Pigments of fungi. Part 43.1,2 Cardinalins 1–6, novel pyranonaphthoquinones from the fungus Dermocybe cardinalis Horak

(Note: The full text of this document is currently only available in the PDF Version )

Malcolm S. Buchanan, Melvyn Gill and Jin Yu


Abstract

The cardinalins 1–6, a series of stereochemically complex, cytotoxic pyranonaphthoquinone dimers and their hydroquinone precursors, have been isolated from the New Zealand toadstool Dermocybe cardinalis and their structures established by spectroscopic methods. The cardinalins are the first pyranonaphthoquinones to be found in the Higher Fungi.


References

  1. For Part 42, see M. Gill and S. Saubern, J. Nat. Prod., 1996, 59, 983 Search PubMed.
  2. Preliminary communication: M. Gill and J. Yu, Nat. Prod. Lett., 1994, 5, 211 Search PubMed.
  3. R. H. Thomson, Naturally Occurring Quinones III, Chapman and Hall, London, 1987 Search PubMed.
  4. E. Horak, Sydowia, 1987, 40, 81 Search PubMed.
  5. G. Keller, M. Moser, E. Horak and W. Steglich, Sydowia, 1987, 40, 168 Search PubMed.
  6. M. Gill and W. Steglich, Prog. Chem. Org. Nat. Prod., 1987, 51, 1 Search PubMed.
  7. M. Gill, Nat. Prod. Rep., 1994, 11, 67 RSC; M. Gill, Nat. Prod. Rep., 1996, 13, 513 RSC.
  8. M. Gill, Aust. J. Chem., 1995, 48, 1 CAS.
  9. R. H. Thomson, J. Chem. Soc., 1950, 1737 RSC.
  10. G. Billen, U. Karl, T. Scholl, K. D. Stroech and W. Steglich, Natural Products Chemistry III, ed. Atta-ur-Rahman and P. W. Le Quesne, Springer, Berlin, 1988, p. 305 Search PubMed.
  11. I. Singh, R. T. Ogata, R. E. Moore, C. W. J. Chang and P. J. Scheuer, Tetrahedron, 1968, 24, 6053 CrossRef CAS.
  12. D. W. Cameron, I. T. Crosby and G. I. Feutrill, Aust. J. Chem., 1992, 45, 2025 CAS.
  13. T. Hanumaiah, D. S. Marshall, B. K. Rao, C. P. Rao, G. S. R. Rao, J. U. M. Rao, K. V. J. Rao and R. H. Thomson, Phytochemistry, 1985, 24, 2373 CrossRef CAS.
  14. E. I. Eliel and S. H. Willen, Stereochemistry of Carbon Compounds, Wiley, New York, 1994, p. 1043 Search PubMed.
  15. M. Gill, A. Gimenez, A. G. Jhingran and A. R. Palfreyman, Tetrahedron: Asymmetry, 1990, 1, 621 CrossRef CAS.
  16. M. Kasai, K. Shirahata, S. Ishii, K. Mineura, H. Marumo, H. Tanaka and S. Omura, J. Antibiot., 1979, 32, 442 CAS.
  17. R. C. Durley, J. MacMillan, T. J. Simpson, A. T. Glen and W. B. Turner, J. Chem. Soc., Perkin Trans. 1, 1975, 163 RSC.
  18. M. E. Stack, R. M. Eppley, P. A. Drufuss and A. E. Pohland, Appl. Environ. Microbiol., 1977, 33, 351 CAS.
  19. M. Moser, Proc. Indian Acad. Sci., Plant Sci., 1985, 94, 381 Search PubMed.
  20. M. A. Brimble, L. J. Duncalf and S. Phythian, Tetrahedron Lett., 1995, 36, 9209 CrossRef CAS.
  21. D. H. Sherman, M. J. Bibb, T. J. Simpson, D. Johnson, F. Malpartida, M. Fernandez-Moreno, E. Martinez, C. R. Hutchinson and D. A. Hopwood, Tetrahedron, 1991, 47, 6029 CrossRef CAS.
  22. H. W. Moore, Science, 1977, 197, 527 CrossRef CAS.
  23. H. W. Moore and R. Czerniak, Med. Res. Rev., 1981, 1, 249 CrossRef CAS.
  24. R. H. Thomson, in The Total Synthesis of Natural Products, ed. J. ApSimon, Wiley, New York, 1992, vol. 8, p. 311 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.