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Phytochemische Untersuchungen Von Zwei Heilpflanzen Zentralamerikas

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Phytochemische Untersuchungen Von Zwei Heilpflanzen Zentralamerikas Phytochemische Untersuchungen von zwei Heilpflanzen Zentralamerikas sowie pharmakologisch‐biologische Untersuchungen von Naturstoffen mit AP‐1, MMPs und Humaner Neutrophiler Elastase als molekulare Targets Inaugural‐Dissertation zur Erlangung der Doktorwürde der Fakultät für Chemie, Pharmazie und Geowissenschaften der Albert‐Ludwigs‐Universität Freiburg im Breisgau vorgelegt von Andrea Hrenn aus Giengen (Brenz) Juni 2008 Dekan: Prof. Dr. A. Bechthold Leiterin der Arbeit: Prof. Dr. I. Merfort Referentin: Prof. Dr. I. Merfort Korreferent: Prof. Dr. A. Bechthold Drittprüfer: Prof. Dr. R. Schubert Tag der Verkündigung des Prüfungsergebnisses: 03.07.2008 Teile dieser Arbeit wurden in folgenden Publikationen und Posterpräsentationen veröffentlicht: Publikationen Hrenn A., Steinbrecher T., Labahn A., Schwager J., Schempp C.M. and Merfort I., Plant phenolics inhibit neutrophil elastase, Planta Medica 72 (12): 1127‐1131 (2006). Lindenmeyer M.T., Hrenn A., Kern C., Castro V., Murillo R., Müller S., Laufer S., Schulte‐ Mönting J., Siedle B. and Merfort I., Sesquiterpene lactones as inhibitors of IL‐8 expression in HeLa cells, Bioorganic & Medicinal Chemistry 14 (8): 2487‐2497 (2006). Siedle B., Hrenn A. and Merfort I., Natural compounds as inhibitors of human neutrophil elastase, Planta Medica 73 (5): 401‐420 (2007). Steinbrecher T.*, Hrenn A.*, Dormann K.L., Merfort I. and Labahn A., Bornyl (3,4,5‐ trihydroxy)‐cinnamate ‐ an optimized human neutrophil elastase inhibitor designed by free energy calculations, Bioorganic & Medicinal Chemistry 16 (5): 2385‐2390 (2008). *These authors contributed equally to this work. Jäger C., Hrenn A., Zwingmann J., Suter A. and Merfort I., Sesquiterpene lactones from Arnica montana inhibit the transcription factors AP‐1 (activator protein‐1) and NF‐κB (nuclear factor‐kappaB) and modulate the activity of MMP1 and MMP13 manuscript in preparation Kurzvorträge Hrenn A., Altevogt D., Interdisziplinäre Zusammenarbeit zwischen Biologie und Chemie: NF‐kappaB und FRET Promovierendenseminar der Pharmazie, Juni 2007, Freiburg, Deutschland Posterpräsentationen Hrenn A., Labahn A., Steinbrecher T., Schwager J., Merfort I., Studies on natural phenolics as inhibitors of elastase Annual Congress of the Society for Medicinal Plant Research, Firenze, Italien, August 2005 Steinbrecher T.*, Hrenn A.*, Merfort I., Dormann K.L., Labahn A., A new human neutrophil elastase inhibitor designed by free energy calculations Bunsentagung, Graz, Österreich, Mai 2007 (*These authors contributed equally to this work.) Steinbrecher T.*, Hrenn A.*, Dormann K.L., Labahn A., Merfort I., Bornyl (3,4,5‐trihydroxy)‐ cinnamate ‐ an optimized human neutrophil elastase inhibitor designed by free energy calculations Irseer Naturstofftage der DECHEMA e.V., Irsee (Allgäu), Deutschland, Februar 2008 (*These authors contributed equally to this work.) Meinen Eltern Probleme kann man niemals mit derselben Denkweise lösen, durch die sie entstanden sind. Albert Einstein Inhaltsverzeichnis I Inhaltsverzeichnis A. Einleitung .............................................................. 1 1. Phytochemische Untersuchungen ................................................. 2 1.1. Hieronyma alchorneoides Fr. Allemão ........................................................... 2 1.2. Siparuna thecaphora (Poepp. et Endl.) A. DC. ................................................ 5 2. Pharmakologisch‐biologische und molekularbiologische Untersuchungen .......................................................................... 10 2.1. Inhibition von Transkriptionsfaktoren (AP‐1, NF‐κB) .................................... 10 2.2. Matrixmetalloproteinasen (MMPs).............................................................. 12 2.3. Untersuchungen zur Elastase‐Hemmung ...................................................... 13 3. Ziele dieser Arbeit ....................................................................... 15 B. Literaturteil ......................................................... 17 1. Definition, Einteilung und Strukturen .......................................... 17 2. Anwendungsgebiete ................................................................... 20 2.1. Wundheilung ............................................................................................... 20 2.1.1. Studien am Menschen ....................................................................................... 20 2.1.2. Studien im Tiermodell und möglicher Mechanismus ........................................ 21 2.1.3. Versorgung von Brandwunden .......................................................................... 23 2.2. Adstringierende Wirkung ............................................................................. 