Non-covalent interaction between procyanidins and apple cell wall material: Part I. Effect of some environmental parameters

Biochimica et Biophysica Acta - General Subjects

Volumn 1672, Issue 3, 2004, Pages 192-202

  Le Bourvellec, C ^a   Guyot, S ^a   Renard, C M G C ^a  

^a CEMAGREF   (France)

Author keywords

gall; Adsorption; AIS; alcohol insoluble material; Apple; cell wall material; Cider; CWM; degree of polymerisation; DP; Grape; molecular weight; Mw; OD; optical density; percentage of galloylation; polyphenol oxydase; Polysaccharide; PPO; Tannin

Indexed keywords

ALCOHOL; CATECHIN; DIOXANE; FLAVANOL DERIVATIVE; HYDROGEN; PROCYANIDIN DERIVATIVE; UREA;

ADSORPTION; APPLE; ARTICLE; CELL WALL; CHEMICAL BOND; CHEMICAL INTERACTION; COMPLEX FORMATION; CONTROLLED STUDY; ENERGY; ENVIRONMENTAL PARAMETERS; GALL (PLANT); HIGH TEMPERATURE; HYDROGEN BOND; HYDROPHOBICITY; IONIC STRENGTH; NONHUMAN; PH; PHYSICAL CHEMISTRY; PLANT CELL; POLYMERIZATION; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUSPENSION; TEMPERATURE;

ADSORPTION; BIFLAVONOIDS; CATECHIN; CELL WALL; ETHANOL; FLAVONOIDS; HYDROGEN BONDING; HYDROGEN-ION CONCENTRATION; HYDROPHOBICITY; MALUS; OSMOLAR CONCENTRATION; PHENOLS; PROANTHOCYANIDINS; PYRUS; SEEDS; TEMPERATURE; VITIS;

MALUS X DOMESTICA; VITIS SP.;

EID: 2942560770     PISSN: 03044165     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbagen.2004.04.001     Document Type: Article

References (56)

