View PDF Version
 
DOI: 10.1039/A701334E (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 1943-1950

Oligomeric flavanoids. Part 26. Structure and synthesis of the first profisetinidins with epifisetinidol constituent units

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

Petrus J. Steynberg, Jan P. Steynberg, E. Vincent Brandt, Daneel Ferreira and Richard W. Hemingway

Abstract

The natural occurrence of the first oligomeric profisetinidins with (2R,3R)-2,3-cis-epifisetinidol chain extender units is demonstrated in the bark of Pithecellobium dulce (Guamúchil). Semi-synthesis using the appropriate flavan-3-ol and flavan-3,4-diol precursors permits unequivocal structural and stereochemical assignment of the novel dimeric epifisetinidol-(4β,8)-catechin and epicatechins 16 and 18, the trimeric bis-epifisetinidol-(4β,6[hair space]:[hair space]4β ,8)-catechin and epicatechins 33 and 35, the fisetinidol-(4α,8)-catechin-(6,4β)- epifisetinidol 37 and fisetinidol-(4α,8)-epicatechin-(6,4β)- epifisetinidol 39.

References

  1. J. J. Botha, D. Ferreira and D. G. Roux, J. Chem. Soc., Perkin Trans. 1, 1981, 1235 RSC.
  2. D. G. Roux and D. Ferreira, Pure Appl. Chem., 1982, 54, 2465 CAS.
  3. D. G. Roux and D. Ferreira, Fortschr. Chem. Org. Naturst., 1982, 41, 47 Search PubMed.
  4. J. J. Botha, P. M. Viviers, D. A. Young, I. C. du Preez, D. Ferreira, D. G. Roux and W. E. Hull, J. Chem. Soc., Perkin Trans. 1, 1982, 527 RSC.
  5. P. M. Viviers, J. J. Botha, D. Ferreira, D. G. Roux and H. M. Saayman, J. Chem. Soc., Perkin Trans. 1, 1983, 17 RSC.
  6. P. M. Viviers, H. Kolodziej, D. A. Young, D. Ferreira and D. G. Roux, J. Chem. Soc., Perkin Trans. 1, 1983, 2555 RSC.
  7. A. Cronjé, J. P. Steynberg, E. V. Brandt, D. A. Young and D. Ferreira, J. Chem. Soc., Perkin Trans. 1, 1993, 2467 RSC.
  8. L. J. Porter, in The Flavonoids. Advances in Research since 1980, ed. J. B. Harborne, Chapman and Hall, London, 1988, p. 21 Search PubMed; and in Flavonoids. Advances in Research since 1986, ed. J. B. Harborne, Chapman and Hall, London, 194, p. 23 Search PubMed.
  9. E. V. Brandt, D. A. Young, D. Ferreira and D. G. Roux, J. Chem. Soc., Perkin Trans. 1, 1987, 2353 RSC.
  10. J. A. Steenkamp, J. C. S. Malan, D. G. Roux and D. Ferreira, J. Chem. Soc., Perkin Trans. 1, 1988, 1325 RSC.
  11. J. P. Steynberg, J. F. W. Burger, J. C. S. Malan, A. Cronjé, D. A. Young and D. Ferreira, Phytochemistry, 1990, 29, 275 CrossRef CAS.
  12. J. C. S. Malan, J. A. Steenkamp, J. P. Steynberg, D. A. Young and D. Ferreira, J. Chem. Soc., Perkin Trans. 1, 1990, 209 RSC.
  13. J. C. S. Malan, D. A. Young, J. P. Steynberg and D. Ferriera, J. Chem. Soc., Perkin Trans. 1, 1990, 227 RSC.
  14. L. Y. Foo, J. Chem. Soc., Chem. Commun., 1986, 236 RSC.
  15. E. Malan and A. Sireeparsad, Phytochemistry, 1995, 38, 237 CrossRef CAS; E. Malan, A. Sireeparsad, J. F. W. Burger and D. Ferreira, Tetrahedron Lett., 1994, 35, 7415 CrossRef CAS.
  16. J. A. Parrotta, Southern Forest Experiment Station, Institute of Tropical Forestry, U.S.D.A. Forest Service, New Orleans, Report SM-40, 1991.
  17. D. G. Roux and E. Paulus, Biochem. J., 1961, 78, 120 CAS.
  18. S. E. Drewes and D. G. Roux, J. Chem. Soc. (C), 1966, 1644 RSC.
  19. R. W. Hemingway, L. Y. Foo and L. J. Porter, J. Chem. Soc., Perkin Trans. 1, 1982, 1209 RSC.
  20. S. E. Drewes and D. G. Roux, Biochem. J., 1965, 96, 681 CAS.
  21. D. G. Roux and E. A. Maihs, Biochem. J., 1960, 74, 44 CAS.
  22. S. E. Drewes and D. G. Roux, Biochem. J., 1965, 94, 482 CAS.
  23. H. K. L. Hundt and D. G. Roux, J. Chem. Soc., Chem. Commun., 1978, 696 RSC; J. Chem. Soc., Perkin Trans. 1, 1981, 1227 Search PubMed.
  24. J. H. van der Westhuizen, D. Ferreira and D. G. Roux, J. Chem. Soc., Perkin Trans. 1, 1981, 1220 RSC.
  25. L. Y. Foo and L. J. Porter, J. Chem. Soc., Perkin Trans. 1, 1983, 1535 RSC.
  26. J. P. Steynberg, E. V. Brandt, D. Ferreira, C. A. Helfer, W. L. Mattice, D. Gornik and R. W. Hemingway, Mag. Reson. Chem., 1995, 33, 611 Search PubMed.
  27. C. A. Hunter and J. K. M. Saunders, J. Am. Chem. Soc., 1990, 112, 5523.
  28. A. C. Fletcher, L. J. Porter, E. Haslam and R. K. Gupta, J. Chem. Soc., Perkin Trans. 1, 1977, 1628 RSC.
  29. M. W. Barrett, W. Klyne, P. M. Scopes, A. C. Fletcher, L. J. Porter and E. Haslam, J. Chem. Soc., Perkin Trans. 1, 1979, 2375 RSC.
Click here to see how this site uses Cookies. View our privacy policy here.