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Einleitung Und Problemstellung 1

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Einleitung Und Problemstellung 1 Phytochemische Untersuchung der Blätter von Eupatorium semialatum Benth., einer in Zentralamerika traditionell verwendeten Arzneipflanze („Bacché“) Inaugural-Dissertation zur Erlangung des Doktorgrades der Mathematisch-Naturwissenschaftlichen Fakultät der Heinrich-Heine-Universität Düsseldorf vorgelegt von Günter Lang aus Bonn Düsseldorf 2001 Gedruckt mit Genehmigung der Mathematisch-Naturwissenschaftlichen Fakultät der Heinrich-Heine-Universität Düsseldorf Referent: Prof. Dr. P. Proksch Korreferent: Priv.-Doz. Dr. C.M. Paßreiter Tag der mündlichen Prüfung: 13. Juli 2001 Die vorliegende Arbeit wurde unter Leitung von Herrn Prof. Dr. P. Proksch am Institut für Pharmazeutische Biologie der Heinrich-Heine-Universität Düsseldorf erstellt. Meinem Doktorvater Herrn Prof. Dr. P. Proksch danke ich sehr herzlich für seine großzügige und wohlwollende Unterstützung meiner Arbeit und die Bereitstellung der vorbildlichen Arbeitsbedingungen. Mein besonderer Dank gilt Herrn Dr. C. M. Paßreiter für seine Freundschaft und vorzügliche Betreuung, seine unermüdliche Diskussionsbereitschaft sowie die vielen wertvollen Anregungen, die für das Gelingen dieser Arbeit unerläßlich waren. Herrn Prof. Dr. G. Willuhn danke ich dafür, mein besonderes Interesse für die pharmazeutische Biologie geweckt und mir die Möglichkeit eröffnet zu haben, die vorliegende Arbeit am Institut für Pharmazeutische Biologie der Heinrich-Heine-Universität Düsseldorf beginnen zu dürfen. Meinen Eltern und meiner Frau Sabine Inhaltsverzeichnis 1 EINLEITUNG UND PROBLEMSTELLUNG 1 2 EIGENE PHYTOCHEMISCHE UNTERSUCHUNGEN 9 2.1 ISOLIERUNG UND IDENTIFIZIERUNG VON SESQUITERPENLACTONEN AUS EUPATORIUM SEMIALATUM 9 2.1.1 Extraktion und Fraktionierung 12 2.1.2 Verbindung SL1 (8β-[2-(2-Hydroxy-1-methoxyethyl)acryloyloxy]reynosin) 13 2.1.3 Verbindung SL2 (8β-[2-(2-Hydroxy-1-methoxyethyl)acryloyloxy]reynosin) 25 2.1.4 Verbindung SL3 (8β-[2-(2-Hydroxy-1-methoxyethyl)acryloyloxy]balchanin) 30 2.1.5 Verbindung SL4 (Trichomatolid D) 34 2.1.6 Verbindung SL5 (8β-[4-Hydroxy-5-(5-hydroxytigloyloxy)tigloyloxy]reynosin) 37 2.1.7 Verbindung SL6 (8β-[5-Hydroxy-4-(5-hydroxytigloyloxy)tigloyloxy]reynosin) 46 2.1.8 Verbindung SL7 (8β-[4-Hydroxy-5-(5-hydroxytigloyloxy)tigloyloxy]balchanin) 52 2.1.9 Verbindung SL8 (8β-[5-Hydroxy-4-(5-hydroxytigloyloxy)tigloyloxy]balchanin) 58 2.1.10 Verbindung SL9 (8β-[4-Hydroxy-5-(5-hydroxytigloyloxy)tigloyloxy]magnolialid) 61 2.1.11 