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Phylogenie Der Verbenaceae : Kladistische Untersuchungen Mit Morphologischen Und Chemischen Merkmalen

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Phylogenie Der Verbenaceae : Kladistische Untersuchungen Mit Morphologischen Und Chemischen Merkmalen Phylogenie der Verbenaceae : Kladistische Untersuchungen mit morphologischen und chemischen Merkmalen Inaugural-Dissertation zur Erlangung der Doktorwürde der Fakultät für Chemie und Pharmazie der Albert-Ludwigs-Universität Freiburg im Breisgau vorgelegt von Ursula von Mulert aus Bad Cannstatt 2001 a Dekan : Prof. Dr. H. Vahrenkamp Leiter der Arbeit : Prof. Dr. H. Rimpler Referent : Prof. Dr. H. Rimpler Korreferent : Prof. Dr. D. Vogellehner Bekanntgabe des Prüfungsergebnisses : 20.12.2001 Diese Arbeit wurde am Institut für Pharmazeutische Biologie der Albert-Ludwigs-Universität unter Leitung von Prof. Dr. H. Rimpler durchgeführt. b dem besten Vadd’r von Welt „Wenn nichts mehr hilft, dann nur noch der Gaschromatograph !!!“ (Dr. Quincy) c INHALTSVERZEICHNIS 1. EINLEITUNG UND PROBLEMSTELLUNG ............................................................... 1 2. LITERATURTEIL ....................................................................................................... 5 2.1. Kladistische Analyse ................................................................................................................ 5 2.1.1. Einführung und Begriffe....................................................................................................................... 5 2.1.2. Polarisierung der Merkmale durch die Außengruppe.................................................................. 7 2.1.3. Methoden.................................................................................................................................................. 7 2.2. Definition und botanische Beschreibung der Verbenaceae ................................................14 2.2.1. Definition der Verbenaceae s. str.....................................................................................................14 2.2.2. Botanische Beschreibung der Verbenaceae s. str.......................................................................15 2.3. Bisherige Gliederungsvorschläge für die Verbenaceae........................................................17 2.3.1. Gliederung der Verbenaceae in Tribus ...........................................................................................17 2.3.2. Gliederung der Gattung Verbena L. ................................................................................................22 2.4. Botanische Beschreibungen der wichtigsten Gattungen der Verbenaceae .......................24 2.5. Iridoide....................................................................................................................................35 2.5.1. Strukturen und Eigenschaften..........................................................................................................35 2.5.2. Biosynthese der Iridoide .....................................................................................................................37 2.5.3. Vorkommen und taxonomische Bedeutung .................................................................................44 3. ERGEBNISSE......................................................................................................... 47 3.1. Phytochemische Untersuchungen.........................................................................................47 3.1.1. Methodik .................................................................................................................................................48 3.1.1.A. Nachweis der Iridoide durch GC/MS .........................................................................................48 3.1.1.B. Nachweis der Iridoide durch Isolierung....................................................................................53 I 3.1.2. Strukturaufklärung einzelner Iridoide............................................................................................55 3.1.2.A. Bekannte Iridoide.............................................................................................................................55 3.1.2.B. Bisher noch nicht bekannte Iridoide..........................................................................................94 3.1.3. Ergebnisse ............................................................................................................................................ 101 3.1.3.A. Acanthaceae JUSS.......................................................................................................................... 103 3.1.3.B. Bignoniaceae JUSS......................................................................................................................... 110 3.1.3.C. Martyniaceae HORAN.................................................................................................................... 118 3.1.3.D. Myoporaceae R. BR....................................................................................................................... 120 3.1.3.E. Orobanchaceae.............................................................................................................................. 122 3.1.3.F. Pedaliaceae R. BR.......................................................................................................................... 123 3.1.3.G. Scrophulariaceae JUSS. ................................................................................................................ 125 3.1.3.H. Verbenaceae s. str......................................................................................................................... 132 3.1.3.I. Zusammenfassung der chemischen Daten ........................................................................... 169 3.1.4. Kodierung der Iridoide...................................................................................................................... 185 3.2. Morphologische Untersuchungen.......................................................................................186 3.2.1. Habitus.................................................................................................................................................. 186 3.2.2. Infloreszenz.......................................................................................................................................... 186 3.2.3. Kelch ...................................................................................................................................................... 190 3.2.4. Krone...................................................................................................................................................... 194 3.2.5. Antheren............................................................................................................................................... 197 3.2.6. Pollen..................................................................................................................................................... 198 3.2.7. Narbe ..................................................................................................................................................... 200 3.2.8. Gynoezeum .......................................................................................................................................... 201 3.2.9. Früchte .................................................................................................................................................. 203 3.2.10. Sonstige Merkmale............................................................................................................................ 204 3.3. Merkmalsliste.......................................................................................................................205 3.4. Kladistische Analyse ............................................................................................................225 3.4.1. Auswertung der chemischen Merkmale..................................................................................... 225 3.4.2. Auswertung der morphologischen Merkmale........................................................................... 228 3.4.3. Auswertung der gesamten Datenmatrix .................................................................................... 231 II 4. DISKUSSION .......................................................................................................243 5. ZUSAMMENFASSUNG.......................................................................................249 6. EXPERIMENTELLER TEIL ....................................................................................251 6.1. Phytochemie.........................................................................................................................251 6.1.1. Material ................................................................................................................................................ 251 6.1.2. Methoden............................................................................................................................................. 252 6.1.2.A. Methoden zum Nachweis der Iridoide durch GC/MS........................................................ 252 6.1.2.B. Methoden zum Nachweis der Iridoide durch Isolierung.................................................. 258 6.1.3. Eigenschaften der Verbindungen.................................................................................................. 267 6.2. Morphologie.........................................................................................................................305 6.2.1. Material ...............................................................................................................................................
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