25 2.3. Antibakterielle, antivirale und antifungale Effekte ...................................... 25 2.3.1. Antibakterielle Aktivität ..................................................................................... 26 2.3.2. Antivirale Aktivität ............................................................................................. 27 2.3.3. Antifungale Aktivität .......................................................................................... 28 2.3.4. Möglicher Mechanismus .................................................................................... 28 2.4. Wirkung bei Hautschädigung durch UV‐Strahlung........................................ 29 2.4.1. Studien am Menschen oder ex‐vivo ................................................................... 30 2.4.2. Studien im Tiermodell ........................................................................................ 31 2.4.3. Möglicher Mechanismus .................................................................................... 32 2.5. Hauttumore ................................................................................................. 34 2.5.1. Studien ............................................................................................................... 34 2.5.2. Möglicher Mechanismus .................................................................................... 36 II Inhaltsverzeichnis 2.6. Weitere Anwendungsgebiete ...................................................................... 39 2.6.1. Atopische Dermatitis und Psoriasis ................................................................... 39 2.6.2. Tannolact® (Firma Galderma) als Beispiel für ein etabliertes Fertigarzneimittel ............................................................................................... 41 2.6.3. Therapie von Feigwarzen ................................................................................... 42 2.6.4. Sonstige Gebiete ................................................................................................ 43 3. Bioverfügbarkeit, Metabolisierung ............................................. 44 4. Zusammenfassung ...................................................................... 46 C. Ergebnisse ........................................................... 49 1. Phytochemische Untersuchungen traditioneller Arznei‐ pflanzen Costa Ricas ................................................................... 49 1.1. Auswahl der Pflanzenextrakte im EMSA ...................................................... 49 1.2. Hieronyma alchorneoides Fr. Allem. ............................................................ 50 1.2.1. Extraktauftrennung durch Säulenchromatographie und Untersuchung der erhaltenen Fraktionen auf Hemmaktivität im NF‐κB‐EMSA .............................. 50 1.2.2. Strukturaufklärung von 7, 4‘‘‐O‐Dimethylamentoflavon (H.1) .......................... 50 1.2.3. Strukturaufklärung von 7‐O‐Monomethylamentoflavon (H.2) ......................... 60 1.2.4. Strukturaufklärung von Amentoflavon (H.3) ..................................................... 69 1.2.5. Untersuchung der biologischen Wirkungen der Biflavonoide ........................... 79 1.2.5.1. NF‐κB‐EMSA 79 1.2.5.2. Luciferase‐Reportergen‐Assay 80 1.2.6. Isolierung und Strukturaufklärung von (+)‐Catechin (H.4) ................................ 81 1.3. Siparuna thecaphora (Poepp. et Endl.) A. DC. .............................................. 89 1.3.1. Extraktauftrennung ............................................................................................ 89 1.3.2. Untersuchung der Aktivität der erhaltenen Fraktionen im NF‐κB‐EMSA .......... 89 1.3.3. Weitere biologisch kontrollierte Auftrennung der Unterfraktion S.t.3 mittels Säulenchromatographie und MTT‐Test ................................................. 89 1.3.4. Detektion einer Dragendorff‐positiven Substanz .............................................. 90 1.3.5. Strukturaufklärung von 3, 7, 4‘‐Trimethylkämpferol (S.1) ................................. 91 1.3.6. Isolierung und Strukturaufklärung von Aristolactam AIIIa (S.2) ........................ 95 2. Pharmakologisch‐biologische Untersuchungen ......................... 105 2.1. Inhibition des Transkriptionsfaktors AP‐1 ................................................... 105 2.1.1. Untersuchung der Hemmkonzentrationen von Sesquiterpenlactonen bei PMA‐Stimulierung in HeLa229‐Zellen sowie in Jurkat‐T‐Zellen ....................... 105 Inhaltsverzeichnis III 2.1.2. Untersuchung der Hemmkonzentrationen von isolierten Sesquiterpen‐ lactonen aus A. montana in Jurkat‐T‐Zellen nach IL‐1β‐Stimulierung ............. 112 2.1.3. Untersuchung von Arnikazubereitungen aus Drogen verschiedener Herkunft ..........................................................................................................
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