Proanthocyanidins and tannin-like compounds - Nature, occurrence, dietary intake and effects on nutrition and health

Journal of the Science of Food and Agriculture

Volumn 80, Issue 7, 2000, Pages 1094-1117

  Santos Buelga, Celestino ^a   Scalbert, Augustin ^b  

^a UNIVERSITY OF SALAMANCA   (Spain)

^b CEMAGREF   (France)

Author keywords

Absorption; Antioxidants; Bioavailability; Black tea; Burden; Cancer; Cardiovascular diseases; Condensed tannins; Fruit juices; Fruits; Metabolism; Metal ion bioavailability; Polyphenols; Proanthocyanidins; Red wine review; Tannin like compounds; Tea; Wine

Indexed keywords

ANTINEOPLASTIC ACTIVITY; BIOAVAILABILITY; CHELATING AGENT; CHEMICAL AND PHYSICAL PROPERTIES; CHRONIC DISEASE; FOOD SOURCE; LOW DENSITY LIPOPROTEIN; OXIDATION; POLYMER; POLYPHENOL DERIVATIVE; PROANTHOCYANIDIN; PROPHYLAXIS; REDUCING AGENT; TANNIN DERIVATIVE; TEA; WINE;

EID: 0034657286     PISSN: 00225142     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1097-0010(20000515)80:7<1094::AID-JSFA569>3.0.CO;2-1     Document Type: Review

References (337)

1. Haslam E, Plant Polyphenols, Vegetable Tannins Revisited. Cambridge University Press, Cambridge (1989).
2. Scalbert A, Antimicrobial properties of tannins. Phytochemistry 30:3875-3883 (1991).
3. Feeny P, Seasonal changes in oak leaf tannins and nutrients as a cause of spring feeding by winter moth caterpillars. Ecology 51:565-581 (1970).
4. Clifford MN and Scalbert A, Ellagitannins - nature, occurrence and dietary burden. J Food Sci Agric 80:1118-1125 (2000).
5. Haslam E, Practical Polyphenolics - from Structure to Molecular Recognition and Physiological Action. Cambridge University Press, Cambridge (1998).
6. Lewis NG and Yamamoto E, Lignin, occurrence, biogenesis and biodegradation. Ann Rev Plant Physiol Plant Mol Biol 41:455-496 (1990).
7. Hashimoto F, Nonaka G-I and Nishioka I, Tannins and related compounds. XC. 8-C-Ascorbyl (-)-epigallocatechin 3-O-gallate and novel dimeric flavan-3-ol, oolonghomobisflavans A and B, from oolong tea. Chem Pharmaceut Bull 37:3255-3263 (1989).
8. Powell C, Clifford MN, Opie SC and Gibson CL, Use of Porter's reagents for the characterisation of thearubigins and other non-proanthocyanidins. J Sci Food Agric 68:33-38 (1995).
9. Powell C, The Polyphenolic Pigments of Black Tea. University of Surrey Press, Guildford (1995).
10. Geiss F, Heinrich M, Hunkler D and Rimpler H, Proanthocyanidins with (+)-epicatechin units from Byrsonima crassifolia bark. Phytochemistry 39:635-643 (1995).
11. Santos-Buelga C, Kolodzieij H and Treutter D, Procyanidin trimers possessing a doubly linked structure from. Aesculus hippocastanum. Phytochemistry 38:499-504 (1995).
12. Porter LJ, Flavans and proanthocyanidins, in The Flavonoids - Advances in Research since 1986, Ed by Harborne JB. Chapman and Hall, London, pp 23-55 (1994).
13. Thompson RS, Jacques D, Haslam E and Tanner RJN, Plant proanthocyanidins - Part 1 - Introduction: the isolation, structure and distribution in nature of plant procyanidins. J Chem Soc, Perkin Trans 1, pp 1387-1399 (1972).
14. Haslam E, Proanthocyanidins, in The Flavonoids: Advances in Research, Ed by Harborne JB and Mabry TJ. Chapman and Hall, London, pp 417-447 (1982).
15. Hemingway RW, Foo LY and Porter LJ, Linkage isomerism in trimeric and polymeric 2,3-cis-procyanidins. J Chem Soc, Perkin Trans 1, pp 1209-1216 (1982).
16. Porter LJ, Flavans and proanthocyanidins, in The Flavonoids -Advances in Research since 1980, Ed by Harborne JB. Chapman and Hall, London, pp 21-62 (1988).
17. Nonaka G-I, Kawahara O and Nishioka I, Tannins and related compounds. XV. A new class of dimeric flavan-3-ol gallates, theasinensins A and B, and proanthocyanidin gallates from green tea leaf. Chem Pharmaceut Bull 31:3906-3914 (1983).
18. Prieur C, Rigaud J, Cheynier V and Moutounet M, Oligomeric and polymeric procyanidins from grape seeds. Phytochemisiry 36:781-784 (1994).
19. Kolodjiej H, Bonefeld M, Burger JFW, Brant EV and Ferreira D, Structure and conformational analysis of procyanidin 3-O-rhamnoside from. Erytroxylum novogranaetense. Phytochemistry 30:1255-1258 (1991).
20. Ishimaru K, Nonaka G-I and Nishioka I, Flavan-3-ol and procyanidin glycosides from. Quercus miyagii. Phytochemistry 26:1167-1170 (1987).
21. Kashiwada Y, Nonaka G and Nishioka I, Tannins and related compounds. XLV. Rhubarb (5) - isolation and characterization of flavan-3-ol and procyanidin glucosides. Chem Pharmaceut Bull 34:3208 (1986).
22. Zhang B, Nonaka G-I and Nishioka I, Potentillanin, a biflavanoid and procyanidin glycoside from. Potentilla viscosa. Phytochemisiry 27:3277-3280 (1988).
23. Achmadi S, Syahbirin G, Choong ET and Hemingway RW, Catechin-3-O-rhamnoside chain extender units in polymeric procyanidins from mangrove bark. Phytochemistry 35:217-219 (1994).
24. Gujer R, Magnolato D and Self R, Glucosylated flavonoids and other phenolic compounds from Sorghum. Phytochemistry 25:1431-1436 (1986).
25. Porter LJ, Foo LY and Furneaux RH, Isolation of three naturally occurring O-β-D-glucopyranosides of procyanidin polymers. Phytochemistry 24:567-569 (1985).
26. Matthews S, Mila I, Scalbert A, Pollet B, Lapierre C, Hervé duPenhoat CLM, Rolando C and Donnelly DMX, Method for estimation of proanthocyanidins based on their acid depolymerization in the presence of nucleophiles. J Agric Food Chem 45:1195-1201 (1997).
27. Déprez S and Scalbert A, [14C]-Biolabelling of (+)-catechin and proanthocyanidin oligomers in willow-tree cuttings. J Agric Food Chem 47:4219-4230 (1999).
28. 12 Procyaniden un Strukturaufklärung neuen Procyanidin. Juslus Liebigs Ann Chem 715:164-171 (1968).
29. Weinges K and Freundenberg K, Condensed proanthocyanidins from cranberries and cola nuts. Chem Commun 2:220-222 (1965).
30. Foo LY and Karchesy JJ, Pracyanidin tetramers and pentamers from Douglas fir bark. Phytochemistry 30:667-670 (1991).
31. Nonaka G-I, Morimoto S and Nishioka I, Tannins and related compounds. Part 13. Isolation and structures of trimeric, tetrameric, and pentameric proanthocyanidins from cinnamon. J Chem Soc, Perkin Trans 1, pp 2139-2145 (1983).
32. Balde AM, Debruyne T, Pieters L, Kolodziej H, Berghe DV, Claeys M and Vlietinck A, Oligomeric proanthocyanidins possessing a doubly linked structure from Pavetta owariensis. Phytochemisiry 38:719-723 (1995).
33. Foo LY and Porter LJ, The structure of tannins of some edible fruits. J Sci Food Agric 32:711-716 (1981).
34. Foo LY, Lu Y, McNabb WC, Waghorn G and Ulyatt MJ, Proanthocyanidins from Lotus pedunculatus. Phytochemistry 45:1689-1696 (1997).
35. Czochanska Z, Foo LY, Newman RH, Porter LJ, Thomas WA and Jones WT, Direct proof of a homogeneous polyflavan-3-ol structure for polymeric proanthocyanidins. J Chem Soc, Chem Commun, pp 375-377 (1979).
36. Souquet JM, Cheynier V, Brossaud F and Moutounet M, Polymeric proanthocyanidins from grape skins. Phytochemistry 43:509-512 (1996).
37. Czochanska Z, Foo LY, Newman RH and Porter LJ, Polymeric proanthocyanidins. Stereochemistry, structural units and molecular weight. J Chem Soc, Perkin Trans 1, pp 2278-2286 (1980).
