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Dentigerumycin: a bacterial mediator of an ant-fungus symbiosis


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.).

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Figure 1: Symbiotic partners: ant, fungi and bacteria.
Figure 2: Structure and activity of dentigerumycin (1).

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  1. Currie, C.R., Scott, J.A., Summerbell, R.C. & Malloch, D. Nature 398, 701–704 (1999).

    Article  CAS  Google Scholar 

  2. Scott, J.J. et al. Science 322, 63 (2008).

    Article  CAS  Google Scholar 

  3. Bérdy, J. J. Antibiot. (Tokyo) 58, 1–26 (2005).

    Article  Google Scholar 

  4. Kaltenpoth, M., Göttler, W., Herzner, G. & Strohm, E. Curr. Biol. 15, 475–479 (2005).

    Article  CAS  Google Scholar 

  5. Schultz, T.R. & Brady, S.G. Proc. Natl. Acad. Sci. USA 105, 5435–5440 (2008).

    Article  CAS  Google Scholar 

  6. Currie, C.R., Poulsen, M., Mendenhall, J., Boomsma, J.J. & Billen, J. Science 311, 81–83 (2006).

    Article  CAS  Google Scholar 

  7. Reynolds, H.T. & Currie, C.R. Mycologia 96, 955–959 (2004).

    Article  Google Scholar 

  8. Matsumori, N., Kaneno, D., Murata, M., Nakamura, H. & Tachibana, K. J. Org. Chem. 64, 866–876 (1999).

    Article  CAS  Google Scholar 

  9. Miller, E.D., Kauffman, C.A., Jensen, P.R. & Fenical, W. J. Org. Chem. 72, 323–330 (2007).

    Article  CAS  Google Scholar 

  10. Fujii, K. et al. Tetrahedron 58, 6873–6879 (2002).

    Article  CAS  Google Scholar 

  11. Schultz, A.W. et al. J. Am. Chem. Soc. 130, 4507–4516 (2008).

    Article  CAS  Google Scholar 

  12. Fujii, K., Ikai, Y., Oka, H., Suzuki, M. & Harada, K. Anal. Chem. 69, 5146–5151 (1997).

    Article  CAS  Google Scholar 

  13. Seco, J.M., Quiñoá, E. & Riguera, R. Tetrahedron Asymmetry 12, 2915–2925 (2001).

    Article  CAS  Google Scholar 

  14. Pennings, M.L.M., Reinhoudt, D.N., Harkema, S. & van Hummel, G.J. J. Org. Chem. 48, 486–491 (1983).

    Article  CAS  Google Scholar 

  15. Snatzke, G., Wagner, U. & Wolff, H.P. Tetrahedron 37, 349–361 (1981).

    Article  CAS  Google Scholar 

  16. Umezawa, K., Nakazawa, K., Ikeda, Y., Naganawa, H. & Kondo, S. J. Org. Chem. 64, 3034–3038 (1999).

    Article  CAS  Google Scholar 

  17. Gräfe, U. et al. J. Antibiot. (Tokyo) 48, 119–125 (1995).

    Article  Google Scholar 

  18. Fischbach, M.A., Walsh, C.T. & Clardy, J. Proc. Natl. Acad. Sci. USA 105, 4601–4608 (2008).

    Article  CAS  Google Scholar 

  19. Oh, D.-C., Scott, J.J., Currie, C.R. & Clardy, J. Org. Lett. 11, 633–636 (2009).

    Article  CAS  Google Scholar 

  20. Currie, C.R. et al. Science 299, 386–388 (2003).

    Article  CAS  Google Scholar 

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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.

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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.

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Correspondence to Cameron R Currie or Jon Clardy.

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Supplementary Figures 1–8, Supplementary Tables 1 and 2, and Supplementary Methods (PDF 1001 kb)

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Oh, DC., Poulsen, M., Currie, C. et al. Dentigerumycin: a bacterial mediator of an ant-fungus symbiosis. Nat Chem Biol 5, 391–393 (2009).

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