Skip to main content

Abstract

Phlobaphenes are reddish-colored, water-insoluble phenolic substances that are believed to be related to co-occurring condensed tannins. The term is also used to describe the red insoluble material produced by treating condensed tannins with mineral acid. The chemical composition of the “natural” phlobaphenes is complex and linked to other extraneous materials in addition to condensed tannins. Phlobaphenes are variable from plant source to plant source and display a variety of functional groups not seen in the condensed tannins. Douglas-fir phlobaphenes are composed of a mixture of polymeric procyanidins, dihydroquercetin, carbohydrate (glucosyl), and methoxyl moieties. Water insolubility appears to be due to the abundance of methoxyl groups.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Stahelin, C.; Hofstetter, J. Chemische untersuchung einiger Rinden. Annal. d. Chemis. u. Pharm. 51: 63 (1844).

    Article  Google Scholar 

  2. Hergert, H.L. Economic importance of flavonoid compounds: wood and bark. In: Geiss-man, T.A. (ed.) The Chemistry of Flavonoid Compounds, The MacMillan Co., New York, pp. 553–592 (1962).

    Google Scholar 

  3. Harvey, A. Tannin Materials with Notes of Tanning Extract Manufacture. Crosby, Lockwood and Son. London, 182p. (1921).

    Google Scholar 

  4. Haslam, E. Chemistry of Vegetable Tannins. Academic Press, New York, 179 p. (1966).

    Google Scholar 

  5. Becker, E.S.; Kurth, E.F. The chemical nature of the extractives from the bark of red fir. Tappi 41: 380 (1958).

    CAS  Google Scholar 

  6. Hergert, H.L.; Blaricom, L.E.; Steinberg, J.C.; Grey, K.R. Isolation and properties of dispersants from western hemlock bark. For. Prod. J. 15: 485 (1965).

    Google Scholar 

  7. Mullick, D.B. Reddish purple pigments in the secondary periderm tissues of western North American conifers. Phytochemistry 8: 2205 (1969).

    Article  CAS  Google Scholar 

  8. Swan, E.P. Characteristics of a phlobaphene from western red cedar bark. For. Prod. J. 13: 195 (1963).

    CAS  Google Scholar 

  9. Zavarin, E.; Snajberk, K. The chemistry of the natural phlobaphenes. III. Pyrolysis of the phlobaphenes from five representative softwood species. Tappi 48: 612 (1965).

    CAS  Google Scholar 

  10. Buchanan, M.A.; Lewis, H.F.; Kurth, E.F. Chemical nature of redwood tannin and phobaphene. Ind. Eng. Chem. 36: 907 (1944).

    Article  CAS  Google Scholar 

  11. Zavarin, E.; Snajberk, K.; Smith, R.M. The chemistry of the natural phlobaphenes. II. Further pyrolysis studies of the phlobaphenes from redwood, (Sequoia sempervirens Endl.) Tappi 48: 574 (1965).

    CAS  Google Scholar 

  12. Zavarin, E.; Snajberk, K. The chemistry of the natural phlobaphenes. I. Pyrolysis of the phlobaphenes from redwood (Sequoia sempervirens Endl.) Tappi 46: 320 (1963).

    CAS  Google Scholar 

  13. Hubbard, J.K.; Kurth, E.F. Douglas-fir bark tannin. J. Am. Leather Chem. Assoc. 44: 604 (1949).

    CAS  Google Scholar 

  14. Hergert, H.L.; Kurth, E.F. The chemical nature of the cork from Douglas-fir bark. Tappi 35: 59 (1952).

    CAS  Google Scholar 

  15. Kurth, E.F.; Aida. K.; Fujii, M. Alcoholysis products from bark flavonoids and polymeric phenolics. Tappi 51: 461 (1968).

    CAS  Google Scholar 

  16. Endres, H.; Stadler, P.; Crone, F.V.D. Uber die Gerbstoffe der Fichtenrinde. X. Mitteilung. Untersuchung uber die Sulfitierung der Phlobaphene des Fichtenrindengerbstoffes. Das Leder 11: 1 (1960).

    CAS  Google Scholar 

  17. Ishak, M.S. Phlobaphenes of Acacia nilotica bark and their sulphitation. Leather Sci. 20: 41 (1973).

    CAS  Google Scholar 

  18. Ishak, M.S. Some aspects on the chemistry of phlobaphenes from Acaia nilotica bark. Egypt. J. Chem. 17: 699 (1974).

    CAS  Google Scholar 

  19. Murko, V.D.; Ramic, S.; Kekic, M. Die Gerbstoffe der Dalmatinischen Salvia officinalis and deren Veranderung wahrend der Lagerung. Planta Medica 25: 295 (1974).

