Natural Product Sciences

  • 제17권2호
  • /
  • Pages.85-89
  • /
  • 2011
  • /
  • 1226-3907(pISSN)
  • /
  • 2288-9027(eISSN)
한국생약학회 (The Korean Society of Pharmacognosy)
권호 표지

Cytotoxicity of Ergosterol Derivatives from the Fruiting Bodies of Hygrophorus russula

  • Lee, Ik-Soo (College of Pharmacy, Chungnam National University) ;
  • Kim, Jin-Pyo (College of Pharmacy, Chungnam National University) ;
  • Na, Min-Kyun (College of Pharmacy, Yeungnam University) ;
  • Jung, Hyun-Ju (College of Pharmacy, Wonkwang University) ;
  • Min, Byung-Sun (College of Pharmacy, Catholic University of Daegu) ;
  • Bae, Ki-Hwan (College of Pharmacy, Chungnam National University)
  • 투고 : 2010.11.30
  • 심사 : 2011.05.09
  • 발행 : 2011.06.30
PDF 다운로드
⟨ 이전 논문 다음 논문 ⟩

초록

Bioassay-guided fractionation of the $CHCl_3$-soluble fraction of a MeOH extract of the fruiting bodies of Hygrophorus russula led to the isolation of five ergosterol derivatives (1 - 5). The structures of these compounds were identified as ergosterol peroxide (1), ergosta-4,6,8(14),22-tetraen-3-one (2), ergosta-7,22-diene-3${\beta}$,5${\alpha}$,6${\alpha}$-triol (3), ergosta-7,22-diene-3${\beta}$,5${\alpha}$,6${\beta}$,9${\alpha}$-tetraol (4), and 5${\alpha}$,6${\alpha}$-epoxy-ergosta-8(14),22-diene-3${\beta}$,7${\alpha}$-diol (5) by comparing their physicochemical and spectral data with those in the literature. These compounds were evaluated for in vitro cytotoxicity against A549 and XF498 cancer cell lines. Most of the tested compounds, except for compound 3, exhibited moderate cytotoxicity against both A549 and XF498 cell lines with $IC_{50}$ values ranging from 10.2 to 18.3 ${\mu}g/ml$ and from 11.4 to 24.6 ${\mu}g/ml$, respectively.

키워드

참고문헌

  1. Abraham, W.R., Bioactive sesquiterpenes produced by fungi: are they useful for humans as well? Curr. Med. Chem. 8, 583-606 (2001). https://doi.org/10.2174/0929867013373147
  2. Adler, J.H., Young, M., and Nes, W.R., Determination of the absolute configuration at C-20 and C-24 of ergosterol in Ascomycetes and Basidiomycetes by proton magnetic resonance spectroscopy. Lipids 12, 364-366 (1977). https://doi.org/10.1007/BF02533639
  3. Brizuela, M.A., Garcia, L., Pérez, L., and Mansur, M., Basidiomicetos: nueva fuente de metabolitos secundarios. Rev. Iberoam. Micol. 15, 69- 74 (1998).
  4. Greca, M.D., Fiorentino, A., Molinaro, A., Monaco, P., and Previ-tera, L., Steroidal 5,6-epoxides from Arum italicum. Nat. Prod. Lett. 2, 27-32 (1993). https://doi.org/10.1080/10575639308043450
  5. Ishizuka, T., Yaoita, Y., and Kikuchi, M., Sterol constituents from the fruit bodies of Grifola frondosa (FR.) S.F. Gray. Chem. Pharm. Bull. 45, 1756-1760 (1998).
  6. Kobayashi, M. and Kanda, F., Isolation and Structure of Four Novel Oxygenated Sterols from a Gorgonian Coral Melithaea ocracea. J. Chem. Soc. Perkin Trans. 1, 1177-1179 (1991).
  7. Kwon, H.C., Zee, S.D., Cho, S.Y., Choi, S.U., and Lee, K.R., Cytotoxic Ergosterols from Paecilomyces sp. J300. Arch. Pharm. Res. 25, 851- 855 (2002). https://doi.org/10.1007/BF02977003
  8. Lee, W.Y., Park, Y., Ahn, J.K., Park, S.Y., and Lee, H.J., Cytotoxic Activity of Ergosta-4,6,8(14),22-tetraen-3-one from the Sclerotia of Polyporus umbellatus. Bull. Korean Chem. Soc. 26, 1464-1466 (2005). https://doi.org/10.5012/bkcs.2005.26.9.1464
  9. Lindequist, U., Niedermeyer, T.H.J., and Jülich, W.D., The pharmacological potential of mushrooms. Evid. Based Complement Alternat. Med. 2, 285-299 (2005). https://doi.org/10.1093/ecam/neh107
  10. Lorenzen, K. and Anke, T., Basidiomycetes as a source for new bioactive natural products. Curr. Org. Chem. 2, 329-364 (1998).
  11. Lubken, T., Schmidt, J., Porzel, A., Arnold, N., and Wessjohann, L.A., Hygrophorones A-G: fungicidal cyclopentenones from Hygrophorus species (Basidiomycetes). Phytochemistry 65, 1061-1071 (2004). https://doi.org/10.1016/j.phytochem.2004.01.023
  12. Mosmann, T.J., Rapid colorimetric assay for cellular growth and survival application to proliferation and cytotoxicicity assays. J. Immunol. Methods 65, 55-63 (1983). https://doi.org/10.1016/0022-1759(83)90303-4
  13. Sheu, J.H., Chang K.C., and Duh, C.Y., A cytotoxic 5,8-epidioxysterol from a soft coral Sinularia species. J. Nat. Prod. 63, 149-151(2000). https://doi.org/10.1021/np9903954
  14. Teichert, A., Lübken, T., Schmidt, J., Porzel, A., Arnold, N., and Wessjohann, L., Unusual bioactive 4-oxo-2-alkenoic fatty acids from Hygrophorus eburneus. Z. Naturforsch. 60b, 25-32 (2005).
  15. Wasser, S.P. and Weis, A.L., Medicinal properties of substances occurring in higher basidiomycetes mushrooms: current perspective (review). Int. J. Med. Mushrooms 1, 31-62 (1999). https://doi.org/10.1615/IntJMedMushrooms.v1.i1.30
  16. Wasser, S.P., Medicinal mushrooms as a source of antitumor and immunomodulating polysaccharides. Appl. Environ. Microbiol. 60, 258-274 (2002).
  17. Yaoita, Y., Amemiya, K., Ohnuma, H., Furumura, K., Masaki, A., Matsuki T., and Kikuchi, M., Sterol constituents from five edible mushrooms. Chem. Pharm. Bull. 46, 944-950 (1998). https://doi.org/10.1248/cpb.46.944
  18. Yassin, M. Mahajna, J.A., and Wasser, S.P., Medicinal mushroom extracts selectively inhibit proliferation and induce differentiation of K562 human chronic myelogenous leukemia blast cells. Int. J. Med. Mushrooms 5, 259-274 (2003).
  19. Zjawiony, J.K., Biologically active compounds from Aphyllophorales (polypore) fungi. J. Nat. Prod. 67, 300-310 (2004). https://doi.org/10.1021/np030372w