Method for Estimation of Proanthocyanidins Based on Their Acid Depolymerization in the Presence of Nucleophiles

Journal of Agricultural and Food Chemistry

Volumn 45, Issue 4, 1997, Pages 1195-1201

  Matthews, Sara ^a   Mila, Isabelle ^a   Scalbert, Augustin ^a   Pollet, Brigitte ^a   Lapierre, Catherine ^a   Hervé Du Penhoat, Catherine L M ^b   Rolando, Christian ^b   Donnelly, Dervilla M X ^c  

^a AGROPARISTECH   (France)

^b ECOLE NORMALE SUPÉRIEURE   (France)

^c UNIVERSITY COLLEGE DUBLIN   (Ireland)

Author keywords

Estimation; Phloroglucinol; Proanthocyanidins; Tannins; Thiolysis

Indexed keywords

EID: 0000959850     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf9607573     Document Type: Article

References (35)

1. Achmadi, S.; Syahbirin, G.; Choong, E. T.; Hemingway, R. W. Catechin-3-O-rhamnoside chain extender units in polymeric procyanidins from mangrove bark. Phytochemistry 1994, 35, 217-219.
2. Aritomi, M.; Donnelly, D. M. X. Stilbene glucosides in the bark of Picea sitchensis. Phytochemistry 1976, 15, 2006-2008.
3. 13C-NMR spectroscopy of cellulose and related carbohydrates. Wood Res. Technol. Notes 1981, 63-93.
4. Baldé, A. M.; Pieters, L. A.; Wray, V.; Kolodziej, H.; Van den Berghe, D. A.; Claeys, M.; Vlietinck, A. J. Dimeric and trimeric proanthocyanidins possessing a doubly linked structure from Pavetta owariensis. Phytochemistry 1991, 30, 4129-4135.
5. 13C assignment of complex polycyclic aromatic hydrocarbons. J. Org. Chem. 1985, 50, 3029-3034.
6. Betts, M. J.; Brown, B. R.; Brown, P. E.; Pike, W. T. Reaction of flavanoids with mercaptoacetic acid. J. Chem. Soc., Chem. Commun. 1967, 1110-1112.
7. Brown, B. R.; Shaw, M. R. Reactions of flavonoids and condensed tannins with sulfur nucleophiles. J. Chem. Soc., Perkin Trans. 1 1974, 2036-2049.
8. Butler, L. G. Relative degree of polymerization of Sorghum tannin during seed development and maturation. J. Agric. Food Chem. 1982, 30, 1090-1095.
9. Butler, L. G.; Price, M. L.; Brotherton, J. E. Vanillin assay for proanthocyanidins (condensed tannins): modification of the solvent for estimation of the degree of polymerization. J. Agric. Food Chem. 1982, 30, 1087-1089.
10. 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.
11. Foo, L. Y. Polymeric proanthocyanidins of Photinia glabrescens, modification of molecular weight and nature of products from hydrogenolysis. Phytochemistry 1982, 21, 1741-1746.
12. Foo, L. Y.; Porter, L. J. Prodelphinidin polymers: definition of structural units. J. Chem. Soc., Perkin Trans. 1 1978, 1186-1190.
13. Foo, L. Y.; Newman, R.; Waghorn, G.; Mcnabb, W. C.; Ulyatt, M. J. Proanthocyanidins from Lotus corniculatus. Phytochemistry 1996, 41, 617-624.
14. Gupta, R. K.; Haslam, E. Plant proanthocyanidins. Part 5 - Sorghum polyphenols. J. Chem. Soc., Perkin Trans. 1 1978, 892-896.
15. Haslam, E. Natural proanthocyanidins. In The Flavonoids; Harborne, J. B., Mabry, T. J., Mabry, H., Eds.; Chapman and Hall: London, 1975; pp 505-559.
16. Haslam, E. Plant Polyphenols, Vegetable Tannins Revisited; Cambridge University Press: Cambridge, U.K., 1989.
17. Hemingway, R. W. Reactions at the interflavonoid bond of proanthocyanidins. In Chemistry and Significance of Condensed Tannins; Hemingway, R. W., Karchesy, J. J., Eds.; Plenum Press: New York, 1989; pp 265-283.
