Next Article in Journal
Introduction to Peptidyl-Prolyl cis/trans Isomerase (PPIase) Series
Next Article in Special Issue
Cytosporone B as a Biological Preservative: Purification, Fungicidal Activity and Mechanism of Action against Geotrichum citri-aurantii
Previous Article in Journal
Protecting Group-Free Synthesis of Glycopolymer-Type Amphiphilic Macromonomers and Their Use for the Preparation of Carbohydrate-Decorated Polymer Particles
Article Menu
Issue 2 (February) cover image

Export Article

Open AccessArticle
Biomolecules 2019, 9(2), 73; https://doi.org/10.3390/biom9020073

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

1
Department of Microbial Drugs, Helmholtz Centre for Infection Research (HZI), Inhoffenstrasse 7, 38124 Braunschweig, Germany
2
University of Applied Sciences Albstadt-Sigmaringen, Faculty of Life Sciences, Anton-Günther-Strasse 51, 72488 Sigmaringen, Germany
3
National Centre for Genetic Engineering and Biotechnology (BIOTEC), NSTDA, 113 Thailand Science Park, Phahonyothin Road, Klong Nueng Klong Luang, Pathum Thani 12120, Thailand
4
Department of Chemistry, Faculty of Science, Aswan University, 81528 Aswan, Egypt
5
Department of Microbiology-Biochemistry, Faculty of Natural and Life Sciences, University of Batna 2, Batna 05000, Algeria
6
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)
  |  
PDF [2831 KB, uploaded 20 February 2019]
  |  

Abstract

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
Figures

Graphical abstract

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).

Supplementary material

SciFeed

Share & Cite This Article

MDPI and ACS Style

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.

Show more citation formats Show less citations formats

Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Biomolecules EISSN 2218-273X Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top