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Convolvulaceae) Neuartige Tropanalkaloide und andere stickstoffhaltige Sekundärstoffe in Windengewächsen (Convolvulaceae) Dissertation zur Erlangung des akademischen Grades des Doktors der Naturwissenschaften (Dr. rer. nat.) eingereicht im Fachbereich Biologie, Chemie, Pharmazie der Freien Universität Berlin vorgelegt von Sonja Christina Ott aus Göppingen Berlin 2011 Diese Dissertationschrift wurde in den Jahren 2000 bis 2011 (mit Unterbrechungen) am Institut für Pharmazie – Pharmazeutische Biologie der Freien Universität Berlin unter der Leitung von Prof. Dr. E. Eich angefertigt. 1. Gutachter: Prof. Dr. Eckart Eich 2. Gutachterin: Prof. Dr. Monika Hilker Tag der Ersteinreichung: 21.10.2011 Tag der Zweiteinreichung: 21.06.2012 Disputation am: 16.08.2012 Danksagung Mein besonderer Dank gilt Herrn Prof. Dr. Eckart Eich für die Überlassung des Themas, die Bereitstellung des Pflanzenmaterials sowie des Saatguts für den Anbau im institutseigenen Gewächshaus und im Wirtschaftshof des Botanischen Garten. Dankenswerterweise durfte ich auch einige seiner fachkundigen Photographien von Convolvulaceae in dieser Arbeit verwenden. Ich danke ihm für die Betreuung meines Dissertationsvorhabens und die wertvollen fachlichen Gespräche. Ausdrücklich möchte ich mich dafür bedanken, daß er die Beendigung meines Dissertationsverfahren auch als Emeritus unterstützt hat. Frau Priv.-Doz. Dr. Kristina Jenett-Siems bin ich für die intensive Betreuung bei der Erstellung der vorliegenden Dissertationsschrift, insbesondere für ihre stete Diskussionsbereitschaft und die wertvollen inhaltlichen Verbesserungsvorschläge, zutiefst dankbar. Auch bezüglich der Spektreninterpretation und der Erstellung der Publikationen war ihre Hilfe unersetzlich. Herrn Dr. K. Siems von der AnalytiCon AG, NL Potsdam, möchte ich für die Aufnahme der NMR-Spektren danken, die aufgrund kleinster Substanzmengen nicht am Institut erstellt werden konnten, und für die hilfreichen Vorschläge zur Strukturaufklärung. Für die Anfertigung der FAB- und HR-Massenspektren und die rege Diskussionsbereitschaft sowie die konstruktiven Vorschläge zur Strukturaufklärung danke ich Frau U. Ostwald und Herrn Dr. G. Holzmann vom Institut für Chemie der FU Berlin. Auch bei der analytischen Abteilung des Instituts für Pharmazie der FU Berlin möchte ich mich für die Erstellung der NMR- und MS-Aufnahmen bedanken. Ein herzliches Dankeschön geht auch an Sara Wagner aus dem Fachbereich Chemie für die tatkräftige Hilfestellung bei der für den Review kurzfristig anberaumten Bestimmung der CD-Werte der Astrimalvine. Dem während der Anfertigung dieser Arbeit plötzlich verstorbenen Herrn Dr. L. Witte vom Arbeitskreis Hartmann der TU Braunschweig sowie dem Arbeitskreis um Frau Prof. Dr. M. Hilker, insbesondere Herrn F. Müller, am Institut für Biologie der FU Berlin danke ich für die reibungslose Kooperation bezüglich der GC-MS- Vermessung der Basen-Extrakte, die die Grundlage der umfangreichen Screening-Arbeiten darstellten. Herrn Prof. Dr. H. H. Pertz danke ich für die fruchtbare Zusammenarbeit und die unersetzliche technische Hilfestellung bei der pharmakologischen Testung der Bonabiline. Für wertvolle Anregungen