Skip to main content
Log in

Flavoglaucin, a metabolite ofEurotium chevalieri, its antioxidation and synergism with tocopherol

  • Technical
  • Published:
Journal of the American Oil Chemists’ Society

Abstract

Screening tests of fungal metabolites were performed for developing new types of antioxidants and synergists for tocopherol (Toc). Flavoglaucin has been found to be an excellent antioxidant and synergist. It is a phenolic compound isolated from mycelial mats ofEurotium chevalieri. Under autoxidation conditions, flavoglaucin remarkably synergized with Toc and stabilized many edible oils and fats. After the addition of flavoglaucin (0.05 %) the vegetable oils retained their original stabilities even after thermal treatment at 180 C for 25 hr. During the oxidation of lard containing Toc (0.04%) under the simulated deep-fat frying conditions, the addition of flavoglaucin didn’t retard the oxidative decomposition of Toc. However, the stability of lard always was higher in the presence of flavoglaucin than in its absence. Flavoglaucin is not mutagenic to Salmonella typhimurium TA 100 and TA 98.

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

  1. Tagaki, T., and T. Iida, JAOCS 57:326 (1980).

    Google Scholar 

  2. Naito, S.; N. Yamaguchi and Y. Yokoo, J. Jpn. Soc. Food Sci. Technol. 28:291,465 (1981).

    Google Scholar 

  3. Fukuda, Y.; T. Osawa and M. Namiki, Ibid. 28:461 (1981).

    CAS  Google Scholar 

  4. Osawa, T., and M. Namiki, Agric. Biol. Chem. 45:735 (1981).

    CAS  Google Scholar 

  5. Hirosue, T.; H. Kawai and Y. Hosogai, J. Jpn. Soc. Food Sci. Technol. 29:418 (1982).

    Google Scholar 

  6. Nose, M., and N. Fujino, Ibid. 29:507 (1982).

    CAS  Google Scholar 

  7. Naito, S., and N. Yamaguchi, Ibid. 29:529 (1982).

    CAS  Google Scholar 

  8. Williams, N.S., and N.D. Harris, J. Food Sci. 48:644 (1983).

    Article  CAS  Google Scholar 

  9. Okada, T., and N. Yamaguchi, J. Jpn. Oil Chem. Soc. 33:305 (1983).

    Google Scholar 

  10. Chipault, J.R., Food Eng. 29:134 (1957).

    CAS  Google Scholar 

  11. Saito, Y., J. Jpn. Oil Chem. Soc. 26:754 (1977).

    CAS  Google Scholar 

  12. Chang, S.S.; B. Ostric-Matijasevic, O.A.-L. Hsieh and C.-L. Huang, J. Food Sci. 42:1102 (1977).

    Article  CAS  Google Scholar 

  13. Bracco, U.; J. Lolinger and J.L. Viret, JAOCS 58:686 (1981).

    CAS  Google Scholar 

  14. Brieskorn, C.H., and H.J. Domling, Z. Lebensmitt-Untersuch. 141:10 (1969).

    Article  CAS  Google Scholar 

  15. Nakatani, N., and R. Inatani, Agric. Biol. Chem. 45:2385 (1981).

    CAS  Google Scholar 

  16. Wu, J.W.; M-H. Lee, C-T. Ho and S.S. Chang, JAOCS 59:339 (1982).

    CAS  Google Scholar 

  17. Inatani, R.; N. Nakatani, H. Fuwa and H. Seto, Agric. Biol. Chem. 46:1661 (1982).

    CAS  Google Scholar 

  18. Inatani, R.; N. Nakatani and H. Fuwa, Ibid. 47:521 (1983).

    CAS  Google Scholar 

  19. Zaika, L.L., and J.L. Smith, J. Sci. Fd. Agric. 26:1357 (1975).

    Article  CAS  Google Scholar 

  20. Aoyama, T.; Y. Nakakita, M. Nakagawa and H. Sakai, Agric. Biol. Chem. 46:2369 (1982).

    CAS  Google Scholar 

  21. Ishikawa, Y., and E. Yuki, Ibid. 39:851 (1975).

    CAS  Google Scholar 

  22. Ishikawa, Y.; E. Yuki, H. Kato and M. Fujimaki, J. Jpn. Oil Chem. Soc. 26:765 (1977).

    CAS  Google Scholar 

  23. Ishikawa, Y., E. Yuki, H. Kato and M. Fujimaki, Agric. Biol. Chem. 42:703,711 (1978).

    CAS  Google Scholar 

  24. Ishikawa, Y., J. Jpn. Oil Chem. Soc. 29:844 (1980).

    CAS  Google Scholar 

  25. Ishikawa, Y.; K. Sugiyama and K. Nakabayashi, JAOCS in press (1984).

