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Bioaktive Sekundärstoffe Aus Endophytischen Pilzen – Isolierung, Strukturaufklärung Und Charakterisierung Der Biologischen Aktivität –

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Bioaktive Sekundärstoffe Aus Endophytischen Pilzen – Isolierung, Strukturaufklärung Und Charakterisierung Der Biologischen Aktivität – Bioaktive Sekundärstoffe aus endophytischen Pilzen – Isolierung, Strukturaufklärung und Charakterisierung der biologischen Aktivität – Inaugural-Dissertation zur Erlangung des Doktorgrades der Mathematisch-Naturwissenschaftlichen Fakultät der Heinrich-Heine-Universität Düsseldorf vorgelegt von Clécia Maria Freitas Richard aus Salvador da Bahia - Brasilien Düsseldorf, November 2011 Aus dem Institut für Pharmazeutische Biologie und Biotechnologie der Heinrich-Heine Universität Düsseldorf Gedruckt mit der Genehmigung der Mathematisch-Naturwissenschaftlichen Fakultät der Heinrich-Heine-Universität Düsseldorf Referent: Prof. Dr. Peter Proksch Koreferent: Dr. Rainer Ebel Tag der mündlichen Prüfung: 04.11.2011 Die vorliegende Arbeit wurde auf Anregung und unter Leitung von Herrn Prof. Dr. P. Proksch am Institut für Pharmazeutische Biologie und Biotechnologie der Heinrich-Heine-Universität Düsseldorf erstellt. Bei Herrn Prof. Dr. P. Proksch möchte ich mich ganz herzlich für die Überlassung des interessanten Themas und das mir entgegengebrachte Vertrauen bedanken. Besonderen Dank auch für die wissenschaftliche Betreuung, sowie die sehr guten Arbeitsbedingungen. Herrn Dr. R. Ebel danke ich sehr herzlich für die Übernahme des Koreferates sowie die intensive wissenschaftliche Betreuung während meiner Promotionszeit. Deficit omne, natus sum! M. FABIVS QVINTILIANVS (c. 35 – c. 100 A.D.) Inhaltsverzeichnis 1. Einleitung 1 1.1. Die Rolle von Naturstoffen bei der Wirkstoffentwicklung 1 1.2. Biologie der Pilze 2 1.3. Klassifizierung der Pilze 3 1.4. Endophytische Pilze 6 1.5. Naturstoffe aus Pilzen 8 1.6. Aufgabenstellung und Zielsetzung dieser Arbeit 20 2. Material und Methoden 21 2.1. Biologisches Material 21 2.1.1. Sammlung des endophytischen Wirtes 21 2.1.2. Isolierung der endophytischen Pilze aus den Wirtspflanzen 21 2.1.3. Identifizierung der isolierten Pilzstämme 23 2.1.4. Beschreibung der bearbeiteten Endophyten 24 2.1.4.1. Stamm SL-5: Pleurophoma cava (Schulzer) Boerema, Loer. & Hamers (1996) 24 2.1.4.2. Stamm HN-B2: Penicillium chrysogenum Thom (1910) 24 2.1.4.3. Stamm BT-3: Botryosphaeria rhodina (Berk. & M. A. Curtis) Arx (1970) 25 2.1.4.4. Stamm NE-8: Neurospora discreta D.D. Perkins & N.B. Raju (1986) 25 2.1.4.5. Stamm MGC-1.3: Fusarium incarnatum (Desm.) Sacc. (1886) 25 2.1.4.6. Stamm MGC-5.1: Neurospora terricola Goch. & Backus (1962) 26 2.1.4.7. Stamm MGC-12.3: Xylaria sp. Hill ex Schrank (1789) 26 2.1.4.8. Stamm BT-III.1: Hypoxylon fragiforme (Pers.) J. Kickx f.