Verbindung SL10 (8β-[5-Hydroxy-4-(5-hydroxytigloyloxy)tigloyloxy]magnolialid) 70 2.1.12 Verbindung SL11 (3β-Hydroxy-8β-[4-hydroxy-5-(5-hydroxytigloyloxy)tigloyloxy]-4α-methoxy- 10(14),11(13)-guaiadien-12,6-olid) 73 2.2 ISOLIERUNG UND IDENTIFIZIERUNG VON FLAVONOID-AGLYKA AUS EUPATORIUM SEMIALATUM 83 2.2.1 Extraktion und Fraktionierung 84 2.2.2 Verbindung FA1 (Hispidulin) 85 2.2.3 Verbindung FA2 (Pectolinarigenin) 94 2.2.4 Verbindung FA3 (Eupafolin) 96 2.2.5 Verbindung FA4 (Desmethoxycentaureidin) 101 2.2.6 Verbindung FA5 (Acacetin) 106 2.2.7 Verbindung FA6 (Patuletin) 108 2.2.8 Verbindung FA7 (Laciniatin) 114 2.2.9 Verbindung FA8 (Mikanin) 119 2.2.10 Verbindung FA9 (Axillarin) 124 2.3 ISOLIERUNG UND IDENTIFIZIERUNG VON FLAVONOID-GLYKOSIDEN AUS EUPATORIUM SEMIALATUM 125 2.3.1 Extraktion und Fraktionierung 125 Inhaltsverzeichnis II 2.3.2 Verbindung FG1 (Eupalin) 125 2.3.3 Verbindung FG2 (Eupalitin 3-rhamnosid-4´-glucosid) 132 2.3.4 Verbindung FG3 (Eupalitin 3-glucosid) 140 2.3.5 Verbindung FG4 (Eupalitin 3-galactosid) 146 2.3.6 Verbindung FG5 (Eupatolin) 150 2.3.7 Verbindung FG6 (6-Methoxykaempferol 3-glucosid) 157 2.3.8 Verbindung FG7 (6-Methoxykaempferol 3-galactosid) 162 2.3.9 Verbindung FG8 (6-Methoxykaempferol 3-rhamnosid) 168 2.3.10 Verbindung FG9 (Patuletin 3-galactosid) 172 2.3.11 Verbindung FG10 (Patuletin 3-rhamnosid) 179 2.3.12 Verbindung FG11 (Patuletin 3-glucosid) 185 2.3.13 Erkenntnisse zur Fragmentierung von 6-Hydroxykaempferol- Dimethylethern bei der LC-MS 190 2.4 ISOLIERUNG UND IDENTIFIZIERUNG VON KAFFEOYL-CHINASÄUREN AUS EUPATORIUM SEMIALATUM 193 2.4.1 Extraktion und Fraktionierung 193 2.4.2 Verbindung KC1 (Chlorogensäuremethylester) 194 2.4.3 Verbindung KC2 (Kryptochlorogensäuremethylester) 205 2.4.4 Verbindung KC3 (Neochlorogensäuremethylester) 207 2.4.5 Verbindung KC4 (Isochlorogensäure b) 209 2.4.6 Verbindung KC5 (Isochlorogensäure b-methylester) 215 2.4.7 Verbindung KC6 (Isochlorogensäure a-methylester) 219 2.4.8 Verbindung KC7 (Isochlorogensäure c) 223 2.4.9 Verbindung KC8 (Isochlorogensäure c-methylester) 225 2.5 EXTRAKTION UND IDENTIFIZIERUNG VON PYRROLIZIDIN-ALKALOIDEN UND MONOTERPENEN AUS EUPATORIUM SEMIALATUM 228 2.5.1 Extraktion 230 2.5.2 Identifizierung der Pyrrolizidinalkaloide PA1 – PA5 (Tussilagin, Isotussilagin, Neotussilagin, Neoisotussilagin und Pyrrolidin-2-essigsäuremethylester) 231 2.5.3 Identifizierung der beiden Monoterpene MO1 und MO2 (trans-Terpin und trans-Sobrerol) 237 2.6 ISOLIERUNG UND IDENTIFIZIERUNG WEITERER VERBINDUNGEN AUS EUPATORIUM SEMIALATUM 239 2.6.1 Extraktion und Fraktionierung 239 2.6.2 Verbindung SE1 (11-Cinnamoyloxyoplopanon) 239 2.6.3 Verbindung TR1 (Oleanolsäure) 247 2.6.4 Verbindung CU1 (Aesculin) 252 Inhaltsverzeichnis III 3 EIGENE PHARMAKOLOGISCHE UNTERSUCHUNGEN 257 3.1 MALARIA – EINE GEIßEL DER MENSCHHEIT 257 3.2 BESTIMMUNG DER ANTIPLASMODIALEN AKTIVITÄT VON SEKUNDÄR-STOFFEN AUS DEM DICHLORMETHAN-EXTRAKT VON E. SEMIALATUM 266 3.2.1 Der pLDH-Test (Parasiten-Lactatdehydrogenase-Test) 266 3.2.2 Ergebnisse 269 4 DISKUSSION 273 5 ZUSAMMENFASSUNG 293 6 EXPERIMENTELLER TEIL 295 6.1 ALLGEMEINES 295 6.2 CHROMATOGRAPHISCHE VERFAHREN 295 6.2.1 Dünnschicht-Chromatographie (DC) 295 6.2.2 Säulenchromatographie (SC) 298 6.2.3 Niederdruck-Flüssigchromatographie (LPLC) 300 6.2.4 Hochleistungs-Flüssigschromatographie (HPLC) 301 6.2.5 Gaschromatographie (GC) 302 6.3 SPEKTROSKOPISCHE VERFAHREN 303 6.3.1 Optische Drehung 303 6.3.2 IR-Spektroskopie 303 6.3.3 UV-Spektroskopie 303 6.3.4 Massenspektrometrie (MS) 304 6.3.5 Kernresonanz-Spektroskopie (NMR) 305 6.4 GEKOPPELTE VERFAHREN 305 6.4.1 GC-MS 305 6.4.2 LC-MS 306 6.5 ISOLIERUNG DER INHALTSSTOFFE AUS EUPATORIUM SEMIALATUM 308 6.5.1 Herkunft des Drogenmaterials 308 6.5.2 Gewinnung der Rohextrakte 308 6.5.3 Fraktionierung des Dichlormethan-Extraktes 308 6.5.3.1 Auftrennung der Fraktion D-II 309 6.5.3.2 Auftrennung der Fraktion D-IV 310 6.5.4 Isolierung und analytische Daten der Sesquiterpenlactone und anderer terpenoider Verbindungen aus dem Dichlormethan-Extrakt 311 6.5.4.1 Verbindung SL1 (8β-[2-(2-Hydroxy-1-methoxyethyl)acryloyloxy]reynosin) 311 6.5.4.2 Verbindung SL2 (8β-[2-(2-Hydroxy-1-methoxyethyl)acryloyloxy]reynosin) 312 6.5.4.3 Verbindung SL3 (8β-[2-(2-Hydroxy-1-methoxyethyl)acryloyloxy]balchanin) 312 Inhaltsverzeichnis IV 6.5.4.4 Verbindung SL4 (Trichomatolid D) 313 6.5.4.5 Verbindung SL5 (8β-[4-Hydroxy-5-(5-hydroxytigloyloxy)tigloyloxy]reynosin) 314 6.5.4.6 Verbindung SL6 (8β-[5-Hydroxy-4-(5-hydroxytigloyloxy)tigloyloxy]reynosin) 315 6.5.4.7 Verbindung SL7 (8β-[4-Hydroxy-5-(5-hydroxytigloyloxy)tigloyloxy]balchanin) 315 6.5.4.8 Verbindung SL8 (8β-[5-Hydroxy-4-(5-hydroxytigloyloxy)tigloyloxy]balchanin) 316 6.5.4.9 Verbindung SL9 (8β-[4-Hydroxy-5-(5-hydroxytigloyloxy)tigloyloxy]magnolialid) 317 6.5.4.10 Verbindung SL10 (8β-[5-Hydroxy-4-(5-hydroxytigloyloxy)tigloyloxy]magnolialid) 317 6.5.4.11 Verbindung SL11 (3β-Hydroxy-8β-[4-hydroxy-5-(5-hydroxytigloyloxy)tigloyloxy]-4α-methoxy- 10(14),11(13)-guaiadien-12,6-olid) 318 6.5.4.12 Verbindung SE1 (11-Cinnamoyloxyoplopanon) 319 6.5.4.13 Verbindung TR1 (Oleanolsäure) 319 6.5.5 Isolierung und analytische Daten der Flavonoid-Aglyka 320 6.5.5.1 Verbindung FA1 (Hispidulin) 