Mycobiology

The Korean Society of Mycology (한국균학회)
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Chemical Constituents of Gymnopilus spectabilis and Their Antioxidant Activity

  • Lee, In-Kyoung (Korea Research Institute of Bioscience and Biotechnology (KRIBB)) ;
  • Cho, Sung-Min (Korea Research Institute of Bioscience and Biotechnology (KRIBB)) ;
  • Seok, Soon-Ja (Rural Development Administration) ;
  • Yun, Bong-Sik (Korea Research Institute of Bioscience and Biotechnology (KRIBB))
  • Published : 2008.03.31
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Abstract

Gymnopilus spectabilis, a hallucinogenic mushroom belonging to the family Cortinariaceae, is found growing in dense clusters on stumps and logs of hardwoods and conifers. It contains the hallucinogenic alkaloid psilocybin and its strongly bitter taste makes it undesirable as an edible. In an effort to identify chemical constituents of Korean native wild mushrooms, 4,6-decadiyne-1,3,8-triol (1), ergosta-4,6,8(14), 22-tetraen-3-one (2), bisnoryangonin (3), and hispidin (4) were isolated from the methanolic extract of the fruiting bodies of G. spectabilis. Their structures were assigned on the basis of various spectroscopic studies. Compounds 3 and 4 displayed significant scavenging activity against the ABTS radical cation, DPPH radical, and superoxide radical anion, while 1 and 2 exhibited no antioxidant activity.

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References

  1. Beauchamp, C. and Fridovich, I. 1971. Superoxide dismutase: improved assay and an assay applicable to acrylamide gels. Anal. Biochem. 44:276-287 https://doi.org/10.1016/0003-2697(71)90370-8
  2. Berger, K. J. and Guss, D. A. 2005. Mycotoxins revisited: Part II. J. Emerg. Med. 28:175-183 https://doi.org/10.1016/j.jemermed.2004.08.019
  3. Blois, M. S. 1958. Antioxidant determinations by the use of a stable free radical. Nature 181:1199-1200 https://doi.org/10.1038/1811199a0
  4. Brady, L. R. and Benedict, R. G. 1972. Occurrence of bisnoryangonin in Pholiota squarroso-adiposa. J. Pharm. Sci. 61:318 https://doi.org/10.1002/jps.2600610251
  5. Davis, N. D., Cole, R. J., Dorner, J. W., Weete, J. D., Backman, P. A., Clark, E. M., King, C. C., Schmidt, S. P. and Diener, U. L. 1986. Steroid metabolites of Acremonium coenophialum, an endophyte of tall fescue. J. Agric. Food Chem. 34:105-108 https://doi.org/10.1021/jf00067a029
  6. Gonindard, C., Bergonzi, C., Denier, C., Sergheraert, C., Klaebe, A., Chavant, L. and Hollande, E. 1997. Synthetic hispidin, a PKC inhibitor, is more cytotoxic toward cancer cells than normal cells in vitro. Cell Biol. Toxicol. 13:141-153 https://doi.org/10.1023/A:1007321227010
  7. Gonzalez, A. G., Barrera, J. B. and Marante, F. T. 1983. The steroids and fatty acids of the basidiomycete Scleroderma polyrhizum. Phytochemistry 22:1049-1050 https://doi.org/10.1016/0031-9422(83)85062-6
  8. Hatfield, G. M. and Brady, L. R. 1969. Occurrence of bis-noryangonin in Gymnopilus spectabilis. J. Pharm. Sci. 58:1298-1299 https://doi.org/10.1002/jps.2600581039
  9. Klaar, M. and Steglich, W. 1977. Isolation of hispidin and 3,14'- bihispidinyl from Phellinus pomaceus. Chem. Ber. 110:1058-1062 https://doi.org/10.1002/cber.19771100327
  10. Kusano, G., Koike, Y., Inoue, H. and Nozoe, S. 1986. The constituents of Gymopilus spectabilis. Chem. Pharm. Bull. 34:3465-3470 https://doi.org/10.1248/cpb.34.3465
  11. Nambudiri, A. M., Vance, C. P. and Towers, G. H. 1974. Styrylpyrone biosynthesis in Polyporus hispidus. II. Enzymic hydroxylation of p-coumaric acid and bis-noryangonin. Biochim. Biophys. Acta. 20:148-55
  12. Nozoe, S., Koike, Y., Tsuji, E., Kusano, G. and Seto, H. 1983. Isolation and structure of gymnoprenols, a novel type of polyisoprenepolyols from Gymopilus spectabilis. Tetrahedron Lett. 24:1731-1734 https://doi.org/10.1016/S0040-4039(00)81756-6
  13. Nozoe, S., Koike, Y., Kusano, G. and Seto, H. 1983. Structure of gymnopilin,a bitter principle of an hallucinogenic mushroom, Gymopilus spectabilis. Tetrahedron Lett. 24:1735-1736 https://doi.org/10.1016/S0040-4039(00)81757-8
  14. Re, R., Pellegrini, N., Proteggente, A., Pannala, A. Yang, M. and Rice-Evans, C. 1999. Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radcal Biol. Med. 26:1231-1237 https://doi.org/10.1016/S0891-5849(98)00315-3
  15. Seitz, L. M. and Paukstelis, J. V. 1977. Metabolites of Alternaria alternata: ergosterol and ergosta-4,6,8(14),22-tetraen-3-one. J. Agric. Food Chem. 25:838-341 https://doi.org/10.1021/jf60212a030
  16. Zjawiony, J. K. 2004. Biologically active compounds from aphyllophorales (polypore) fungi. J. Nat. Prod. 67:300-310 https://doi.org/10.1021/np030372w

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  2. Gymnopilin K: a new cytotoxic gymnopilin from Gymnopilus spectabilis vol.65, pp.3, 2012, https://doi.org/10.1038/ja.2011.122
  3. Detection of Hispidin by a Luminescent System from Basidiomycete Armillaria borealis vol.480, pp.1, 2018, https://doi.org/10.1134/S1607672918030146