Advertisement

Abstract

The nonadrides are a small group of fungal metabolites characterised chemically by the presence of a nine-membered alicyclic ring and two five-ring anhydride functions. The first two members, glauconic and glaucanic acids, were isolated by Wijkman (18) in 1931 from a fungus described as Pé nicillium glaucum and in 1934 by Yuill (19) from a P. purpurogenum species. The third nonadride, byssochlamic acid, was obtained from Byssochlamys fulva by Raistrick and Smith (14) in 1933. Although extensive chemical work was carried out on glauconic acid by Wijkman, Kraft, Sutter and their co-workers (16, 17, 15, 12, 11) and on byssochlamic acid by Raistrick’s group (14) and by Cook, Loudon and Paton (7), the structures of the metabolites were not elucidated until the early sixties when these problems were solved chemically by Barton, Sutherland and their collaborators (1) and X-ray crystallographically by Robertson and Sim and their group (8, 9).

Keywords

Maleic Anhydride Absolute Configuration Labelling Pattern Succinic Anhydride Glutaric Acid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Baldwin, J. E., D. H. R. Barton, J. L. Bloomer, L. M. Jackman, L. Rodriguez-Hahn and J. K. Sutherland: The Constitutions of Glauconic, Glau-canic, and Byssochlamic Acids. Experientia 18, 345 (1962).CrossRefGoogle Scholar
  2. 2.
    Baldwin, J. E., D. H. R. Barton and J. K. Sutherland: The Nonadrides. IV. The Constitution and Stereochemistry of Byssochlamic Acid. J. Chem. Soc. (London) 1965, 1787.Google Scholar
  3. 3.
    Barton, D. H. R., L. D. S. Godinho and J. K. Sutherland: The Nonadrides. III. The Absolute Configuration of Glauconic and Glaucanic Acids. J. Chem. Soc. (London) 1965, 1779.Google Scholar
  4. 4.
    Barton, D. H. R., L. M. Jackman, L. Rodriguez-Hahn and J. K. Sutherland: The Nonadrides. II. The Constitutions of Glauconic and Glaucanic Acids. J. Chem. Soc. (London) 1965, 1772.Google Scholar
  5. 5.
    Barton, D. H. R. and J. K. Sutherland: The Nonadrides. I. Introduction and General Survey. J. Chem. Soc. (London) 1965, 1769.Google Scholar
  6. 6.
    Bloomer, J. L., C. E. Moppett and J. K. Sutherland: The Biosynthesis of Glauconic Acid. Chem. Commun. 1965, 619.Google Scholar
  7. 7.
    Cook, J. W., J. D. Loudon and R. P. Paton; see R. P. Paton: Thesis, Univ. Glasgow. 1954.Google Scholar
  8. 8.
    Ferguson, G., J. M. Robertson and G. A. Sim: The Stereochemistry of Glauconic Acid. Proc. Chem. Soc. (London) 1962, 385.Google Scholar
  9. 9.
    Hamor, T. A., I. C. Paul, J. M. Robertson and G. A. Sim: Fungal Metabolites. II. The Structure of Byssochlamic Acid: X-Ray Analysis of Byssochlamic Acid Bis-p-bromophenyl Hydrazide. J. Chem. Soc. (London) 1963, 5502.Google Scholar
  10. 10.
    Hoffmann, R. and R. B. Woodward: Selection Rules for Concerted Cycloaddition Reactions. J. Amer. Chem. Soc. 87, 2046 (1965).CrossRefGoogle Scholar
  11. 11.
    Kraft, K.: Zur Konstitution der Glaukonsäuren. VI. Liebigs Ann. Chem. 530, 20 (1937)CrossRefGoogle Scholar
  12. 12.
    Kraft, K. und H. Porsch: Zur Konstitution der Glaukonsäuren. V. Untersuchungen am Glaukonin. Liebigs Ann. Chem. 527, 168 (1936).Google Scholar
  13. 13.
    Moppett, C. E. and J. K. Sutherland: unpublished.Google Scholar
  14. 14.
    Raistrick, H. and G. Smith: Studies in the Biochemistry of Micro-organisms. XXXV. The Metabolic Products of Byssochlamys fulva Olliver and Smith. Biochem. J. 27, 1814 (1933); and unpublished observations.Google Scholar
  15. 15.
    Sutter, H., F. Rottmayr und H. Porsch: Zur Konstitution der Glaukonsäuren. IV. Liebigs Ann. Chem. 521, 189 (1936).CrossRefGoogle Scholar
  16. 16.
    Sutter, H. und N. Wijkman: Über einige neue, durch Schimmelpilze gebildete Substanzen. II. Zur Konstitution der Glaukonsäuren. Liebigs Ann. Chem. 505, 248 (1933)CrossRefGoogle Scholar
  17. 17.
    Zur Konstitution der Glaukonsäuren. III. Liebigs Ann. Chem. 519, 97 (1935)Google Scholar
  18. 18.
    Wijkman, N.: Über einige neue, durch Schimmelpilze gebildete Substanzen. Liebigs Ann. Chem. 485, 61 (1931).CrossRefGoogle Scholar
  19. 19.
    Yuill, J. L.: The Acids Produced from Sugar by a Pé nicillium Parasitic upon Aspergillus niger. Biochem. J. 28, 222 (1934).Google Scholar

Copyright information

© Springer-Verlag / Wien 1967

Authors and Affiliations

  • J. K. Sutherland
    • 1
  1. 1.LondonUK

Personalised recommendations