38. Haslam E, Symmetry and promiscuity in procyanidin biochemistry. Phytochemistry 16:1625-1640 (1977).
39. De Freitas V, Glories Y and Laguerre M, Characterization of oligomeric and polymeric procyanidins from grape seeds by LSIMS. Phytochemistry 49:1435-1441 (1998).
40. Cheynier V, Doco T, Fulcrand H, Guyot S, Le Roux E, Souquet JM, Rigaud J and Moutounet M, ESI-MS analysis of polyphenolic oligomers and polymers. Analusis 25:M32-M37 (1997).
41. Guyot S, Doco T, Souquet JM, Moutounet M and Drilleau JF, Characterization of highly polymerized procyanidins in cider apple (Malus sylvestris var kermerrien) skin and pulp. Phytochemistry 44:351-357 (1997).
42. Matthews S, Mila I, Scalbert A and Donnelly DMX, Extractible and non-extractible proanthocyanidins in barks. Phytochemistry 45:405-410 (1997).
43. Guyot S, Marnet N, Laraba D, Sanoner P and Drilleau J-F, Reversed-phase HPLC following thiolysis for quantitative estimation and characterization of the four main classes of phenolic compounds in different tissue zones of a French cider apple variety (Malus domestica Var. Kermerrien). J Agric Food Chem 46:1698-1705 (1998).
44. Guyot S, Vercauteren J and Cheynier V, Structural determination of colourless and yellow dimers resulting from (+)-catechin coupling catalysed by grape polyphenoloxidase. Phytochemistry 42:1279-1288 (1996).
45. Davis AL, Lewis JR, Cai Y, Powell C, Davies AP, Wilkins JPG, Pudney P and Clifford MN, A polyphenolic pigment from black tea. Phytochemistry 46:1397-1402 (1997).
46. Takino Y, Ferretti A, Flanagan V, Gianturco M and Vogel M, Structure of theaflavin, apolyphenol of black tea. Tetrahedron Lett, pp 4019-4025 (1965).
47. Davis AL, Cai Y and Davies AP, H-1 and C-13 NMR assignment of theaflavin, theaflavin monogallate and theaflavin digallate. Magn Reson Chem 33:549-552 (1995).
48. Hara Y, Luo SJ, Wickremasinghe RL and Yamanishi T, Special issue on tea. Food Rev Int 11:371-542 (1995).
49. Roberts EAH, Economic importance of flavonoid substances: tea fermentation, in The Chemistry of Flavonoid Compounds, Ed by Geissman TA. Pergamon, Oxford, pp 468-512 (1962).
50. Clifford MN and Powell C, A partial resolution of 'black tea tannins' by HPLC. Proc 18th Int Conf on Polyphenols, Bordeaux, pp 217-218 (1996).
51. Fulcrand H, Doco T, Essafi NE, Cheynier V and Moutounet M, Study of the acetaldehyde induced polymerisation of flavan-3-ols by liquid chromatography ion spray mass spectrometry. J Chromatogr A 752:85-91 (1996).
52. Saucier C, Bourgeois G, Vitry C, Roux D and Glories Y, Characterization of (+)-catechin-acetaldehyde polymers: a model for colloidal state of wine polyphenols. J Agric Food Chem 45:1045-1049 (1997).
53. Saucier C, Guerra C, Pianet I, Laguerre M and Glories Y, (+)-Catechin-acetaldehyde condensation products in relation to wine-ageing. Phytochemistry 46:229-234 (1997).
54. Bakker J, Picinelli A and Bridle P, Model wine solutions: colour and composition changes during ageing. Vitis 32:111-118 (1993).
55. Escribano-Bailon T, Dangles O and Brouillard R, Coupling reactions between flavylium ions and catechin. Phytochemistry 41:1583-1592 (1996).
56. Rivas-Gonzalo JC, Bravo-Haro S and Santos-Buelga C, Detection of compounds formed through the reaction of malvidin 3-monoglucoside and catechin in the presence of acetaldehyde. J Agric Food Chem 43:1444-1449 (1995).
57. Roggero JP, Archier P, Coen S and Rocheville-Divorne C, Etude par HPLC de la réaction glucoside de malvidine-acetaldehyde-composé phénolique. Conn Vigne Vin 21:163-168 (1987).
58. Timberlake CF and Bridle P, Interactions between anthocyanins, phenolic compounds and acetaldehyde and their significance in red wines. Am J Enol Vitic 27:97-105 (1976).
59. Wildenradt HL and Singleton VL, The production of aldehydes as a result of oxidation of polyphenolic compounds and its relation to wine ageing. Am J Enol Vitic 25:119-126 (1974).
60. Singleton VL, Oxygen with phenols and related reactions in musts, wines, and model systems: observations and practical implications. Am J Enol Vitic 38:69-77 (1987).
61. Fulcrand H, Cheynier V, Oszmianski J and Moutounet M, An oxidized tartaric acid residue as a new bridge potentially competing with acetaldehyde in flavan-3-ol condensation. Phytochemistry 46:223-227 (1997).
62. Francia-Aricha EM, Guerra MT, Rivas-Gonzalo JC and Santos-Buelga C, New anthocyanin pigments formed after condensation with flavanols. J Agric Food Chem 45:2262-2266 (1997).
63. Santos-Buelga C, Francia-Aricha EM, de Pascual-Teresa S and Rivas-Gonzalo JC, Contribution to the identification of the pigments responsible for the browning in anthocyanin-flavanol solutions. Z Lebensm Untersuch Forsch 209:411-415.
64. Fulcrand H, Es-Safi EN, Cheynier V and Moutounet M, A new oxidative pathway contributing to wine browning. Proc 19th Im Conf on Polyphenols, Lille, pp 257-258 (1998).
65. Es-Safi EN, Le Guernevé C, Labarbe B, Fulcrand H, Cheynier V and Moutounet M, Structure of a new xanthylium salt derivative. Tetrahedron Lett 40:5869-5872 (1999).
66. Jurd L and Somers TC, The formation of xanthylium salts from proanthocyanidins. Phytochemistry 9:419-427 (1970).
67. Jurd L, Anthocyanins and related compounds. XI. Catechin flavylium salt condensation reactions. Tetrahedron 23:1057-1064 (1967).
68. Jurd L and Waiss AC, Anthocyanins and related compounds. VI. Flavylium salt phloroglucinol condensation products. Tetrahedron 21:1471-1483 (1965).
69. Santos-Buelga C, Bravo-Haro S and Rivas-Gonzalo JC, Interactions between catechin and malvidin 3-monoglucoside in model solution. Z Lebensm Untersuch Forsch 201:269-274 (1995).
70. Liao H, Cai Y and Haslam E, Polyphenol interactions. Anthocyanins: copigmentation and colour changes in red wines. J Sci Food Agric 59:299-305 (1992).
71. Francia-Aricha EM, Rivas-Gonzalo JC and Santos-Buelga C, Effect of malvidin-3-monoglucoside on the browning of monomeric and dimeric flavanols. Z Lebensm Untersuch Forsch 207:223-228 (1998).
72. Somers TC, The polymeric nature of wine pigments. Phytochemistry 10:2175 (1971).
73. Vivar-Quintana AM, Santos-Buelga C, Francia-Aricha E and Rivas-Gonzalo JC, Formation of anthocyanin-derived pigments in experimental red wines. Food Sci Technol Int 5:347-352.
74. Bakker J, Bridle P, Honda T, Kuwano H, Saito N, Terahara N and Timberlake CF, Identification of an anthocyanin occurring in some red wines. Phytochemistry 44:1375-1382 (1997).
75. Bakker J and Timberlake CF, Isolation, identification and characterization of new color-stable anthocyanins occurring in some red wines. J Agric Food Chem 45:35-43 (1997).
76. Fulcrand H, Dossantos PJC, Sarnimanchado P, Cheynier V and Favrebonvin J, Structure of new anthocyanin-derived wine pigments. J Chem Soc, Perkin Trans 1, pp 735-739 (1996).
77. Fulcrand H, Benaddeljalil C, Rigaud J, Cheynier V and Moutounet M, A new class of wine pigments generated by reaction between pyruvic acid and grape anthocyanins. Phytochemistry 47:1401-1407 (1998).
78. Tanaka T, Takahashi R, Kouno I and Nonaka G, Chemical evidence for the de-astringency (insolubilization of tannins) of persimmon fruit. J Chem Soc, Perkin Trans 1, pp 3013-3022 (1994).
79. Lea AGH, Bridle P, Timberlake CF and Singleton VL, The procyanidins of white grapes and wines. Am J Enol Vitic 30:289-300 (1979).
80. Lea AGH, Reversed-phase gradient high-performance liquid chromatography of procyanidins and their oxidation products in ciders and wines, optimized by Snyder's procedure. J Chromatogr 194:62-68 (1980).
81. Treutter D, Santos-Buelga C, Gutmann M and Kolodziej H, Identification of flavan-3-ols and procyanidins by high-performance liquid chromatography and chemical reaction detection. J Chromatogr A 667:290-297 (1994).
