Caripyrin, a new inhibitor of infection-related morphogenesis in the rice blast fungus Magnaporthe oryzae

Journal of Antibiotics

Volumn 63, Issue 6, 2010, Pages 285-289

  Rieger, Patrick H ^a   Liermann, Johannes C ^b   Opatz, Till ^b   Anke, Heidrun ^a   Thines, Eckhard ^a  

^a Institute of Biotechnology and Drug Research   (Germany)

^b UNIVERSITY OF HAMBURG   (Germany)

Author keywords

antifungal activity; basidiomycetes; Caripia montagnei; caripyrin; Magnaporthe oryzae; plant protection; pyridyloxirane

Indexed keywords

ANTIFUNGAL AGENT; CARIPYRIN A; FUSARIC ACID; UNCLASSIFIED DRUG; EPOXIDE; PYRIDINE DERIVATIVE; TRANS 5 (3 METHYLOXIRANYL)PYRIDINCARBOXYLIC ACID METHYL ESTER; TRANS-5-(3-METHYLOXIRANYL)PYRIDINCARBOXYLIC ACID METHYL ESTER;

ARTICLE; BASIDIOMYCETES; CARIPIA MONTAGNEI; CONIDIUM; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; FUNGAL PLANT DISEASE; GERMINATION; MAGNAPORTHE ORYZAE; MITOCHONDRIAL RESPIRATION; MORPHOGENESIS; NONHUMAN; PHYTOTOXICITY; PRIORITY JOURNAL; RICE BLAST; ROOT GROWTH; SPROUT; DRUG EFFECT; FERMENTATION; GROWTH, DEVELOPMENT AND AGING; ISOLATION AND PURIFICATION; MAGNAPORTHE; METABOLISM; MICROBIOLOGY; PLANT DISEASE; RICE;

BASIDIOMYCOTA; CARIPIA MONTAGNEI; FUNGI; MAGNAPORTHE GRISEA; MAGNAPORTHE ORYZAE;

ANTIFUNGAL AGENTS; BASIDIOMYCOTA; EPOXY COMPOUNDS; FERMENTATION; MAGNAPORTHE; MORPHOGENESIS; ORYZA SATIVA; PLANT DISEASES; PYRIDINES;

EID: 77954161160     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2010.31     Document Type: Article

References (27)

