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Complexation of Condensed Tannins with Metal Ions

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Plant Polyphenols

Part of the book series: Basic Life Sciences ((BLSC,volume 59))

Abstract

The ortho-dihydroxyl group on the flavonoid B-ring of condensed tannins is the main group involved in metal complexation. Potentimetric and spectrophotometric studies have shown that iron(III) forms mono-di-, and trisdentate complexes with tannins and o-diphenol ligands as the pH is increased. These colored complexes have been found to owe their intense coloration to charge transfer processes. Similar types of complexes are formed with aluminum(III) ions although these are colorless. The germanium(IV)-o-diphenol complex is a tris-chelate, whereas, that with boric acid is a mono-chelated complex with tetrahedral symmetry. Formation constants of the above metal complexes are shown to be related to the ligand ionization constants and those metal ions that form soluble tannin complexes have been found to conform to the normal complexation behavior of o-diphenol ligands. A number of divalent metal complexes form well-defined complexes with o-diphenols although the tannin complexes with these metal ions are less well studied. The order of tannin complex stability has, however, been determined by the pH of incipient precipitation and some interesting orders of stability established. Titanium(IV), molybdenum(VI), and tungsten(VI) ions have also been found to form highly colored (charge transfer) complexes with condensed tannins.

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References

  1. Mabry, T.J.; Markham, K.R.; Thomas, M.B. The systematic identification of flavonoids. Springer-Verlag, Berlin, pp. 50–56 (1970).

    Book  Google Scholar 

  2. Schoeller, W.R.; Powell, A.R. The analysis of minerals and ores of the rarer elements, 3rd Ed. Griffin and Co. Ltd., London, p. 8 (1955).

    Google Scholar 

  3. Slabbert, N.P. Ionisation of some flavanols and dihydroflavonols. Tetrahedron 33:821 (1977).

    Article  CAS  Google Scholar 

  4. Slabbert, N.P. Metal complexes of black wattle tannins and related model polyphenols. PhD Thesis, Rhodes University, Grahamstown, South Africa, (1972).

    Google Scholar 

  5. Roux, D.G.; Drewes, S.E.; Saayman, H.M. Simple interrelationships within the complexity of wattle (Mimosa) extract composition. J. Soc. Leather Trades’ Chem. 49:416 (1965).

    CAS  Google Scholar 

  6. Abe, I.; Funaoka, M.; Kodama, M. Phenolic nuclei of condensed tannins. Japan Wood Res. Soc. 33:582 (1986).

    Google Scholar 

  7. Bizri, Y.; Chromer, M.; Ezzat, A.; Scharff, J. Metal complexation by natural polymeric materials: interactions of chestnut tannins with copper(II) ions. J. Chem. Research (S):306 (1984).

    Google Scholar 

  8. Bartusek, A.; Zelinka, J. Potentiometrische unterzuchung der berylliumkomplexe mit o-diphenolen, 1,8-dihydroxynaphthalinderivatenund o-phenolcarbonsauren. Coll.Czech. Chem. Comm. 32:992 (1967).

    Article  CAS  Google Scholar 

  9. Harvey, A.E.; Manning, D.L. Spectrophotometric methods of establishing empirical formulas of colored complexes in solution. J. Amer. Chem. Soc. 72:4488 (1950).

    Article  CAS  Google Scholar 

  10. Schwarzenbach, G.; Willi, A. Metallindikatoren III. Die Komplexbildung der Brenzcatechin-3,5-disulfosaure met dem eisen(III)-ion. Helv. Chim. Acta. 61:528 (1951).

    Article  Google Scholar 

  11. Sommer, L. Uber die genaue spektrophotometriche eisen (III)-und titan(IV)-bestimmung met polyphenolen und verwandten Verbindungen. Acta Chim. Hung. 33:23 (1962).

    CAS  Google Scholar 

  12. Jorgensen, C.K. Absorption spectra and chemical bonding in complexes. Pergamon Press, Oxford, p. 146 (1962).

    Google Scholar 

  13. King, H.G.C.; White, T. The chemistry of vegetable tannins. Croydon, p. 42 (1956).

    Google Scholar 

  14. Roux, D.G. Photometric methods of tannin analysis for black wattle tannin. J. Soc. Leather Trades’ Chem. 35:322 (1951).

    CAS  Google Scholar 

  15. Seavell, A. J. Anticorrosive properties of mimosa (wattle) tannin. J. Oil Col. Chem. Assoc. 61:439 (1978).

    CAS  Google Scholar 

  16. Draper, P.A. Performance of a novel corrosion inhibiting pigment of low toxicity, in ferrous metal primers, applied to marginally prepared surfaces. In: Proceedings of the Oil and Colour Chemists’ Assoc. Biannual Conference, Edinburgh, p. 49 (1985).

