Pink discoloration of canned pears: Role of procyanidin chemical depolymerization and procyanidin/cell wall interactions

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 27, 2013, Pages 6679-6692

  Le Bourvellec, Carine ^a,b   Gouble, Barbara ^a,b   Bureau, Sylvie ^a,b   Loonis, Michèle ^a,b   Plé, Yves ^c   Renard, Catherine M G C ^a,b  

^a UMR A 408 INRA University of Avignon   (France)

^b UNIVERSITY OF AVIGNON   (France)

^c CTCPA   (France)

Author keywords

condensed tannins; covalent binding; polyphenol; polysaccharide; processing; Pyrus communis L.

Indexed keywords

ACIDIC PH VALUES; CELL WALL-DEGRADING ENZYMES; CONDENSED TANNINS; COVALENT BINDING; ENZYME TREATMENT; PINK DISCOLORATION; POLYPHENOLS; PYRUS COMMUNIS L;

ANTHOCYANINS; COLOR; DISCOLORATION; PH; POLYSACCHARIDES; PROCESSING; TANNINS;

FRUITS;

BIFLAVONOID; CATECHIN; PIGMENT; PROANTHOCYANIDIN; PROCYANIDIN;

ARTICLE; CELL WALL; CHEMISTRY; FRUIT; POLYMERIZATION; PYRUS;

BIFLAVONOIDS; CATECHIN; CELL WALL; FRUIT; PIGMENTS, BIOLOGICAL; POLYMERIZATION; PROANTHOCYANIDINS; PYRUS;

EID: 84880024033     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf4005548     Document Type: Article

References (76)

