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Phytochemische, Pharmakologische Und Chemoökologische Untersuchungen Zu Sesquiterpenlactonen Aus Kamille, Schafgarbe Und Arnika

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Phytochemische, Pharmakologische Und Chemoökologische Untersuchungen Zu Sesquiterpenlactonen Aus Kamille, Schafgarbe Und Arnika Phytochemische, pharmakologische und chemoökologische Untersuchungen zu Sesquiterpenlactonen aus Kamille, Schafgarbe und Arnika Dissertation zur Erlangung des Doktorgrades der Naturwissenschaften (Dr. rer. nat.) der Fakultät Chemie und Pharmazie der Universität Regensburg vorgelegt von Marcel Flemming aus Schneizlreuth Die vorliegende Arbeit wurde im Zeitraum von Mai 2010 bis April 2014 am Lehrstuhl für Pharmazeutische Biologie der Universität Regensburg unter Anleitung von Herrn Prof. Dr. Jörg Heilmann angefertigt. Promotionsgesuch eingereicht am: 11.08.2014 Datum der mündlichen Prüfung: 25.09.2014 Prüfungsausschuss: Prof. Dr. Arnold Pfitzner (Vorsitzender) Prof. Dr. Jörg Heilmann (Erstgutachter) Prof. Dr. Christian Zidorn (Zweitgutachter) Prof. Dr. Joachim Wegener (Drittprüfer) Danksagung Zuerst möchte ich mich an Herrn Prof. Dr. Jörg Heilmann richten. Lieber Jörg, vielen, lieben Dank für die große Freiheit, die du mir gelassen hast und für das damit verbundene, mir entgegengebrachte Vertrauen! Danke für dein gutes Händchen beim Zusammenstellen des Lehrstuhls, an dem man sich nur wohlfühlen und gute Freunde finden konnte und danke für dein Lenken hin zu spannenden Forschungsthemen. Und vor allem danke dafür, dass du immer mehr Freund warst als Chef. Frau Dr. Birgit Kraus möchte ich danken für die Unterstützung bei den zellbiologischen Arbeiten, den fachlichen Anregungen und für die gute und freundschaftliche Zusammenarbeit beim Betreuen des Praktikums Pharmazeutische Biologie I. Und natürlich auch, liebe Birgit, für den Trost, wenn die Zellen nicht so wollten, wie man das von ihnen erwartete. Herrn Dr. Guido Jürgenliemk möchte ich danken für viele fachliche Ratschläge im Bereich der Analytik. Außerdem, lieber Guido, vielen Dank für die vielen humorvollen Mensagänge und Kaffeepausen, Berg- und Bergausrüstungsgespräche und nicht zuletzt für eine rote Mammutjacke. Danke auch an Frau Ohli, Frau Hirsch, Frau Bauer und Frau Nömeier, die mich erfolgreich durch den universitären Verwaltungsapparat führten. Besonderer Dank gebührt dem guten Geist im Labor, Gabi Brunner. Liebe Gabi, ohne dich hätte ich nie etwas gefunden! Vielen Dank für die Beantwortung unzähliger Fragen, v.a. wo etwas ist und wie etwas geht und für die Unterstützung bei der Laborarbeit. Vielen Dank auch an Anne Grashuber für die Hilfe im Praktikum und bei sämtlichen Laborbelangen. Danke an die Mitarbeiter der zentralen Analytik, v.a. an Herrn Josef Kiermaier und Herrn Wolfgang Söllner für ihre Hilfe bei der Auswertung der Massenspektren. Vielen Dank an Frau Simone Fuchs vom Lehrstuhl Pharmazeutische Biologie der Goethe- Universität Frankfurt am Main für das Durchführen des Luciferase-Assays. Herzlichen Dank an Herrn Dr. Fred Eickmeyer, der mich mit seinem unschätzbaren Wissen bei der Anzucht von Arnikapflanzen unterstützt hat und freundlicherweise die Aufzucht der Arnikaklone in seinem Gewächshaus übernommen hat. Danke auch an Frau Dr. Heidi Heuberger, die mich mit vielen Informationen zur Kultivierung von Arnika versorgt hat und mich tatkräftig bei der Veröffentlichung des Beitrags zum Anbau von Arnika in Rumänien unterstützt hat. Großer Dank gebührt meinen Freunden, den Parkmitarbeitern von Parcul Natural Munţii Maramureşului Costel Bucur, Gabriel Covaza, Catalina Bogdan, Anton Brenner, Christina Pop und ihrem Vater Mr. Pop und allen Parkranger. Außerdem danke an Emil Pop für seine Unterstützung bei der Überzeugungsarbeit der Bauern und für seinen Zuspruch. Vielen Dank auch an Dr. Dieter Gerard von der Firma FLAVEX in Rehlingen, der sich mit großem Pioniergeist, Vertrauen und Großzügigkeit bei der Finanzierung des Projekts zum nachhaltigen Anbau und Schutz von Arnika in Maramureş beteiligt hat. Vielen Dank auch an Herrn Bert Schumann, der das Projekt zum nachhaltigen Anbau und Schutz von Arnika in Maramureş mit seinem Engagement stark unterstützt hat. Ganz besonderer Dank gebührt meinen lieben Laborkollegen, die alle zusammen wie die Zutaten in einem guten Eintopf waren…jede anders an Charakter und Geschmack, doch zusammen sehr harmonisch. Es war sehr, sehr lustig mit euch! Vielen Dank an: Dr. Daniel Bücherl für die Hilfe im Labor und v.a.: Humor! Ich mag Sie! Eine Liste aller Zitate würde den Rahmen dieser Arbeit sprengen. Dr. Katharina Zenger. Liebe Kathi, vielen Dank für die gute Zeit vom ersten Tag an. Für Berg und Bouldern, deinen guten Humor, und deine Loyalität. Dr. Rosmarie Scherübel, für ihr Lachen, das einen jeden befällt und von Trübsinn befreit, v.a. beim Durchführen von Praktika. Beata Kling, meine liebe Laborkollegin, mit der unzählige running gags geteilt wurden und die mich immer brav