Biogenesis of Condensed Tannins — An Overview

  • Herbert L. Hergert


There are currently four hypotheses as to how condensed tannins are produced in nature. In order to explain the 2,3-cis configuration of frequently encountered proanthocyanidin polymers, each of these biosynthetic proposals invoke isomerase enzymes or chemical intermediates not yet encountered in nature. Thus, substantial further study is required to clarify the pathways involved. An experimental program is proposed to achieve this objective.


Condensed Tannin Shikimic Acid Coniferyl Alcohol Quinone Methide Chain Terminator 
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  1. 1.
    Freudenberg, K.; Neish, A.C. Constitution and Biosynthesis of Lignin. Springer-Verlag, Heidelberg. pp 82–97 (1968).Google Scholar
  2. 2.
    Sarkanen, K.V. Precursors and their polymerization. In: Sarkanen, K.V.; Ludwig, C.H. (eds) Lignins. Wiley-Interscience, New York. pp. 95–163 (1971).Google Scholar
  3. 3.
    Goldschmid, O.; Hergert, H.L. TAPPI 44 (12): 858 (1961).Google Scholar
  4. 4.
    Hergert, H.L. Economic importance of flavonoid compounds: wood and bark. In: Geissman, T.A. (ed.) The Chemistry of Flavonoid Compounds. Pergamon Press, Oxford. pp 553–592 (1962).Google Scholar
  5. 5.
    Hasegawa, M.; Hasue, M. J. Jap. For. Soc. 44 (9): 244 (1962).Google Scholar
  6. 6.
    Samejima, M.; Yoshimoto, T. Systematic studies on the stereochemical composition of proanthocyanidins from coniferous bark. Mokuzai Gakkaishi 28 (1): 67 (1982).Google Scholar
  7. 7.
    Roux, D.G.; Ferreira, D. α-hydroxychalcones as intermediates in flavanoid biogenesis: the significance of recent chemical analogies. Phytochemistry 13: 2039 (1974).CrossRefGoogle Scholar
  8. 8.
    Hillis, W.E. Biosynthesis of tannin. In: Higuchi, T. (ed.) Biosynthesis and Biodegradation of Wood Components. Academic Press, New York, pp. 325–347 (1985).Google Scholar
  9. 9.
    Haslam, E. Proanthocyanidins. In: Harborne, J.B.; Mabry, T.J. (eds.) The Flavonoids: Advances in Research. Chapman and Hall, London. pp. 417–447 (1982).Google Scholar
  10. 10.
    Platt, R.V.; Opie, C.T.; Haslam, E. Plant proanthocyanidins. Part 8. Biosynthesis of flavan-3-ols and other secondary plant products from 2S-phenylalanine. Phytochemistry 23: 2211 (1984).CrossRefGoogle Scholar
  11. 11.
    Stafford, H.A. Enzymic regulation of procyanidin biosynthesis: lack of a flav-3-en-3-ol intermediate. Phytochemistry 22: 2643 (1983).CrossRefGoogle Scholar
  12. 12.
    Stafford, H.A.; Lester, H.H.; Porter, L.J. Chemical and enzymatic synthesis of monomeric procyanidins (leucocyanidins or 3’,4’,5,7-tetrahydroxyflavan-3,4-diols) from (2R,3R)dihydroquercetin. Phytochemistry 24: 333 (1985).CrossRefGoogle Scholar
  13. 13.
    Hemingway, R.W., Laks, P.E. Condensed tannins: a proposed route to 2R,3R-(2,3-cis)proanthocyanidins. J. Chem. Soc. Chem. Commun.: 746 (1985).Google Scholar
  14. 14.
    Hemingway, R.W., Foo, L.Y. Condensed tannins: quinone methide intermediates in procyanidin synthesis. J. Chem. Soc. Chem. Commun.: 1035 (1983).Google Scholar
  15. 15.
    Attwood, M.R., Brown, B.R., Lisseter, S.G., Torrero, C.L., Weaver, P.M. Spectral evidence for the formation of quinone-methide intermediates from 5- and 7-hydroxyflavonoids. J. Chem. Soc. Chem. Commun.:177 (1984).Google Scholar
  16. 16.
    Wong, E.; Birch, E. J. J. Chem. Soc. Chem. Comm.: 979 (1975).Google Scholar
  17. 17.
    Bohm, B.A. The minor flavonoids. In: Harborne, J.B.; Mabry, T.J. (eds.) The Flavonoids: Advances in Research. Chapman and Hall, London. pp 313–416 (1982).Google Scholar
  18. 18.
    Malan, E.; Roux, D.G. (+)-trans-Pubeschin, the first catechin analogue of peltygynoids from Peltogyne pubescens and P. venosa. Phytochemistry 13: 1575 (1974).CrossRefGoogle Scholar
  19. 19.
    Foo, L.Y. Configuration and conformation of dihydroflavonols from Acacia melanoxylon. Phytochemistry 26(3): 813 (1987).CrossRefGoogle Scholar
  20. 20.
    Lundgren, L.N., Theander, O. Cis and trans-dihydroquercetin glucosides from needles of Pinus sylvestris. Phytochemistry 27: 829 (1988).Google Scholar

Copyright information

© Plenum Press, New York 1989

Authors and Affiliations

  • Herbert L. Hergert
    • 1
  1. 1.Repap Technologies Inc.Valley ForgeUSA

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