bezüglich der isolierten neuen Naturstoffe möchte ich mich bei Herrn Dr. M. Kaloga bedanken. Außerdem danke ich den Mitarbeitern des Instituts für Pharmazie, die auf verschiedenste Weise zum Gelingen dieser Arbeit beigetragen haben, insbesondere Frau M. Meyer für die wertvollen Tipps und Tricks im Laboralltag sowie Frau Dr. Julia Lazar-Schurreit und Frau Sahin für die tröstenden Worte in schweren Zeiten. Herrn B. Kamann danke ich für die interessanten Sicherheitsbegehungen. Meinen ehemaligen Doktorandinnenkolleginnen Inga Köhler, Carola Schubert und Sonja Frölich sowie meinen Kondoktoranden Oliver Radtke und Ronald Keipert danke ich für die freundschaftliche und stets angenehme Arbeitsatmosphäre, ihr kollegiales Verhalten, die anregenden Gespräche und die schönen Erinnerungen an meine Laborzeit. Herrn Prof. Dr. M. F. Melzig danke für die Nutzung der Räumlichkeiten und technischen Ausstattung auch nach der Auflösung des Arbeitskreises Eich am Institut für Pharmazie – Pharmazeutische Biologie. Frau Wilke und Herrn M. Meyer vom Wirtschaftshof des Botanischen Garten der FU Berlin möchte ich für die Unterstützung beim Anbau der Pflanzen im Freiland und die Auseinzelung zur Vermehrung von Falkia repens danken. Bei Frau Dr. B. Jeckel vom Pflanzenschutzamt Berlin möchte ich mich für die fachkundige Beratung zur biologischen Schädlingsbekämpfung bedanken. Meinem ehemaligen Ethik-Lehrer am Simon-Marius-Gymnasium Gunzenhausen Herrn Peter Voss danke ich für die ausgewählte Literatur zum Thema Hexenprozesse. Nina Marxen möchte ich für die wunderschöne Zeichnung von Ipomoea tricolor cv. “Heavenly Blue” danken, die ich für die Widmung verwenden durfte. Steff Weißhäupl danke ich für die Umsetzung der graphischen Bildbearbeitung trotz erschwerter Bedingungen. An meine Patentante Prof. Dr. Elke Platz-Waury ergeht ein inniger Dank für die sprachliche Korrektur und die formale Hilfestellung bei der Dissertationsschrift. Die richtigen Fragen zur richtigen Zeit und die tolle Teamarbeit beim Erstellen der englischen Version der Zusammenfassung empfand ich als sehr wertvoll. Meiner Schreibstubengefährtin Friede Krebs danke ich für die liebevolle mentale Unterstützung und vor allem für die lebensrettenden Eintöpfe in der Endphase der Arbeit. Meinem geschätzten Bruder Dr. Claus-Eric Ott danke ich aus ganzem Herzen für den essentiellen Beistand in der Endphase dieser Arbeit: für die intelligenten Kommentare beim Korrekturlesen, für das Tiffisieren der C-Design-Formeln und für die Unterstützung bei dem Unterfangen, aus der Druckvorlage ein in sich abgerundetes Buch werden zu lassen. Ihm und Gina Yadegari möchte ich auch für den unermüdlichen Arbeitseinsatz bei der letzten Ernte im Gewächshaus danken. Und – last but not least – möchte ich meinen Freunden und meiner Familie danken, die mich in all den Jahren stets unterstützt und an mich geglaubt haben, allen voran meinen beiden Jungs, dem Kleinen und dem Großen, Ede Ott und Jan Krüger, die mir stets den Rücken gestärkt haben und oft auf mich verzichten mussten. Publikationsliste Originalarbeiten: Ott, S. C., Jenett-Siems, K., Siems, K., Müller, F., Hilker, M., Eich, E. (2013) Ipvelutine, 7-acetoxy-2-(tigloyloxy)tropane, an unusual tropane alkaloid from Ipomoea velutina