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Boswellia Spp.) Unter Department Chemie der Technischen Universität München Untersuchungen zum Harz des Weihrauchbaums (Boswellia spp.) unter besonderer Berücksichtigung der Säurefraktion Jochen Helge Bergmann Vollständiger Abdruck der von der Fakultät für Chemie der Technischen Universität München zur Erlangung des akademischen Grades eines Doktors der Naturwissenschaften genehmigten Dissertation. Vorsitzender: Univ.-Prof. Dr. W. Hiller Prüfer der Dissertation: 1. Univ.-Prof. Dr. J. Jauch, Universität des Saarlandes - Saarbrücken 2. Univ.-Prof. Dr. P. Schieberle Die Dissertation wurde am 5.5.2004 bei der Technischen Universität München eingereicht und durch die Fakultät für Chemie am 23.6.2004 angenommen. Der experimentelle Teil der vorliegenden Arbeit wurde von August 2000 bis Dezember 2003 am Lehrstuhl I für Organische Chemie des Departments Chemie der Technischen Uni- versität München durchgeführt und von Herrn Priv.-Doz. Dr. Johann Jauch betreut. Ich danke Herrn Professor Dr. Thorsten Bach, Ordinarius am oben genannten Lehrstuhl, für die Bereit- stellung des Labors und insbesondere den Zugang zu den NMR-Geräten. Diese Arbeit wurde großzügig gefördert durch den „Bund der Freunde der Technischen Universität München“ und die Technische Universität München (Promotionsstipendien von August 2000 bis Dezember 2001), die Deutsche Forschungsgemeinschaft (Personal- und Sachmittel; Januar 2002-März 2004), die Dr.-Ing.-Leonhard-Lorenz-Stiftung der Technischen Universität München (Sachmittel) sowie die BASF AG und Degussa AG (Chemikalien- und Gerätespenden). Für die Harzproben der unterschiedlichen Weihrauch-Arten möchte ich mich bei den ein- zelnen Spendern bedanken, insbesondere Dr. M. Al-Amri (Ministry of Agriculture, Rumais Research Station, Muscat, Oman), Professor Dr. M. Thulin (Uppsala Universitet, Schweden) und Frau J. Steele (Economic Botany Collection, Kew Gardens, GB). Dr. N. Kilian und Dr. R. Vogt vom Botanischen Garten und Botanischen Museum in Berlin-Dahlem schließlich haben mir großzügigen Zugang zur dortigen Harzsammlung und der Bibliothek gewährt. Die Aufnahme der Massenspektren verdanke ich Herrn H. Krause und die der FAME-GC- MS-Chromatogramme in Kapitel 3.2.1 Herrn Michael Lindenmeier. Bei Frau E. Kaldyk und Dr. Ulrich Reiser bedanke ich mich für die Hilfe bei den Schwierigkeiten am Anfang meiner Doktorarbeit, bei Herrn Dr. W. Eisenreich und Frau C. Schwarz für die 2D-NMR-Messungen und Herrn C. Krombach (Merck-VWR) für die Überlassung eine Chromolith-Säule für die HPLC. Frau Dr. A. Weeks (University of Texas, Austin) und Herrn Prof. Dr. M. Thulin (Uppsala Universitet, Schweden) sei für die ausführlichen Erläuterungen zur Botanik der Burseraceen und der Weihrauchbäume gedankt. Im Rahmen von Fortgeschrittenenpraktika in der Organischen Chemie wurden von den folgenden Studierenden der TU München Teilgebiete der vorliegenden Arbeit bearbeitet: Peter Kaden, Maike Müller (Isolierung und Strukturaufklärung von Boswelliasäuren). Josef Mitterpleininger, Christoph Rentsch, Georg Wuitschik (Methodenentwicklung bei der Partialsynthese von Boswelliasäuren). Ihnen sei an dieser Stelle herzlich für ihre Anregungen und tatkräftige Mithilfe gedankt. Für gelegentliche Hilfe bei der Literaturbeschaffung, kollegiale Gespräche und gründli- ches Korrekturlesen bedanke ich mich bei Patrick Gruber, Claudia Kahle, Birgit Kindermann, Michael Lindenmeier, Dr. Anja Setrdle und Dr. Carsten Wallner. Schließlich möchte ich mich herzlich bei meinem Betreuer, Herrn Prof. Dr. Johann Jauch, für eine Betreuung und eine Arbeitsatmosphäre bedanken, wie ich sie mir nicht besser hätte wünschen können. Inhaltsverzeichnis I Inhaltsverzeichnis Inhaltsverzeichnis........................................................................................................................I Abkürzungen und Symbole......................................................................................................IV Abbildungsverzeichnis.............................................................................................................VI Tabellenverzeichnis..................................................................................................................IX 1 Einleitung.......................................................................................................................... 1 1.1 Pflanzliche Harze.......................................................................................................... 1 1.1.1 Harzliefernde Pflanzen der Burseraceae-Familie.................................................... 2 1.1.2 Weihrauchharz......................................................................................................... 3 1.1.2.1 Chemie des Weihrauchharzes, insbesondere der sauren Bestandteile........... 6 1.1.2.2 Medizinische Verwendung von Weihrauch................................................. 12 1.1.2.3 Pharmakologische Wirkung von Weihrauchinhaltsstoffen ......................... 14 1.2 Identifizierung der verschiedenen Weihrauch-Arten.................................................. 16 1.3 Identifizierung unerwünschter Beimischungen im Weihrauchharz............................ 20 1.4 Die Verwendung von Ionenaustauschern bei der Isolierung von Naturstoffen.......... 20 1.5 Isolierung und Partialsynthese von Boswelliasäuren und deren Derivaten................ 22 1.6 Analytische Aspekte der Weihrauchchemie ............................................................... 24 1.6.1 Dünnschicht-Chromatographie.............................................................................. 24 1.6.2 Hochleistungsflüssig-Chromatographie an monolithischer stationärer Phase....... 25 1.6.3 NMR-Spektroskopie .............................................................................................. 25 1.6.4 FAME-GC-MS zur Analytik organischer Säuren ................................................. 25 2 Fragestellung................................................................................................................... 27 3 Ergebnisse und Diskussion............................................................................................. 28 3.1 Identifizierung der Weihrauch-Art bei unbekannten Proben...................................... 28 3.1.1 Unterscheidung anhand Geruch, Extrakt- und Säureanteil.................................... 28 3.1.2 Unterscheidung der Boswellia-Spezies mittels Dünnschicht-Chromatographie der Säurefraktion.......................................................................................................... 38 3.1.3 Unterscheidung der Boswellia-Spezies mittels HPLC der Säurefraktion.............. 43 3.1.4 Unterscheidung der Boswellia-Spezies durch Kombination verschiedener Methoden ............................................................................................................... 51 3.1.5 HPLC-Übersichtschromatogramm der Säurefraktion auf monolithischer stationärer RP-18-Phase......................................................................................... 57 3.2 Identifizierung und Quantifizierung von Kolophoniumbestandteilen im Weihrauchharz ............................................................................................................ 60 3.2.1 Isolierung von Kolophoniumbestandteilen aus Probe 1 (Bser Gr1)...................... 60 3.2.2 Quantifizierung von Kolophoniumbestandteilen in Probe 1 (Bser Gr1)............... 65 3.2.3 Trennung von DhAbiA 38 und β-KBA 6 auf monolithischer RP-18-Phase ......... 71 3.3 Isolierung der Säurefraktion aus dem Weihrauchharz mittels Ionenaustauscher ....... 72 3.4 Isolierung und Partialsynthese von Boswelliasäuren und deren Derivaten................ 86 3.4.1 Partialsynthese einzelner Boswelliasäuren aus anderen Boswelliasäuren............. 86 3.4.2 Partialsynthese einzelner Boswelliasäuren aus der gesamten Säurefraktion......... 91 3.4.3 Effiziente Gewinnung und Aufreinigung einzelner Boswelliasäuren ................... 93 3.5 NMR-Spektroskopie von Boswelliasäuren und deren Derivaten ............................... 97 3.5.1 Strukturaufklärung der Boswelliasäuren am Beispiel von β-ABA 2 .................... 97 3.5.2 Vergleichende NMR-Spektroskopie von natürlichen und nicht-natürlichen Boswelliasäuren................................................................................................... 103 3.5.3 Diskrepanzen zwischen eigenen Messungen und Literaturwerten ...................... 107 II Inhaltsverzeichnis 4 Experimenteller Teil..................................................................................................... 111 4.1 Allgemeine Angaben................................................................................................ 111 4.2 Chemikalien.............................................................................................................. 112 4.3 Material..................................................................................................................... 112 4.4 Geräte........................................................................................................................ 113 4.5 Arbeitsvorschriften ................................................................................................... 115 4.5.1 Identifizierung der Weihrauch-Art bei unbekannten Proben............................... 115 4.5.1.1 Herstellung von Weihrauch-Extrakten aus großen Probenmengen........... 115 4.5.1.2 Herstellung von Weihrauch-Extrakten aus kleinen Probenmengen .......... 116 4.5.1.3 Bestimmung der Effizienz verschiedener Lösungsmittel bei der Extraktion von Weihrauchharz
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