1. Oerke, E. C., Dehne, H. W., Schonbeck, F. & Weber, A. Crop Protection & Crop Production. 808 pp (Elsevier, Amsterdam, 1994).
2. Talbot, N. J., Ebbole, D. J. & Hamer, J. E. Identification and characterization of MPG1, a gene involved in pathogenicity from the rice blast fungus Magnaporthe grisea. Plant Cell 5, 1575-1590 (1993).
3. Howard, R. J., Ferrari, M. A., Roach, D. H. & Money, N. P. Penetration of hard surfaces by a fungus employing enormous turgor pressures. Proc. Natl Acad. Sci. USA 88, 11281-11284 (1991).
4. Howard, R. J. & Ferrari, M. A. Role of melanin in appressorium function. Exp. Mycol. 13, 403-418 (1989).
5. Thompson, J. E. et al. The second naphthol reductase of fungal melanin biosynthesis in Magnaporthe grisea. J. Biol. Chem. 275, 34867-34872 (2000).
6. Wei, C. Z., Katoh, H., Nishimura, K. & Ishii, H. Site-directed mutagenesis of the cytochrome b gene and development of diagnostic methods for identifying QoI resistance of rice blast fungus. Pest Manag. Sci. 65, 1344-1351 (2009).
7. Schwarz,M.,Köpcke, B., Weber, R. W. S., Sterner, O. & Anke, H. 3-Hydroxypropionic acid as a nematicidal principle of endophytic fungi. Phytochemistry 65, 2239-2245 (2004).
8. Kettering, M., Valdivia, C., Sterner, O., Anke, H. & Thines, E. Heptemerones A-G, seven novel diterpenoids from Coprinus heptemerus: producing organism, fermentation, isolation and biological activities. J. Antibiot. 58, 390-396 (2005).
9. Anke, H., Bergendorff, O. & Sterner, O. Assay of the biological activity of guaiane sesquiterpenoids isolated from the fruit bodies of edible Lactarius species. Food Chem. Toxicol. 27, 393-398 (1989).
10. Gottlieb, H. E., Kotlyar, V. & Nudelman, A. NMR chemical shifts of common laboratory solvents as trace impurities. J. Org. Chem. 62, 7512-7515 (1997).
11. Singer, R. The Agaricales in Modern Taxonomy (Koeltz Scientific Books, Königsstein, Germany, 1986).
12. National Center for Biotechnology Information (NCBI), accession number DQ449988, 2009.
13. Renslo, A. R. & Danheiser, R. L. Synthesis of substituted pyridines via regiocontrolled [4+2] cycloadditions of oximinosulfonates. J. Org. Chem. 63, 7840-7850 (1998).
14. Ichikawa, K., et al. Novel cytokine production inhibitors produced by a basidiomycete, Marasmiellus sp. J. Antibiot. 54, 703-709 (2001). (Pubitemid 32962795)
15. Skaltsounis, A. L. et al. Plantes de Nouvelle-Calédonie. 94e Communication. Alcaloïdes monoterpéniques de Scaevola racemigera DÄ NIKER. Helv. Chim. Acta. 68, 1679-1685 (1985).
16. Fernandez-Pol, J. A., Klos, D. J. & Hamilton, P. D. Cytotoxic activity of fusaric acid on human adenocarcinoma cells in tissue culture. Anticancer Res. 1, 57-64 (1993).
17. Hirai, T., Fukushima, K., Kumamoto, K. & Iwahashi, H. Effects of some naturally occurring iron ion chelators on in vitro superoxide radical formation. Biol. Trace Elem. Res. 108, 77-85 (2005).
18. Thines, E., Anke, H. & Weber, R. W. S. Fungal secondary metabolites as inhibitors of infection-related morphogenesis in phytopathogenic fungi. Mycol.Res. 108, 14-25 (2004).
19. Chapman & Hall Database 2010.
20. Bacon, C. W., Porter, J. K., Norred, W. P. & Leslie, J. F. Production of fusaric acid by Fusarium species. Appl. Environ. Microbiol. 62, 4039-4043 (1996).
21. Choi, Y-E. et al. AC1, a gene encoding a putative GTPase-activating protein, regulates bikaverin biosynthesis in Fusarium verticillioides. Mycologia 100, 701-709 (2008).
22. Jain, M. Handbook of Enzyme Inhibitors (John Wiley & Sons, New York, 1982).
23. Alabouvette, C. et al. Diversity and interactions among strains of Fusarium oxysporum: application to biological control. In Biotic Interactions in Plant Pathogen Associations (eds Jegger, M. J. & Spence, N. J.) 131-157 (CAB International, London, 2001).
24. Son, S. W. et al. Bikaverin and fusaric acid from Fusarium oxysporum show antioomycete activity against Phytophthora infestans. J. Appl. Microbiol. 104, 692-698 (2008).
25. 2O-soluble metabolites of Fusarium against Lemna minor L. (Duckweed). Mycopathologia 118, 185-189 (1992).
26. Iwahashi, H., Kawamori, H. & Fukushima, K. Quinolinic acid, alpha-picolinic acid, fusaric acid, and 2,6-pyridinedicarboxylic acid enhance the Fenton reaction in phosphate buffer. Chem. Biol. Interact. 118, 201-215 (1999).
27. Bouizgarne, B. et al. Early physiological responses of Arabidopsis thaliana cells to fusaric acid: toxic and signalling effects. New Phytol. 169, 209-218 (2006).