Kollegen aus der BUZ, Stefan Wiesneth. Auch „Danke sagen“ möchte ich Matej Barbic, Susann Haase, Sarah Sutor, Anne Freischmidt, Sebastian Schwindl und dem Hieu. Ebenfalls danken möchte ich den Gastwissenschaftlern Dr. Andrija Smelcerovic und Dr. Louh Gabin für die fruchtbaren Diskussionen und die Möglichkeit etwas aus deren Land und Kultur zu erfahren. Gerne habe ich die Master- und Bachelor-Arbeiten von Julia Paterson, Angeliki Mathioudaki und Sandra Seidl mit begleitet. Ich danke den Wahlpflichtstudentinnen, Alexia Zamanikas und Karin Gold sowie der „Frau Schiller“ für die angenehme Zusammenarbeit und deren Hilfe. Nicht vergessen möchte ich Natalie Asthausen, die mir die Zeichnung von H. empetrifolium dankenswerterweise angefertigt hat. Vielen Dank auch an Daniela Schneider, der Mama meines Patenkindes, die mit Ihren liebevollen „Durchhaltepaketen“ für die körperliche Grundsicherung für die Stunden vor dem PC gesorgt hat. Das Team der Anthemis Apotheken und insbesondere deren Chefin Carole Holzhäuer verdient meinen Dank, nicht zuletzt für die exquisiten und geselligen Weihnachtsfeiern! „Last but not least“ gilt mein ganz besonderer Dank meinen Freunden, allen voran Tobias Elflein, seiner lieben Frau Caro mit Emilio und Daniel Schmitt. Ihr seid immer für mich da gewesen, egal in welcher Lebenssituation. Publikationsliste Teile dieser Arbeit wurden bereits veröffentlicht: Publikationen Schmidt, Sebastian; Jürgenliemk, Guido; Skaltsa, Helen; Heilmann, Jörg (2012): Phloroglucinol derivatives from Hypericum empetrifolium with antiproliferative activity on endothelial cells. In: Phytochemistry 77, S. 218-225 Schmidt, Sebastian; Jürgenliemk, Guido; Schmidt, Thomas J.; Skaltsa, Helen; Heilmann, Jörg (2012): Bi-, tri-, and polycyclic acylphloroglucinols from Hypericum empetrifolium. In: J. Nat. Prod. 75 (10), S. 1697-1705 Poster Schmidt, Sebastian; Jürgenliemk, Guido; Skaltsa, Helen; Heilmann, Jörg (2010): Two novel phloroglucinols from Hypericum empetrifolium with antiproliferative activity on endothelial cells. In: Planta Med. 76 (12), P-597 7th Tannin Conference (Presymposium) and 58th International Congress and Annual Meeting of the Society for Medicinal Plant and Natural Product Research Berlin, Germany, 29th August - 2nd September 2010 Schmidt, Sebastian; Jürgenliemk, Guido; Skaltsa, Helen; Heilmann, Jörg (2012): Neue trizyklische Acylphloroglucinole aus Hypericum empetrifolium mit in vitro antiproliferativer Aktivität an Endothelzellen. In: Z. Phytother. 33 (S1), P-17 Phytotherapeutika 2012, 17.-19. Mai 2012, Wien Für meine Mama und meinen Papa, meine Schwester Kerstin, meine Brüder Thomas, Ralf und Rainer sowie mein Patenkind Kaja-Luna Inhaltsverzeichnis 1 EINLEITUNG ............................................................................................................................... 1 1.1 Die Gattung Hypericum L. .......................................................................................... 1 1.1.1 Botanik, Taxonomie, Phytochemie und Chemotaxonomie ....................................... 1 1.1.2 Die Sektion 19 Coridium SPACH ................................................................................... 5 1.1.3 Hypericum empetrifolium subsp. empetrifolium WILLD. ............................................ 6 1.1.3.1 Etymologie, Botanik und Taxonomie ................................................................. 6 1.1.3.2 Bioaktivität und Phytochemie .......................................................................... 12 1.1.4 Acylphloroglucinole .................................................................................................. 14 1.2 Die Angiogenese ...................................................................................................... 19 1.2.1 Physiologie der Angiogenese ................................................................................... 19 1.2.2 Anti-Angiogenese als therapeutisches Target ......................................................... 20 1.2.2.1 Tumortherapie ................................................................................................. 21 1.2.2.2 Therapie der altersbedingten Makuladegeneration ........................................ 22 1.2.3 Anti-angiogene Aktivität ausgewählter Naturstoffe ................................................ 23 1.3 Zielsetzung .............................................................................................................. 26 1.3.1 Isolierung von Acylphloroglucinolen aus Hypericum empetrifolium ....................... 26 1.3.2 Testung auf eine mögliche anti-angiogene Aktivität ............................................... 26 2 MATERIAL UND METHODEN ............................................................................................. 27 2.1 Phytochemische Methoden ..................................................................................... 27 2.1.1 Geräte, Gefäße und Software .................................................................................. 27 2.1.2 Chemikalien und Lösungsmittel ............................................................................... 29 2.1.3 Pflanzenmaterial ...................................................................................................... 30 2.1.4 Extraktion des Pflanzenmaterials ............................................................................. 30 2.1.5 Fraktionierung und Isolierung .................................................................................. 30 2.1.5.1 Flash-Chromatographie .................................................................................... 30 2.1.5.2 Fraktionskontrolle ............................................................................................ 32 2.1.5.2.1 Dünnschichtchromatographie ...................................................................... 32 2.1.5.2.2 1H-NMR Spektroskopie ................................................................................. 34 2.1.5.3 Semi-präparative HPLC ..................................................................................... 34 2.1.6 Strukturaufklärung und Charakterisierung .............................................................
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