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Hydroxylated anthraquinones produced by Geosmithia species

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Abstract

Geosmithia fungi are little known symbionts of bark beetles. Secondary metabolites of lilac colored species G. lavendula and other nine Geosmithia species were investigated in order to elucidate their possible role in the interactions of the fungi with environment. Hydroxylated anthraquinones (yellow, orange, and red pigments), were found to be the most abundant compounds produced into the medium during the submerged cultivation. Three main compounds were identified as 1,3,6,8-tetrahydroxyanthraquinone (1), rhodolamprometrin (1-acetyl-2,4,5,7-tetrahydroxyanthraquinone; 2), and 1-acetyl-2,4,5,7,8-pentahydroxyanthraquinone (3). Compounds 2 and 3 (representing the majority of produced metabolites) inhibited the growth of G+-bacteria Staphylococcus aureus and Bacillus subtilis with minimum inhibitory concentration of 64–512 μg/mL. Anti-inflammatory activity detected as inhibition of cyclooxygenase-2 was found only for compound 3 at 1 and 10 μg/mL. Compound 2 interfered with the morphology, compound 3 with cell-cycle dynamics of adherent mammalian cell lines.

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Abbreviations

AQ(s):

anthraquinone(s)

COX-1:

cyclooxygenase-1

COX-2:

cyclooxygenase-2

CZD:

Czapek-Dox (medium)

DAPI:

4′,6-diamidino-2-phenylindole

LOD:

limit of detection

LOQ:

limit of quantification

MEA:

malt extract (medium)

MIC(s):

minimal inhibitory concentration(s)

PBS:

phosphate-buffered saline

UPLC:

ultra-performance liquid chromatography

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Authors and Affiliations

  1. Department of Biogenesis and Biotechnology, Institute of Microbiology, Academy of Sciences of the Czech Republic v.v.i., 142 20, Prague 4, Czech Republic

    E. Stodůlková, M. Kolařík, Z. Křesinová, M. Kuzma, M. Šulc, P. Man, P. Novák, J. Olšovská, M. Chudíčková, S. Pažoutová & M. Flieger

  2. Laboratory of Plant Biotechnologies, Joint Laboratory of the Institute of Experimental Botany, Academy of Sciences of the Czech Republic v.v.i., and Research Institute of Crop Production v.v.i., 166 00, Prague 6, Czech Republic

    P. Maršík & P. Landa

  3. Department of Cell Biology, Faculty of Science, Charles University, 128 00, Prague 2, Czech Republic

    J. Černý

  4. School of Chemistry, The University of Edinburgh, Edinburgh, EH9 3JJ, UK

    J. Bella

Authors
  1. E. Stodůlková
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  2. M. Kolařík
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  3. Z. Křesinová
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  4. M. Kuzma
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  5. M. Šulc
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  6. P. Man
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  7. P. Novák
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  8. P. Maršík
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  9. P. Landa
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  10. J. Olšovská
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  11. M. Chudíčková
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  12. S. Pažoutová
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  13. J. Černý
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  14. J. Bella
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  15. M. Flieger
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Correspondence to M. Flieger.

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Stodůlková, E., Kolařík, M., Křesinová, Z. et al. Hydroxylated anthraquinones produced by Geosmithia species. Folia Microbiol 54, 179–187 (2009). https://doi.org/10.1007/s12223-009-0028-3

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  • DOI: https://doi.org/10.1007/s12223-009-0028-3

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