Abstract
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.
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References
Freudenberg, K.; Neish, A.C. Constitution and Biosynthesis of Lignin. Springer-Verlag, Heidelberg. pp 82–97 (1968).
Sarkanen, K.V. Precursors and their polymerization. In: Sarkanen, K.V.; Ludwig, C.H. (eds) Lignins. Wiley-Interscience, New York. pp. 95–163 (1971).
Goldschmid, O.; Hergert, H.L. TAPPI 44 (12): 858 (1961).
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).
Hasegawa, M.; Hasue, M. J. Jap. For. Soc. 44 (9): 244 (1962).
Samejima, M.; Yoshimoto, T. Systematic studies on the stereochemical composition of proanthocyanidins from coniferous bark. Mokuzai Gakkaishi 28 (1): 67 (1982).
Roux, D.G.; Ferreira, D. α-hydroxychalcones as intermediates in flavanoid biogenesis: the significance of recent chemical analogies. Phytochemistry 13: 2039 (1974).
Hillis, W.E. Biosynthesis of tannin. In: Higuchi, T. (ed.) Biosynthesis and Biodegradation of Wood Components. Academic Press, New York, pp. 325–347 (1985).
Haslam, E. Proanthocyanidins. In: Harborne, J.B.; Mabry, T.J. (eds.) The Flavonoids: Advances in Research. Chapman and Hall, London. pp. 417–447 (1982).
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).
Stafford, H.A. Enzymic regulation of procyanidin biosynthesis: lack of a flav-3-en-3-ol intermediate. Phytochemistry 22: 2643 (1983).
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).
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).
Hemingway, R.W., Foo, L.Y. Condensed tannins: quinone methide intermediates in procyanidin synthesis. J. Chem. Soc. Chem. Commun.: 1035 (1983).
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).
Wong, E.; Birch, E. J. J. Chem. Soc. Chem. Comm.: 979 (1975).
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).
Malan, E.; Roux, D.G. (+)-trans-Pubeschin, the first catechin analogue of peltygynoids from Peltogyne pubescens and P. venosa. Phytochemistry 13: 1575 (1974).
Foo, L.Y. Configuration and conformation of dihydroflavonols from Acacia melanoxylon. Phytochemistry 26(3): 813 (1987).
Lundgren, L.N., Theander, O. Cis and trans-dihydroquercetin glucosides from needles of Pinus sylvestris. Phytochemistry 27: 829 (1988).
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© 1989 Plenum Press, New York
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Hergert, H.L. (1989). Biogenesis of Condensed Tannins — An Overview. 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_4
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DOI: https://doi.org/10.1007/978-1-4684-7511-1_4
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