(1835) 26 2.1.4.9. Stamm BT-1: Eurotium rubrum W. Bremer (1901) 27 2.2. Kultivierungsmethoden und verwendete Nährmedien 27 2.2.1. Anlage von Flüssigkulturen 27 2.2.2. Anlage von Festkulturen 28 2.2.3. Zusammensetzung der verwendeten Nährmedien 28 2.3. Extraktion der Standkulturen 29 I Inhaltsverzeichnis 2.3.1. Extraktion der Small-Scale-Kulturen 29 2.3.2. Extraktion der Large-Scale-Kulturen 30 2.4. Isolierung biologisch aktiver Verbindungen aus endophytischen Pilzen 31 2.5. Strukturaufklärung der biologisch aktiven Verbindungen 31 2.6. Primärscreening zur Ermittlung biologisch bzw. chemisch interessanter Extrakte 32 2.7. Biologische Charakterisierung der isolierten Reinsubstanze 32 2.8. Beschreibung der Tests auf biologische Aktivität 33 2.8.1. Antibiotische und fungizide Aktivität 33 2.8.1.1. Zusammensetzung der verwendeten Nährmedien 34 2.8.2. Zytotoxizität 36 2.8.3. Proteinkinase Assays 37 2.9. Allgemein verwendete Analysen- und Meßmethoden 38 2.9.1. Chromatographische Methoden 38 2.9.1.1. Dünnschichtchromatographie (DC) 38 2.9.1.2. Säulenchromatographie (SC) 38 2.9.1.3. Hochleistungsflüssigchromatographie (HPLC = high performance liquid chromatography) 39 2.9.2. UV-Vis-Spektroskopie 43 2.9.3. Massenspektrometrie (MS) 43 2.9.4. Kernresonanzspektroskopie (NMR - Nuclear Magnetic Resonance) 44 2.9.5. Optische Drehung 45 2.10. Allgemein verwendete Geräte und Chemikalien 46 2.10.1. Geräte 46 2.10.2. Chemikalien 47 3. Ergebnisse 48 3.1. Inhaltsstoffe aus Pleurophoma cava (SL-5) 48 3.1.1. Aposphaerin A 49 II Inhaltsverzeichnis 3.2. Inhaltsstoffe aus Penicillium chrysogenum (HN-B2) 54 3.2.1. Terrestrinsäure 55 3.2.2. Viridicatol 61 3.2.3. Viridicatin 64 3.2.4. Roquefortin 67 3.3. Inhaltsstoffe aus Botryosphaeria rhodina (BT-3) 71 3.3.1. Griseofulvin 73 3.3.2. Dechlorgriseofulvin 76 3.3.3. Cycloaspeptid A 79 3.3.4. Sclerotigenin 83 3.4. Inhaltsstoffe aus Neurospora discreta (NE-8) 88 3.4.1. Kojisäure 89 3.5. Inhaltsstoffe aus Fusarium incarnatum (MGC-1.3) 92 3.5.1. Fusapyron 93 3.5.2. Desoxyfusapyron 97 3.5.3. Equisetin 100 3.6. Inhaltsstoffe aus Neurospora terricola (MGC-5.1) 103 3.6.1. Diaportinol 104 3.6.2. Diaportinsäure 107 3.6.3. 8-Hydroxy-3-(2,4-dihydroxypentyl)-6-methoxyisochromen-1-on (neuer Naturstoff) 109 3.7. Inhaltsstoffe aus Xylaria sp. (MGC-12.3) 115 3.7.1. (E)- Methyl 3-(4-methoxyphenoxy)-propenoat 116 3.7.2. Cytochalasin E 120 3.7.3. 5-Carboxymellein 124 3.7.4. 1,3-Dihydro-4-hydroxy-1-(1-hydroxyethyl)-3-oxoisobenzofuran-5-carbonsäure (neuer Naturstoff) 127 3.8. Inhaltsstoffe aus Hypoxylon fragiforme (BT-III.1) 132 3.8.1. Orsellinsäure 133 3.8.2. 3-Ethyl-7-methoxy-1,3-dihydro-2-benzofuran-1-on (neuer Naturstoff) 136 III Inhaltsverzeichnis 3.8.3. Scytalon 141 3.8.4. 