1. Chandler, B. V.; Clegg, K. M. Pink discoloration in canned pears. I. Role of tin in pigment formation J. Sci. Food Agric. 1970, 21 (6) 315-319
2. Chandler, B. V.; Clegg, K. M. Pink discoloration in canned pears. II. Measurement of potential and developed color in pear samples J. Sci. Food Agric. 1970, 21 (6) 319-323
3. Chandler, B. V.; Clegg, K. M. Pink discoloration in canned pears. III. Inhibition by chemical additives J. Sci. Food Agric. 1970, 21 (6) 323-328
4. Czerkaskyj, A. Pink discoloration in canned Williams' Bon Chretien pears J. Food Sci. 1970, 35 (5) 608-611
5. Hamauzu, Y.; Kume, C.; Yasui, H.; Fujita, T. Reddish coloration of Chinese quince (Pseudocydonia sinensis) procyanidins during heat treatment and effect on antioxidant and antiinfluenza viral activities J. Agric. Food Chem. 2007, 55 (4) 1221-1226
6. Adams, J. B.; Brown, H. M. Discoloration in raw and processed fruits and vegetables Crit. Rev. Food Sci. Nutr. 2007, 47 (3) 319-333
7. Luh, B. S.; Leonard, S. J.; Patel, D. S. Pink discoloration in canned Bartlett pears Food Technol. 1960, 14, 53-56
8. Bate-Smith, E. C. Leuco-anthocyanins. 1. Detection and identification of anthocyanidins formed leuco-anthocyanins in plant tissues Biochemical J. 1954, 58 (1) 122-125
9. Thompson, R. S.; Jacques, D.; Haslam, E.; Tanner, R. J. N. Plant proanthocyanidins. Part I. Introduction: the isolation, structure and distribution in nature of plant procyanidins J. Chem. Soc., Perkin Trans. 1 1972, 1387-1399
10. Beart, J. E.; Lilley, T. H.; Haslam, E. Polyphenol interactions.2. Covalent binding of procyanidins to proteins during acid-catalysed decomposition, observation on some polymeric proathocyanidins J. Chem. Soc., Perkin Trans. 2 1985, 9) 1439-1443
11. Porter, L. J.; Hrstich, L. N.; Chan, B. G. The conversion of of procyanidins and prodelphinidins to cyanidin and delphinidin Phytochemistry 1986, 25 (1) 223-230
12. Haslam, E. In vino veritas: oilgomeric procyanidins and the aging of red wines Phytochemistry 1980, 19, 2577-2582
13. Haslam, E. Plant Polyphenols. Vegetable Tannins Revisited; Cambridge University Press: Cambridge, UK, 1989.
14. Le Bourvellec, C.; Renard, C. M. G. C. Interactions between polyphenols and macromolecules: quantification methods and mechanisms Crit. Rev. Food Sci. Nutr. 2012, 52 (1-3) 213-248
15. Esatbeyoglu, T.; Wray, V.; Winterhalter, P. Dimeric procyanidins: screening for B1 to B8 and semisynthetic preparation of B3, B4, B6, and B8 from a polymeric procyanidin fraction of white willow bark (Salix alba) J. Agric. Food Chem. 2010, 58 (13) 7820-7830
16. Serrano, J.; Puupponen-Pimia, R.; Dauer, A.; Aura, A.-M.; Saura-Calixto, F. Tannins: current knowledge of food sources, intake, bioavailability and biological effects Mol. Nutr. Food Res. 2009, 53, S310-S329
17. Lea, A. G. H.; Arnold, G. M. Phenolics of ciders-bitterness and astringency J. Sci. Food Agric. 1978, 29 (5) 478-483
18. Ribéreau-Gayon, P. The anthocyanins of grapes and wines. In Anthocyanins as Food Colors; Academic Press: New York, 1982.
19. Es-Safi, N.-E.; Guyot, S.; Ducrot, P.-H. NMR, ESI/MS, and MALDI-TOF/MS analysis of pear juice polymeric proanthocyanidins with potent free radical scavenging activity J. Agric. Food Chem. 2006, 54 (19) 6969-6977
20. Ferreira, D.; Guyot, S.; Marnet, N.; Delgadillo, I.; Renard, C. M. G. C.; Coimbra, M. A. Composition of phenolic compounds in a Portuguese pear (Pyrus communis L. var. S. Bartolomeu) and changes after sun-drying J. Agric. Food Chem. 2002, 50 (16) 4537-4544
