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Chemische Zusammensetzung Und Antimikrobielle Eigenschaften Der Ätherischen Öle Von Leptospermum Scoparium J

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Chemische Zusammensetzung Und Antimikrobielle Eigenschaften Der Ätherischen Öle Von Leptospermum Scoparium J Chemische Zusammensetzung und antimikrobielle Eigenschaften der ätherischen Öle von Leptospermum scoparium J. R. et G. Forst. und anderer Teebaumöle der Gattungen Kunzea, Leptospermum und Melaleuca unter besonderer Berücksichtigung von Handelsölen DISSERTATION zur Erlangung des naturwissenschaftlichen Doktorgrades des Fachbereiches Chemie der Universität Hamburg vorgelegt von Frank Christoph aus Hamburg Hamburg 2001 Leptospermum scoparium J. R. et G. Forst. (Manuka) Zeichnung: F. Osborne aus BROOKER et al. (1987) Die vorliegende Arbeit entstand in der Zeit von Oktober 1997 bis Mai 2001 am Institut für Pharmazie, Abteilung für Pharmazeutische Biologie der Universität Hamburg unter der Leitung von Frau Prof. Dr. E. Stahl-Biskup, der ich für die vertrauensvolle Zusammenarbeit und die wohlwollende Förderung meiner Arbeit herzlich danken möchte 1. Gutachter: Prof. Dr. E. Stahl-Biskup 2. Gutachter: Prof. Dr. K.-H. Kubeczka Tage der mündlichen Prüfungen: 12. Juli, 16. Juli, 23. Juli 2001 II Meiner Großmutter Upon the hills are Myrtles blooming – Dark tea–tree glades Toss their light foam like banners triumphing, White Burgan wades Knee-deep in summer grass, a mounth ago Heath-myrtle sweet Laughed and turned rosy – crimsoning her snow On flying feet. Of scent she brought dear memories. The gums Star-crowned and tall Baring their limbs as every zephyr comes, Sing over all. N.N. III Danksagungen Herrn Prof. Dr. K.-H. Kubeczka danke ich sehr herzlich für die Überlassung des Arbeitsplatzes und für die Übernahme des Koreferates. Auch für die hilfreiche Unterstützung bei analytischen Fragestellungen möchte ich mich nochmals bedanken. Herrn Prof. Dr. P.-M. Kaulfers, Institut für Mikrobiologie und Immunologie des Universitätsklinikums Hamburg - Eppendorf, danke ich für spontane Bereitstellung von Arbeitsplatz und –material und seine freundliche Unterstützung bei den mikrobiologischen Fragestellungen, sowie seinen Mitarbeiterinnen und Mitarbeitern danke ich für die sehr angenehme Zusammenarbeit bei den antimikrobiellen Untersuchungen. Frau Sabine Krause danke ich für die diesbezügliche technische Assistenz besonders herzlich. Frau Kerstin Blum gilt mein besonderer Dank für geleistete technische Assistenz auf chemisch-analytischem Gebiet. Herrn Prof. Dr. W. A. König, Institut für Organische Chemie der Universität Hamburg, danke ich für die Isomerenbestimmung von trans-Calamenen. Seinem technischen Mitarbeiter Herrn M. Preusse gilt mein Dank für die Durchführung der GC-MS-Messungen. Frau Prof. Dr. I. Merfort, Universität Freiburg, danke ich für die Durchführung der Untersuchungen zur Hemmung der NF-kB Aktivität. Herrn PD Dr. H. Häberlein, Universität Marburg, danke ich für die Beschaffung von Pflanzenmaterial. Frau Dr. J. Holthuijzen, Freiburg, danke ich ebenfalls für die Beschaffung von Pflanzenmaterial. Besonderer Dank an Herrn K.-D. Protzen für wichtige Ratschläge, Anregungen und hilfreiche Gespräche, die zum Gelingen dieser Arbeit beitrugen, sowie für die Beschaffung von Literatur. Herrn R. Storm gilt ebenfalls mein Dank für die Beschaffung von Literatur. Meinen Dank richte ich zudem an Herrn H. Müggenburg für die allgemeine Förderung unseres Arbeitskreises. IV Folgenden Firmen danke ich für deren freundliche Bereitstellung der ätherischen Handelsöle: Adrian (Germany) GmbH (Hamburg), Aromara GmbH (St. Blasien), Coast Biologicals Ltd. (Manukau City, NZ), H. E. Daniel Ltd. (Royal Tunbridge Wells, UK), Düllberg Konzentra GmbH & Co. (Hamburg), Frey & Lau GmbH (Henstedt-Ulzburg), Eduard Gerlach GmbH (Lübbecke), Paul Kaders GmbH (Hamburg), Melaleuka GmbH (Saarbrücken), C. Melchers Essential Oils Handels-GmbH (Bremen), Neumond Düfte der Natur GmbH (Raisting), Nordmann Rassmann GmbH & Co. (Hamburg), Phoenix Natural Products Ltd. (Southall, UK), Primavera Life (Sulzberg), Taoasis GmbH (Lemgo), R. C. Treatt & Co. Ltd. (Bury St Edmunds, UK), Worlée E. H. & Co. Drogenhandelsges.mbH (Hamburg) V Abkürzungsverzeichnis Abb. Abbildung ACIAR Australian Centre for International Agricultural Research Aqua dest. Aqua destillata, Destilliertes Wasser ATCC American Type Culture Collection ATTIA Australian Tea Tree Industry Association BA Blutagar BfArM Bundesinstitut für Arzneimittel und Medizinprodukte BHIB Brain Heart Infusion Bouillon BP British Pharmakopoeia c.i. clinical isolate, klinisches Isolat CV coefficient of variation d Tag DAB Deutsches Arzneibuch DAC Deutscher Arzneimittel Codex DC Dünnschichtchromatograhie DNA Desoxyribonucleinsäure EINECS European Inventory of Existing Commercial Chemical Substances ELINCS European List of Notified New Chemical Substances EMSA Gel-Elektromobilitätsshift-Assay EuAB Europäisches Arzneibuch