R. BR. (Convolvulaceae). Scientia Pharmaceutica 81 (2), 543-548. Ott, S. C., Jenett-Siems, K., Eich, E. (2013) Stereochemistry of consabatine from Convolvulus sabatius VIV. (Convolvulaceae). Scientia Pharmaceutica 81 (1), 247-250. Ott, S. C., Jenett-Siems, K., Pertz, H. H., Siems, K., Witte, L., Eich, E. (2013) Bonabiline A, a monoterpenoid 3-acyloxytropane from the roots of Bonamia spectabilis showing M3 receptor antagonist activity. Erratum. Planta Medica 79 (6), 512. Ott, S. C., Tofern-Reblin, B., Jenett-Siems, K., Siems, K., Müller, F., Hilker, M., Onegi, B., Witte, L., Eich, E. (2007) Unusual tropane alkaloid pattern in two African convolvulaceous species. Phytochemistry and chemotaxonomy of the Convolvulaceae, part 20. Zeitschrift für Naturforschung 62b, 285-288. Ott, S. C., Jenett-Siems, K., Pertz, H. H., Siems, K., Witte, L., Eich, E. (2006) Bonabiline A, a monoterpenoid 3-acyloxytropane from the roots of Bonamia spectabilis showing M3 receptor antagonist activity. Planta Medica 72, 1403-1406. Jenett-Siems, K., Ott, S. C., Schimming, T., Siems, K., Müller, F., Hilker, M., Witte, L., Hartmann, T., Austin, D. F., Eich, E. (2005) Ipangulines and minalobines, chemotaxonomic markers of the infrageneric Ipomoea taxon subgenus Quamoclit, section Mina. Phytochemistry 66, 223-231. Jenett-Siems, K., Weigl, R., Böhm, A., Mann, P., Tofern-Reblin, B., Ott, S. C., Ghomian, A., Kaloga, M., Siems, K., Witte, L., Hilker, M., Müller, F., Eich, E. (2005) Chemotaxonomy of the pantropical genus Merremia (Convolvulaceae) based on the distribution of tropane alkaloids. Phytochemistry 66, 1448-1464. Posterpräsentationen: Ott, S. C., Jenett-Siems, K., Tofern, B., Siems, K., Müller, F., Hilker, M., Witte, L., Eich, E. (2004) Tropane alkaloids from the South African perennial herb Falkia repens (Convolvulaceae). 52nd Annual GA-Congress at the International Congress on Natural Products Research, Phoenix, Arizona, USA. Ott, S. C.,Jenett-Siems, K., Müller, F., Hilker, M., Witte, L., Eich, E. (2004) Neuartige Tropanalkaloide aus afrikanischen Convolvulaceae. Deutsche Pharmazeutische Gesellschaft (DPhG), Landesgruppe Berlin-Brandenburg: Der wissenschaftliche Nachwuchs stellt sich vor, Berlin. Ott, S. C., Jenett-Siems, K., Pertz, H. H., Eich, E. (2003) Muscarinic M3 receptor properties of bonabiline A from Bonamia spectabilis (Convolvulaceae). 51st Annual Congress of the Society for Medicinal Plant Research, Kiel. Ott, S. C., Jenett-Siems, K., Siems, K., Müller, F., Hilker, M., Onegi, B., Eich, E. (2003) Astrimalvine, a new tropane alkaloid from Astripomoea malvacea (Convolvulaceae). 51st Annual Congress of the Society for Medicinal Plant Research, Kiel. Ott, S. C., Jenett-Siems, K., Siems, K., Witte, L., Eich, E. (2002) Bonabiline, einzigartige Tropanalkaloide aus Bonamia spectabilis (Convolvulaceae). DPhG-Jahrestagung, Berlin. Ott, S. C., Jenett-Siems, K., Siems, K., Witte ,L., Eich, E. (2002) Bonabilines, unique tropane alkaloids from Bonamia spectabilis (Convolvulaceae). 50th Annual Congress of the Society for Medicinal Plant Research, Barcelona, Spain. Schimming, T., Tofern, B., Ott, S. C., Jenett-Siems, K., Gupta, M. P., Johnson, R. W., Milson,
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