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Acmella Ciliata (H.B.K.) Cassini

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Acmella Ciliata (H.B.K.) Cassini A Acmella ciliata (H.B.K.) Cassini Phytochemische und enzymatische Untersuchungen, galenische Präformulierungen 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 RONALD KEIPERT aus Berlin März, 2009 B C Die Arbeit wurde angefertigt in den Jahren 2003 - 2009 unter Leitung von Herrn Prof. Dr. M. F. Melzig. 1. Gutachter: Prof. Dr. Melzig 2. Gutachter: PD Dr. Jenett-Siems Disputation am: 24.06.2009 D E Meinen Eltern F G Danksagung Mein besonderer Dank gilt Herrn Prof. Dr. M. F. Melzig* für die Überlassung dieses vielseitigen Themas, seine stete Unterstützung der Arbeit und Bereitschaft zur Diskussion. Außerdem bin ich ihm dankbar für die Freiräume, die Arbeit den Erfordernissen entsprechend anpassen und erweitern zu können. Frau PD Dr. K. Jenett-Siems* danke ich für die große Hilfe bei der Strukturaufklärung, insbesondere bei der Auswertung von NMR-Spektren, sowie für wertvolle phytochemische Tipps. Mein Dank gilt weiter Frau Dr. R. Schenk und Mitarbeitern, Landwirtschaftlich-Gärtnerische Fakultät der Humboldt-Universität, Berlin, die durch Aufzucht und Anbau von Acmella ciliata die Arbeit primär ermöglichten. Bei Herrn Dr. W. Mehnert** möchte ich mich herzlich für die Mitarbeit und Unterstützung bei den galenischen Themen und statistischen Auswertungen bedanken. Frau Dr. K. Wölkart, Mathematisch-Naturwissenschaftliche Fakultät der Karl-Franzens- Universität‚ Graz, danke ich ganz besonders für die HPLC-MS-Analysen zweier Acmella ciliata-Fraktionen und für die Anregungen zu deren Auswertung. Frau Dr. B. Rennert(*) danke ich für die Einführung in die Elastaseanalytik. Weiterhin danke ich den Diplomandinnen Frau F. Gollesch* und Frau K. Henke* für die Messung von Acmella-Proben im Trypsin- bzw. Thrombin-Assay. Den Studierenden Frau J. Stratmann, Frau A. Reibert, Frau C. Behrends, Herr C. Dehne gilt mein Dank für ihr Mitwirken im Rahmen ihrer Wahlpflichtarbeit, Frau Dr. J. Lazar- Schurreit* für die Hilfe bei der mikroskopischen Auswertung, Frau P. Schlupp** für die Herstellung der Nanoemulsion, Herrn Dr. B. Schwabe** für die Mitarbeit bei der Tablettenherstellung, Herrn Prof. Dr. B. Müller und Mitarbeitern, Christian-Albrechts- Universität, Kiel, für die Herstellung der CO2-Extrakte, Herrn Dr. K. Siems, AnalytiCon AG, Potsdam, für die Hilfe bei NMR-Problemen, Herrn Dr. M. Fengler für wertvolle Statistiktipps und meinem Bruder T. Keipert für die Hilfe in Gestaltungsfragen der Arbeit. Schließlich gilt mein Dank den Mitarbeitern des Arbeitskreises von Prof. Melzig für ihre Kollegialität und besonders Frau M. Mayer und Frau S. Ott für wertvolle Tipps im Laboralltag. Mein herzlichster Dank gebührt meinen Eltern, meiner Lebensgefährtin Jeannette und meinem Sohn Manuel, die mir stets geistige und moralische Unterstützung bei der Durchführung und Fertigstellung meiner Arbeit gewährten und viel Geduld aufbrachten. * Institut für Pharmazie, Pharmazeutische Biologie im Fachbereich Biologie, Chemie, Pharmazie der Freien Universität, Berlin ** Institut für Pharmazie, Pharmazeutische Technologie im Fachbereich Biologie, Chemie, Pharmazie der Freien Universität, Berlin H I Inhaltsverzeichnis Einleitung .............................................................................................................................. 1 Problemstellung .................................................................................................................. 3 Allgemeiner Teil.................................................................................................................. 4 1. Beschreibung der Pflanze ..................................................................................... 4 1.1. Taxonomie............................................................................................................... 4 1.2. Vorkommen............................................................................................................. 8 1.3. Makroskopische Beschreibung............................................................................... 9 1.4. Mikroskopische Beschreibung.............................................................................. 14 2. Gewinnung des Pflanzenmaterials..................................................................... 20 2.1. Anbau / Aufzucht .................................................................................................. 20 2.2. Ernte und Trocknung............................................................................................. 22 2.3. Extraktion.............................................................................................................. 22 3. Phytochemische Untersuchungen ...................................................................... 