Dokument: Biodiversity of marine-derived fungi and identification of their metabolites
| Titel: | Biodiversity of marine-derived fungi and identification of their metabolites | |||||||
| Weiterer Titel: | Biodiversität von Pilzen mariner Herkunft und Identifizierung ihrer Sekundärstoffe | |||||||
| URL für Lesezeichen: | https://docserv.uni-duesseldorf.de/servlets/DocumentServlet?id=7333 | |||||||
| URN (NBN): | urn:nbn:de:hbz:061-20080331-102412-5 | |||||||
| Kollektion: | Dissertationen | |||||||
| Sprache: | Englisch | |||||||
| Dokumententyp: | Wissenschaftliche Abschlussarbeiten » Dissertation | |||||||
| Medientyp: | Text | |||||||
| Autor: | Indriani, Ine Dewi [Autor] | |||||||
| Dateien: |
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| Beitragende: | Prof. Dr. Proksch Peter [Betreuer/Doktorvater] Prof. Dr. Ebel, Rainer [Gutachter] | |||||||
| Stichwörter: | Fungus, marine, secondary metabolites, molecular biology | |||||||
| Dewey Dezimal-Klassifikation: | 500 Naturwissenschaften und Mathematik » 570 Biowissenschaften; Biologie | |||||||
| Beschreibungen: | Insgesamt wurden 31 Verbindungen aus Pilzen isoliert, die aus 12 verschiedenen marinen Organismen stammen, darunter Vertreter unterschiedlicher Substanzklassen wie Alkaloide, Polyketide und Terpene. Eine Verbindung, ein Pyranacetal, erwies sich dabei als neuer Naturstoff. Die Strukturen der Verbindungen wurden durch massenspektrometrische Verfahren sowie ein- und zweidimensionale NMR-Spektroskopie aufgeklärt.
1. Pilze aus der Klasse Eurotiomycetes Sechs stickstoffhaltige Verbindungen wurden aus Penicillium polonicum, isoliert aus dem marinen Schwamm Tethya sp., erhalten. Fünf davon, Cyclopenin, Cyclopenol, Viridicatol, Viridicatin sowie 3-Methylviridicatin waren biogenetisch verwandt. Meleagrin, Roquefortin, Citrinin, Citrininhydrat und die Diastereomere Quinolactacin A1 und A2 wurden aus Penicillium citrinum erhalten, welcher aus der marinen Alge Sargassum sp. isoliert wurde. Meleagrin, Roquefortin und Citrininhydrat zeigten eine beachtliche zytotoxische Wirkung gegen die murine Lymphomazelllinie L5178Y, wohingegen Citrinin nicht aktiv war. Das Anthrachinon Skyrin und die Preanthrachinone Atrovirin B1 und B2 wurden aus einem Extrakt des aus dem Schwamm Aplysina aerophoba isolierten Talaromyces wortmanii erhalten. Zwei bekannte Verbindungen, Tenuazonsäure und Alternariol, wurden aus dem Pilz Alternaria compacta erhalten, der aus dem marinen Schwamm Suberites domuncula isoliert wurde. 2. Pilze aus der Klasse Sordariomycetes Drei verwandte Alkaloide, Chaetomin, Cochliodinol und Semicochliodinol wurden vom aus dem marinen Schwamm Tethya sp. isolierten Pilz Chaetomium sp. erhalten. Alle zeigten starke zytotoxische Aktivität gegenüber L5178Y-Zellen und zeigten inhibitorische Aktivität gegenüber Proteinkinasen. Ein neues, mit der Familie der Cholesterolsynthesehemmstoffe Agistatine verwandtes Pyranacetal wurde vom Pilz Xylaria sp. erhalten, der aus der marinen Alge Padina australis isoliert wurde. Diese Verbindung wurde 3-Methyl-methoxyagistatin D genannt, basierend auf der Methylmethoxygruppe in Position C-3. Daldinia escholzii aus der marinen Alge Halimeda berneoensis produzierte die bekannte Verbindung 4,4’,5,5’-tetrahydroxy-1,1’-binaphthyl. Diese Verbindung zeigte eine beträchtliche zytotoxische Aktivität gegenüber L5178Y-Zellen und erwies darüber hinaus als Inhibitor von Proteinkinasen auf; beide Eigenschaften wurden bisher noch nicht in der Literatur beschrieben. Das Makrolid Zearalenon wurde von dem aus Sargassum sp. isolierten Pilz Fusarium equiseti erhalten. Indol-3-carbonsäure und das Diterpen Myrocin A wurden aus Arthrinium sp. gewonnen, der aus Tethya sp. isoliert wurde. Myrocin A bewies zytotoxische Wirkung und Aktivität als Inhibitor von Proteinkinasen. Die chemotaxonomische Markersubstanz 5-Carboxymellein wurde aus dem Pilzstamm PV 1.1 erhalten. Aufgrund dieser chemischen Befunde ist anzunehmen, dass dieser Pilz aus der Familie der Xylariaceae stammt. 3. Pilze aus der Klasse Dothideomycetes Die antimykotische Verbindung Griseofulvin wurde vom aus dem marinen Schwamm Suberites domuncula isolierten Pilz Botryosphaeria stevensii erhalten; damit erwies sich dieser Pilz als einer der wenigen bekannten Griseofulvin-Produzenten außerhalb der Gattung Penicillium. Der aus dem marinen Schwamm Petrosia ficiformis isolierte Pilz Paraphaeosphaera michotii produzierte die Substanzen Cyclopenin, Cyclopenol, Viridicatol, Viridicatin und 3,4,8-Trihydroxy-1-tetralon. Die Bestimmung der Diversität der Pilze in marinen Organismen wurde mithilfe der Polymerasekettenreaktion (PCR) unter Verwendung von Primern, die auf konservierte, taxonomisch signifikante Gene gerichtet waren, durchgeführt, gefolgt von denaturierender Gradientengelelektrophorese (DGGE). Das universelle Pilzprimerpaar ITS1 und ITS4 erzeugte DNA-Amplifikate, die sich per DGGE trennen ließen und eine Identifizierung der zugrunde liegenden Pilzstämme auf breiter Basis erlaubten. Es konnte gezeigt werden, dass die DGGE unter Verwendung dieses Primerpaares eine zuverlässige und aussagekräftige Methode zur Erfassung der Diversität von Pilzen in komplexen biologischen Proben darstellt, insbesondere, was Mangrovenpflanzen betrifft. Pilz-Sequenzen konnten aus den DGGE-Experimenten mit Mangrovenpflanzen erhalten werden, wobei zweifelsfrei nachgewiesen wurde, dass eine Bande jeweils auf einen Pilzstamm zurückzuführen ist. Zwei Banden mit vergleichbarer Laufstrecke in Proben der Rinde und Blätter von Avicennia marina wurden sequenziert und mittels BLAST-Suche jeweils dem Pilz Alternaria sp. zugeordnet. Eine weitere, aus den Blättern von Avicennia marina stammende Bande wurde nach Sequenzierung als Fusarium sp. identifiziert. Im Rahmen dieser Arbeit wurde erstmalig der erfolgreiche Nachweis von Pilz-DNA im Gesamt-DNA-Extrakt von marinen Schwämmen auf der Basis von PCR und DGGE geführt. Dabei zeigte sich, dass neben den Banden, welche Pilze repräsentieren, auch solche auftraten, die auf DNA des Schwammes zurückgehen. Allerdings ließen sich Banden von Schwamm-DNA von denen der Pilze durch ihre unterschiedlichen Laufstrecken in den DGGE-Gelen sicher unterscheiden. Anhand der Sequenzen aller im Rahmen dieser Arbeit untersuchten Pilzstämme, die auf Amplifikation mit dem Primerpaar ITS1 und ITS4 zurückgehen, wurde eine phylogenetische Analyse durchgeführt. Der aus diesen Sequenzen konstruierte phylogenetische Baum wurde mithilfe bioinformatischer Methoden validiert, und es konnte gezeigt werden, dass er die Evolutionsgeschichte und Verwandtschaft innerhalb des Reichs der Pilze bis herunter zur Gattungsebene wider gibt.A total number of 31 compounds was isolated comprising diverse structural groups including alkaloids, polyketides and terpenes, from 12 marine organism-derived fungi; one of which was a new pyranacetal derivative. The structures of the compounds were elucidated by performing mass spectrometry as well as one- and two-dimensional nuclear magnetic resonance (NMR) experiments. 1. Fungi from class Eurotiomycetes Six nitrogen containing compounds were isolated from Penicillium polonicum derived from the marine sponge Tethya sp. Five of which, cyclopenin, cyclopenol, viridicatol, viridicatin and 3-methyl viridicatin, were biogenetically related. Meleagrin, roquefortine, citrinin, citrinin hydrate and the diastereomers quinolactacin A1 and A2 were isolated from Penicillium citrinum derived from the marine alga Sargassum sp. Meleagrine, roquefortine and citrinin hydrate showed relatively high cytotoxic activity against the mouse lymphoma cell line L5178Y, whereas citrinin was inactive. The anthraquinone skyrin and the preanthraquinones atrovirin B1 and atrovirin B2 were obtained from the extract of Talaromyces wortmanii derived from the marine sponge Aplysina aerophoba. Two known compounds, tenuazonic acid and alternariol, were isolated from Alternaria compacta derived from the marine sponge Suberites domuncula. 