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Untersuchungen Zu Den Inhaltsstoffen Von Echinacea Atrorubens Sowie

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Untersuchungen Zu Den Inhaltsstoffen Von Echinacea Atrorubens Sowie Untersuchungen zu den Inhaltsstoffen von Echinacea atrorubens sowie zur Wirkung und Bioverfügbarkeit von Alkamiden Birgit Dietz Untersuchungen zu den Inhaltsstoffen von Echinacea atrorubens sowie zur Wirkung und Bioverfügbarkeit von Alkamiden Inaugural Dissertation zur Erlangung des Doktorgrades der Mathematisch-Naturwissenschaftlichen Fakultät der Heinrich-Heine-Universität Düsseldorf Vorgelegt von Birgit Dietz aus Dortmund Düsseldorf 2002 Gedruckt mit Genehmigung der Mathematisch-Naturwissenschaftlichen Fakultät der Heinrich-Heine-Universität Düsseldorf Referent: Prof. Dr. R. Bauer Korreferent: Prof. Dr. B.C. Lippold Tag der mündlichen Prüfung: 09.07.2002 Die vorliegende Arbeit wurde auf Anregung und unter Leitung von Herrn Prof. Dr. R. Bauer am Institut für Pharmazeutische Biologie der Heinrich-Heine-Universität Düsseldorf angefertigt. Mein besonderer Dank gilt meinem Doktorvater, Herrn Prof. Dr. R. Bauer, für die hilfreiche Betreuung, seine große Diskussionsbereitschaft, für die Schaffung eines harmonischen Arbeitsklimas und für seinen unermüdlichen Einsatz besonders auch über die Entfernung von Graz nach Düsseldorf in der letzten Phase der Arbeit. Weiterhin danke ich Herrn Prof. Dr. P. Proksch und Herrn Prof. Dr. G. Willuhn sehr herzlich, dass sie mir die Arbeit am Institut für Pharmazeutische Biologie ermöglichten. Herrn Prof. Dr. B.C. Lippold danke ich besonders für die Übernahme des Korreferates. Meinen Eltern I Inhaltsverzeichnis 1 EINLEITUNG UND PROBLEMSTELLUNG..................................................................... 1 2 DIE GATTUNG ECHINACEA ............................................................................................. 2 2.1. SYSTEMATIK UND VERBREITUNG..................................................................................... 2 2.1.1. Systematik.............................................................................................................................. 2 2.1.2. Verbreitung ........................................................................................................................... 5 2.2. BISHER BEKANNTE INHALTSSTOFFE ............................................................................... 6 2.2.1. Alkamide................................................................................................................................ 6 2.2.2. Polyacetylene ...................................................................................................................... 10 2.2.3. Kaffeesäurederivate ............................................................................................................ 11 2.2.4. Flavonoide........................................................................................................................... 13 2.2.5. Polysaccharide und Glykoproteine ..................................................................................... 13 2.2.6. Alkaloide ............................................................................................................................. 14 2.2.7. Ätherisches Öl ..................................................................................................................... 15 2.2.8. Sonstige Inhaltsstoffklassen................................................................................................. 16 2.3. TRADITIONELLE UND HEUTIGE ANWENDUNG............................................................ 17 2.3.1. Traditionelle Anwendung .................................................................................................... 17 2.3.2. Heutige Anwendung ............................................................................................................ 18 2.3.3. Klinische Studien mit Zubereitungen aus E. angustifoliae radix......................................... 18 2.3.4. Klinische Studien mit Zubereitungen aus E. pallidae radix ................................................ 18 2.3.5. Klinische Studien mit Zubereitungen aus E. purpureae radix............................................. 19 2.3.6. Klinische Studien mit Zubereitungen aus E. purpureae herba........................................... 19 2.3.7. Klinische Studien mit Zubereitungen aus mehreren Echinacea-Arten................................ 20 2.4. BISHERIGE PHARMAKOLOGISCHE UNTERSUCHUNGEN............................................ 21 2.4.1. Pharmakologische Wirkungen von E. angustifoliae radix .................................................. 21 2.4.2. Pharmakologische Wirkungen von E. pallidae radix.......................................................... 22 2.4.3. Pharmakologische Wirkungen von E. purpureae radix ...................................................... 