25 3.1. Inhaltsstoffe allgemein .......................................................................................... 25 3.2. DC-Screening........................................................................................................ 26 3.2.1. Acmella ciliata-Droge ........................................................................................... 27 3.2.2. Acmella ciliata / Acmella oleracea-Vergleich – Frischpflanzen .......................... 31 3.3. Alkamide ............................................................................................................... 34 3.3.1. Literaturüberblick.................................................................................................. 34 3.3.1.1. Vorkommen / Strukturen....................................................................................... 34 3.3.1.2. Anwendung / Wirkung.......................................................................................... 39 3.3.1.2.1. Traditionelle Anwendung...................................................................................... 39 3.3.1.2.2. Potentielle Wirkungen / Wirkprinzip .................................................................... 41 3.3.2. Isolierung............................................................................................................... 43 3.3.3. Strukturaufklärung ................................................................................................ 45 3.3.3.1. +ESI-MS-Fragmentierung der Amidreste............................................................. 50 3.3.3.2. Undeca-2E,4E-dien-8,10-diinsäure-isobutylamid (Verbindung A1) .................... 52 3.3.3.3. Nona-2E-en-6,8-diinsäure-phenylethylamid (Verbindung A2) ............................ 56 3.3.3.4. 7-Hydroxy-dodeca-2E,4E,8Z,10E-tetraensäure-isobutylamid (Verbindung A3) . 59 3.3.3.5. 2,4-Dihydroxy-nona-6,8-diinsäure-phenylethylamid (Verbindung A4) ............... 61 II 3.3.3.6. Dodeca-2E-en-8,10-diinsäure-isobutylamid (Verbindung A5)............................. 63 3.3.3.7. 2-Hydroxy-undeca-7Z,9E-diensäure-isobutylamid (Verbindung A61) Undeca-2E,7Z,9E-triensäure-isobutylamid (Verbindung A62) ............................. 64 3.3.3.8. Nona-2Z-en-6,8-diinsäure-isobutylamid (Verbindung A7) und 2,3(c)-Epoxy-nona-6,8-diinsäure-phenylethylamid (Verbindung A8).................. 66 3.3.3.9. Nona-2Z-en-6,8-diinsäure-phenylethylamid (Verbindung A9)............................. 68 3.3.3.10. Undeca-2E-en-8,10-diinsäure-isobutylamid (Verbindung A10)........................... 69 3.3.3.11. Undeca-2E,4E-dien-8,10-diinsäure-methylbutylamid (Verbindung A11)............ 71 3.3.3.12. Weitere Verbindungen aus Sammelfraktion 2 (Retentionszeiten 20,95; 21,67 und 23,98 min)...................................................................................................... 73 3.3.3.13. 2,5-Dihydroxy-deca-6Z,8E-diensäure-isobutylamid (2,5-Dihydroxyhydro- spilanthol) (Verbindung A12) ............................................................................... 74 3.3.3.14. Spilanthol (Deca-2E,6Z,8E-triensäure-isobutylamid) (Verbindung A13) ............ 76 3.3.3.15. Trideca-5Z-en-10,12-diinsäure-isobutylamid (Verbindung A14)......................... 78 3.3.3.16. Hydrospilanthol (Deca-6Z,8E-diensäure-isobutylamid) (Verbindung A15)......... 79 3.3.3.17. Weitere Verbindungen aus Sammelfraktion 3 ...................................................... 81 3.3.3.18. Dodeca-2E,4E,8Z,10E-tetraensäure-isobutylamid (Verbindung A16) ................. 82 3.3.3.19. Resümee ................................................................................................................ 84 3.4. Phenolische Verbindungen.................................................................................... 86 3.4.1. Allgemeines........................................................................................................... 86 3.4.2. Isolierung............................................................................................................... 88 3.4.3. Strukturaufklärung ................................................................................................ 92 3.4.3.1. Phenol-Monocarbonsäuren.................................................................................... 93 3.4.3.1.1. p-Hydroxybenzoesäure (Verbindung P1) ............................................................. 93 3.4.3.1.2. Protocatechusäure (Verbindung P2) ..................................................................... 94 3.4.3.1.3. cis-/trans-p-Cumarsäure (Verbindung P3)............................................................ 95 3.4.3.1.4. trans-Kaffeesäure (Verbindung P4).....................................................................
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