Experientia

, Volume 31, Issue 11, pp 1250–1251 | Cite as

Zonaroic acid from the brown seaweedDictyopteris undulata (=zonarioides)

  • G. Cimino
  • S. de Stefano
  • W. Fenical
  • L. Minale
  • J. J. Sims
Specialia Chimica, Biochimica

Summary

A sesquiterpene-substituted 4-hydroxybenzoic acid, zonaroic acid (5), is described from the brown seaweedDictyopteris undulata (=zonarioides). The absolute stereochemistry in the zonarol (1)-chromazonarol (2) and zonaroic acid (5) series has also been defined. The occurrence of5 along with zonarol (1), the corresponding sesquiterpene-substituted hydroquinone, suggests that 4-hydroxybenzoic acid is the ring precursor as in ubiquinone biogenesis.

Keywords

Hydroquinone Ubiquinone Absolute Stereochemistry Ring Precursor 

References

  1. 1.
    W. Fenical, J. J. Sims, R. M. Wing andP. Radlik, J. org. Chem.38, 2383 (1973).CrossRefPubMedGoogle Scholar
  2. 2.
    W. Fenical andO. Mcolnnell, Experientia31, 1004 (1975).Google Scholar
  3. 3.
    G. Cimino, S. De Stefano andL. Minale, Experientia31, in press (1975).Google Scholar
  4. 4.
    G. Cimino, S. De Stefano andL. Minale, Experientia28, 1401 (1972).Google Scholar
  5. 5.
    Hydrogenation of zonarol was carried out as described for the ester6.Fenical et al. (ref.1) on hydrogenation (PtO2 as catalyst) of zonarol followed by oxidative cleavage of the hydroquinone moiety obtained an epimeric mixture at C-8 (60∶40) of dihydrotauranic acid.Google Scholar
  6. 6.
    L. Ruzicka, O. Dürst andO. Jeger, Helv. chim. Acta30, 353 (1947).CrossRefGoogle Scholar
  7. 7.
    J. D. Cocker andT. G. Halsall, J. chem. Soc.1956, 4262.Google Scholar
  8. 8.
    G. Büchi andK. Biemann, Croat. chem. Acta29, 163 (1957);J. D. Cocker andT. G. Halsall, J. chem. Soc.1957, 4401.Google Scholar
  9. 9.
    W. Klyne andJ. Buckingham, inAtlas of stereochemistry (Chapman and Hall, London 1974), p. 110 and 119.Google Scholar
  10. 10.
    D. R. Threlfall andG. R. Whistance, inAspect of Terpenoid Chemistry and Biochemistry (Ed.T. W. Goodwin, Academic Press, London and New York 1971), p. 357.Google Scholar

Copyright information

© Birkhäuser Verlag 1975

Authors and Affiliations

  • G. Cimino
    • 1
    • 2
    • 3
  • S. de Stefano
    • 1
    • 2
    • 3
  • W. Fenical
    • 1
    • 2
    • 3
  • L. Minale
    • 1
    • 2
    • 3
  • J. J. Sims
    • 1
    • 2
    • 3
  1. 1.Laboratorio per la Chimica di molecole di interesse biologico del C.N.R.NapoliItaly
  2. 2.Institute of Marine ResourcesScripps Institution of OceanographyLa JollaUSA
  3. 3.Department of Plant PathologyUniversity of CaliforniaRiversideUSA

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