    Article  PubMed  CAS  Google Scholar 

  20. Styles, E.D.; Oldriska, C. Genetic control of 3-hydroxy-and 3-deoxy-flavonoids in Zea mays. Phytochemistry 14: 413 (1975).

    Article  CAS  Google Scholar 

  21. Styles, E.D.; Oldriska, C. The genetic control of flavonoid synthesis in maize. Can. J. Genet. Cytol. 19: 289 (1977).

    CAS  Google Scholar 

  22. Mathur, J.M.S.; Sharma, N.D. Unusual occurrence of phlobaphenes: the non-anthocyanic co-pigments in maize embryo. Maize Genetics Cooperation Newsletter 50: 48 (1976).

    Google Scholar 

  23. Bate-Smith, E.C. Luteoforol (3’,4,4’,5,7-pentahydroxyflavan) in Sorghum vulgare L. Phytochemistry 8: 1803 (1969).

    Article  CAS  Google Scholar 

  24. Dhake, J.D.; Girhe, S.N. Chemical nature of extraneous components of Bija Pterocarpus marsupium Roxb. IPPTA 21: 63 (1984).

    CAS  Google Scholar 

  25. Duran, N.; Rojas, H.; Nascimento, M.G.; Freer, J.; Baeza, J. Biomass photochemistry II. Chemiluminescence in the peroxidation of tannin, phlobaphene and catechin. Cellulose Chem. Technol. 18: 411 (1984).

    CAS  Google Scholar 

  26. Duran, N.; Baeza, J.; Freer, J.; Rojas, N.; Nascimento, M.G. Biomass photochemistry, VI: Light-induced oxidation of phlobaphene from wood. Polymer Photochem. 6: 393 (1985).

    Article  CAS  Google Scholar 

  27. Baeza, J.; Freer, J.; Rojas, N.; Duran, N. Conductimetric method for the determination of phenolic groups in phlobaphene and tannin from Pinus radiata D. Don: solvent effect. Analyst 110: 1407 (1985).

    Article  CAS  Google Scholar 

  28. Young, D.A.; Cronje, A.; Botes, A.L.; Ferreira, D.; Roux, D.G. Synthesis of condensed tannins. Part 14. Biflavanoid profisetinidins as synthons. The acid induced `phlobaphene’ reaction. J. Chem. Soc. Perkin Trans. 1: 2521 (1985).

    Article  Google Scholar 

  29. Steenkamp, J.A.; Steynberg, J.P.; Brandt, E.V.; Ferreira, D.; Roux, D.G., Phlobatannins, a novel class of ring-isomerized condensed tannins. J. Chem. Soc. Chem. Commun.: 1678 (1985).

    Google Scholar 

  30. Steynberg, J.P.; Young, D.A.; Burger, J.F.W.; Ferreira, D.; Roux, D.G. Phlobatannins via facile ring isomerizations of profisetinidin and prorobinetinidin condensed tannin units. J. Chem. Soc. Chem. Commun.: 1013 (1986).

    Google Scholar 

  31. Foo, L.Y.; Karchesy, J.J. Procyanidin polymers of Douglas-fir bark. Structure from degradation with phloroglucinol. Phytochemistry (in press).

    Google Scholar 

  32. Porter, L.J.; Newman, R.H.; Foo, L.Y.; Wong, H.; Hemingway, R.W. Polymeric proanthocyanidins. 13C-NMR studies of procyanidins. J. Chem. Soc. Perkin Trans. 1:1217 (1982).

    Google Scholar 

  33. Markham, K.R.; Chari, V.M.; Mabry, T.J. Carbon-13 NMR spectroscopy of flavonoids. In: Harborne, J.B.; Mabry, T. J. (eds.) The Flavonoids: Advances in Research. Chapman and Hall, London, pp. 19–134 (1982).

    Google Scholar 

  34. Foo, L.Y.; Karchesy, J.J. Polyphenolic glycosides from Douglas-fir inner bark. Phytochemistry (in press).

    Google Scholar 

  35. Agrawal, P.K., Thakur, R.S., 13C NMR spectroscopy of lignin and neolignan derivatives. Magnetic Resonance in Chemistry 23: 389 (1985).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1989 Plenum Press, New York

About this chapter

Cite this chapter

Foo, L.Y., Karchesy, J.J. (1989). Chemical Nature of Phlobaphenes. In: Hemingway, R.W., Karchesy, J.J., Branham, S.J. (eds) Chemistry and Significance of Condensed Tannins. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-7511-1_6

Download citation

  • DOI: https://doi.org/10.1007/978-1-4684-7511-1_6

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4684-7513-5

  • Online ISBN: 978-1-4684-7511-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics