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Botanica Marina

Editor-in-Chief: Dring, Matthew


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1437-4323
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Sponge-associated fungi and their bioactive compounds: the Suberites case

Peter Proksch1 / Rainer Ebel2 / RuAngelie Edrada3 / Frank Riebe4 / Hongbing Liu5 / Arnulf Diesel6 / Mirko Bayer7 / Xiang Li8 / Wen Han Lin9 / Vladislav Grebenyuk10 / Werner E.G. Müller11 / Siegfried Draeger12 / Alga Zuccaro13 / Barbara Schulz14

1Institut für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, Geb. 26.23, 40225 Düsseldorf, Germany

Present address: Department of Chemistry, University of Aberdeen, Meston Building, Meston Walk, Old Aberdeen, AB24 3UE Scotland, UK.
2Institut für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, Geb. 26.23, 40225 Düsseldorf, Germany

3Institut für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, Geb. 26.23, 40225 Düsseldorf, Germany

4Institut für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, Geb. 26.23, 40225 Düsseldorf, Germany

5Institut für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, Geb. 26.23, 40225 Düsseldorf, Germany

6Institut für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, Geb. 26.23, 40225 Düsseldorf, Germany

7Institut für Pharmazeutische Biologie und Biotechnologie, Heinrich-Heine-Universität Düsseldorf, Universitätsstr. 1, Geb. 26.23, 40225 Düsseldorf, Germany

8National Research Laboratory of Natural and Biomimetic Drugs, Peking University, 100083 Beijing, P.R. China

9National Research Laboratory of Natural and Biomimetic Drugs, Peking University, 100083 Beijing, P.R. China

10Institut für Physiologische Chemie und Pathobiochemie, Johannes-Gutenberg-Universität, Duesbergweg 6, 55128 Mainz, Germany

11Institut für Physiologische Chemie und Pathobiochemie, Johannes-Gutenberg-Universität, Duesbergweg 6, 55128 Mainz, Germany

12Institut für Mikrobiologie, Technische Universität Carolo-Wilhelmina zu Braunschweig, Spielmannstraße 7, 38106 Braunschweig, Germany

13Institut für Mikrobiologie, Technische Universität Carolo-Wilhelmina zu Braunschweig, Spielmannstraße 7, 38106 Braunschweig, Germany

14Institut für Mikrobiologie, Technische Universität Carolo-Wilhelmina zu Braunschweig, Spielmannstraße 7, 38106 Braunschweig, Germany

Corresponding author

Citation Information: Botanica Marina. Volume 51, Issue 3, Pages 209–218, ISSN (Online) 1437-4323, ISSN (Print) 0006-8055, DOI: https://doi.org/10.1515/BOT.2008.014, March 2008

Publication History

Received:
2007-06-19
Accepted:
2008-01-21
Published Online:
2008-03-07

Abstract

Specimens of Suberites domuncula that had been cultured in aquaria for 4 weeks were analyzed for their associated fungi. A total of 81 fungal strains belonging to 20 different genera was isolated and identified by morphological and molecular methods. The most frequently isolated taxa were Cladosporium spp., Penicillium spp., Petriella sp., Phialophora spp. and Engyodontium album. Based on chromatographic and mass spectrometric analysis of fungal extracts, as well as on bioassay results, Aspergillus ustus, Penicillium sp., Petriella sp. and Scopulariopsis sp. were selected for in-depth analysis of their natural products. A total of 19 different fungal metabolites, including three new natural products, was isolated and structurally identified. A. ustus yielded two sesquiterpenes, a drimane derivative and deoxyuvidin, as well as a sesterterpene ophiobolin H. The drimane derivative had an ED50 value against L5178Y cells of 1.9 μg ml-1 in vitro. The crude extract of Petriella sp. was also strongly cytotoxic against the L5178Y cell line. The cyclic tetrapeptide WF-3161 was primarily responsible for the activity; the ED50 value was <0.1 μg ml-1. It was identical to the known compound WF-3161 and had been previously isolated from Petriella guttulata. In addition to WF-3161, three further natural products were obtained and unequivocally identified as new derivatives of infectopyrone by one- and two-dimensional NMR spectroscopy and by mass spectroscopy. Of the new compounds, only dihydroinfectopyrone was active against L5178Y cells; the ED50 value was 0.2 μg ml-1. Penicillium sp. yielded the largest number of metabolites. Viridicatin, viridicatol, cyclopenin and cyclopenol suppressed larval growth of the polyphagous pest insect Spodoptera littoralis when incorporated into an artificial diet at an arbitrarily chosen concentration of 237 ppm. Viridicatol was the most active compound and had an ED50 value of ca. 50 ppm. Scopulariopsis sp. yielded three metabolites, including the known acetylcholinesterase inhibitors quinolactacin A1 and A2.

Keywords: marine natural products; sponge-associated fungal metabolites; Suberites domuncula

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