zum Bouldern begleitet hat. Dr. Sebastian Schmidt für seine Unterstützung bei der Laborarbeit und v.a. für seine gute Laune und die vielen gemeinsamen, zumindest für uns guten Witze. Monika Untergehrer für die wirklich sehr wertvolle Hilfe bei den Zell-Assays, die vielen guten Gespräche und Witze und die Verbindung ins ferne Oberbayern. Petr Jirásek für seinen trockenen Humor, seine Sprachgewandtheit und seine schiere Körpergröße. Außerdem möchte ich mich für die kollegiale und schöne Zusammenarbeit bedanken bei, Markus Löhr, Stefan Wiesneth, Eva Lotter, Edna Makule, Tri Hieu Nguyen, Ilya Volkov, Christian Zeh, Katharina Schiller, Sebastian Schwindl, Daniela Pemp, Dr. Sarah Sutor, Dr. Anne Freischmidt und Dr. Magdalena Motyl und Dr. Matej Barbič und bei meinen Praktikanten und Praktikantinnen für die wertvolle Mitarbeit. Außerdem ganz besonders bei meinen Eltern, die mich immer unterstützt haben und bei Chrisi, Henri, Nico, Alex und Andi dafür, dass ihr immer zu mir gehalten habt und mir meine Freizeit verschönt habt. Pubilkationen Teile dieser Arbeit wurden bereits veröffentlicht: Flemming, M.; Heilmann, J. (2014): Nachhaltiger Anbau und Schutz von Arnica montana L. in Maramures (Rumänien). In: Zeitschrift für Arznei- und Gewürzpflanzen 19(1), S. 52-53. Poster: Flemming, M.; Heilmann, J. (2013): Protection and Sustainable Cultivation of Arnica montana L. in Maramureş (Romania). In: Planta Medica 79, S. 1256. 61 st International Congress and Annual Meeting of the GA, 1 st -5st September, Münster, Germany. Meinen lieben Eltern. Wer einen Tag lang glücklich sein will der betrinke sich. Wer einen Monat lang glücklich sein will der schlachte ein Schwein. Wer ein Jahr lang glücklich sein will, der heirate. Wer aber ein Leben lang glücklich sein will, der werde Gärtner. Chinesisches Sprichwort Inhalt A Allgemeine Einleitung ................................................................................................ 1 B Phytochemische und pharmakologische Untersuchungen von Proazulenen aus Kamille und Schafgarbe ................................................................................................................. 9 B.1 Einleitung .......................................................................................................... 9 B.1.1 Artbescheibung der Kamille ............................................................................. 9 B.1.1.1 Botanik der Kamille .......................................................................................... 9 B.1.1.2 Phytochemie der Kamille ............................................................................... 11 B.1.2 Artbeschreibung der Schafgarbe.................................................................... 15 B.1.2.1 Botanik der Schafgarbe .................................................................................. 15 B.1.2.2 Phytochemie der Schafgarbe ......................................................................... 18 B.1.3 Einführung zur Pharmakologie von Proazulenen aus Kamille und Schafgarbe . ........................................................................................................................ 31 B.1.4 Kurze Einführung zur Molekularbiologie von Entzündungsprozessen .......... 36 B.1.4.1 Entzündungsprozesse und die Rolle des Adhäsionsmoleküls ICAM-1 ........... 36 B.1.4.2 Entzündungsprozesse und die Rolle der Translokation von NF-κB ................ 39 B.1.4.3 Die Rolle von NO-Radikalen im Enzündungsgeschehen ................................ 42 B.1.5 Zielsetzung ...................................................................................................... 45 B.2 Material und Methoden ................................................................................. 46 B.2.1 Präparativ-analytischer Teil............................................................................ 46 B.2.1.1 Isolierung und Identifizierung von Matricin aus Kamillenblüten ................... 46 B.2.1.1.1 Herstellung eines Kamillenblütenextrakts ................................... 46 B.2.1.1.2 Chromatographische Isolierung des Matricins ............................ 47 B.2.1.1.3 Identifizierung des Matricins ........................................................ 49 B.2.1.1.4 Reinheitsbestimmung des Matricins ............................................ 51 B.2.1.2 Chamazulen .................................................................................................... 51 B.2.1.3 Aktivitätsgeleitete Fraktionierung eines Schafgarbenblütenextrakts ........... 52 B.2.1.3.1 Herstellung eines Schafgarbenblütenextrakts ............................. 52 B.2.1.3.2 Fraktionierung des Schafgarbenblütenextrakts ........................... 52 B.2.1.4 Isolierung von 8-Desacetyl-8-angeloyl-4-epi-matricin ................................... 53 B.2.1.4.1 Herstellung eines Schafgarbenkrautextrakts ............................... 53 B.2.1.4.2 Chromatographische Aufarbeitung
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