82. Treutter D, Chemical reaction detection of catechins and proanthocyanidins with 4-dimethylaminocinnamaldehyde. J Chromatogr 467:185-193 (1989).
83. Mayr U, Treutter D, Santos-Buelga C, Bauer H and Feucht W, Developmental changes in the phenol concentrations of 'Golden Delicious' apple fruits and leaves. Phytochemistry 38:1151-1155 (1995).
84. De Pascual-Teresa S, Treutter D, Rivas-Gonzalo JC and Santos-Buelga C, Qualitative and quantitative analysis of dietary flavanols. Proc 19th Int Conf on Polyphenols, Lille, pp 257-258 (1998).
85. De Pascual-Teresa S, Mendez-Arroyo A, Santos-Buelga C and Rivas-Gonzalo JC, Determination of flavan-3-ols in some Spanish wines. Proc 19th Int Conf on Polyphenols, Lille, pp 333-334 (1998).
86. De Pascual-Teresa S, Treutter D, Rivas-Gonzalo JC and Santos-Buelga C, Analysis of flavanols in beverages by high-performance liquid chromatography with chemical reaction detection. J Agric Food Chem 46:4209-4213 (1998).
87. Scalbert A, Quantitative methods for the estimation of tannins in plant tissues, in Plant Polyphenols, Synthesis, Properties, Significance, Ed by Hemingway RW and Laks PE. Plenum, New York, pp 259-280 (1992).
88. Swain T and Hillis WE, The phenolic constituents of Prunus domestica - I - The quantitative analysis of phenolic constituents. J Sci Food Agric 10:63-68 (1959).
89. Price ML and Butler LG, Rapid visual estimation and spectrophotometric determination of tannin content of Sorghum grain. J Agric Food Chem 25:1268-1273 (1977).
90. Graham HD, Stabilization of the Prussian blue color in the determination of polyphenols. J Agric Food Chem 40:801-805 (1992).
91. Hagerman AE and Butler LG, Tannins and lignins, in Herbivores: Their Interactions with Secondary Plant Metabolites, Ed by Rosenthal GA and Berenbam MR. Academic Press, London, pp 355-388 (1991).
92. Hagerman AE, Radial diffusion method for determining tannin in plant extracts. J Chem Ecol 13:437-449 (1987).
93. Makkar HPS, Protein precipitation methods for quantitation of tannins: a review. J Agric Food Chem 37:1197-1202 (1989).
94. Bacon JR and Rhodes MJC, Development of a competitive assay for the evaluation of the binding of human parotid salivary proteins to dietary complex phenols and tannins using a peroxidase-labeled tannin. J Agric Food Chem 46:5083-5088 (1999).
95. Garcia-Parilla MC, Heredia FJ, Troncoso AM and Gonzalez AG, Spectrophotometric determination of total procyanidins in wine vinegar. Talanta 44:119-123 (1997).
96. Deshpande SS, Cheryan M and Salunkhe DK, Tannin analysis of food products. CRC Crit Rev Food Sci Nutr 24:401-449 (1986).
97. Broadhurst RB and Jones WT, Analysis of condensed tannins using acidified vanillin. J Sci Food Agric 29:788-794 (1978).
98. Delcour JA and Varebeke DJ, A new colorimetric assay for flavonoids in pilsner beers. J Inst Brew 91:37-40 (1985).
99. Porter LJ, Hrstich LN and Chan BG, The conversion of procyanidins and prodelphinidins to cyanidin and delphinidin. Phytochemistry 25:223-230 (1986).
100. Bate-Smith EC, Astringency in foods. Food 23:124-135 (1954).
101. Déprez S, Mila I and Scalbert A, Complete qualitative and quantitative analysis of procyanidins and prodelphinidins in plant extracts by thiolysis (submitted).
102. Bate-Smith EC, Tannins in herbaceous leguminosae. Phytochemistry 12:1809-1812 (1973).
103. Tabera J, Frias J, Estrella I, Villa R and Vidalvalverde C, Natural fermentation of lentils - influence of time, concentration and temperature on protein content, trypsin inhibitor activity and phenolic compound content. Z Lebensm Untersuch Forsch 201:587-591 (1995).
104. Vidal-Valverde C, Frias J, Estrella MI, Gorospe MJ, Ruiz R and Bacon J, Effect of processing on some antinutritional factors of lentils. J Agric Food Chem 42:2291-2295 (1994).
105. Bartolome B, Estrella I and Hernandez T, Changes in phenolic compounds in lentils (Lens culinaris) during germination and fermentation. Z Lebensm Untersuch Forsch 205:290-294 (1997).
106. Helsper JPFG, Kolodziej H, Hoogendijk JM and Van Norel A, Characterization and trypsin inhibitor activity of proanthocyanidins from Vicia faba. Phytochemistry 34:1255-1260 (1993).
107. Elkin RG, Freed MB, Hamaker BR, Zhang Y and Parsons CM, Condensed tannins are only partially responsible for variations in nutrient digestibilities of sorghum grain cultivars. J Agric Food Chem 44:848-853 (1996).
108. Jerumanis J, Quantitative analysis of flavanoids in barley, hops and beer by high-performance liquid chromatography. J Inst Brew 91:250-252 (1985).
109. Lees GL, Wall KM, Beveridge TH and Suttill NH, Localization of condensed tannins in apple fruit peel, pulp, and seeds. Can J Bot 73:1897-1904 (1995).
110. Mayr U and Treutter D, Vorkommen und Gehalte von Flavanolen in Apfelfrüchten und -säften. Proc XXXI Vortragstagung, Deutsche Gesellschaft für Qualitätforschung (Pflanzliche Nahrungsmittel), Kiel, pp 113-118 (1996).
111. Suarez-Valles B, Sanatamaria J, Mangas JJ and Blanco D, HPLC of the neutral phenolic compounds of low molecular weight in apple juices. J Agric Food Chem 42:2732-2736 (1994).
112. Amiot MJ, Tacchini M, Aubert S and Oleszek W, Influence of cultivar, maturity stage, and storage conditions on phenolic composition and enzymatic browning of pear fruits. J Agric Food Chem 43:1132-1137 (1995).
113. Bourzeix M, Weyland D and Heredia N, Etude des catéchines et des procyanidols de la grappe de raisin, du vin et d'autres dérivés de la vigne. Bull OIV 669-670:1171-1254 (1986).
114. Ricardo da Silva JM, Rosec JP, Bourzeix M, Mourgues J and Moutounet M, Dimer and trimer procyanidins in Carignan and Mourvedre grapes and red wines. Vitis 31:55-63 (1992).
115. Heinonen IM, Meyer AS and Frankel EN, Antioxidant activity of berry phenolics on human low-density lipoprotein and liposome oxidation. J Agric Food Chem 46:4107-4112 (1998).
116. Mangas JJ, Suarez B, Picinelli A, Moreno J and Blanco D, Differentiation of phenolic profiles of apple juices prepared according to two membrane techniques. J Agric Food Chem 45:4777-4784 (1997).
117. Spanos GA, Wrolstad RE and Heatherbell DA, Influence of processing and storage on the phenolic composition of apple juice. J Agric Food Chem 38:1572-1579 (1990).
118. Bengoechea ML, Sancho AI, Bartolome B, Estrella Y, Gomez-Cordoves C and Hernandez T, Phenolic composition of industrially manufactured purees and concentrates from peach and apple fruits. J Agric Food Chem 45:4071-4075 (1997).
119. Spanos GA and Wrolstad RE, Influence of variety, maturity, processing, and storage on the phenolic composition of pear juice. J Agric Food Chem 38:817-824 (1990).
120. Jaworski AW and Lee CY, Fractionation and HPLC determination of grape phenolics. J Agric Food Chem 35:257-259 (1987).
121. Lea AGH and Timberlake CF, The phenolics of ciders. 1. Procyanidins. J Sci Food Agric 24:1537-1545 (1974).
122. Lea AGH and Arnold GM, The phenolics of ciders: bitterness and astringency. J Sci Food Agric 29:478-483 (1978).
123. Auw JM, Blanco V, O'Keefe SF and Sims CA, Effect of processing on the phenolics and color of Cabernet Sauvignon, Chambourcin, and Noble wines and juices. Am J Enol Vitic 47:279-286 (1996).
124. Ghiselli A, Nardini M, Baldi A and Scaccini C, Antioxidant activity of different phenolic fractions separated from an Italian wine. J Agric Food Chem 46:361-367 (1998).
125. Kovac V, Alonso E, Bourzeix M and Revilla E, Effect of several enological practices on the content of catechins and proanthocyanidins of red wines. J Agric Food Chem 40:1953-1957 (1992).
126. Ricardo da Silva JM, Cheynier V, Souquet JM, Moutounet M, Cabanis JC and Bourzeix M, Interaction of grape seed procyanidins with various proteins in relation to wine fining. J Sci Food Agric 56:111-125 (1991).
