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Issue 11, 2006
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Polyketides from the marine-derived fungus Ascochyta salicorniae and their potential to inhibit protein phosphatases

Simon F. Seibert,a  Ekaterina Eguereva,a  Anja Krick,a  Stefan Kehraus,a  Elena Voloshina,b  Gerhard Raabe,b  Jörg Fleischhauer,b  Eckhard Leistner,a  Michael Wiese,c  Heino Prinz,d  Kirill Alexandrov,d  Petra Janning,d  Herbert Waldmannd  and  Gabriele M. König*a 
Author affiliations

* Corresponding authors

a Institute for Pharmaceutical Biology, University of Bonn, Nußallee 6, D-53115 Bonn, Germany
E-mail: g.koenig@uni-bonn.de
Fax: +49 228 733250
Tel: +49 228 733747

b Institute for Organic Chemistry, Rheinisch-Westfälische Technische Hochschule Aachen, Landoltweg 1, D-52074 Aachen, Germany

c Pharmaceutical Institute, University of Bonn, An der Immenburg 4, D-53121 Bonn, Germany

d Max Planck Institute of Molecular Physiology, Otto-Hahn-Straße 11, D-44227 Dortmund, Germany

Abstract

Chemical investigation of the marine fungus Ascochyta salicorniae led to the isolation of two new epimeric compounds, ascolactones A (1) and B (2), in addition to the structurally-related polyketides hyalopyrone (3), ascochitine (4), ascochital (5) and ascosalipyrone (6). The absolute configurations of the epimeric compounds 1 and 2 were assigned as (1R,9R) and (1S,9R), respectively, through simulation of the chiroptical properties using quantum-chemical CD calculations, and chiral GC–MS subsequent to oxidative cleavage (Baeyer–Villiger oxidation) of the side chain.

In silico screening using the PASS software identified some of the A. salicorniae compounds (1–6) as potential inhibitors of protein phosphatases. Compound 4 was found to inhibit the enzymatic activity of MPtpB with an IC50 value of 11.5 μM.

Graphical abstract: Polyketides from the marine-derived fungus Ascochyta salicorniae and their potential to inhibit protein phosphatases

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Publication details

The article was received on 30 Jan 2006, accepted on 20 Mar 2006 and first published on 03 May 2006


Article type: Paper
DOI: 10.1039/B601386D
Citation: Org. Biomol. Chem., 2006,4, 2233-2240
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    Polyketides from the marine-derived fungus Ascochyta salicorniae and their potential to inhibit protein phosphatases

    S. F. Seibert, E. Eguereva, A. Krick, S. Kehraus, E. Voloshina, G. Raabe, J. Fleischhauer, E. Leistner, M. Wiese, H. Prinz, K. Alexandrov, P. Janning, H. Waldmann and G. M. König, Org. Biomol. Chem., 2006, 4, 2233
    DOI: 10.1039/B601386D

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