Brief Communication | Published:

Dentigerumycin: a bacterial mediator of an ant-fungus symbiosis

Nature Chemical Biology volume 5, pages 391393 (2009) | Download Citation

Subjects

Abstract

Fungus-growing ants engage in mutualistic associations with both the fungus they cultivate for food and actinobacteria (Pseudonocardia spp.) that produce selective antibiotics to defend that fungus from specialized fungal parasites. We have analyzed one such system at the molecular level and found that the bacterium associated with the ant Apterostigma dentigerum produces dentigerumycin, a cyclic depsipeptide with highly modified amino acids, to selectively inhibit the associated parasitic fungus (Escovopsis sp.).

  • Compound

    Dentigerumycin

  • Compound

    N-alpha-(2,4-Dinitro-5-fluorophenyl)leucineamide

  • Compound

    N-alpha-(2,4-Dinitro-6-fluorophenyl)leucineamide

  • Compound

    S-Piperazic acid

  • Compound

    R-Piperazic acid

  • Compound

    7-S-methoxy-trifluoromethylphenylacetyl dentigerumycin ester

  • Compound

    7-R-Methoxy-trifluoromethylphenylacetyl dentigerumycin ester

  • Compound

    15-N-Deoxydentigerumycin

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Acknowledgements

We thank the Smithsonian Tropical Research Institute for providing facilities in which to work in Panama, the Autoridad Nacional del Ambiente y el Mar for sampling and export permits, J. Heemstra and C. Walsh (Harvard Medical School) for providing synthetic piperazic acids, and A. Adams, S. Marsh, A. Pinto-Tomas and G. Suen (University of Wisconsin–Madison) for comments on a manuscript draft. This work was supported by funding from the Lundbeck and Carlsberg Foundations to M.P., from the US National Science Foundation (MCB07020255) to C.R.C. and from the US National Institutes of Health (CA24487) to J.C.

Author information

Author notes

    • Dong-Chan Oh
    •  & Michael Poulsen

    These authors contributed equally to this work.

Affiliations

  1. Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, Boston, Massachusetts, USA.

    • Dong-Chan Oh
    •  & Jon Clardy
  2. Department of Bacteriology, University of Wisconsin-Madison, Madison, Wisconsin, USA.

    • Michael Poulsen
    •  & Cameron R Currie

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Contributions

D.-C.O., M.P., C.R.C. and J.C. designed experiments and wrote the manuscript. D.-C.O. performed the structural determination and biological activity analysis on dentigerumycin. M.P. isolated the cultivar, the parasite and the Pseudonocardia symbionts and performed bioassay parings.

Corresponding authors

Correspondence to Cameron R Currie or Jon Clardy.

Supplementary information

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    Supplementary Text and Figures

    Supplementary Figures 1–8, Supplementary Tables 1 and 2, and Supplementary Methods

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DOI

https://doi.org/10.1038/nchembio.159