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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

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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 GCMS 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 (16) 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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