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

Simon F. Seibert; Ekaterina Eguereva; Anja Krick; Stefan Kehraus; Elena Voloshina; Gerhard Raabe; Jörg Fleischhauer; Eckhard Leistner; Michael Wiese; Heino Prinz; Kirill Alexandrov; Petra Janning; Herbert Waldmann; Gabriele M. König

doi:10.1039/B601386D

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 Waldmann^d and Gabriele M. König*^a

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^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

Organic & Biomolecular Chemistry

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

Abstract

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

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