24 2.4.4. Pharmakologische Wirkungen von E. purpureae herba...................................................... 26 2.4.5. Pharmakologische Untersuchungen von nicht näher definierten Echinacea-Präparaten .. 28 2.5. VERTRÄGLICHKEIT UND TOXIZITÄT VON ECHINACEA-PRÄPARATEN................. 30 2.6. BISHERIGE PHARMAKOKINETISCHE UNTERSUCHUNGEN........................................ 32 2.7. BISHERIGER STAND DER ANALYTIK .............................................................................. 33 3 ALLGEMEINES ZU ECHINACEA ATRORUBENS ....................................................... 40 II Inhaltsverzeichnis 3.1. BOTANISCHE BESCHREIBUNG UND VERBREITUNG ................................................... 40 3.1.1. Habitus der Pflanze .............................................................................................................40 3.1.2. Makroskopische Beschreibung von Echinaceae atrorubens radix ...................................... 41 3.2. MIKROSKOPISCHE BESCHREIBUNG ................................................................................ 42 3.2.1. Mikroskopische Beschreibung des Krautes ......................................................................... 42 3.2.2. Eigene mikroskopische Untersuchungen des Blattes und der Wurzel ................................. 42 3.3. BISHER BEKANNTE PHARMAKOLOGISCHE UNTERSUCHUNGEN............................ 44 4 EIGENE PHYTOCHEMISCHE UNTERSUCHUNGEN................................................... 45 4.1. ANALYTIK.............................................................................................................................. 45 4.1.1. HPLC-Analyse..................................................................................................................... 45 4.1.2. Dünnschichtchromatographische Analyse .......................................................................... 54 4.2. ISOLIERUNG UND STRUKTURAUFKLÄRUNG VON ALKAMIDEN AUS ECHINACEAE ATRORUBENS RADIX ................................................................................ 59 4.2.1. Fraktionierung..................................................................................................................... 59 4.2.2. Probleme bei der Isolierung von Alkamiden ....................................................................... 62 4.2.3. Undeca-2E,4E/Z-dien-8,10-diinsäure-isobutylamide (Verbindungen A1/2) ....................... 62 4.2.4. Undeca-2E-en-8,10-diinsäure-isobutylamid (Verbindung A3)............................................ 67 4.2.5. Dodeca-2E,4Z-dien-8,10-diinsäure-isobutylamid (Verbindung A4) ................................... 70 4.2.6. Dodeca-2E-en-8,10-diinsäure-isobutylamid (Verbindung A5)............................................ 71 4.2.7. Dodeca-2E,4Z,10Z-trien-8-insäure-isobutylamid (Verbindung A6).................................... 72 4.2.8. Trideca-2E,7Z-dien-10,12-diinsäure-isobutylamid (Verbindung A7) ................................. 75 4.2.9. Dodeca-2E,4E,8Z,10Z/E-tetraensäure-isobutylamide (Verbindungen A8/9)...................... 79 4.2.10. Dodeca-2E,4E,8Z-triensäure-isobutylamid (Verbindung A10)........................................... 82 4.2.11. Dodeca-2E,4E-diensäure-isobutylamid (Verbindung A11)................................................. 85 4.2.12. Dodeca-2E,4Z,10Z-trien-8-insäure-2-methylbutylamid (Verbindung A12) ........................ 88 4.2.13. Dodeca-2E,4Z-dien-8,10-diinsäure-2-methylbutylamid (Verbindung A13)........................ 92 4.2.14. Dodeca-2E,10E/Z-dien-8-insäure-isobutylamide (Verbindungen A14/15) ......................... 96 4.2.15. Pentadeca-2E,9Z-dien-12,14-diinsäure-isobutylamid (Verbindung A16)........................... 99 4.2.16. Dodeca-2E,4E-diensäure-2-methylbutylamid (Verbindung A17)...................................... 103 4.2.17. Dodeca-2E,4E,8Z-triensäure-2-methylbutylamid (Verbindung A18)................................ 106 4.2.18. Dodeca-2E,4E,8Z,10Z/E-tetraensäure-2-methylbutylamide (Verbindungen A19/20)....... 107 4.3. IDENTIFIZIERUNG WEITERER LIPOPHILER VERBINDUNGEN ................................. 110 4.3.1. Identifizierung der Triterpene β-Sitosterol, Stigmasterol und Campesterol...................... 110 4.4. ISOLIERUNG UND STRUKTURAUFKLÄRUNG EINER HYDROPHILEN VERBINDUNG AUS ECHINACEAE ATRORUBENS HERBA .................................................................... 111 Inhaltsverzeichnis III 4.4.1. Narcissin (Verbindung FG1): 3,4´,5,7-Tetrahydroxy-3´-methoxyflavon-3-β-[6-O-α-L- rhamnopyranosyl-D-glucopyranose] ................................................................................ 111 4.5. ISOLIERUNG UND STRUKTURAUFKLÄRUNG EINES FLAVONOIDS AUS DEM PRESSSAFT VON ECHINACEAE PURPUREAE HERBA ................................................ 114 4.5.1. Robinetin (Verbindung F1): 3´,4´,5´,7-Tetrahydroxyflavonol..........................................
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