Skip to main content
Log in

Alternariol monomethyl ether and α, β-dehydrocurvularin from endophytic fungi Alternaria spp. Inhibit appressorium formation of Magnaporthe grisea

  • Bioactive Material
  • Article
  • Published:
Journal of the Korean Society for Applied Biological Chemistry Submit manuscript

Abstract

Appressorium formation pathway of Magnaporthe grisea (M. grisea) is a new target for developing rice blast controlling agent. Inhibitory activity of endophytic fungi against the appressorium formation of M. grisea was screened. Two compounds displaying the activity were isolated from Alternaria tenuissima and Alternaria sp. isolated from the leaves of Acacia mangium and were identified as alternariol monomethyl ether and (4S)-α, β-dehydrocurvularin with IC50s of 51.0 and 10.6 μg/mL, respectively. These compounds were of no practical implication due to its low activity. However, they would serve as biochemical tool to study appressorium development.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  • Almassi F, Ghisalberti EL, Skelton BW, and White AH (1994) Structural study of dehydrocurvularin, an inhibitor of microtubule assembly. Aust J Chem 47, 1193–1197.

    Article  CAS  Google Scholar 

  • An YH, Zhao TZ, Miao J, Liu GT, Zheng Y-Z, Xu Y-M, and Van Etten RL (1989) Isolation, identification, and mutagenicity of alternariol monomethyl ether. J Agric Food Chem 37, 1341–1343.

    Article  CAS  Google Scholar 

  • Caputo O and Viola F (1977) Isolation of α, β-dehydrocurvularin from Aspergillus aureofulgens. Planta Med 31, 31–32.

    Article  CAS  Google Scholar 

  • Cromer D and Waber J (1974) In International Tables for X-ray Crystallography, Vol. IV, Table 2.2A, Table 2.3.1. Kynoch Press, Birmingham, England.

    Google Scholar 

  • Deising HB, Werner S, and Wernitz M (2000) The role of fungal appressoria in plant infection. Microb Infect 2, 1631–1641.

    Article  CAS  Google Scholar 

  • Hyeon SB, Ozaki A, Suzuki A, and Tamura S (1976) Isolation of α, β-dehydrocurvularin and â-hydroxycurvularin from Alternaria tomato as sporulation suppressing factors. Agr Biol Chem 40, 1663–1664.

    Article  CAS  Google Scholar 

  • Kim S-U, Strobel G, and Ford E (1999) Screening of taxolproducing endophytic fungi from Ginkgo biloba and Taxus cuspidata in Korea. Agric Chem Biotechnol 42, 97–99.

    CAS  Google Scholar 

  • Kobayashi A, Hino T, Yata S, Itoh T J, Sato H, and Kawazu K (1988) Unique spindle poisons, curvularin and its derivatives, isolated from Penicillium species. Agr Biol Chem 52, 3119–3123.

    Article  CAS  Google Scholar 

  • Kusano M, Nakagami K, Fujioka S, Kawano T, Shimada A, and Kimura Y (2003) α, β-Dehydrocurvularin and related compounds as nematocides of Pratylenchus penetrans from the fungus Aspergillus sp. Biosci Biotech Biochem 67, 1413–1416

    Article  CAS  Google Scholar 

  • Lee YH and Oh HS (2000) A target-site-specific screening system for antifungal compounds on appressorium formation in Magnaporthe grisea. Phytopathology 90, 1162–1168.

    Article  Google Scholar 

  • Munro HD, Musgrave OC, and Templeton gnR (1967) Curvularin. Part V. The compound C16H18O5, a,b-dehydrocurvularin. J Chem Soc (C) 947–948.

  • Park SY, Milgroom MG, Han S, Kang S, and Lee YH (2003) Diversity of pathotypes and DNA fingerprint haplotypes in populations of Magnaporthe grisea in Korea over two decades. Phytopathology 93, 1378–1385.

    Article  CAS  Google Scholar 

  • Pinkerton R and Strobel G (1976) Serinol as an activator of toxin production in attenuated cultures of H. sacchari. Proc Natl Acad Sci USA 73, 4007–4011.

    Article  CAS  Google Scholar 

  • Pollock GA, DiSabatino CE, Heimsch RC, and Hilbelink DR (1982) The subchronic toxicity and teratogenicity of alternariol monomethyl ether produced by Alternaria solani. Food Chem Toxicol 20, 899–902.

    Article  CAS  Google Scholar 

  • Raistrick H, Stickings CE, and Thomas R (1953) Studies in the biochemistry of micro-organisms. Biochem J 55, 421–433.

    CAS  Google Scholar 

  • Robeson DJ and Strobel GA (1981) α, β-Dehydrocurvularin and curvularin from Alternaria cinerariae. Z Naturforsch 36c, 1081–1083.

    CAS  Google Scholar 

  • Scott PM and Stoltz DR (1980) Mutagens produced by Alternaria alternata. Mutat Res 78, 33–40.

    Article  CAS  Google Scholar 

  • Sheldick GM (1997) SHELX-97, Program for Crystal Structure Refinement. University of Gottingen, Gottingen, Germany.

    Google Scholar 

  • Strobel G (2003) Endophytes as sources of bioactive products. Microb Infect 5, 535–544.

    Article  CAS  Google Scholar 

  • Talbot NJ (2003) On the trail of a cereal killer: exploring the biology of Magnaporthe grisea. Annu Rev Microbiol 57, 177–202.

    Article  CAS  Google Scholar 

  • Tan N, Tao Y, Pan J, Wang S, Xu F, She Z, Lin Y, and Jones EBG (2008) Isolation, structure elucidation, and mutagenicity of four alternariol derivatives produced by the mangrove endophytic fungus No. 2240. Chem Nat Comp 44, 296–300.

    Article  CAS  Google Scholar 

  • Vurro M, Evidente A, Andolfi A, Zonno MC, Giordano F, and Motta A (1998) Brefeldin A and a,b-dehydrocurvularin, two Phytotoxins from Alternaria zinniae, a biocontrol agent of Xanthium occidentale. Plant Sci 138, 67–79.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Pham QT.

Additional information

YTJ and KHR contributed equally to the work.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Jeon, YT., Ryu, KH., Kang, MK. et al. Alternariol monomethyl ether and α, β-dehydrocurvularin from endophytic fungi Alternaria spp. Inhibit appressorium formation of Magnaporthe grisea . J. Korean Soc. Appl. Biol. Chem. 53, 39–42 (2010). https://doi.org/10.3839/jksabc.2010.007

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.3839/jksabc.2010.007

Key words

Navigation