127. Treutter D and Santos-Buelga C, Sensitive detection and identification of catechins and proanthocyanidins by HPLC and post-column-derivatization, in Flavonoids and Bioflavonoids, Ed by Antus S, Gabor M and Vetschera K. Akademiai Kiado, Budapest, pp 203-209 (1995).
128. Betes-Saura C, Andres-Lacueva C and Lamuela-Raventos RM, Phenolics in white free run juices and wines from Penedes by high-performance liquid chromatography: changes during vinification. J Agric Food Chem 44:3040-3046 (1996).
129. Ricardo da Silva JM, Cheynier V, Samsom A and Bourzeix M, Effect of pomace contact, carbonic maceration and hyper-oxidation on the procyanidin composition of Grenache blanc wines. Am J Enol Vitic 44:168-172 (1993).
130. Baron R, Mayen M, Merida J and Medina M, Changes in phenolic compounds and browning during biological aging of sherry-type wine. J Agric Food Chem 45:1682-1685 (1997).
131. McMurrough I, Madigan DT and Smyth MR, Semipreparative chromatographic procedure for the isolation of dimeric and trimeric proanthocyanidins from barley. J Agric Food Chem 44:1731-1735 (1996).
132. McMurrough I, Madigan DT and Kelly RJ, The role of flavonoid polyphenols in beer stability. J Am Soc Brew Chem 54:141-148 (1996).
133. Porter LJ, Ma Z and Chan BG, Cacao procyanidins: major flavanoids and identification of some minor metabolites. Phytochemistry 30:1657-1663 (1991).
134. Kühnau J, The flavonoids: a class of semi-essential food components: their role in human nutrition. World Rev Nutr Diet 24:117-191 (1976).
135. McMurrough I and Baert T, Identification of proanthocyanidins in beer and their direct measurement with a dual electrode electrochemical detector. J Inst Brew 100:409-116 (1994).
136. Luck G, Liao H, Murray NJ, Grimmer HR, Warminski EE, Williamson MP, Lilley TH and Haslam E, Polyphenols, astringency and proline-rich proteins. Phytochemistry 37:357-371 (1994).
137. Charlton AJ, Baxter NJ, Lilley TH, Haslam E, Mcdonald CJ and Williamson MP, Tannin interactions with a full-length human salivary proline-rich protein display a stronger affinity than with single proline-rich repeats. FEBS Lett 382:289-292 (1996).
138. Hagerman AE, Tannin-protein interactions, in Phenolic Compounds in Food and Their Effects on Health. I. Analysis, Occurrence and Chemistry, Ed by Ho CT, Lee CY and Huang MT. American Chemical Society, Washington, DC, pp 236-247 (1992).
139. Hagerman AE and Butler LG, Condensed tannin purification and characterization of tannin-associated proteins. J Agric Food Chem 28:947-952 (1980).
140. Hagerman AE and Butler LG, The specificity of proanthocyanidin-protein interactions. J Biol Chem 256:4494-4497 (1981).
141. Asquith TN, Uhlig J, Mehansho H, Putman L, Carlson DM and Butler L, Binding of condensed tannins to salivary proline-rich glycoproteins: the role of carbohydrate. J Agric Food Chem 35:331-334 (1987).
142. Komninos J, Kekos D, Macris BJ and Galiotou-Panayotou M, Tannin-resistant a-amylase from Calvatia gigantea. Biotechnol Bioengng 32:939-941 (1988).
143. Strumeyer DH and Malin MJ, Resistance of extracellular yeast invertase and other glycoproteins to denaturation by tannins. Biochem J 118:899-900 (1970).
144. Haslam E, Polyphenol-protein interactions. Biochem J 139:285-288 (1974).
145. Sami-Manchado P, Cheynier V and Moutounet M, Interactions of grape seed tannins with salivary proteins. J Agric Food Chem 47:42-47 (1999).
146. Okuda T, Mori K and Hatano T, Relationship of the structures of tannins to the binding activities with hemoglobin and methylene blue. Chem Pharmacent Bull 33:1424-1433 (1985).
147. Kawamoto H, Nakatsubo F and Murakami K, Relationship between the B-ring hydroxylation pattern of condensed tannins and their protein-precipitating capacity. J Wood Chem Technol 10:401-409 (1990).
148. Mole S, Rogler JC and Butler LG, Growth reduction by dietary tannins: different effects due to different tannins. Biochem Syst Ecol 21:667-677 (1993).
149. Vallet J, Rouanet J-M and Besançon P, Dietary grape seed tannins: effects on nutritional balance and on some enzymic activities along the crypt-villus axis of rat samll intestine. Ann Nutr Metab 38:75-84 (1994).
150. Hussein L and Abbas H, Nitrogen balance studies among boys fed combinations of faba beans and wheat differing in polyphenolic contents. Nutr Rep Int 31:67-81 (1985).
151. Butler LG and Rogler JC, Biochemical mechanisms of the antinutritional effects of tannins, in Phenolic Compounds in Food and Their Effects on Health. I. Analysis, Occurrence and Chemistry, Ed by Ho CT, Lee CY and Huang MT. American Chemical Society, Washington, DC, pp 298-304 (1992).
152. Lizardo R, Peiniau J and Aumaitre A, Effect of sorghum on performance, digestibility of dietary components and activities of pancreatic and intestinal enzymes in the weaned piglet. Anim Feed Sci Technol 56:67-82 (1995).
153. Glick Z and Joslyn MA, Effect of tannic acid and related compounds on the absorption and utilization of proteins in the rat. J Nutr 100:516-520 (1970).
154. Majumdar S and Moudgal RP, Effect of tannic acid on activities of certain digestive enzymes and alkaline phosphatase in intestine and glucose absorption in adult chickens. J Appl Anim Res 6:105-112 (1994).
155. Ahmed AE, Smithard R and Ellis M, Activities of enzymes of the pancreas, and the lumen and mucosa of the small intestine in growing broiler cockerels fed on tannin-containing diets. Brit J Nutr 65:189-197 (1991).
156. Horigome T, Kumar R and Okamoto K, Effects of condensed tannins prepared from leaves of fodder plants on digestive enzymes in vitro and in the intestine of rats. Bru J Nutr 60:275-285 (1988).
157. Tebib K, Rouanet JM and Besancon P, Effect of grape seed tannins on the activity of some rat intestinal enzyme activities. Enzyme & Protein 48:51-60 (1994).
158. Mole S, Butler LG and Iason G, Defense against dietary tannin in herbivores: a survey for proline rich salivary proteins in mammals. Biochem Syst Ecol 18:287-293 (1990).
159. Hagerman AE and Robbins CT, Specificity of tannin-binding salivary proteins relative to diet selection by mammals. Can J Zool 71:628-633 (1993).
160. Ann DK and Lin HH, Regulation of salivary gland-specific gene expression. Crit Rev Oral Biol Med 8:244-252 (1997).
161. Mehansho H, Asquith TH, Butler LG, Rogler JC and Carlson DM, Tannin-mediated induction of proline-rich protein synthesis. J Agric Food Chem 40:93-97 (1992).
162. Jansman AJM, Frohlich AA and Marquardt RR, Production of proline-rich proteins by parotid glands of rats is enhanced by feeding diets containing tannins from faba beans (Vicia faba L.). J Nutr 124:249-258 (1994).
163. Mehansho H, Butler LG and Carlson DM, Dietary tannins and salivary proline-rich proteins: interactions, induction, and defense mechanisms. Ann Rev Nutr 7:423-440 (1987).
164. Déprez S, Biomarquage de Tanins Condensés et Etude de Leur Biodisponibitité dans l'Organisme Humain. Institut National Agronomique Paris-Grignon, Paris (1999).
165. Oh HI and Hoff JE, Effect of condensed grape tannins on the in vitro activity of digestive proteases and activation of their zymogens. J Food Sci 51:577-580 (1986).
166. Mila I, Etude des Effets Modulateurs des Proanthocyanidines sur l'Absorption du Glutamate et du Fer par l'Epithelium Intestinal Caco-2. Conservatoire National des Arts et Métiers, Paris (1999).
167. Honda M and Hara Y, Inhibition of rat small intestinal sucrase and α-glucosidase activities by tea polyphenols. Biosci BiotechnolBiochem 57:123-124 (1993).
168. Loeb H, Vandenplas Y, Wursch P and Guesry P, Tannin-rich carob pod for the treatment of acute-onset. J Pediatr Gastroenterol Nutr 8:480-485 (1989).
169. Janower ML, Robbins LL and Wenlund DE, A review of the use of tannic acid in patients with ulcerative colitis. Radiology 89:42-43 (1967).
170. Hör M, Rimpler H and Heinrich M, Inhibition of intestinal chloride secretion by proanthocyanidins from Guazuma ulmifolia. Planta Med 61:208-212 (1995).
