Precipitation of metal ions by plant polyphenols: Optimal conditions and origin of precipitation

Journal of Agricultural and Food Chemistry

Volumn 44, Issue 2, 1996, Pages 599-606

  McDonald, Mark ^a   Mila, Isabelle ^a   Scalbert, Augustin ^a  

^a AGROPARISTECH   (France)

Author keywords

Complexation; Copper; Metal ions; Polyphenols; Precipitation; Tannins; Zinc

Indexed keywords

EID: 0001368233     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf950459q     Document Type: Article

References (38)

1. Abakumov, G. A.; Lobanov, A. V.; Cherkasov, V. K.; Bazuvaev, G. A. The synthesis and properties of o-semiquinolate copper complexes. Inorg. Chim. Acta 1981, 49, 135-138.
2. Aplincourt, M.; Bee, A.; Gerard, C.; Hugel, R. P.; Njomgang, R.; Prudhomme, J.-C. Modelling of the interactions of metal cations with soil organic matter. Part 3. Thermodynamic stability of copper(II) and iron(III) complexes with 3,4-dihydroxybenzoic acid. J. Chem. Res. (S) 1987, 398-399.
3. Balla, J.; Kiss, T.; Jameson, R. F. Copper(II)-catalyzed oxidation of catechol by molecular oxygen in aqueous solution. Inorg. Chem. 1992, 31, 58-62.
4. Brune, M.; Rossander, L.; Hallberg, L. Iron absorption and phenolic compounds: importance of different phenolic structures. Eur. J. Clin. Nutr. 1989, 43, 547-558.
5. Chaberek, S.; Martell, A. E. Organic Sequestring Agents; Wiley: New York, 1959.
6. Chang, C. W.; Anderson, J. U. Flocculation of clays and soils by organic compounds. Soil Sci. Soc. Am. Proc. 1968, 32, 23-27.
7. Czochanska, Z.; Foo, L. Y.; Newman, R. H.; Porter, L. J. Polymeric proanthocyanidins. Stereochemistry, structural units and molecular weight. J. Chem. Soc., Perkin Trans. 1 1980, 2278-2286.
8. Durkee, G. E. Micronutrient foliar sprays. Agrichem. West 1965, 1, 17-19.
9. Gerega, K.; Kozlowski, H.; Kiss, T.; Micera, G.; Strinna Erre, L.; Cariati, F. Cupric complexes with 3,4-dihydroxybenzoic acid. Inorg. Chim. Acta 1987, 138, 31-34.
10. Gray, V. E. The acidity of wood. J. Inst. Wood Sci. 1958, 1, 58-64.
11. Grimshaw, J. Phenolic aralkylamines, monohydric alcohols, monocarbaldehydes, monoketones and monocarboxylic acids. In Rodd's Chemistry, 2nd ed.; Coffey, S., Ed.; Elsevier: Amsterdam, 1976; pp 141-202.
12. Haddock, E. A.; Al-Shafi, S. M. K.; Gupta, R. K.; Magnolato, D.; Haslam, E. The metabolism of gallic acid and hexahydroxydiphenic acid in plants. Part 1. Introduction. Naturally occurring galloyl esters. J. Chem. Soc., Perkin Trans. 1 1982, 2515-2524.
13. Hagerman, A. E.; Butler, L. G. Condensed tannin purification and characterization of tannin-associated proteins. J. Agric. Food Chem. 1980, 28, 947-952.
14. Haslam, E. Plant polyphenols (syn. vegetable tannins) and chemical defense - a reappraisal. J. Chem. Ecol. 1988, 14, 1789-1805.
15. Haslam, E. Plant Polyphenols, Vegetable Tannins Revisited; Cambridge University Press: Cambridge, U.K., 1989.
16. Haslam, E.; Haworth, R. D.; Mills, S. D.; Rogers, H. J.; Armitage, R.; Searle, T. Gallotannins. Part II. Some esters and depsides of gallic acid. J. Chem. Soc. 1961, 1836-1842.
17. Kennedy, J. A.; Powell, K. J. Polyphenol interactions with aluminium(III) and iron(III): their possible involvement in the podzolization process. Aust. J. Chem. 1985, 38, 879-888.
18. Laks, P. E.; McKaig, P. A.; Hemingway, R. W. Flavonoid biocides: wood preservatives based on condensed tannins. Holzforschung 1988, 42, 299-306.
