Antifungal Cyclopeptolide from Fungal Saprophytic Antagonist Ulocladium atrum

  • Yun, Bong-Sik (Functional Metabolomics Research Center, KRIBB) ;
  • Kwon, Eun-Mi (Department of Applied Biology, Chungnam National University) ;
  • Kim, Jin-Cheol (Biological Function Research Team, KRICT) ;
  • Yu, Seung-Hun (Department of Applied Biology, Chungnam National University)
  • Published : 2007.07.31

Abstract

The saprophytic fungus Ulocladium atrum Preuss is a promising biological control agent for Botrytis cinerea in greenhouse- and field-grown crops. However, despite its known potent antifungal activity, no antifungal substance has yet been reported. In an effort to characterize the antifungal substance from U. atrum, we isolated an antibiotic peptide. Based on extensive spectroscopic analyses, its structure was established as a cyclopeptolide with a high portion of N-methylated amino acids, and its $^1H$ and $^{13}C$ chemical shifts were completely assigned based on extensive 1D and 2D NMR experiments. Compound 1 exhibited potent antifungal activity against the plant pathogenic fungus Botrytis cinerea and moderate activity against Alternaria alternate and Magnaporthe grisea.

Keywords

References

  1. Agrios, G. N. 2005. Plant Pathology, 5th Ed., pp. 922-945
  2. Berto, P, J. M. Hai'ssam, and P. Lepoivre. 2001. Possible role of colonization and cell wall-degrading enzymes in the differential ability of three Ulocladium atrum strains to control Botrytis cinerea on necrotic strawberry leaves. Phytopathology 91: 1030-1036 https://doi.org/10.1094/PHYTO.2001.91.11.1030
  3. Boff, P., J. Kohl, M. Gerlagh, and J. de Kraker. 2002. Biocontrol of grey mold by Ulocladium atrum applied at different flower and fruit stages of strawberry. Biocontrol 47: 193-206 https://doi.org/10.1023/A:1014553221510
  4. Boff, P., J. Kohl, W. A. G. M. Jansen, P. J. F. M. Horsten, C. H. Lombaers-van der Plas, and M. Gerlagh. 2002. Biological control of grey mould with Ulocladium atrum in annual strawberry crops. Plant Dis. 86: 220-224 https://doi.org/10.1094/PDIS.2002.86.3.220
  5. Elad, Y, N. E. Malathrakis, and A. J. Dik. 1996. Biological control of Botrytis-incited diseases and powdery mildews in greenhouse crops. Crop Prot. 15: 229-240 https://doi.org/10.1016/0261-2194(95)00129-8
  6. Emmer, G., M. A. Grassberger, J. G. Meingassner, G. Schulz, and M. Schaude. 1994. Derivatives of a novel cyclopeptolide. 1. Synthesis, antifungal activity and structure-activity relationships. J Med. Chem. 37: 1908-1917 https://doi.org/10.1021/jm00039a002
  7. Kessel, G. J. T., B. H. de Hass, C. H. Lombaers-van der Plass, E. M. J. Meijer, F. M. Dewey, J. Goudrian, W. van der Werf, and J. Kohl. 1999. Quantification of mycelium of Botrytis spp. and the antagonist Ulocladium atrum in necrotic leaf tissue of cyclamen and lily by fluorescence microscopy and image analysis. Phytopathology 89: 868-876 https://doi.org/10.1094/PHYTO.1999.89.10.868
  8. Kessel, G. J. T., B. H. de Haas, C. H. Lombaers-van der Plass, J. E. van den Ende, M. G. Pennock-Vos, W. van der Werf, and J. Kohl. 2001. Comparative analysis of the role of substrate specificity in biological control of Botrytis elliptica in lily and B. cinerea in cyclamen with Ulocladium atrum. Eur. J. Plant Pathol. 107: 273-284 https://doi.org/10.1023/A:1011273613406
  9. Kohl, J. and W. M. L. Molhoek. 2001. Effect of water potential on conidial germination and antagonism of Ulocladium atrum against Botrytis cinerea. Phytopathology 91: 485-491 https://doi.org/10.1094/PHYTO.2001.91.5.485
  10. Kohl, J., R. Belanger, and N. J. Fokkenma. 1997. Interaction of four antagonistic fungi with Botrytis aclada in dead onion leaves: A comparative microscopic and ultrastructural study. Phytopathology 87: 634-642 https://doi.org/10.1094/PHYTO.1997.87.6.634
  11. Kohl, J., W. M. L. Molhoek, C. H. van der Plas, and N. J. Fokkema. 1995. Effect of Ulocladium atrum and other antagonists on sporulation of Botrytis cinerea on dead lily leaves exposed to field conditions. Phytopathology 85: 393-401 https://doi.org/10.1094/Phyto-85-393
  12. Kohl, J., W. M. L. Molhoek, H. M. Goosson-van de Geijn, and C. H. Lombaers-van der Plas. 2003. Potential of Ulocladium atrum for biocontrol of onion leaf spot through suppression of sporulation of Botrytis spp. BioControl 48: 349-359 https://doi.org/10.1023/A:1023614622179
  13. Lee, N. Y., E. M. Kwon, J. C. Kim, and S. H. Yu. 2004. Biological control of Botrytis leaf blight of lily and Botrytis gray mold of cucumber by Ulocladium atrum. Res. Plant Dis. 10: 319-323 https://doi.org/10.5423/RPD.2004.10.4.319