320 6.5.5.2 Verbindung FA2 (Pectolinarigenin) 321 6.5.5.3 Verbindung FA3 (Eupafolin) 321 6.5.5.4 Verbindung FA4 (Desmethoxycentaureidin) 321 6.5.5.5 Verbindung FA5 (Acacetin) 322 6.5.5.6 Verbindung FA6 (Patuletin) 322 6.5.5.7 Verbindung FA7 (Laciniatin) 323 6.5.5.8 Verbindung FA8 (Mikanin) 323 6.5.5.9 Verbindung FA9 (Axillarin) 323 6.5.6 Fraktionierung des Methanol-Extraktes 324 6.5.6.1 Auftrennung der Fraktion M-II 324 6.5.6.2 Auftrennung der Fraktion M-IV 325 6.5.6.3 Auftrennung der Fraktion M-V 325 6.5.6.4 Auftrennung der Fraktion M-VII 326 6.5.6.5 Auftrennung der Fraktion M-VIII 326 6.5.7 Isolierung und analytische Daten der Flavonoid-Glykoside und Kaffeoyl- Chinasäuren sowie eines Coumarin-Glykosids aus dem Methanol-Extrakt 327 6.5.7.1 Verbindung FG1 (Eupalin) 327 6.5.7.2 Verbindung FG2 (Eupalitin 3-rhamnosid-4´-glucosid) 327 6.5.7.3 Verbindung FG3 (Eupalitin 3-glucosid) 328 6.5.7.4 Verbindung FG4 (Eupalitin 3-galactosid) 328 6.5.7.5 Verbindung FG5 (Eupatolin) 329 6.5.7.6 Verbindung FG6 (6-Methoxykaempferol 3-glucosid) 329 6.5.7.7 Verbindung FG7 (6-Methoxykaempferol 3-galactosid) 330 6.5.7.8 Verbindung FG8 (6-Methoxykaempferol 3-rhamnosid) 330 6.5.7.9 Verbindung FG9 (Patuletin 3-galactosid) 331 6.5.7.10 Verbindung FG10 (Patuletin 3-rhamnosid) 331 6.5.7.11 Verbindung FG11 (Patuletin 3-glucosid) 332 6.5.7.12 Verbindung KC1 (Chlorogensäuremethylester) 332 6.5.7.13 Verbindung KC2 (Kryptochlorogensäuremethylester) 333 6.5.7.14 Verbindung KC3 (Neochlorogensäuremethylester) 333 6.5.7.15 Verbindung KC4 (Isochlorogensäure b) 334 6.5.7.16 Verbindung KC5 (Isochlorogensäure b-methylester) 334 6.5.7.17 Verbindung KC6 (Isochlorogensäure a-methylester) 335 Inhaltsverzeichnis V 6.5.7.18 Verbindung KC7 (Isochlorogensäure c) 336 6.5.7.19 Verbindung KC8 (Isochlorogensäure c-methylester) 336 6.5.7.20 Verbindung CU1 (Aesculin) 337 6.5.8 Aufreinigung der 140 g-Portion des Methanol-Extraktes zum Nachweis der Pyrrolizidin-Alkaloide 337 6.5.9 Analytische Daten der Pyrrolizidin-Alkaloide aus Fraktion I und der in Fraktion II vorliegenden Monoterpene 338 6.6 PHARMAKOLOGISCHE ARBEITSMETHODEN 341 6.6.1 Allgemeines 341 6.6.2 Reagenzien und Mischungen 341 6.6.3 Herkunft der Parasiten-Isolate 342 6.6.4 Gewinnung des Blut-Serums 342 6.6.5 Aufbereitung der Erythrozyten 342 6.6.6 Kultivierung der Plasmodien 342 6.6.7 Blutaustriche und Zählung der Parasiten 343 6.6.8 Durchführung des modifizierten pLDH-Assays 343 6.6.9 Berechung der IC50 344 6.6.10 Statistischer Vergleich der Mittelwerte 344 7 LITERATUR 345 Abkürzungsverzeichnis A.
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