Biosynthesis of longianone from Xylaria longiana: a metabolite with a biosynthetic relationship to patulin

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

Rebecca J. M. Goss, Jens Fuchser and David O’Hagan


Abstract

Longianone, a metabolite of Xylaria longiana, is an isomer of the well known fungal toxin, patulin; it is demonstrated that longianone is biosynthesised from 6-methylsalicylic acid in a pathway closely related to that found in patulin biosynthesis.


References

  1. R. L. Edwards, D. J. Maitland, C. L. Oliver, M. C. Pacey, L. Shields and A. J. S. Whalley, J. Chem. Soc., Perkin Trans. 1, 1999, 715 RSC.
  2. S. L. Midland, N. T. Keen and J. J. Sims, J. Org. Chem., 1995, 60, 1118 CrossRef CAS.
  3. S. L. Midland, N. T. Keen, J. J. Sims, M. M. Midland, M. M. Stayton, M. J. Smith, E. P. Mazzola, K. J. Graham and J. Clardy, J. Org. Chem., 1993, 58, 2940 CrossRef CAS.
  4. M. Tada, M. Nagai, C. Okumura, J. Osano and T. Matsuzaki, Chem. Lett., 1989, 683 CAS.
  5. H. Iijima, H. Noguchi, Y. Ebizuka, U. Sankawa and H. Seto, Chem. Pharm. Bull., 1983, 31, 362 CAS.
  6. S. W. Tanenbaum and E. W. Bassett, J. Biol. Chem., 1959, 234, 1861 CAS.
  7. A. I. Scott and M. Yalpani, J. Chem. Soc., Chem. Commun., 1967, 945 RSC.
  8. J. Sekiguchi, G. M. Gaucher and Y. Yamada, Tetrahedron Lett., 1979, 41 CrossRef CAS.
  9. F. M. Hauser and S. A. Pogany, Synthesis, 1980, 814 CrossRef CAS.
  10. K. Wähälä, I. Ojanperä, L. Häyri and T. A. Hase, Synth. Commun., 1987, 137 CAS.
  11. J. Sekiguchi and G. M. Gaucher, Biochemistry, 1978, 17, 1785 CrossRef.
  12. M. Bennet, G. B. Gill, G. Pattenden, A. J. Shuker and A. Stapelton, J. Chem. Soc., Perkin Trans. 1, 1991, 929 RSC.
Click here to see how this site uses Cookies. View our privacy policy here.