21. Le Bourvellec, C.; Guyot, S.; Renard, C. M. G. C. Non-covalent interaction between procyanidins and apple cell wall material. Part I. Effect of some environmental parameters Biochim. Biophys. Acta 2004, 1672 (3) 192-202
22. Renard, C. M. G. C. Effects of conventional boiling on the polyphenols and cell walls of pears J. Sci. Food Agric. 2005, 85 (2) 310-318
23. Renard, C.; Vanleeuwen, M.; Voragen, A. G. J.; Thibault, J. F.; Pilnik, W. Studies on apple protopectin. 2. Apple cell wall degradation by pure polysaccharidases and their combinations Carbohydr. Polym. 1990, 14 (3) 295-314
24. Renard, C. M. G. C. Variability in cell wall preparations: quantification and comparison of common methods Carbohydr. Polym. 2005, 60 (4) 515-522
25. Guyot, S.; Marnet, N.; Laraba, D.; Sanoner, P.; 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. 1998, 46 (5) 1698-1705
26. Micard, V.; Renard, C. M. G. C.; Thibault, J. F. Enzymatic saccharification of sugar-beet pulp Enzym. Microb. Technol. 1996, 19 (3) 162-170
27. Renard, C. M. G. C.; Baron, A.; Guyot, S.; Drilleau, J. F. Interactions between apple cell walls and native apple polyphenols: quantification and some consequences Int. J. Biol. Macromol. 2001, 29 (2) 115-125
28. Le Bourvellec, C.; Bouzerzour, K.; Ginies, C.; Regis, S.; Ple, Y.; Renard, C. M. G. C. Phenolic and polysaccharidic composition of applesauce is close to that of apple flesh J. Food Compos. Anal. 2011, 24 (4-5) 537-547
29. Seaman, J. F.; Moore, W. E.; Mitchell, A. E.; Millett, M. A. Techniques for the determination of flesh constituents by quantitative paper chromatography Tappi, J. Tech. Assoc. Pulp Paper Ind. 1954, 37, 336-343
30. Englyst, H.; Wiggins, H. S.; Cummings, J. H. Determination of the non-starch polysaccharides in plant foods by gas-liquid chromatography of constituent sugars as alditol acetates Analyst 1982, 107, 307-318
31. Blumenkrantz, N.; Asboe-Hansen, G. New method for quantitative determination of uronic acids Anal. Biochem. 1973, 54 (2) 484-489
32. Renard, C. M. G. C.; Ginies, C. Comparison of the cell wall composition for flesh and skin from five different plums Food Chem. 2009, 114 (3) 1042-1049
33. CIE, International Commission on Illumination. Recommendations on Uniform Colour Spaces, Colour, Difference Equations, Psychometric Colour Terms; Bureau Central de la CIE: Paris, France, 1978; CIE Publication 15 (Suppl. 2), (E-1.31) 1971/(TC-1.3).
34. McGuire, R. G. Reporting of objective color measurements HortScience 1992, 27 (12) 1254-1255
35. Box, G. E. P.; Hunter, J. S.; Hunter, W. G. Statistics for Experimenters, An Introduction to Design, Data Analysis and Model Building; Wiley: New York, 1978.
36. Galvis Sanchez, A. C.; Gil-Izquierdo, A.; Gil, M. I. Comparative study of six pear cultivars in terms of their phenolic and vitamin C contents and antioxidant capacity J. Sci. Food Agric. 2003, 83 (10) 995-1003
37. Oleszek, W.; Amiot, M. J.; Aubert, S. Y. Identification of some phenolic in pear fruit J. Agric. Food Chem. 1994, 42 (6) 1261-1265
38. Spanos, G. A.; Wrolstad, R. E. Influence of variety, maturity, processing, and storage on the phenolic composition of pear juice J. Agric. Food Chem. 1990, 38 (3) 817-824
39. Vidal, S.; Cartalade, D.; Souquet, J. M.; Fulcrand, H.; Cheynier, V. Changes in proanthocyanidin chain length in winelike model solutions J. Agric. Food Chem. 2002, 50 (8) 2261-2266
40. Asami, D. K.; Hong, Y. J.; Barrett, D. M.; Mitchell, A. E. Processing-induced changes in total phenolics and procyanidins in clingstone peaches J. Sci. Food Agric. 2003, 83 (1) 56-63