4-Hydroxyscytalon 146 3.8.5. RF-3192-C 149 3.8.6. (+)-Mitorubrinsäure 152 3.8.7. (-)-Mitorubrinol 157 3.8.8. Cytochalasin H 160 3.9. Inhaltsstoffe aus Eurotium rubrum (BT-1) 164 3.9.1. Cochliodinol 165 3.9.2. Chaetomin 169 3.10. Untersuchung auf Biologische Aktivitäten der aus Endophytischen Pilze erhaltenen Inhaltsstoffe 173 3.10.1. Biologische Aktivität der Inhaltsstoffe aus Pleurophoma cava (SL-5) 173 3.10.2. Biologische Aktivität der Inhaltsstoffe aus Penicillium chrysogenum (HN-B2) 173 3.10.3. Biologische Aktivität der Inhaltsstoffe aus Botryosphaeria rhodina (BT-3) 174 3.10.4. Biologische Aktivität der Inhaltsstoffe aus Neurospora discreta (NE-8) 175 3.10.5. Biologische Aktivität der Inhaltsstoffe aus Fusarium incarnatum (MGC-1.3) 175 3.10.6. Biologische Aktivität der Inhaltsstoffe aus Neurospora terricola (MGC-5.1) 176 3.10.7. Biologische Aktivität der Inhaltsstoffe aus Xylaria sp. (MGC-12.3) 177 3.10.8. Biologische Aktivität der Inhaltsstoffe aus Hypoxylon fragiforme (BT-III.1) 178 3.10.9. Biologische Aktivität der Inhaltsstoffe aus Eurotium rubrum (BT-1) 179 4. Diskussion 183 4.1. Der Pilz Pleurophoma cava (SL-5) und seine Naturstoffe 185 4.2. Der Pilz Penicillium chrysogenum (HN-B2) und seine Naturstoffe 186 4.3. Der Pilz Botryosphaeria rhodina (BT-3) und seine Naturstoffe 190 4.4. Der Pilz Neurospora discreta (NE-8) und seine Naturstoffe 192 4.5. Der Pilz Fusarium incarnatum (MGC-1.3) und seine Naturstoffe 194 4.6. Der Pilz Neurospora terricola (MGC-5.1) und seine Naturstoffe 198 4.7. Die Xylariaceae spp. und ihre Naturstoffe 199 IV Inhaltsverzeichnis 4.7.1. Der Pilz Xylaria sp. (MGC-12.3) und seine Naturstoffe 200 4.7.2. Der Pilz Hypoxylon fragiforme (BT-III.1) und seine Naturstoffe 206 4.8. Der Pilz Eurotium rubrum (BT-1) und seine Naturstoffe 209 5. Zusammenfassung 213 6. Literaturverzeichnis 219 7. Abkürzungen 243 8. Anhang 246 9. Danksagung 254 10. Curriculum Vitae 256 11. Erklärung 257 V Einleitung 1. Einleitung 1.1. Die Rolle von Naturstoffen bei der Wirkstoffentwicklung Die zunehmende Entwicklung von Resistenzen bei humanpathogenen Bakterien gegen bereits angewandte Wirkstoffe, das Wiederaufleben und die weitere Ausbreitung bereits ausgerottet geglaubter Krankheiten, die Resistenzbildung bei Schädlingen gegenüber Pestiziden, dies alles nicht zuletzt auch durch das kontinuierliche Wachstum der Weltbevölkerung und die zunehmende Schädigung der Umwelt verursacht, lassen die große Notwendigkeit der Entwicklung neuer Wirkstoffe und Methoden zur Bekämpfung von Krankheiten und Schädlingen erkennen (Strobel, 2002; Vieira et al., 2001). Seit Jahrhunderten werden Naturstoffe, vor allem pflanzlicher Herkunft, erfolgreich zur Behandlung von Krankheiten eingesetzt. Und bis in die heutige Zeit sind sowohl Naturstoffe aus Pflanzen, aus Mikroorganismen, marinen Organismen, Insekten sowie aus Tieren aus unserem gegenwärtigen Arzneimittelrepertoire sowie bei der Entwicklung neuer Arzneistoffe nicht wegzudenken (Scheuer, 1978; Natori et al., 1981). Bisher wurden schon mehr als 100.000 Sekundärstoffe mit einem Molekulargewicht von unter 2.500 Dalton (im englischen Sprachgebrauch auch als „small molecules“ bezeichnet) isoliert und identifiziert, zumeist