  26. Yuki, E.; Y. Ishikawa and T. Yoshiwa, J. Jpn. Oil Chem. Soc. 23:497,714 (1974).

    CAS  Google Scholar 

  27. Hamasaki, T.; Y. Kimura, Y. Hatsuda and M. Nagao, Agric. Biol. Chem. 45:313 (1981).

    CAS  Google Scholar 

  28. Hamasaki, T.; M. Fukunaga, Y. Kimura and Y. Hatsuda, Ibid. 44:1685 (1980).

    CAS  Google Scholar 

  29. Hamasaki, T.; K. Nagayama and Y. Hatsuda, Ibid. 40:203 (1976).

    CAS  Google Scholar 

  30. Hamasaki, T., K. Nagayama and Y. Hatsuda, Ibid. 40:2487 (1976).

    CAS  Google Scholar 

  31. Hamasaki, T.; H. Kuwano, K. Isono, Y. Hatsuda, K. Fukuyama, T. Tsukihara and Y. Katsube, Ibid. 39:749 (1975).

    CAS  Google Scholar 

  32. Chexal, K.K.; C. Fouweather, J.S.E. Holker, T.J. Simpson and K. Young, J. Chem. Soc. Perkin Trans. I. 1974, p. 1584 [Ishida, M.; T. Hamasaki and Y. Hatsuda, Agric. Biol. Chem. 39:2181 (1975)].

    Article  Google Scholar 

  33. Kitamura, Z.; U. Kurimoto and M. Yokoyama, J. Pharm. Soc. Jpn. 76:972 (1956).

    CAS  Google Scholar 

  34. Hamasaki, T.; Y. Sata, Y. Hatsuda, M. Tanabe and L.W. Cary, Tetrahedron Lett. No. 9:659 (1975).

    Google Scholar 

  35. Fukuyama, K.; T. Tsukihara, Y. Katsube, T. Hamasaki and Y. Hatsuda, Agric. Biol. Chem. 40:1053 (1976).

    CAS  Google Scholar 

  36. Hamasaki, T.; K. Nagayama and Y. Hatsuda, Ibid. 42:37 (1978).

    CAS  Google Scholar 

  37. Ishikawa, Y., JAOCS 59:505 (1982).

    CAS  Google Scholar 

  38. Martin, J.B., US Patent 2,634,213 (1953).

  39. Yuki, E., and K. Morimoto, J. Jpn. Oil Chem. Soc. 31:915 (1982).

    CAS  Google Scholar 

  40. Yuki, E., and Y. Ishikawa, Ibid. 53:673 (1976).

    CAS  Google Scholar 

  41. Yoshihira, K.; C. Takahashi, S. Sekita and S. Natori, Chem. Pharm. Bull. 20:2727 (1972).

    CAS  Google Scholar 

  42. Turner, W.B., Fungal Metabolites, Academic Press Inc., London and New York, 1971, p. 141.

    Google Scholar 

  43. Winarno, F.G., JAOCS 56:363 (1979).

    CAS  Google Scholar 

  44. György, P.; K. Murata and Y. Sugimoto, JAOCS 51:377 (1974).

    Google Scholar 

  45. György, P., US Patent 3,855,256 (1974).

  46. Ikehata, H.; M. Wakaizumi and K. Murata, Agric. Biol. Chem. 32:740 (1968).

    CAS  Google Scholar 

  47. Yoshida, H., and G. Kajimoto, J. Jpn. Soc. Food Nutr. 25:415 (1972).

    CAS  Google Scholar 

  48. Yamaguchi, N.; Y. Yokoo and M. Fujimaki, J. Jpn. Food Sci. Technol. 26:71 (1979).

    CAS  Google Scholar 

  49. Yamaguchi, N.; Y. Yokoo and M. Fujimaki, Ibid. 29:407 (1982).

    CAS  Google Scholar 

  50. Ishikawa, Y.; K. Morimoto and S. Iseki, Abstract of the Annual Meeting of Jpn. Oil Chem. Soc. 1982, p. 56.

  51. Olcott, H.S., Lipids and Their Oxidation, edited by H.W. Schultz, E.A. Day and R.O. Sinnhuber, Avi Pub. Co., 1962, p. 173.

  52. Motosugi, M.; S. Dohi, T. Suzuki and M. Ishikawa, J. Tech. Exp. Stn. Shizuoka Pref. (Jpn.). 25:117 (1981).

    Google Scholar 

  53. Ames, B.N., Science 221:1256 (1983).

    Article  CAS  Google Scholar 

  54. Yuki, E., J. Jpn. Soc. Food Sci. Technol. 9:149 (1962).

    Google Scholar 

  55. Nakanishi, K., Jpn. Patent No. 48-7907 (1973).

  56. Ishikawa, Y., and K. Itoh, J. Jpn. Oil Chem. Soc. 30:767 (1981).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

About this article

Cite this article

Ishikawa, Y., Morimoto, K. & Hamasaki, T. Flavoglaucin, a metabolite ofEurotium chevalieri, its antioxidation and synergism with tocopherol. J Am Oil Chem Soc 61, 1864–1868 (1984). https://doi.org/10.1007/BF02540819

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02540819

Keywords

Navigation