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DOI: 10.1039/A808340A (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 119-126

Pigments of fungi. Part 50.1 Structure, biosynthesis and stereochemistry of new dimeric dihydroanthracenones of the phlegmacin type from Cortinarius sinapicolor Cleland

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Catherine Elsworth, Melvyn Gill, Alberto Giménez, Nives M. Milanovic and Evelin Raudies

Abstract

(3S,3′S,P[hair space])-Anhydrophlegmacin-9,10-quinone 8′-O-methyl ether 2 and its (2′S[hair space])-hydroxy derivative 3 are isolated from the bright yellow, glutinous fruiting bodies of the Australian toadstool Cortinarius sinapicolor and their structures and absolute stereochemistry are deduced by spectroscopic, chemical and isotopic labelling methods. The biosynthesis of the phlegmacin derivatives 2 and 3 in C. sinapicolor has been studied by feeding experiments using sodium [2-13C]acetate, [Me-13C]methionine and 6-O-[Me-13C]-torosachrysone 8-O-β-D-gentiobioside 5.

References

  1. Part 49 M. Gill, A. Gimenez, A. G. Jhingran, N. M. Milanovic and A. R. Palfreyman, J. Chem. Soc., Perkin Trans. 1, 1998, 3431 Search PubMed.
  2. M. Gill and W. Steglich, Prog. Chem. Org. Nat. Prod., 1987, 51, 1 Search PubMed.
  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; B. Fuhrer, A Field Companion to Australian Fungi, Kyodo Printing, Singapore, 1995 Search PubMed.
  5. M. Gill, A. Gimenez, A. G. Jhingran and A. F. Smrdel, Phytochemistry, 1989, 28, 2647 CrossRef CAS.
  6. S. F. Mason, R. H. Seal and D. R. Roberts, Tetrahedron, 1974, 30, 1671 CrossRef CAS.
  7. N. Harada and K. Nakanishi, Circularly Dichroic Spectroscopy-Exciton Coupling in Organic Stereochemistry, University Science Books, Mill Valley, 1983 Search PubMed.
  8. K. Nakanishi and N. Berova, The Exciton Chirality Method in Circular Dichroism, ed. K. Nakanishi, N. Berova and R. W. Woody, VCH, Weinheim, New York, 1994 Search PubMed.
  9. V. Prelog and G. Helmchen, Angew. Chem., 1982, 94, 614 CAS.
  10. B. Oertel, Dissertation, Rheinischen Friedrich-Wilhelms-Universität, Bonn, 1984.
  11. S. Takahashi, S. Kitanaka, M. Takido, U. Sankawa and S. Shibata, Phytochemistry, 1977, 16, 999 CrossRef CAS.
  12. W. Steglich and B. Oertel, Sydowia, 1984, 37, 284 Search PubMed.
  13. P. M. Morgan, PhD Thesis, University of Melbourne, 1998.
  14. M. S. Buchanan, M. Gill, P. M. Millar, S. Phonh-Axa, E. Raudies and J. Yu, J. Chem. Soc., Perkin Trans. 1, to be submitted Search PubMed.
  15. K. Arai, Y. Aoki and Y. Yamamoto, Chem. Pharm. Bull., 1989, 37, 621 CAS.
  16. M. Gill, A. Gimenez, A. G. Jhingran and A. R. Palfreyman, Tetrahedron: Asymmetry, 1990, 1, 621 CrossRef CAS.
  17. M. Müller, Dissertation, Ludwig-Maximillians-Universität, München, 1995.
  18. J. W. Cornforth, Aust. J. Chem., 1993, 46, 157 CAS.
  19. M. Endo and H. Naoki, Tetrahedron, 1980, 36, 2449 CrossRef CAS.
  20. S. N. Eagle, M. Gill, S. Saubern and J. Yu, Nat. Prod. Lett., 1993, 2, 151 Search PubMed.
  21. C. Elsworth, PhD Thesis, University of Melbourne, in preparation.
  22. M. S. Buchanan, M. Gill and A. Gimenez, Aust. J. Chem., 1998, 51, 103 CAS.
  23. G. P. Bakhaeva, Y. A. Berlin, O. A. Chuprunova, M. N. Kolosov, G. Y. Peck, L. A. Piotrovich, M. M. Schemyakin and I. V. Vasina, J. Chem. Soc., Chem. Commun., 1967, 10 RSC.
  24. D. L. Dreyer, I. Arai, C. D. Bachman, W. R. Anderson, Jr., R. G. Smith and G. D. Daves, Jr., J. Am. Chem. Soc., 1975, 97, 4985 CrossRef.
  25. W. Steglich, E. Töpfer-Petersen and I. Pils, Z. Naturforsch., Teil C, 1973, 28, 354 Search PubMed.
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