171. Verhaeron EHC and Lemli J, The effect of gallotannins and (+)-catechin on the stimulated fluid secretion on the colon, following a rhein perfusion in guinea pigs. Planta Med, no 4, pp 269-272 (1986).
172. Galvez J, Zarzuelo A, Crespo ME, Utrilla MP, Jimenez J, Spiessens C and de Witte P, Antidiarrhoeic activity of Sclerocarya birrea bark extract and its active tannin constituent in rats. Phytother Res 5:276-278 (1991).
173. Sakanaka S and Kim M, Green tea polyphenols to prevent dental caries. Polyphénols Actualités, no 18, pp 18-21 (1998).
174. Hattori M, Kusumoto Y, Namba T, Ishigami T and Hara Y, Effect of tea polyphenols on glucan synthesis by glucosyl-transferase from Streptococcus mutans. Chem Pharmacent Bull 38:717-720 (1990).
175. Sakanaka S, Sato T, Kim M and Yamamoto T, Effects of green tea polyphenols on glucan synthesis and cellular adherence of cariogenic streptococci. Agric Biol Chem 54:2925 (1990).
176. Sami-Manchado P, Korompli MH, Michaïlesco P and Cheynier V, Inhibition of Streptococcus mutans growth by grape seed procyanidins. Proc 19th Int Conf on Polyphenols, Lille, pp 115-116 (1998).
177. Sakanaka S, Kim M, Taniguchi M and Yamamoto T, Antibacterial substances in Japanese green tea extract against Streptococcus mutans, a cariogenic bacterium. Agric Biol Chem 54:2925-2932 (1989).
178. Manach C, Morand C, Texier O, Favier ML, Agullo G, Demigne C, Regerat F and Remesy C, Quercetin metabolites in plasma of rats fed diets containing rutin or quercetin. J Nutr 125:1911-1922 (1995).
179. Kennedy JA and Powell KJ, Polyphenol interactions with aluminium(III) and iron(III): their possible involvement in the podzolization process. Aust J Chem 38:879-888 (1985).
180. Marmolle F, Leize E, Mila I, Van Dorsselaer A, Scalbert A and Albrecht-Gary AM, Polyphenol metallic complexes: characterization by electrospray mass spectrometric and spectrophotometric methods. Analusis 25:M53-M55 (1997).
181. Powell HKJ and Rate AW, Aluminium-tannin equilibria: a potentiometric study. Aust J Chem 40:2015-2022 (1987).
182. McDonald M, Mila I and Scalbert A, Precipitation of metal ions by plant polyphenols: optimal conditions and origin of precipitation. J Agric Food Chem 44:599-606 (1996).
183. Scalbert A, Mila I, Expert D, Marmolle F, Albrecht A-M, Hurrell R, Huneau J-F and Tome D, Polyphenols, metal ion complexation and biological consequences, in Plant Polyphenols. 2. Chemistry and Biology, Ed by Gross GG, Hemingway R and Yoshida T. Plenum, New York, in press.
184. Cook JD, Reddy MB and Hurrell RF, The effect of red and white wines on nonheme-iron absorption in humans. Am J Clin Nutr 61:800-804 (1995).
185. Hurrell RF, Reddy M and Cook JD, Inhibition of non-heme iron absorption in man by herb teas, coffee and black tea. Br J Nutr 81:289-295 (1998).
186. Disler PB, Lynch SR, Torrance JD, Sayers MH, Bothwell TH and Charlton RW, The mechanism of the inhibition of iron absorption by tea. S Afr J Med Sci 40:109-116 (1975).
187. South PK, House WA and Miller DD, Tea consumption does not affect iron absorption in rats unless tea and iron are consumed together. Nutr Res 17:1303-1310 (1997).
188. Hallberg L and Rossander L, Effect of different drinks on the absorption of non-heme iron from composite meals. Human Nutr Appl Nutr36A:116-123 (1982).
189. Disler PB, Lynch SR, Charlton RW, Torrance JD, Bothwell TH, Walker RB and Mayet F, The effect of tea on iron absorption. Gut 16:193-200 (1975).
190. Siegenberg D, Baynes RD, Bothwell TH, Macfarlane BJ, Lamparelli RD, Car NG, Macphail P, Schmidt U, Tal A and Mayet F, Ascorbic acid prevents the dose dependent inhibitory effects of polyphenols and phytates on nonhemeiron absorption. Am J Clin Nutr 53:537-541 (1991).
191. Brune M, Rossander L and Hallberg L, Iron absorption and phenolic compounds: importance of different phenolic structures. Eur J Clin Nutr 43:547-558 (1989).
192. De Alarcon PA, Donovan ME, Forbes GB, Landaw SA and Stockman JA, Iron absorption in the thalassemia syndromes and its inhibition by tea. New Engl J Med 300:5-8 (1979).
193. Drewitt PN, Butterworth KR, Springall CD and Moorhouse SR, Plasma levels of aluminium after tea ingestion in healthy volunteers. Food Chem Toxicol 31:19-23 (1993).
194. Fairweather-Tait S, Piper Z, Fatemi SJA and Moore GR, The effect of tea on iron and aluminium metabolism in the rat. Br J Nutr 65:61-68 (1991).
195. Müller M, Anke M and Illing-Günther H, Availability of aluminium from tea and coffee. Z Lebensm Untersuch Forsch 205:170-173 (1997).
196. 27Al NMR. Phytochemistry 31:1215-1218 (1992).
197. De Veto E and Yokel RA, The biological speciation and toxicokinetics of aluminum. Environ Health Perspect 102:940-951 (1994).
198. Orgogozo J-M, Dartigues J-F, Lafont S, Letenneur L, Commenges D, Salamon R, Renaud S and Breteler MB, Wine consumption and dementia in the elderly: a prospective community study in the Bordeaux area. Rev Neurol (Paris) 153:185-192 (1997).
199. Vaquero MP, Veldhuizen M, Van Dokkum W, Van den Hamer CJA and Schaafsma G, Copper bioavailability from breakfasts containing tea. Influence of the addition of milk. J Sci Food Agric 64:475-481 (1994).
200. Greger JL and Lyle BJ, Iron, copper and zinc metabolism of rats fed various levels and types of tea. J Nutr 118:52-60 (1988).
201. Hamdaoui M, Hedhili A, Doghri T and Tritar B, Effect of tea decoction given to rats ad libitum for a relatively long time on body weight gains and iron, copper, zinc, magnesium concentrations in blood, liver, duodenum and spleen. Ann Nutr Metabol 41:196-202 (1997).
202. Ganji V and Kies CV, Zinc bioavailability and tea consumption: studies in healthy humans consuming self-selected and laboratory-controlled diets. Plant Foods Human Nutr 46:267-276 (1994).
203. Flanagan PR, Cluett J, Chamberlain MJ and Valberg LS, Dual-isotope method for determination of human zinc absorption: the use of a test meal of turkey meat. J Nutr 115:111-122 (1985).
204. Kehrer JP and Smith CV, Free radicals in biology: sources, reactivities, and roles in the etiology of human diseases, in Natural Antioxidants, Ed by Frei B. Academic Press, New York, pp 25-62 (1994).
205. Gutteridge JMC and Halliwell B, Antioxidants in Nutrition, Health, and Disease. Oxford University Press, Oxford (1994).
206. Jovanovic SV, Steenken S, Simic MG and Hara Y, Antioxidant properties of flavonoids: reduction potentials and electron transfer reactions of flavonoid radicals, in Flavonoids in Health and Disease, Ed by Rice-Evans C and Packer L. Marcel Dekker, New York, pp 137-161 (1998).
207. Bors W and Saran M, Radical scavenging by flavonoid antioxidants. Free Radic Res Commun 2:289-294 (1987).
208. Rice-Evans CA, Miller NJ and Paganga G, Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic Biol Med 20:933-956 (1996).
209. Saint-Cricq de Gaulejac N, Provost C and Vivas N, Comparative study of polyphenol scavenging activities by different methods. J Agric Food Chem 47:425-431 (1999).
210. Ricardo da Silva JM, Darmon N, Fernandez Y and Mitjavila S, Oxygen free radical scavenger capacity in aqueous models of different procyanidins from grape seeds. J Agric Food Chem 39:1549-1552 (1991).
211. Plumb GW, De Pascual-Teresa S, Santos-Buelga C, Cheynier V and Williamson G, Antioxidant properties of catechins and proanthocyanidins: effect of polymerisation, galloylation and glycosylation. Free Radic Res 29:351-358 (1998).
212. Miller NJ, Castelluccio C, Tijburg L and Riceevans C, The antioxidant properties of theaflavins and their gallate esters-radical scavengers or metal chelators?. FEBS Lett 392:40-44 (1996).
213. Saint-Cricq de Gaulejac N, Vivas N, de Freitas V and Bourgeois G, The influence of various phenolic compounds on scavenging activity assessed by an enzymatic method. J Sci Food Agric 79:1081-1090 (1999).
