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DOI: 10.1039/A808845D (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1999, 715-720

Metabolites of the higher fungi. Part 31.1 Longianone, a C7H6O4 spiro bicyclic lactone from the fungus Xylaria longiana (Rehm.)

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Raymond L. Edwards, Derek J. Maitland, Claire L. Oliver, Michael S. Pacey, Len Shields and Anthony J. S. Whalley

Abstract

Longianone 1 from Xylaria longiana is identified as 1,7-dioxaspiro[4,4]non-2-ene-4,8-dione by chemical and physical methods. The possible biosynthetic origin is discussed.

References

  1. Part 30: M. O. Adeboya, R. L. Edwards, T. Laessoe, D. J. Maitland and A. J. S. Whalley, Leibigs Ann. Chem., 1996, 1437 Search PubMed.
  2. A. Brack, Helv. Chem. Acta, 1947, 30, 2 CrossRef.
  3. J. C. Sheehan, W. B. Lawson and R. J. Gaul, J. Am. Chem. Soc., 1958, 80, 5536 CrossRef CAS.
  4. F. M. Dean, Naturally Occurring Oxygen Ring Compounds, Butterworths, London, 1963, p. 518 and references therein Search PubMed.
  5. J. Sekiguchi, G. M. Gaucher and Y. Yamada, Tetrahedron Lett., 1979, 41 CrossRef CAS.
  6. F. Brunner and O. Petrini, Mycol. Res., 1992, 96, 723.
  7. F. S. N. Gonzalez and J. D. Rodgers, Mycotaxon, 1989, 34, 263 Search PubMed.
  8. Rhem, Ann. Mycol., 1904, 2, 175 Search PubMed.
  9. J. F. Grove, J. Chem. Soc., 1951, 883 RSC.
  10. M. Bennett, G. B. Gill, G. Pattenden, A. J. Shuker and A. Stapleton, J. Chem. Soc., Perkin Trans. 1, 1991, 929 RSC.
  11. F. Sher, J. L. Isidor, H. R. Taneja and R. M. Carlson, Tetrahedron Lett., 1973, 8, 577 CrossRef.
  12. R. E. Rowenkranz, K. Alner, R. Good, W. V. Philipsborn and C. H. Eugster, Helv. Chim. Acta, 1963, 46, 1259 CAS.
  13. A. San-Martin, J. Rovirosa, O. Munoz, M. H. M. Chen, R. D. Guneratne and J. Clardy, Tetrahedron Lett., 1983, 24, 4063 CrossRef CAS.
  14. A. San-Martin, J. Rovirosa, C. Xu, H. S. M. Lu and J. Clardy, Tetrahedron Lett., 1987, 28, 6013 CrossRef CAS.
  15. P. Bloch, C. Tamm, P. Bollinger, T. J. Petcher and H. P. Weber, Helv. Chim. Acta, 1976, 59, 133 CAS.
  16. P. Bloch and J. C. Tamm, Helv. Chim. Acta, 1981, 64, 304 CAS.
  17. W. Breitenstein, K. K. Chexal, P. Mohr and C. Tamm, Helv. Chim. Acta, 1981, 64, 379 CAS.
  18. M. Dolder, X. Chao and C. Tamm, Helv. Chim. Acta, 1990, 73, 63 CAS.
  19. M. Tada, M. Nagai, C. Okumura, J. Osano and T. Matsuzaki, Chem. Lett., 1989, 683 CAS.
  20. Y. Aramaki, K. Chiba and M. Tada, Phytochemistry, 1995, 38, 1419 CrossRef CAS.
  21. W. B. Turner and D. C. Aldridge, Fungal Metabolites II, Academic Press, London and New York, 1983, pp. 72–73 and references cited therein Search PubMed.
  22. W. F. Reynolds, S. McLean, M. Perpick-Dumont and R. G. Enriquez, Magn. Reson. Chem., 1989, 27, 162 CAS.
  23. G. M. Sheldrick, SHELXS-97, University of Göttingen, 1997.
  24. G. M. Sheldrick, SHELXL-97, University of Göttingen, 1997.
  25. J. R. Anderson, R. L. Edwards and A. J. S. Whalley, J. Chem. Soc., Perkin Trans. 1, 1983, 2185 RSC.
  26. R. J. Cole, J. H. Moore, N. D. Davis, J. W. Kirksey and U. L. Diener, J. Agric. Food Chem., 1971, 19, 909 CrossRef CAS.
  27. The United Kingdom Chemical Database Service D. A. Fletcher, R. F. Meeking and D. J. Parkin, Chem. Inf. Comput. Sci., 1966, 36, 746 Search PubMed.
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