41. Brownmiller, C.; Howard, L. R.; Prior, R. L. Processing and storage effects on procyanidin composition and concentration of processed blueberry products J. Agric. Food Chem. 2009, 57 (5) 1896-1902
42. Hong, Y. J.; Barrett, D. M.; Mitchell, A. E. Liquid chromatography/mass spectrometry investigation of the impact of thermal processing and storage on peach procyanidins J. Agric. Food Chem. 2004, 52 (8) 2366-2371
43. Hernandez, T.; Ausin, N.; Bartolome, B.; Bengoechea, L.; Estrella, I.; Gomez Cordoves, C. Variations in the phenolic composition of fruit juices with different treatments Z. Lebensm. Unters. -Forsch. A (Food Res. Technol.) 1997, 204 (2) 151-155
44. Vallejo, F.; Tomas-Barberan, F. A.; Garcia-Viguera, C. Phenolic compound contents in edible parts of broccoli inflorescences after domestic cooking J. Sci. Food Agric. 2003, 83 (14) 1511-1516
45. O'Connell, J. E.; Fox, P. F. Proposed mechanism for the effect of polyphenols on the heat stability of milk Int. Dairy J. 1999, 9 (8) 523-536
46. Diem, S.; Bergmann, J.; Herderich, M. Tryptophan- N -glucoside in fruits and fruit juices J. Agric. Food Chem. 2000, 48 (10) 4913-4917
47. Gutsche, B.; Grun, C.; Scheutzow, D.; Herderich, M. Tryptophan glycoconjugates in food and human urine Biochem. J. 1999, 343, 11-19
48. Frear, D. S.; Swanson, H. R.; Mansager, E. R. Picloram metabolism in leafy spurge-isolation and identification of glucose and gentiobiose conjugates J. Agric. Food Chem. 1989, 37 (5) 1408-1412
49. Guyot, S.; Marnet, N.; Drilleau, J. F. Thiolysis-HPLC characterization of apple procyanidins covering a large range of polymerization states J. Agric. Food Chem. 2001, 49 (1) 14-20
50. Hamauzu, Y.; Takedachi, N.; Miyasaka, R.; Makabe, H. Heat treatment of Chinese quince polyphenols increases rat plasma levels of protocatechuic and vanillic acids Food Chem. 2010, 118 (3) 757-763
51. Guyot, S.; Doco, T.; Souquet, J. M.; Moutounet, M.; Drilleau, J. F. Characterization of highly polymerized procyanidins in cider apple (Malus sylvestris var kermerrien) skin and pulp Phytochemistry 1997, 44 (2) 351-357
52. Koehler, N.; Wray, V.; Winterhalter, P. New approach for the synthesis and isolation of dimeric procyanidins J. Agric. Food Chem. 2008, 56 (13) 5374-5385
53. Esatbeyoglu, T.; Winterhalter, P. Preparation of dimeric procyanidins B1, B2, B5, and B7 from a polymeric procyanidin fraction of black chokeberry (Aronia melanocarpa) J. Agric. Food Chem. 2010, 58 (8) 5147-5153
54. Salas, E.; Fulcrand, H.; Meudec, E.; Cheynier, V. Reactions of anthocyanins and tannins in model solutions J. Agric. Food Chem. 2003, 51 (27) 7951-7961
55. Salas, E.; Atanasova, V.; Poncet-Legrand, C.; Meudec, E.; Mazauric, J. P.; Cheynier, V. Demonstration of the occurrence of flavanol-anthocyanin adducts in wine and in model solutions Anal. Chim. Acta 2004, 513 (1) 325-332
56. Murakami, M.; Yamaguchi, T.; Takamura, H.; Matoba, T. Effects of thermal treatment on radical-scavenging activity of single and mixed polyphenolic compounds J. Food Sci. 2004, 69 (1) FCT7-FCT15
57. n determination of direct condensation flavanol-anthocyanin adducts in pressure extracted pomegranate (Punica granatum L.) Juice J. Agric. Food Chem. 2010, 58 (19) 10560-10567
58. Macz-Pop, G. A.; Gonzalez-Paramas, M.; Perez-Alonso, J. J.; Rivas-Gonzalo, J. C. New flavanol-anthocyanin condensed pigments and anthocyanin composition in Guatemalan beans (Phaseolus spp.) J. Agric. Food Chem. 2006, 54 (2) 536-542
59. Friedrich, W.; Eberhardt, A.; Galensa, R. Investigation of proanthocyanidins by HPLC with electrospray ionization mass spectrometry Eur. Food Res. Technol. 2000, 211 (1) 56-64