aus Pflanzen und Mikroorganismen. Davon wurden ca. 50.000 von Mikroorganismen produziert, und von den 12.000 Antibiotika, die bis 1995 entdeckt wurden, stammen 22% aus filamentösen Pilzen. Die Biodiversität von Mikroorganismen ist enorm, und nur ein geringer Teil davon wurde bisher überhaupt auf Sekundärmetabolite untersucht. Im Bereich der Pilze geht man davon aus, dass bislang lediglich 5% der Artenvielfalt entdeckt sowie beschrieben wurde, wovon wiederum maximal 16% chemischen Studien unterzogen wurden (Demain, 1999; Pearce, 1997). In den letzten Jahren ist ein erneutes Interesse am Entdecken von biologisch aktiven Verbindungen ausgehend von natürlichen Quellen zu beobachten, unabhängig von den beeindruckenden Fortschritten neuer konkurrierender Methoden wie der kombinatorischen Chemie, „high throughput screening“ (vollautomatischen Screening- und Analysemethoden) oder der Gentechnik. Es ist somit unbestritten, dass naturstoff-basierte Wirkstoffe einen signifikanten Beitrag zu modernen Therapiemethoden leisten. Beispielsweise basieren ca. 40% der verschriebenen Medikamente auf diesen Naturstoffen. Darüber hinaus waren über 1 Einleitung 50%
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  • Diversity and Enzyme Activity of Fungal Species Associated with Macroalgae, Agarum Clathratum
    저작자표시-비영리-변경금지 2.0 대한민국 이용자는 아래의 조건을 따르는 경우에 한하여 자유롭게 l 이 저작물을 복제, 배포, 전송, 전시, 공연 및 방송할 수 있습니다. 다음과 같은 조건을 따라야 합니다: 저작자표시. 귀하는 원저작자를 표시하여야 합니다. 비영리. 귀하는 이 저작물을 영리 목적으로 이용할 수 없습니다. 변경금지. 귀하는 이 저작물을 개작, 변형 또는 가공할 수 없습니다. l 귀하는, 이 저작물의 재이용이나 배포의 경우, 이 저작물에 적용된 이용허락조건 을 명확하게 나타내어야 합니다. l 저작권자로부터 별도의 허가를 받으면 이러한 조건들은 적용되지 않습니다. 저작권법에 따른 이용자의 권리는 위의 내용에 의하여 영향을 받지 않습니다. 이것은 이용허락규약(Legal Code)을 이해하기 쉽게 요약한 것입니다. Disclaimer 이학석사 학위논문 Diversity and enzyme activity of fungal species associated with macroalgae, Agarum clathratum . 구멍쇠 미역(Agarum clathratum) 에서 분리한 진균의 다양성과 효소활성 2017년 8월 서울대학교 대학원 생명과학부 이 서 빈 Diversity and enzyme activity of fungal species associated with macroalgae, Agarum clathratum Seobihn Lee Advisor: Professor Young Woon Lim, Ph.D. A thesis submitted in partial satisfaction of the Requirements for the degree Master of Science in Biological Sciences August 2017 Graduate School of Biological Sciences Seoul National University Diversity and enzyme activity of fungal species associated with macroalgae, Agarum clathratum Seobihn Lee Graduate School of Biological Science Seoul National University Abstract Agarum clathratum is one of brown macroalgae species. Recently, it has risen as a serious environmental issue being accumulated on coast in Korea. In order to discover fungal candidates to solve this problem, fungal diversity associated with A. clathratum in decay was investigated and their enzyme activities were confirmed; alginase, β-glucosidase and endoglucanase which participated in degrading alginate and cellulose of A.
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