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Isolierung Und Strukturaufklärung Terpenoider Inhaltsstoffe Aus Montanoa Hibiscifolia Und Oyedaea Verbesinoides

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Isolierung Und Strukturaufklärung Terpenoider Inhaltsstoffe Aus Montanoa Hibiscifolia Und Oyedaea Verbesinoides Isolierung und Strukturaufklärung terpenoider Inhaltsstoffe aus Montanoa hibiscifolia und Oyedaea verbesinoides sowie Untersuchungen ihrer biologischen Aktivität Inaugural-Dissertation zur Erlangung der Doktorwürde der Fakultät für Chemie, Pharmazie und Geowissenschaften der Albert-Ludwigs-Universität Freiburg im Breisgau vorgelegt von Stefan Müller aus Haunstetten April 2004 Dekan: Prof. Dr. K. Bucher Leiterin der Arbeit: Prof. Dr. I. Merfort Referentin: Prof. Dr. I. Merfort Korreferent: Prof. Dr. R. Schubert Dritter Prüfer: Prof. Dr. A. Bechthold Tag der Verkündigung des Prüfungsergebnisses: 8. Juli 2004 Teile dieser Arbeit wurden in folgenden Publikationen und Posterpräsentationen ver- öffentlicht. Publikationen: Müller, S., Tirapelli, C.R., de Oliveira, A.M., Murillo, R., Castro, V., Merfort, I., 2003. Studies of ent-Kaurane diterpenes from Oyedaea verbesinoides for their in- hibitory activity on vascular smooth muscle contraction. Phytochemistry 63, 391-396. Müller, S., Murillo, R., Castro, V., Brecht, V., Merfort, I., 2004. Sesquiterpene lac- tones from Montanoa hibiscifolia inhibit the transcription factor NF-κB. Journal of Natural Products 67, 622-630. Müller, S., Hildebrandt, S., Klaas, C.A., Tubaro, A., Altinier, G., Merfort, I., Structural requirements of sesquiterpene lactones for NF-κB inhibition and for reduction of the mouse ear edema, in Vorbereitung. Posterpräsentationen Müller, S., Murillo, R., Castro, V., Mora, G. and Merfort, I., Ent-Kauranes from Oye- daea verbesinoides. Annual Congress of the Society for Medicinal Plant Re- search, 2001, Erlangen, Deutschland Müller, S., Murillo, R., Castro, V. and Merfort, I., Unusual Sesquiterpene Lactones from Montanona hibiscifolia. Annual Congress of the Society for Medicinal Plant Research, 2002, Barcelona, Spanien Müller, S., Lindenmeyer, M.T., Murillo, R., Castro, V., Altinier, G., Tubaro, A., Della Loggia, R., Prahst, C.and Merfort, I., Sesquiterpene Lactones from Montanoa hibiscifolia with Antiinflammatory Activity. Annual Congress of the Society for Medicinal Plant Research, 2003, Kiel, Deutschland Für meine Eltern παντα ρηει (Alles ist im Fluß) Heraklit (544-483 v. Chr.) Inhaltsverzeichnis I A. EINLEITUNG ....................................................................................................1 B. ERGEBNISSE ................................................................................................11 1. Inhaltsstoffführung der oberirdischen Teile von Montanoa hibiscifolia ..........................11 1.1 Extraktion und Fraktionierung des lipophilen Extraktes....................................................11 1.2 Sesquiterpenlactone .........................................................................................................11 1.2.1 Strukturaufklärung von 8α-(2’R,3’R-Epoxy-2’-methylbutyryloxy)-4α,9α-epidioxy-9ß-hydroxy- 5ßH-eudesm-1Z,11(13)-dien-6ß,12-olid (1)...............................................................................12 1.2.2 Strukturaufklärung von 8α-(2’S,3’S-Epoxy-2’-methylbutyryloxy)-4α,9α-epidioxy-9ß-hydroxy- 5ßH-eudesm-1Z,11(13)-dien-6ß,12-olid (2)...............................................................................22 1.2.3 Strukturaufklärung von 8α-(2’S,3’S-Epoxy-2’-methylbutyryloxy)-4α,9α-epidioxy-9ß-hydroxy- 5ßH-eudesm-1Z-en-6ß,12-olid (3).............................................................................................33 1.2.4 Strukturaufklärung von 8α-(2’R,3’R-Epoxy-2’-methylbutyryloxy)-4α-hydroxy-9-oxo-5ßH- eudesm-1Z,11(13)-dien-6ß,12-olid (4).......................................................................................41 1.2.5 Strukturaufklärung von 8α-(2’R,3’R-Epoxy-2‘-methylbutyryloxy)-9α-hydroxy-(11,13)- dehydromontahibisciolid (5).......................................................................................................50 1.2.6 Strukturaufklärung von 8α-(2’R,3’R-Epoxy-2‘-methylbutyryloxy)-9α-hydroxy- montahibisciolid (6) ...................................................................................................................58 1.2.7 Strukturaufklärung von 8α-(2’R,3’R-Epoxy-2’-methylbutyryloxy)-9α-hydroxy-1α-methoxy- 1,10α-dihydromontahibisciolid (7) .............................................................................................66 1.2.8 Strukturaufklärung von 8α-(2’R,3’R-Epoxy-2’-methylbutyryloxy)-9ß-hydroxy-germacra- 4E,1(10)E-dien-6ß,12-olid (8)....................................................................................................75 1.2.9 Strukturaufklärung von 8α-(2’S,3’S-Epoxy-2’-methylbutyryloxy)-9ß-hydroxy-germacra- 4E,1(10)E-dien-6ß,12-olid (9)....................................................................................................83 1.2.10 Strukturaufklärung von 9ß-(2’S,3’S-Epoxy-2’-methylbutyryloxy)-8α-hydroxy-germacra- 4E,1(10)E-dien-6ß,12-olid (10)..................................................................................................88 1.2.11 Strukturaufklärung von 8α-(2’S,3’S-Epoxy-2’-methylbutyryloxy)-9-oxo-germacra-4E, 1(10)Z-dien-6ß,12 olid (11)........................................................................................................95 1.2.12 Strukturaufklärung von 8α-(2’S,3’S-Epoxy-2’-methylbutyryloxy)-1α-methoxy-9-oxo-10αH- germacra-4E-en-6ß,12-olid (12) ..............................................................................................103 1.2.13 Strukturaufklärung von 8α-(2’R,3’R-Epoxy-2’-methylbutyryloxy)-1α-methoxy-9-oxo-10αH- germacra-4E-en-6ß,12-olid (13) ..............................................................................................110 1.2.14 Strukturaufklärung von 8α-Hydroxy-9ß-tigloyloxy-germacra-4E,1(10)E-dien-6ß,12-olid (14)..112 1.2.15 Strukturaufklärung von 3α-Acetoxy-costunolid (15).................................................................120 2. Inhaltsstoffführung der Blätter von Oyedaea verbesinoides ........................................124 2.1 Extraktion und Fraktionierung des lipophilen Extraktes................................................. 124 2.2 Kaurane und Sesquiterpene .......................................................................................... 125 2.2.1 Identifizierung der ent-Kaur-16-en-19-säure (16) ....................................................................125 2.2.2 Identifizierung von ent-Kaur-16-en-19-al (17)..........................................................................127 2.2.3 Identifizierung von ent-19-Hydroxy-kaur-16-en (18) ................................................................130 2.2.4 Identifizierung von ent-Kaur-16ß-ol (19)..................................................................................134 2.2.5 Identifizierung von ent-15ß-Tigloyloxy-9α-hydroxy-kaur-16-en-19-säure (20).........................138 II Inhaltsverzeichnis 2.2.6 Identifizierung von ent-15ß-Angeloyloxy-9α-hydroxy-kaur-16-en-19-säure (21) .....................143 2.2.7 Identifizierung von ent-15ß-Angeloyloxy-7α,9α-dihydroxy-kaur-16-en-19-säure (22) .............148 2.2.8 Identifizierung von ent-9α-Hydroxy-kaur-16-en-19-säure (23).................................................153 2.2.9 Identifizierung von ent-9(11)-Dehydrokaur-16-en-19-säure (24) .............................................155 2.2.10 Identifizierung von 1α-Angeloyloxy-carotol (25) ......................................................................157 2.3 Identifizierung der sonstigen Verbindungen (26 - 30).................................................... 160 3. Sesquiterpenlactone aus Saussurea lappa .................................................................163 3.1 Identifizierung von Dehydosaussurealacton (31) und Costunolid (32).......................... 163 4. Pharmakologisch-biologische Untersuchungen...........................................................169 4.1 Untersuchung von aus M. hibiscifolia und S. lappa isolierten Sesquiterpenlactonen auf die Hemmung des Transkriptionsfaktors NF-κB im Electrophoretic Mobility Shift Assay (EMSA) ...................................................................................................... 169 4.1.1 Einfluss der Sesquiterpenlactone auf die NF-κB-DNA-Bindung in Jurkat T-Zellen ..................170 4.1.2 Einfluss der Sesquiterpenlactone auf die NF-κB-DNA-Bindung in RAW 264.7-Zellen .............172 4.1.3 Einfluss der Sesquiterpenlactone aus Saussurea lappa auf die NF-κB-DNA-Bindung ............174 4.2 Einfluss von Sesquiterpenlactonen auf das Croton-Öl induzierte Mausohr-Ödem ....... 176 4.3 Untersuchungen auf Hemmung der NF-κB-DNA-Hemmung eines Spiroketal- Enol-Ethers .................................................................................................................... 178 4.4 Untersuchung von den aus O. verbesinoides isolierten Kauranen auf ihre pharmakologische Wirkung............................................................................................ 169 4.4.1 Einfluss von Kauranen auf ihre Hemmungsaktivität bei der Kontraktion der glatten Gefäßmuskulatur......................................................................................................................181 4.4.2 Einfluss von Kauranen auf die NF-κB-DNA-Bindung in RAW 264.7-Zellen..............................184 C. CIRCULARDICHROISMUS..........................................................................185 1. Grundlagen ..................................................................................................................185 1.1 Polarisation des Lichts ..................................................................................................
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