18. Hergert, H. L. Hemlock and spruce tannins: an odyssey. In Chemistry and Significance of Condensed Tannins; Hemingway, R. W., Karchesy, J. J., Eds.; Plenum Press: New York, 1989; pp 3-20.
19. Hergert, H. L. The nature of non-proanthocyanidin units in "condensed tannins" from conifer wood and bark. In Plant Polyphenols, Synthesis, Properties, Significance; Hemingway, R. W., Laks, P. E., Eds.; Plenum Press: New York, 1992; pp 385-409.
20. Jacques, D.; Haslam, E.; Bedford, G. R.; Greatbanks, D. Plant proanthocyanidins. Part II - Proanthocyanidin A2 and its derivatives. J. Chem. Soc., Perkin Trans. 1 1974, 2663-2671.
21. Kolodziej, H. Thiolysis of birch bark procyanidins: structural dependence in formation of 2,3-cis-3,4-cis-flavan-4-benzyl-thioethers from procyanidins. Phytochemistry 1990, 29, 1671-1674.
22. Koupai-Abyazani, M. R.; McCallum, J.; Böhm, B. A. Identification of the constituent flavanoid units in sainfoin proanthocyanidins by reverse phase high-performance liquid chromatography. J. Chromatogr. 1992, 594, 117-123.
23. Matthews, S.; Mila, I.; Scalbert, A.; Donnelly, D. M. X. Extractible and non-extractible proanthocyanidins in barks. Phytochemistry 1997, in press.
24. Porter, L. J. Structure and chemical properties of the condensed tannins. In Plant Polyphenols, Synthesis, Properties, Significance; Hemingway, R. W., Laks, P. E., Eds.; Plenum Press: New York, 1992; pp 245-258.
25. Porter, L. J.; Hrstich, L. N.; Chan, B. G. The conversion of procyanidins and prodelphinidins to cyanidin and delphinidin. Phytochemistry 1986, 25, 223-230.
26. Prieur, C.; Rigaud, J.; Cheynier, V.; Moutounet, M. Oligomeric and polymeric procyanidins from grape seeds. Phytochemistry 1994, 36, 781-784.
27. Samejima, M.; Yoshimoto, T. High performance liquid chromatography of proanthocyanidins and related compounds. Mokuzai Gakkaishi 1981, 27, 658-662.
28. Scalbert, A. Quantitative methods for the estimation of tannins in plant tissues. In Plant Polyphenols, Synthesis, Properties, Significance; Hemingway, R. W., Laks, P. E., Eds.; Plenum Press: New York, 1992; pp 259-280.
29. Scalbert, A.; Monties, B.; Janin, G. Tannins in wood: comparison of different estimation methods. J. Agric. Food Chem. 1989, 37, 1324-1329.
30. Scalbert, A.; Duval, L.; Peng, S.; Monties, B. Polyphenols of Quercus robur L. II. Preparative isolation by low-pressure and high-pressure liquid chromatography of heartwood ellagitannins. J. Chromatogr. 1990, 502, 107-119.
31. Steynberg, J. P.; Ferreira, D.; Roux, D. G. The first condensed tannins based on a stilbene. Tetrahedron Lett. 1983, 24, 4147-4150.
32. Swain, T.; Hillis, W. E. The phenolic constituents of Prunus domestica. I-The quantitative analysis of phenolic constituents. J. Sci. Food Agric. 1959, 10, 63-68.
33. Tanaka, T.; Takahashi, R.; Kouno, I.; Nonaka, G. Chemical evidence for the de-astringency (insolubilization of tannins) of persimmon fruit. J. Chem. Soc., Perkin Trans. 1 1994, 3013-3022.
34. Thompson, R. S.; Jacques, D.; Haslam, E.; Tanner, R. J. N. Plant proanthocyanidins. Part 1 - Introduction: the isolation, structure and distribution in nature of plant procyanidins. J. Chem. Soc., Perkin Trans. 1 1972, 1387-1399.
35. Viriot, C.; Scalbert, A.; Hervé du Penhoat, C.; Rolando, C.; Moutounet, M. Methylation, acetylation and gel permeation chromatography of hydrolysable tannins. J. Chromatogr. 1994, 662, 77-85.