FID Flammenionisationsdetektor GC Gaschromatographie h Stunde IL Interleukin ISO International Standards Organisation kA keine Angabe KBE Kolonien-bildende Einheiten Lsg. Lösung MBK Minimale Bakterizide Konzentration MHB Mueller Hinton Bouillon MHK Minimale Hemmkonzentration min Minute VI MMK Minimale Mikrobizide Konzentration MS Massenspektrometrie MTKW Monoterpenkohlenwasserstoffe NCCLS National Committee for Clinical Laboratory Standards nd nicht detektiert NF-kB Nuclear factor kB NMR Nuclear Magnetic Resonance, Kernresonanz OTC Over The Counter ox. MT oxygenierte Monoterpene ox. ST oxygenierte Sesquiterpene PMA Phorbol-12-myristat-13-acetat präp. GC Präparative Gaschromatographie S. Seite s.l. sensu lato, im weiteren Sinne von SDA Sabouraud Dextrose Agar SDB Sabouraud Dextrose Bouillon Sp Spur(en) º <0.05% s.str. sensu stricto, im engeren Sinne von STKW Sesquiterpenkohlenwasserstoffe subsp. Subspecies, Unterart t Tonne(n) Tab. Tabelle TGA Therapeutic Goods Act TNF Tumornekrosefaktor TSA Tryptophan Soja Agar TSB Tryptophan Soja Bouillon TSC Trockensäulenchromatographie U Umdrehung ü.NN über Normal Null USP United States Pharmakopoeia var. varietas, Varietät WHO World Health Organization VII VIII Inhaltsverzeichnis Inhaltsverzeichnis A EINLEITUNG..................................................................................................................... 1 1 Zielsetzung dieser Arbeit .................................................................................................1 2 Die Familie der Myrtaceae................................................................................................3 2.1 Systematik und Verbreitung.........................................................................................3 2.1.1 Unterfamilie Myrtoideae...................................................................................3 2.1.2 Unterfamilie Leptospermoideae ........................................................................3 2.2 Morphologie und Anatomie ..........................................................................................4 2.3 Chemische Merkmale..................................................................................................5 2.3.1 Nicht flüchtige Inhaltsstoffe ..............................................................................5 2.3.2 Flüchtige Inhaltsstoffe......................................................................................5 3 Pflanzenarten, deren ätherische Öle unter dem Namen Teebaumöle s.l. bekannt sind ....6 3.1 Leptospermum scoparium J. R. et G. Forst...................................................................6 3.1.1 Morphologie und Anatomie ..............................................................................7 3.1.2 Verbreitung .....................................................................................................7 3.1.3 Chemische Merkmale ......................................................................................8 3.2 Kunzea ericoides (A. Rich.) J. Thompson .....................................................................9 3.2.1 Morphologie und Anatomie ..............................................................................9 3.2.2 Verbreitung ................................................................................................... 10 3.2.3 Chemische Merkmale .................................................................................... 10 3.3 Melaleuca alternifolia Cheel ....................................................................................... 11 3.3.1 Morphologie und Anatomie ............................................................................ 11 3.3.2 Verbreitung ................................................................................................... 11 3.3.3 Chemische Merkmale .................................................................................... 12 3.3.4 Monographien ............................................................................................... 13 3.4 Melaleuca cajuputi subsp. cajuputi Powell .................................................................. 13 3.4.1 Morphologie und Anatomie ............................................................................ 14 3.4.2 Verbreitung und chemische Merkmale der drei Subspecies.............................. 14 3.4.3 Monographien ............................................................................................... 15 3.5 Melaleuca quinquenervia (Cav.) S. T. Blake................................................................ 16 3.5.1 Morphologie und Anatomie ............................................................................ 16 3.5.2 Verbreitung ................................................................................................... 17 3.5.3 Chemische Merkmale ...................................................................................
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