60. Remy, S.; Fulcrand, H.; Labarbe, B.; Cheynier, V.; Moutounet, M. First confirmation in red wine of products resulting from direct anthocyanin-tannin reactions J. Sci. Food Agric. 2000, 80 (6) 745-751
61. Es-Safi, N. E.; Fulcrand, H.; Cheynier, V.; Moutounet, M. Studies on the acetaldehyde-induced condensation of (-)-epicatechin and malvidin 3- O -glucoside in a model solution system J. Agric. Food Chem. 1999, 47 (5) 2096-2102
62. Le Bourvellec, C.; Guyot, S.; Renard, C. M. G. C. Interactions between apple (Malus × domestica Borkh.) polyphenols and cell walls modulate the extractability of polysaccharides Carbohydr. Polym. 2009, 75 (2) 251-261
63. Martin Cabrejas, M. A.; Waldron, K. W.; Selvendran, R. R.; Parker, M. L.; Moates, G. K. Ripening-related changes in the cell-walls of Spanish pear (Pyrus communis) Physiol. Plant. 1994, 91 (4) 671-679
64. Isherwood, F. A.; Jermyn, M. A. Changes in the cell wall of the pear during ripening Biochem. J. 1956, 64 (1) 123-132
65. Ferreira, D.; Barros, A.; Coimbra, M. A.; Delgadillo, I. Use of FT-IR spectroscopy to follow the effect of processing in cell wall polysaccharide extracts of a sun-dried pear Carbohydr. Polym. 2001, 45 (2) 175-182
66. Ahmed, A. E.; Labavitch, J. M. Cell-wall metabolism in ripening fruit. 1. Cell-wall changes in ripening Bartlett pears Plant Physiol. 1980, 65 (5) 1009-1013
67. Bindon, K. A.; Smith, P. A.; Kennedy, J. A. Interaction between grape-derived proanthocyanidins and cell wall material. 1. Effect on proanthocyanidin composition and molecular mass J. Agric. Food Chem. 2010, 58 (4) 2520-2528
68. Le Bourvellec, C.; Renard, C. M. G. C. Non-covalent interaction between procyanidins and apple cell wall material. Part II: Quantification and impact of cell wall drying Biochim. Biophys. Acta 2005, 1725 (1) 1-9
69. Le Bourvellec, C.; Watrelot, A. A.; Ginies, C.; Imberty, A.; Renard, C. M. G. C. Impact of processing on the noncovalent interactions between procyanidin and apple cell wall J. Agric. Food Chem. 2012, 60 (37) 9484-9494
70. Bindon, K. A.; Kennedy, J. A. Ripening-induced changes in grape skin proanthocyanidins modify their interaction with cell walls J. Agric. Food Chem. 2011, 59 (6) 2696-2707
71. Rentzsch, M.; Schwarz, M.; Winterhalter, P. Pyranoanthocyanins-an overview on structures, occurrence, and pathways of formation Trends Food Sci. Technol. 2007, 18 (10) 526-534
72. Williamson, G.; Clifford, M. N. Colonic metabolites of berry polyphenols: the missing link to biological activity? Br. J. Nutr. 2010, 104, S48-S66
73. Del Rio, D.; Costa, L. G.; Lean, M. E. J.; Crozier, A. Polyphenols and health: what compounds are involved? Nutr. Metab. Cardiovasc. Dis. 2010, 20 (1) 1-6
74. Donovan, J. L.; Manach, C.; Rios, L.; Morand, C.; Scalbert, A.; Remesy, C. Procyanidins are not bioavailable in rats fed a single meal containing a grapeseed extract or the procyanidin dimer B-3 Br. J. Nutr. 2002, 87 (4) 299-306
75. Bazzocco, S.; Mattila, I.; Guyot, S.; Renard, C. M. G. C.; Aura, A. M. Factors affecting the conversion of apple polyphenols to phenolic acids and fruit matrix to short-chain fatty acids by human faecal microbiota in vitro Eur. J. Nutr. 2008, 47 (8) 442-452
76. Aura, A.-M.; Mattila, I.; Hyotylainen, T.; Gopalacharyulu, P.; Cheynier, V.; Souquet, J.-M.; Bes, M.; Le Bourvellec, C.; Guyot, S.; Oresic, M. Characterization of microbial metabolism of Syrah grape products in an in vitro colon model using targeted and non-targeted analytical approaches Eur. J. Nutr. 2013, 52 (2) 833-846