    Google Scholar 

  17. Sharphouse, J.H. Leather technician’s handbook. Vernon Lock Ltd., London, p. 178 (1983).

    Google Scholar 

  18. Pitchet, P; Benoit, R.L. Complexes of germanium(IV) with anions of o-diphenols and their stability constants. Inorg. Chtm. 6:1505 (1967).

    Article  Google Scholar 

  19. Stejsak, V.; Bartusek, M. Germanium(IV)-chelate met o-diphenolen. Col November 18, 19911. Czech. Chem. Comm. 38:3103 (1973).

    Article  Google Scholar 

  20. Bevillar, P. Les acides phenolgermaniques. Bull. Soc. Chim. France:296 (1954).

    Google Scholar 

  21. Roux, D.G. The purification of black wattle tannin and its effect on combustion analysis. J. Soc. Leather Trades2019; Chem. 33:393 (1949).

    CAS  Google Scholar 

  22. Havelkova, L.; Bartusek, M. Potentiometric investigation of the complexes of aluminium with o-diphenols, chromotropic acid and o-diphenol carboxylic acids. Coll. Czech. Chem. Comm. 34:3722 (1969).

    Article  CAS  Google Scholar 

  23. Porter, L.J.; Markham K.R. The aluminium(III) complexes of hydroxy-flavones in absolute methanol. J. Chem. Soc. (C):344 (1970).

    Google Scholar 

  24. Slabbert, N.P. Mimosa-Al tannages-an alternative to chrome tanning. J. Amer. Leather Chem. Assoc. 76:231 (1981).

    CAS  Google Scholar 

  25. Antikainen, P.J.; Oksanen, H. On the oxyanion chelates of o-diphenols. Acta Chem. Stand. 22:2867 (1968).

    Article  CAS  Google Scholar 

  26. Timberlake, C.F. A potentiometric and polarographic study of copper-catechol complexes. J. Chem. Soc.:4987 (1957).

    Google Scholar 

  27. Murakami, Y.; Nahamura, K.; Takunaga, M. Stability order in metal chelate compounds. Bull. Chem. Soc. Japan 36:669 (1963).

    Article  CAS  Google Scholar 

  28. Jameson, R.F.; Neillie, W.F.S. Complexes formed by adrenaline and related compounds with transitional-metal ions. J. Inorg. Nucl. Chem. 28:2667 (1966).

    Article  CAS  Google Scholar 

  29. Tyson, C.A.; Martell, A.E. Equilibria of metal ions with pyrocatechol and 3,5-di-t-butylpyro-catechol. J. Amer. Chem. Soc. 90:3379 (1968).

    Article  CAS  Google Scholar 

  30. Athavale, V.T.; Prabhu, L.H.; Vartak, D.G. Solution stability constants of some metal complexes of derivatives of catechol. J. Inorg. Nucl. Chem. 28:1237 (1966).

    Article  CAS  Google Scholar 

  31. Martell, A.E.; Calvin, M. Chemistry of the metal chelate compounds. Prentice Hall, New York, p. 186 (1952).

    Google Scholar 

  32. Irvine, H.; Williams, R.J.P. The stability of transition-metal complexes. J. Chem. Soc.:3192 (1953).

    Google Scholar 

  33. Schmidt, E.L.; Lotz, W.R. Tropical wood or bark extracts as preservatives for southern pine: a preliminary laboratory evaluation. Amer. Wood-Preservers’ Assoc.:173 (1988).

    Google Scholar 

  34. Laks, P.E. Wood preservation as trees do it. Amer. Wood Preservers’ Assoc.:147 (1988).

    Google Scholar 

  35. Pizzi, A.; Conradie, W.E.; Jansen, A. Polyflavonoid tannins-a main cause of soft-rot failure in CCA-treated timber. Wood Sci. Technol. 20:71 (1986).

    Article  CAS  Google Scholar 

  36. Khayat, Y.; Cromer-Morin, M.; Scharff, J.P. Interactions of Pb(II) ions with 3,5-pyrocate-choldisulphonic and 3,4-dihydroxybenzoic acids. J. Inorg. Nucl. Chem. 43:627 (1981).

    Article  CAS  Google Scholar 

  37. Sommer, L. Titan(IV)-chelate mit brenzcatechin, brenzcatechin-3,5-disulfonsaure und protocatechusaure. Coll. Czech. Chem. Comm. 28:2102 (1963).

    CAS  Google Scholar 

  38. Brown, D.H. Tungstate complexes with catechol. J. Inorg. Nucl. Chem. 17:146 (1961).

    Article  CAS  Google Scholar 

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© 1992 Springer Science+Business Media New York

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Slabbert, N. (1992). Complexation of Condensed Tannins with Metal Ions. In: Hemingway, R.W., Laks, P.E. (eds) Plant Polyphenols. Basic Life Sciences, vol 59. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-3476-1_23

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  • DOI: https://doi.org/10.1007/978-1-4615-3476-1_23

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-6540-2

  • Online ISBN: 978-1-4615-3476-1

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