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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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Article information


Submitted
30 Jan 2006
Accepted
20 Mar 2006
First published
03 May 2006

Org. Biomol. Chem., 2006,4, 2233-2240
Article type
Paper

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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