A highly diverse spectrum of naphthoquinone derivatives produced by the endophytic fungus Biatriospora sp. CCF 4378

Abstract

A strain of Biatriospora sp. CCF 4378 was tested for the production of secondary metabolites under submerged fermentation conditions. Eleven compounds were isolated from the culture broth, and the structures of these compounds were determined using HRMS, NMR and X-ray analysis. In addition to six known naphthoquinone derivatives, i.e. ascomycone A, ascomycone B, 6-deoxyfusarubine, 6-deoxyanhydrofusarubine, herbarine and balticol A, one derivative of 2-azaanthraquinone, 6-deoxybostrycoidine, was also identified. Four new natural pyranonaphthoquinones were found, and these natural products were pleorubrin A, pleorubrin B, pleorubrin C and pleorubrin D. The toxicity on human cell lines of the crude naphthoquinone fraction and pure 6-deoxybostrycoidin, ascomycone B, pleorubrin B and 6-deoxyfusarubin was tested. Ascomycone B and 6-deoxyfusarubin elicited rapid cytotoxicity at micromolar concentrations.

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Abbreviations

DMSO:

Dimethyl sulfoxide

ESI:

Electrospray Ionisation

HMBC:

Heteronuclear multiple-bond correlation

HPLC:

High-performance liquid chromatography

HRMS:

High-resolution mass spectrometry

ITS:

Internal transcribed spacer

LDI:

Laser desorption/ionisation

LSU rDNA:

Large-subunit ribosomal DNA

NMR:

Nuclear magnetic resonance

PBS:

Phosphate-buffered saline

SSU rDNA:

Small-subunit ribosomal DNA

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Acknowledgments

This work was supported by the LD-COST CZ project LD13039, Czech Science Foundation project No. 13-16565S, Long-Term Research Plans of the Ministry of Education, Youth and Sports of the Czech Republic No. MSM0021620858, and Charles University projects UNCE 204013/2012. Access to instrumental and other facilities was also supported by the EU (Operational Program Prague–Competitiveness project CZ.2.16/3.1.00/24023) and by the IMIC institutional research concept RVO61388971.

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Correspondence to Miroslav Flieger.

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Stodůlková, E., Man, P., Kuzma, M. et al. A highly diverse spectrum of naphthoquinone derivatives produced by the endophytic fungus Biatriospora sp. CCF 4378. Folia Microbiol 60, 259–267 (2015). https://doi.org/10.1007/s12223-014-0366-7

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Keywords

  • Endophytic Fungus
  • HMBC Correlation
  • Naphthoquinone Derivative
  • Submerged Fermentation Condition
  • Ulmus Laevis