Pigments of fungi. Part 49.1 Structure and biosynthesis of dermocanarin 4, a naphthoquinone-dihydroanthracenone dimer from the fungus Cortinarius sinapicolor Cleland

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Melvyn Gill, Alberto Gimenez, Akhil G. Jhingran, Nives M. Milanovic and Anna R. Palfreyman


Abstract

Dermocanarin 4 3, a novel naphthoquinone-dihydroanthracenone dimer containing a nine membered lactone ring has been isolated from the fruit bodies of the Australasian fungus Cortinarius sinapicolor and the structure and axial stereochemistry have been determined by spectroscopic methods. The biosynthesis of dermocanarin 4 has been studied in intact toadstools by feeding experiments involving [Me-13C]methionine, sodium [2-13C]acetate and sodium [1,2-13C2[hair space]]acetate.


References

  1. M. Gill and A. Gimenez, J. Chem. Soc., Perkin Trans. 1, 1995, 645 RSC.
  2. M. Gill and A. Gimenez, Tetrahedron Lett., 1990, 31, 3505 CrossRef CAS.
  3. E. Horak and A. E. Wood, Sydowia, 1988, 40, 81 Search PubMed.
  4. M. Cole, B. Fuhrer and A. Holland, A. Field Guide to the Common Genera of Gilled Fungi in Australia, Inkata Press, Melbourne, 1984 Search PubMed.
  5. B. Fuhrer, A Field Companion to Australian Fungi, Kyodo Printing, Singapore, 1995 Search PubMed.
  6. C. A. Grgurinovic, Mycotaxon, 1988, 36, 47 Search PubMed.
  7. M. Moser, in The Agaricales in Modern Taxonomy, R. Singer, Scientific Books, Koeltz, 1986, pp. 653–656 Search PubMed.
  8. M. Gill, Beih. Sydowia, 1995, 10, 73 Search PubMed.
  9. M. Gill and W. Steglich, Prog. Chem. Org. Nat. Prod., 1987, 51, 1 Search PubMed.
  10. R. H. Thomson, Naturally Occurring Quinones, 2nd edn., Academic Press, London, 1971 Search PubMed.
  11. M. Gill, A. Gimenez, A. G. Jhingran and A. F. Smrdel, Phytochemistry, 1989, 28, 2647 CrossRef CAS.
  12. G. Billen, U. Karl, T. Scholl, K. D. Stroech and W. Steglich, Natural Products Chemistry III, eds. Atta-ur-Rahman and P. W. Le Quesne, Springer, Berlin, 1988, p. 305 Search PubMed.
  13. E. Horak, personal communication.
  14. M. Gill, A. Giménez and R. Watling, J. Nat. Prod., 1992, 55, 372 CrossRef CAS.
  15. N. Imamura, K. Kakinuma, N. Ikekawa, H. Tanaka and S. Omura, J. Antibiot., 1982, 35, 602 CAS.
  16. J. K. M. Sanders and B. K. Hunter, Modern NMR Spectroscopy, Oxford University, Oxford, 1987 Search PubMed.
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