214. Fujita Y, Komagoe K, Niwa Y, Uehara I, Hara R, Mon H, Okuda T and Yoshida T, Studies on inhibition mechanism of autoxidation by tannins and flavonoids. III. Inhibition mechanism of tannins isolated from medicinal plants and related compounds on autoxidation of methyl linoleate. Yakugaku Zasshi 108:528-537 (1988).
215. Ariga T and Hamamo M, Antioxidative properties of proanthocyanidins - 2 - Radical scavenging action and its mode in procyanidin-B1 and procyanidin-B3 from Azuki beans to peroxyl radicals. Agric Biol Chem 54:2499-2504 (1990).
216. Bos MA, Vennat B, Meunier MT, Pouget MP, Pourrat A and Fialip J, Procyanidins from tormentil: antioxidant properties towards lipoperoxidation and anti-elastase activity. Biol Pharmaceut Bull 19:146-148 (1996).
217. Aust SD, Assessing the antioxidant activities of polyphenols. Polyphénols Actualités (16):9-11 (1997).
218. Frei B, Cardiovascular disease and nutrient antioxidants: role of low-density lipoprotein oxidation. Crit Rev Food Sci Nutr 35:83-98 (1995).
219. Vinson JA and Hontz BA, Phenol antioxidant index: comparative antioxidant effectiveness of red and white wines. J Agric Food Chem 43:401-403 (1995).
220. Miyagi Y, Miwa K and Inoue H, Inhibition of human low-density lipoprotein oxidation by flavonoids in red wine and grape juice. Am J Cardiol 80:1627 (1997).
221. Frankel EN, Kanner J, German JB, Parks E and Kinsella JE, Inhibition of oxidation of human low-density lipoprotein by phenolic substances in red wine. Lancet 341:454-156 (1993).
222. Abu-Amsha R, Croft KD, Puddey IB, Proudfoot JM and Beilin LJ, Phenolic content of various beverages determines the extent of inhibition of human serum and low-density lipoprotein oxidation in vitro: identification and mechanism of action of some cinnamic acid derivatives from red wine. Clin Sci 91:449-458 (1996).
223. Teissedre PL, Frankel EN, Waterhouse AL, Peleg H and German JB, Inhibition of in vitro human LDL oxidation by phenolic antioxidants from grapes and wines. J Sci Food Agric 70:55-61 (1996).
224. Mazur A, Bayle D, Lab C, Rock E and Rayssiguier Y, Inhibitory effect of procyanidin-rich extracts on LDL oxidation in vitro. Atherosclerosis 145:421-422 (1999).
225. Frankel EN, Waterhouse AL and Teissedre PL, Principal phenolic phytochemicals in selected California wines and their antioxidant activity in inhibiting oxidation of human low-density lipoproteins. J Agric Food Chem 43:890-894 (1995).
226. Harmand MF and Blanquet P, The fate of total flavanolic oligomers (OFT) extracted from Vitis vinifera L. in the rat. Eur J. Drug Metabol Pharmacokinet 3:15-30 (1978).
227. Laparra J, Michaud J and Masquelier J, Etude pharmacocinétique des oligomères flavanoliques. Plant Med Phytother 11:133-142 (1977).
228. Michaud J, Lacaze P and Masquelier J, Fractionnement des oligomères flavanoliques du raisin, Bull Soc Pharm Bordeaux 110:111-116 (1971).
229. Jimenez-Ramsey LM, Rogler JC, Housley TL, Butler LG and Elkin RG, Absorption and distribution of C-14-labelled condensed tannins and related sorghum phenolics in chickens. J Agric Food Chem 42:963-967 (1994).
230. 14C-labelled condensed tannins in the gastrointestinal tract of sheep. Br J Nutr 72:467-477 (1994).
231. Groenewoud G and Hundt HKL, The microbial metabolism of condensed (+)-catechins by rat-caecal microflora. Xenobiotica 16:99-107 (1986).
232. Scheline RR, CRC Handbook of Mammalian Metabolism of Plant Compounds. CRC Press, Boca Raton, FL (1991).
233. Scalbert A and Williamson G, Polyphenol intake and bioavailability. J Nutr in press.
234. Monks TJ, Hanzlik RP, Cohen GM, Ross D and Graham DG, Quinone chemistry and toxicity. Toxicol Appl Pharmacol 112:2-16 (1992).
235. Manach C, Morand C, Crespy V, Demigné C, Texier O, Régérat F and Rémésy C, Quercetin is recovered in human plasma as conjugated derivatives which retain antioxidant properties. FEBS Lett 426:331-336 (1998).
236. Sakagami H, Kuribayashi N, Iida M, Sakagami T, Takeda M, Fukuchi K, Gomi K, Ohata H, Momose K, Kawazoe Y, Hatano T, Yoshida T and Okuda T, Induction of DNA fragmentation by tannin- and lignin-related substances. Anticancer Res 15:2121-2128 (1995).
237. Kashiwada Y, Nonaka G, Nishioka I, Chang JJ and Lee KH, Antitumor agents, 129. Tannins and related compounds as selective cytotoxic agents. J Nat Prod 55:1033-1043 (1992).
238. Kolodziej H, Haberland C, Woerdenbag HJ and Konings AWT, Moderate cytotoxicity of proanthocyanidins to human tumour cell lines. Phytother Res 9:410-415 (1995).
239. Kashiwada Y, Nonaka G-I, Nishioka I, Ballas LM, Jiang JB, Janzen WP and Lee K-H, Tannins as selective inhibitors of protein kinase C. Bioorg Med Chem Lett 2:239-244 (1992).
240. Bomser JA, Singletary KW, Wallig MA and Smith MA, Inhibition of TPA-induced tumor promotion in CD-1 mouse epidermis by a polyphenolic fraction from grape seeds. Cancer Lett 135:151-157 (1999).
241. Gali HU, Perchellet EM, Gao XM, Karchesy JJ and Perchellet JP, Comparison of the inhibitory effects of monomeric, dimeric, and trimeric procyanidins on the biochemical markers of skin tumor promotion in mouse epidermis in vivo. Planta Med 60:235-239 (1994).
242. Miyamoto K, Kishi N, Koshiura R, Yoshida T, Hatano T and Okuda T, Relationship between the structures and the anti-tumor activities of tannins. Chem Pharmacent Bull 35:814-822 (1987).
243. Katiyar SK and Mukhtar H, Tea in chemoprevention of cancer: epidemiologic and experimental studies (review). Int J Oncol 8:221-238 (1996).
244. Huang MT, Xie JG, Wang ZY, Ho CT, Lou YR, Wang CX, Hard GC and Conney AH, Effects of tea, decaffeinated tea, and caffeine on UVB light-induced complete carcinogenesis in SKH-1 mice: demonstration of caffeine as a biologically important constituent of tea. Cancer Res 57:2623-2629 (1997).
245. Huber WW, McDaniel LP, Kaderlik KR, Teitel CH, Lang NP and Kadlubar FF, Chemoprotection against the formation of colon DNA adducts from the food-borne carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in the rat. Mutat Res 376:115-122 (1997).
246. Cao J, Xu Y, ChenJS and Klaunig JE, Chemopreventive effects of green and black tea on pulmonary and hepatic carcinogenesis. Fund Appl Toxicol 29:244-250 (1996).
247. Chung FL, Wang M, Rivenson A, Iatropoulos MJ, Reinhardt JC, Pittman B, Ho CT and Amin SG, Inhibition of lung carcinogenesis by black tea in Fischer rats treated with a tobacco-specific carcinogen: caffeine as an important constituent. Cancer Res 58:4096-4101 (1998).
248. Bu-Abbas A, Nunez X, Clifford MN, Walker R and Ioannides C, A comparison of the antimutagenic potential of green, black and decaffeinated teas: contribution of flavanols to the antimutagenic effect. Mutagenesis 11:597-603 (1996).
249. Catterall F, Copeland E, Clifford MN and Ioannides C, Contribution of theafulvins to the antimutagenicity of black tea: their mechanism of action. Mutagenesis 13:631-636 (1998).
250. Apostolides Z, Balentine DA, Harbowy ME, Hara Y and Weisburger JH, Inhibition of PhIP mutagenicity by catechins, and by theaflavins and gallate esters. Mutat Res 389:167-172 (1997).
251. Weisburger JH, Rivenson A, Kingston DG, Wilkins TD, Van Tassell RL, Nagao M, Sugimura T and Hara Y, Dietary modulation of the carcinogenicity of the heterocyclic amines. Princess Takamatsu Symp 23:240-250 (1995).
252. Dong Z, Ma W, Huang C and Yang CS, Inhibition of tumor promoter-induced activator protein 1 activation and cell transformation by tea polyphenols, (-)-epigallocatechin gallate, and theaflavins. Cancer Res 57:4414-4419 (1997).
253. Liang YC, Chen YC, Lin YL, Lin-Shiau SY, Ho CT and Lin JK, Suppression of extracellular signals and cell proliferation by the black tea polyphenol, theaflavin-3,3′-digallate. Carcinogenesis 20:733-736 (1999).
254. Saeki K, Sano M, Miyase T, Nakamura Y, Hara Y, Aoyagi Y and Isemura M, Apoptosis-inducing activity of polyphenol compounds derived from tea catechins in human histiolytic lymphoma U937 cells. Biosci Biotechnol Biochem 63:585-587 (1999).
255. Hibasami H, Komiya T, Achiwa Y, Ohnishi K, Kojima T, Nakanishi K, Sugimoto Y, Hasegawa M, Akatsuka R and Hara Y, Black tea theaflavins induce programmed cell death in cultured human stomach cancer cells. Int J Mol Med 1:725-727 (1998).
256. Morse MA, Kresty LA, Steele VE, Kelloff GJ, Boone CW, Balentine DA, Harbowy ME and Stoner GD, Effects of theaflavins on N-nitrosomethylbenzylamine-induced esophageal tumorigenesis. Nutr Cancer 29:7-12 (1997).
257. Yang GY, Liu Z, Seril DN, Liao J, Ding W, Kim S, Bondoc F and Yang CS, Black tea constituents, theaflavins, inhibit 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-induced lung tumorigenesis in A/J mice. Carcinogenesis 18:2361-2365 (1997).
258. Yang CS and Wang ZY. Tea and cancer. J Natl Cancer Inst 85:1038-1049 (1993).
259. Goldbohm RA, Hertog MGL, Brants HAM, Van Poppel G and Van den Brandt PA, Consumption of black tea and cancer risk: a prospective cohort study. J Natl Cancer Inst 88:93-100 (1996).
260. Yang CS, Lee MJ, Chen LS and Yang GY, Polyphenols as inhibitors of carcinogenesis. Environ Health Perspect 105:971-976 (1997).
261. Blot WJ, McLaughlin JK and Chow WH, Cancer rates among drinkers of black tea. Crit Rev Food Sci Nutr 37:739-760 (1997).
262. Waddell WJ, Borzelleca JF, Doull J, Grasso P, LeBourhis B, Levy PS and Tamburro CH, Alcohol and cancer [letter; comment]. Br J Cancer 66:1200-1203 (1992).
263. Tuyns AJ, Alcohol and cancer. Proc Nutr Soc 49:145-151 (1990).
264. Kato I, Nomura AM, Stemmermann GN and Chyou PH, Prospective study of the association of alcohol with cancer of the upper aerodigestive tract and other sites. Cancer Causes Control 3:145-151 (1992).
265. Gronbaek M, Becker U, Johansen D, Tonnesen H, Jensen G and Sorensen TIA, Population based cohort study of the association between alcohol intake and cancer of the upper digestive tract. Br Med J 317:844-847 (1998).
266. Berger A, Beer and spirits, but not wine, raise the risk of upper digestive tract cancer. Br Med J 317:848 (1998).
267. Clifford AJ, Ebeler SE, Ebeler JD, Bills ND, Hinrichs SH, Teissedre PL and Waterhouse AL, Delayed tumor onset in transgenic mice fed an amino acid-based diet supplemented with red wine solids. Am J Clin Nutr 64:748-756 (1996).
268. Jang M, Cai L, Udeani GO, Slowing KV, Thomas CF, Beecher CWW, Fong HHS, Farnsworth NR, Kinghorn AD, Mehta RG and Pezzuto JM, Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 275:218 (1997).
269. Prescott E, Gronbaek M, Becker U and Sorensen TI, Alcohol intake and the risk of lung cancer: influence of type of alcoholic beverage. Am J Epidemiol 149:463-470 (1999).
270. Carpenter CL, Morgenstern H and London SJ, Alcoholic beverage consumption and lung cancer risk among residents of Los Angeles County. J Nutr 128:694-700 (1998).
271. Chung K-T, Wong TY, Wei C-I and Huang Y-W, Tannins and human health: a review. Crit Rev Food Sci Nutr 38:421-464 (1998).
272. Morton JF, Further associations of plant tannins and human cancer. Q J Crude Drug Res 12:1829-1841 (1972).
273. Ranadive KJ, Ranadive SN, Shivapurkar NM and Gothoskar SV, Betel quid chewing and oral cancer: experimental studies on hamsters. Int J Cancer 24:835-843 (1979).
274. Patrineli A, Clifford MN and Ioannides C, Contribution of phenols, quinones and reactive oxygen species to the mutagenicity of white grape juice in the Ames test. Food Chem Toxicol 34:869-872 (1996).
275. Nagabhushan M, Sarode AV, Nair J, Amonkar AJ, AV DS and Bhide SV, Mutagenicity and carcinogenicity of tea, Camellia sinensis. Indian J Exp Biol 29:401-406 (1991).
276. Wang C-K and Lee W-H, Separation, characteristics, and biological activities of phenolics in areca fruits. J Agric Food Chem 44:2014-2019 (1996).
277. Yu CL and Swaminathan B, Mutagenicity of proanthocyani-dins. Food Chem Toxicol 25:135-139 (1987).
278. Kirby KS, Induction of tumours by tannin extracts. Br J Cancer 14:147-150 (1960).
279. Korpassy B and Mosonyi M, The carcinogenic activity of tannic acid. Liver tumors induced in rats by prolonged subcutaneous administration of tannic acid solutions. Br J Cancer 4:411-420 (1950).
280. Kapadia GJ, Paul BD, Chung EB, Ghosh B and Pradhan SN, Carcinogenicity of Camellia sinensis (tea) and some tannin-containing folk medicinal herbs administered subcutaneously in rats. J Natl Cancer Inst 57:207-209 (1976).
281. Onodera H, Kitaura K, Mitsumori K, Yoshida J, Yasuhara K, Shimo T, Takahashi M and Hayashi Y, Study on the carcinogenicity of tannic acid in F344 rats. Food Chem Toxicol 32:1101-1106 (1994).
282. Johnson IT and Gee JM, Biological effects of food-borne polyphenols in the gastrointestinal tract, in Polyphenols 98, Ed by Ibrahim R, Rolando C and Scalbert A. INRA Editions, Paris, in press.
283. Zhu BT, Ezell EL and Liehr JG, Catechol-O-methyltransferase-catalyzed rapid O-methylation of mutagenic flavonoids. Metabolic inactivation as a possible reason for their lack of carcinogenicity in vivo. J Biol Chem 269:292-299 (1994).
284. Wang C-K, Lee W-H and Peng C-H, Contents of phenolics and alkaloids in Areca catechu Linn, during maturation. J Agric Food Chem 45:1185-1188 (1997).
285. Oterdoom HJ, Tannin, sorghum, and oesophageal cancer [letter]. Lancet 2:330 (1985).
286. Chen F, Cole P, Mi Z and Xing LY, Corn and wheat-flour consumption and mortality from esophageal cancer in Shanxi, China. Int J Cancer 53:902-906 (1993).
287. Van Rensburg SJ, Epidemiologic and dietary evidence for a specific nutritional predisposition to esophageal cancer. J Natl Cancer Inst 67:243-251 (1981).
288. Tijburg LBM, Mattern T, Folts JD, Weisgerber UM and Katan MB, Tea flavonoids and cardiovascular diseases: a review. Crit Rev Food Sci Nutr 37:771-785 (1997).
289. Boffetta P and Garfinkel L, Alcohol drinking and mortality among men enrolled in an American Cancer Society prospective study. Epidemiology 1:342-348 (1990).
290. Thun MJ, Peto R, Lopez AD, Monaco JH, Henley SJ, Heath Jr CW and Doll R, Alcohol consumption and mortality among middle-aged and elderly U.S. adults. New Engl J Med 337:1705-1714 (1997).
291. Renaud SC, Gueguen R, Schenker J and d'Houtaud A, Alcohol and mortality in middle-aged men from eastern France. Epidemiology 9:184-188 (1998).
292. StLeger AS, Cochrane AL and Moore F, Factors associated with cardiac mortality in developed countries with particular reference to the consumption of wine. Lancet, pp 1017-1020 (1979).
293. Renaud S and De Lorgeril M, Wine, alcohol, platelets, and the French paradox for coronary heart disease. Lancet 339:1523-1526 (1992).
294. Criqui MH and Ringel BL, Does diet or alcohol explain the French paradox?. Lancet 344:1719-1723 (1994).
295. Rimm EB, Klatsky A, Grobee D and Stampfer MJ, Review of moderate alcohol consumption and reduced risk of coronary heart disease: is the effect due to beer, wine, or spirits?. Br Med J 312:731-736 (1996).
296. Klatsky AL and Armstrong MA, Alcoholic beverage choice and risk of coronary artery disease mortality: do red wine drinkers fare best?. Am J Cardiol 71:467-469 (1993).
297. Gronbaek M, Deis A, Sorensen TIA, Becker U, Schnohr P and Jensen G, Mortality associated with moderate intakes of wine, beer, or spirits, Br Med J 310:1165-1169 (1995).
