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Biomolecules 2019, 9(2), 73;

The Effect of Cytochalasans on the Actin Cytoskeleton of Eukaryotic Cells and Preliminary Structure–Activity Relationships

Department of Microbial Drugs, Helmholtz Centre for Infection Research (HZI), Inhoffenstrasse 7, 38124 Braunschweig, Germany
University of Applied Sciences Albstadt-Sigmaringen, Faculty of Life Sciences, Anton-Günther-Strasse 51, 72488 Sigmaringen, Germany
National Centre for Genetic Engineering and Biotechnology (BIOTEC), NSTDA, 113 Thailand Science Park, Phahonyothin Road, Klong Nueng Klong Luang, Pathum Thani 12120, Thailand
Department of Chemistry, Faculty of Science, Aswan University, 81528 Aswan, Egypt
Department of Microbiology-Biochemistry, Faculty of Natural and Life Sciences, University of Batna 2, Batna 05000, Algeria
Department of Cell Biology, Helmholtz Centre for Infection Research (HZI), Inhoffenstraße 7, 38124 Braunschweig, Germany
Authors to whom correspondence should be addressed.
Received: 21 January 2019 / Revised: 14 February 2019 / Accepted: 14 February 2019 / Published: 19 February 2019
(This article belongs to the Special Issue Biology, Biotechnology and Bioprospecting of Microbial Biomolecules)
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In our ongoing search for new bioactive fungal metabolites, two new cytochalasans were isolated from stromata of the hypoxylaceous ascomycete Hypoxylon fragiforme. Their structures were elucidated via high-resolution mass spectrometry (HR-MS) and nuclear magnetic resonance (NMR) spectroscopy. Together with 23 additional cytochalasans isolated from ascomata and mycelial cultures of different Ascomycota, they were tested on their ability to disrupt the actin cytoskeleton of mammal cells in a preliminary structure–activity relationship study. Out of all structural features, the presence of hydroxyl group at the C7 and C18 residues, as well as their stereochemistry, were determined as important factors affecting the potential to disrupt the actin cytoskeleton. Moreover, reversibility of the actin disrupting effects was tested, revealing no direct correlations between potency and reversibility in the tested compound group. Since the diverse bioactivity of cytochalasans is interesting for various applications in eukaryotes, the exact effect on eukaryotic cells will need to be determined, e.g., by follow-up studies involving medicinal chemistry and by inclusion of additional natural cytochalasans. The results are also discussed in relation to previous studies in the literature, including a recent report on the anti-Biofilm activities of essentially the same panel of compounds against the pathogenic bacterium, Staphylococcus aureus. View Full-Text
Keywords: actin cytoskeleton; Ascomycota; chromatography; secondary metabolites; structure elucidation; Xylariales actin cytoskeleton; Ascomycota; chromatography; secondary metabolites; structure elucidation; Xylariales

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Kretz, R.; Wendt, L.; Wongkanoun, S.; Luangsa-ard, J.J.; Surup, F.; Helaly, S.E.; Noumeur, S.R.; Stadler, M.; Stradal, T.E. The Effect of Cytochalasans on the Actin Cytoskeleton of Eukaryotic Cells and Preliminary Structure–Activity Relationships. Biomolecules 2019, 9, 73.

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