19. McGraw, G. W.; Rials, T. G.; Steynberg, J. P.; Hemingway, R. W. Chemistry of pecan tannins and analysis of cure of pecan tannin-based cold-setting adhesives with a DMA microbeam test. In Plant Polyphenols, Synthesis, Properties, Significance; Hemingway, R. W., Laks, P. E., Eds.; Plenum Press: New York, 1992; pp 979-990.
20. Meunier, L.; Vaney, C. La Tannerie; Gauthier-Villars: Paris, 1903.
21. Mila, I.; Scalbert, A. Tannin antimicrobial properties through iron deprivation: a new hypothesis. Acta Hortic. 1994, 381, 749-755.
22. - . A potentiometric study in 0.6 M Na(Cl). Acta Chem. Scand. 1981, A35, 201-212.
23. Öhman, L.-O.; Sjöberg, S. Equilibrium and structural studies of silicon(IV) and aluminium(III) in aqueous solution. 4. A potentiometric study of polynuclear aluminium(III) hydroxo complexes with gallic acid in hydrolyzed aluminium(III) solutions. Acta Chem. Scand. 1982, A36, 47-53.
24. Okuda, T.; Mori, K.; Shiota, M.; Ida, K. Effect of the interaction of tannins with coexisting substances. II. Reduction of heavy metal ions and solubilization of precipitates. Yakugaku Zasshi 1982, 102, 735-742.
25. Powell, H. K. J.; Rate, A. W. Aluminium-tannin equilibria: a potentiometric study. Aust. J. Chem. 1987, 40, 2015-2022.
26. Randall, J. M.; Bermann, R. L.; Garrett, V.; Waiss, A. C. J. Use of bark to remove heavy metal ions from waste solutions. For. Prod. J. 1974, 24, 80-84.
27. 4) type: synthesis and properties of complexes derived from pyrocatechol and tetrachloropyrocatechol. Inorg. Chem. 1966, 5, 1542-1551.
28. Sampat, S. S.; Vora, J. C. Influence of colloids on the corrosion of 3S aluminium in low flow velocity water. Indian J. Technol. 1975, 13, 476.
29. Scalbert, A. Antimicrobial properties of tannins. Phytochemistry 1991, 30, 3875-3883.
30. Scalbert, A.; Monties, B.; Janin, G. Tannins in wood: comparison of different estimation methods. J. Agric. Food Chem. 1989, 37, 1324-1329.
31. Seavell, A. J. Anticorrosive properties of mimosa (wattle) tannin. J. Oil Col. Chem. Assoc. 1978, 61, 439-462.
32. Slabbert, N. P. Mimosa-Al tannages - an alternative to chrome tanning. J. Am. Leather Chem. Assoc. 1981, 76, 231-244.
33. Slabbert, N. Complexation of condensed tannins with metal ions. In Plant Polyphenols; Hemingway, R. W., Laks, P. E., Eds.; Plenum Press: New York, 1991; pp 421-445.
34. Spencer, C. M.; Cai, Y.; Martin, R.; Gaffney, S. H.; Goulding, P. N.; Magnolato, D.; Lilley, T. H.; Haslam, E. Polyphenol complexation - some thoughts and observations. Phytochemistry 1988, 27, 2397-2409.
35. Steinhaus, R. K.; Barsuhn, C. L. Kinetics of the metal-exchange reaction between N,N′-bis(2-picolyl)ethylenediamineniekel(II) and copper(II). Inorg. Chem. 1974, 13, 2922-2929.
36. Sykes, R. L.; Hancock, R. A.; Orsulick, S. T. Tannage with aluminium salts. Part II. Chemical basis for the reactions with polyphenols. J. Soc. Leather Technol. Chem. 1980, 64, 32-37.
37. Viriot, C.; Scalbert, A.; Hervé du Penhoat, C. L. M.; Moutounet, M. Ellagitannins in woods of sessile oak and sweet chestnut - dimerization and hydrolysis during wood ageing. Phytochemistry 1994, 36, 1253-1260.
38. Weber, G. Investigation of Cu(II)-catechin interactions by means of liquid chromatography with electrochemical detection. Anal. Chim. Acta 1990, 232, 377-383.