2. Fungi from class Sordariomycetes Three related alkoloids, chaetomin, cochliodinol and semicochliodinol, were isolated from Chaetomium sp. derived from the marine sponge Tethya sp. All of them showed high cytotoxic activity against L5178Y cells and also displayed protein kinase inhibitory activity. One new pyranacetal related to the family of cholesterol synthesis inhibitors agistatines was isolated from Xylaria sp. derived from the marine algaa Padina australis. This compound was named 3-methyl methoxy agistatine D based on the methyl methoxy moiety at position C-3. Daldinia escholzii derived from the marine alga Halimeda borneoensis was found to produce the known compound 4,4’,5,5’-tetrahydroxy-1,1’-binaphthyl. This compound showed very high cytotoxic activity against L5178Y cells and also had protein kinase inhibitory activity, both of which had not been reported before. The macrolide zearalenone was isolated from the fungus Fusarium equiseti derived from the alga Sargassum sp. Indole-3-carboxylic acid and the diterpene myrocin A were obtained from Arthrinium sp. derived from Tethya sp. Myrocin A had cytotoxic activity and protein kinase inhibitory activity. A chemotaxonomic marker compound, 5-carboxymellein, was isolated from the fungus PV 1.1. Based on the results of the chemical analysis, it can be assumed that PV1.1 was a fungus that belonged to the family Xylariaceae. 3. Fungi from class Dothideomycetes The antifungal compound griseofulvin was isolated from Botryosphaeria stevensii derived from the marine sponge Suberites domuncula and made this fungus one of the few griseofulvin producers outside the genus Penicillium. The fungus Paraphaeosphaera michotii derived from the marine sponge Petrosia ficiformis was found to produce cyclopenin, cyclopenol, viridicatol, viridicatin and 3,4,8-trihydroxy-1-tetralone. Fungal diversity in marine organisms was assessed by performing polymerase chain reaction (PCR) using primers that target conserved, taxonomically significant genes, coupled with denaturing gradient gel electroforesis (DGGE). The universal fungal primer pair ITS 1 and ITS 4 generated fungal DNA products which were suitable for DGGE analysis allowing broad-based molecular identification. DGGE using this primer pair was proven a trustworthy and reliable tool for determining fungal diversity in complex biological samples, most notably mangrove plants. Fungal sequences could be recovered from the DGGE experiment involving mangrove plants, clearly demonstrating the each band represented one fungal strain. Two bands with similar migration distance in a bark sample of Avicennia marina and a leaf sample of the same plant were sequenced, and upon BLAST search were revealed to belong to the same fungus, Alternaria sp. Another band was recovered from a DGGE experiment of a leaf sample of Avicennia marina, and after sequencing, it was identified as Fusarium sp. Detection of fungal DNA in the total DNA extract of marine sponge was carried out for the first time by employing PCR and DGGE techniques. The results showed that in this case there were also other bands representing sponge DNA sequences, besides bands representing fungal DNA. However, sponge-derived bands and fungi-derived bands can be distinguished in the DGGE gel based on their migration distances. A phylogenetic analysis was performed using the DNA sequences of all fungal strains under investigation, amplified by the primer pair ITS 1 and ITS 4. The phylogenetic tree hence constructed was validated by bioinformatical methods and was shown to represent the evolutionary history and relationship within the kingdom fungi down to the genus level. | |||||||
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| Lizenz: |  Urheberrechtsschutz | |||||||
| Bezug: | 11/2003 - 12/2007 | |||||||
| Fachbereich / Einrichtung: | Mathematisch- Naturwissenschaftliche Fakultät » WE Pharmazie » Pharmazeutische Biologie und Biotechnologie | |||||||
| Dokument erstellt am: | 26.03.2008 | |||||||
| Dateien geändert am: | 26.03.2008 | |||||||
| Promotionsantrag am: | 30.10.2007 | |||||||
| Datum der Promotion: | 11.12.2007 |