298. Woodward M and Tunstall-Pedoe H, Alcohol consumption, diet, coronary risk factors, and prevalent coronary heart disease in men and women in the Scottish heart health study. J Epidemiol Community Health 49:354-362 (1995).
299. Rosenberg L, Slone D, Shapiro S, Kaufman DW, Miettinen OS and Stolley PD, Alcoholic beverages and myocardial infarction in young women. Am J Public Health 71:82-85 (1981).
300. Stensvold I, Tverdal A, Solvoll K and Foss OP, Tea consumption, relationship to cholesterol, blood pressure, and coronary and total mortality. Prevent Med 21:546-553 (1992).
301. Green MS and Jucha E, Association of serum lipids with coffee, tea, and egg consumption in free-living subjects. J Epidemiol Community Health 40:324-329 (1986).
302. Lin BB, Chen HL and Huang PC, Effects of instant Pauchong tea, catechin, and caffeine on serum cholesterol and serum low-density lipoprotein in mice. Nutr Rep Int 34:821-829 (1986).
303. Tebib K, Besancon P and Rouanet JM, Dietary grape seed tannins affect lipoproteins, lipoprotein lipases and tissue lipids in rats fed hypercholesterolemic diets. J Nutr 124:2451-2457 (1994).
304. Hodgson JM, Puddey IB, Burke V, Beilin LJ and Jordan N, Effects on blood pressure of drinking green and black tea. J Hypertens 17:457-463 (1999).
305. Bingham SA, Vorster H, Jerling JC, Magee E, Mulligan A, Runswick SA and Cummings JH, Effect of black tea drinking on blood lipids, blood pressure and aspects of bowel habit. Br J Nutr 78-41-55 (1997).
306. Van het Hof KH, deBoer HSM, Wiseman SA, Lien N, Weststrate JA and Tijburg LBM, Consumption of green or black tea does not increase resistance of low-density lipoprotein to oxidation in humans. Am J Clin Nutr 66:1125-1132 (1997).
307. Loktionov A, Bingham SA, Vorster H, Jerling JC, Runswick SA and Cummings JH, Apolipoprotein E genotype modulates the effect of black tea drinking on blood lipids and blood coagulation factors: a pilot study. Br J Nutr 79:133-139 (1998).
308. Princen HM, van Duyvenvoorde W, Buytenhek R, Blonk C, Tijburg LB, Langius JA, Meinders AE and Pijl H, No effect of consumption of green and black tea on plasma lipid and antioxidant levels and on LDL oxidation in smokers. Arterioscler Thromb Vasc Biol 18:833-841 (1998).
309. Naismith DJ, Akinyanju PA and Yudkin J, Influence of caffeine-containing beverage on the growth, food utilization and plasma lipids of the rat. J Nutr 97:375-381 (1969).
310. Fears R, The hypercholesterolaemic effect of caffeine in rats fed on diets with and without supplementary cholesterol. Br J Nutr 39:363-374 (1978).
311. Fuster V, Lewis A. Conner Memorial Lecture. Mechanisms leading to myocardial infarction: insights from studies of vascular biology [published erratum appears in. Circulation 91:256 (1995). Circulation 90:2126-2146 (1994).
312. Maxwell S, Cruickshank A and Thorpe G, Red wine and antioxidant activity in serum. Lancet 344:193-194 (1994).
313. Duthie GG, Pedersen MW, Gardner PT, Morrice PC, Jenkinson AM, McPhail DB and Steele GM, The effect of whisky and wine consumption on total phenol content and antioxidant capacity of plasma from healthy volunteers. Eur J Clin Nutr 52:733-736 (1998).
314. Whitehead TP, Robinson D, Allaway S, Syms J and Hale A, Effect of red wine ingestion on the antioxidant capacity of serum. Clin Chem 41:32-35 (1995).
315. Serafini M, Maiani G and Ferro-Luzzi A, Alcohol-free red wine enhances plasma antioxidant capacity in humans. J Nutr 128:1003-1007 (1998).
316. Carbonneau MA, Leger CL, Monnier L, Bonnet C, Michel F, Fouret G, Dedieu F and Descomps B, Supplementation with wine phenolic compounds increases the antioxidant capacity of plasma and vitamin E of low-density lipoprotein without changing the lipoprotein Cu(2+)-oxidizability: possible explanation by phenolic location. Eur J Clin Nutr 51:682-690 (1997).
317. Serafini M, Ghiselli A and Ferro-Luzzi A, In vivo antioxidant effect of green and black tea in man. Eur J Clin Nutr 50:28-32 (1996).
318. Rice-Evans C and Miller NJ, Total antioxidant status in plasma and body fluids. Methods Enzymol 234:279-293 (1994).
319. Kondo K, Matsumoto A, Kurata H, Tanahashi H, Koda H, Amachi T and Itakura H, Inhibition of oxidation of low-density lipoprotein with red wine. Lancet 344:1152 (1994).
320. Fuhrman B, Lavy A and Aviram M, Consumption of red wine with meals reduces the susceptibility of human plasma and low-density lipoprotein to lipid peroxidation. Am J Clin Nutr 61:549-554 (1995).
321. De Rijke YB, Demacker PNM, Assen NA, Sloots LM, Katan MB and Stalenhoef AFH, Red wine consumption does not affect oxidizability of low-density lipoproteins in volunteers. Am J Clin Nutr 63:329-334 (1996).
322. Sharpe PC, McGrath LT, McClean E, Young IS and Archbold GP, Effect of red wine consumption on lipoprotein (a) and other risk factors for atherosclerosis. Q J Med 88:101-108 (1995).
323. Jialal I, Vega GL and Grundy SM, Physiologic levels of ascorbate inhibit the oxidative modification of low density lipoprotein. Atherosclerosis 82:185-191 (1990).
324. Yoshino K, Tomita I, Sano M, Oguni I, Hara Y and Nakano M, Effects of long-term dietary supplement of tea polyphenols on lipid peroxide levels in rats. Age 17:79-85 (1994).
325. Lauque D, Prevost MC, Carles P and Chap H, Signal transducing mechanisms in human platelets stimulated by cotton bract tannin. Am J Respir Cell Mol Biol 4:65-71 (1991).
326. Rohrbach MS, Rolstad RA, Tracy PB and Russell JA, Platelet 5-hydroxytryptamine release and aggregation promoted by cotton bracts tannin. J Lab Clin Med 103:152-160 (1984).
327. Rohrbach MS, Kreofsky TJ and Chan BG, Structural determinants of the platelet agonist activity of cotton bract condensed tannin. Environ Res 52:199-209 (1990).
328. Rohrbach MS, Rolstad RA and Russell JA, Protection by plasma proteins against condensed tannin-mediated platelet activation. Biochem Med 34:189-194 (1985).
329. Sagesaka-Mitane Y, Miwa M and Okada S, Platelet aggregation inhibitors in hot water extract of green tea. Chem Pharmaceut Bull 38:790-793 (1990).
330. Wollny T, Aiello L, Di Tommaso D, Bellavia V, Rotilio D, Donati MB, de Gaetano G and lacoviello L, Modulation of haemostatic function and prevention of experimental thrombosis by red wine in rats: a role for increased nitric oxide production. Br J Pharmacol 127:747-755 (1999).
331. Demrow HS, Slane PR and Folts JD, Administration of wine and grape juice inhibits in vivo platelet activity and thrombosis in stenosed canine coronary arteries. Circulation 91:1182-1188 (1995).
332. Ruf JC, Berger JL and Renaud S, Platelet rebound effect of alcohol withdrawal and wine drinking in rats - relation to tannins and lipid peroxidation. Arterioscl Thromb Vasc Biol 15:140-144 (1995).
333. Osman HE, Maalej N, Shanmuganayagam D and Folts JD, Grape juice but not orange or grapefruit juice inhibits platelet activity in dogs and monkeys. J Nutr 128:2307-2312 (1998).
334. Xia J, Allenbrand B and Sun GY, Dietary supplementation of grape polyphenols and chronic ethanol administration on LDL oxidation and platelet function in rats. Life Sci 63:383-390 (1998).
335. Lavy A, Fuhrman B, Markel A, Dankner G, Ben-Amotz A, Presser D and Aviram M, Effect of dietary supplementation of red or white wine on human blood chemistry, hematology and coagulation: favorable effect of red wine on plasma high-density lipoprotein. Ann Nutr Metab 38:287-294 (1994).
336. Pace-Asciak CR, Rounova O, Hahn SE, Diamandis EP and Goldberg DM, Wines and grape juices as modulators of platelet aggregation in healthy human subjects. Clin Chim Acta 246:163-182 (1996).
337. Pellegrini N, Pareti FI, Stabile F, Brusamolino A and Simonetti P, Effects of moderate consumption of red wine on platelet aggregation and haemostatic variables in healthy volunteers. Eur J Clin Nutr 50:209-213 (1996).