1. Haslam E. Polyphenol-protein Interactions. Biochem. J. 139:1974;285-288
2. Hagerman A.E., Butler L.G. The specificity of procyanidin-protein interactions. J. Biol. Chem. 256:1981;4494-4497
3. McManus J.P., Davis K., Beart J.E., Gaffney S.H., Lilley T.H., Haslam E. Polyphenol interactions: Part I. Introduction. Some observation on the reversible complexation of polyphenols with proteins and polysaccharides. J. Chem. Soc., Perkin Trans. 2:1985;1429-1438
4. Helsper J.P.F.G., Kolodziej H., Hoogendijj J.M., Van Norel A. Characterization and trypsin inhibitor activity of proanthocyanidins from Vicia faba. Phytochemistry. 34:1993;1255-1260
5. Baxter N.J., Lilley T.H., Haslam E., Williamson M.P. Multiple interactions between polyphenols and a salivary proline-rich protein repeat result in complexation and precipitation. Biochemistry. 36:1997;5566-5577
6. De Freitas V., Mateus M. Nephelometry study of salivary protein-tannin aggregates. J. Sci. Food Agric. 82:2001;113-119
7. 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. 29:2001;115-125
8. Guyot S., Marnet N., Sanoner P., Drilleau J.F. Variability of the polyphenolic composition of cider apple (Malus domestica) fruits and juices. J. Agric. Food Chem. 51:2003;6240-6247
9. Lea A.G.H., Arnold G.M. The phenolics of ciders: bitterness and astringency. J. Sci. Food Agric. 29:1978;478-483
10. Szejtli J. Cyclodextrins in drugs formulation: Part I. J. Pharm. Technol. Int. 3:1991;15-22
11. Fayad N., Marchal L., Billaud C., Nicolas J. Comparison of β-cyclodextrin effect on polyphenol oxidation catalyzed by purified polyphenol oxidase from different sources. J. Agric. Food Chem. 45:1997;2442-2446
12. Irwin P.L., Pfeffer P.E., Doner L.W., Sapers G.M., Brewster D., Nagahashi G., Hicks K.B. Binding geometry, stoichiometry, and thermodynamics of cyclomalto-oligosaccharide (cyclodextrin) inclusion complex formation with chlorogenic acid, the major substrate of apple polyphenol oxidase. Carbohydr. Res. 25:1994;13-27
13. Ficcara R., Tommasini S., Raneri D., Calabro M.L., Di Bella M.R., Rustichelli C., Gamberini M.C., Ficarra P. Study of flavonoids/β- cyclodextrins inclusion complexes by NMR, FT-IR, DSC, X-ray investigation. J. Pharm. Biotech. Anal. 29:2002;1005-1014
14. Ishizu T., Kintsu K., Yamamoto H. NMR study of the solution structures of the inclusion complexes of β-cyclodextrin with (+)-catechin and (-)-epicatechin. J. Phys. Chem., B. 103:1999;8992-8997
15. Caccia F., Dispenza R., Fronza G., Fuganti C., Malpezzi L., Mele A. Structure of neohesperidin dihydrochalcone/β-cyclodextrin inclusion complex: NMR, MS and X-ray spectrocopic investigation. J. Agric. Food Chem. 46:1998;1500-1505
16. Hostettmann K., Lederer M., Marston A., Leipzig-Pagani E. A study of the cyclodextrin complexes of flavonoids by thin layer chromatography. Phytochem. Anal. 8:1997;173-175
17. Gaffney S.H., Martin R., Lilley T.H., Haslam E., Magnoloto D. The association of polyphenols with caffeine and α- and β-cyclodextrin in aqueous media. J. Chem. Soc., Chem. Commun. 1986;107-109
18. Cai Y., Lilley T.H., Haslam E., Gaffney S.H. Carbohydrate-polyphenol complexation. Hemingway R.W., Karchesy J.J. Chemistry and Significance of Condensed Tannins. 1989;307-322 Plenum, New York
19. Guyot S., Doco T., Souquet J.M., Moutounet M., Drilleau J.-F. Characterisation of highly polymerised procyanidins in cider apple (Malus domestica, var. Kermerrien) skin and pulp. Phytochemistry. 44:1997;351-357
20. Guyot S., Marnet N., Drilleau J.F. Thioacidolysis-HPLC characterisation of apple procyanidins covering a large range of polymerisation state. J. Agric. Food Chem. 49:2001;14-20
21. Souquet J.M., Labarbe B., Le Guernevé C., Cheynier V., Moutounet M. Phenolic composition of grape stems. J. Agric. Food Chem. 48:2000;1076-1080
22. Dubois M., Gilles K.A., Hamilton J.K., Rebers P.A., Smith F. Colorimetric method for the determination of sugars and related substances. Anal. Chem. 28:1956;350-356
23. Vidal S., Francis L., Guyot S., Marnet N., Kwiatkowski M., Gawel R., Cheynier V., Waters E.J. The mouth-feel properties of grape and apple proanthocyanidins in a wine-like medium. J. Sci. Food Agric. 83:2003;564-573
24. Thibault J.F. Automatisation du dosage des substances pectiques par la méthode au méta-hydroxydiphényl. Lebensm.-Wiss. Technol. 12:1979;247-251
25. Seaman J.F., Moore W.E., Mitchell R.L., Millet M.A. Techniques for the determination of pulp constituents by quantitative paper chromatography. Tappi. 37:1954;336-343
26. Englist 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. 107:1984;307-318
27. Klavons J.A., Bennet R.D. Determination of methanol using alcohol oxidase and its application to methyl ester content of pectins. J. Agric. Food Chem. 34:1986;597-599
28. Hach C.C., Brayton S.V., Kopelove A.B. A powerful Kjeldahl nitrogen method using peroxymonosulfuric acid. J. Agric. Food Chem. 33:1985;1117-1123
29. Sanoner P., Guyot S., Marnet N., Molle D., Drilleau J.F. Polyphenol profiles of French cider apple varieties (Malus domestica sp.). J. Agric. Food Chem. 47:1999;4847-4853
30. Selvendran R.R., O'Neill M.A. Isolation and analysis of cell walls from plant material. Methods Biochem. Anal. 32:1987;25-153
31. Renard C.M.G.C., Voragen A.G.J., Thibault J.F., Pilnik W. Studies on apple protopectin: I. Extraction of insoluble pectin by chemical means. Carbohydr. Polym. 12:1990;9-25
32. Massiot P., Renard C.M.G.C. Composition, physico-chemical properties and enzymatic degradation of fibres prepared from different tissues of apple. Lebensm. Wiss. Technol. 30:1997;800-806
33. Renard C.M.G.C., Voragen A.G.J., Thibault J.F., Pilnik W. Studies on apple protopectin IV: apple xyloglucans and influence of pectin extraction treatments on their solubility. Carbohydr. Polym. 15:1991;387-403
34. Renard C.M.G.C., Voragen A.G.J., Thibault J.F., Pilnik W. Studies on apple protopectin V: structural studies on enzymatically extracted pectins. Carbohydr. Polym. 16:1991;137-154
35. Voragen G.J., Heutink R., Pilnik W. Solubilization of apple cell walls with polysaccharide-degrading enzymes. J. Appl. Biochem. 2:1980;452-468
36. De Vries J.A., Rombouts F.M., Voragen A.G.J., Pilnik W. Enzymic degradation of apple pectins. Carbohydr. Polym. 2:1982;25-33
37. Guyot S., Marnet N., Laraba D., Sanoner P., Drilleau J.F. Reversed-phase HPLC following thioacidolysis for quantitative estimation and caracterisation of the four main classes of phenolic compounds in different tissue zone of a french cider apple variety (Malus domestica var. Kermerrien). J. Agric. Food Chem. 46:1998;1698-1705
38. Guyot S., Marnet N., Le Bourvellec C., Drilleau J.F. Highly polymerised procyanidins in fruits and juices of perry pear (Pyrus communis) varieties. El Hadrami I. Polyphenols Communications 2002. Marrakech. 2002;463-464 Université Cadi Ayyad
39. 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. 50:2002;4537-4544
40. Prieur C., Rigaud J., Cheynier V., Moutounet M. Oligomeric and polymeric procyanidins from grape seeds. Phytochemistry. 36:1994;781-784
41. Labarbe B., Cheynier V., Brossaud F., Souquet J.M., Moutounet M. Quantitative fractionation of grape proanthocyanidins according to their degree of polymerization. J. Agric. Food Chem. 47:1999;2719-2723
42. Oh H.I., Hoff J.E., Armstrong G.S., Haff L.A. Hydrophobic interaction in tannin-protein complexes. J. Agric. Food Chem. 28:1980;394-398
43. Asano K., Shinagawa K., Hashimoto N. Characterization of haze-forming proteins of beer and their roles in chill haze formation. J. Am. Soc. Brew. Chem. 40:1982;147-154
44. Siebert K.J., Carrasco A., Lynn P.Y. Formation of protein-polyphenol haze in beverages. J. Agric. Food Chem. 44:1996;1997-2005
45. Serafini M., Maiani G., Ferro-Luzzi A. Effect of ethanol on red wine tannin-protein (BSA) interactions. J. Agric. Food Chem. 45:1997;3148-3151
46. Vernhet A., Pellerin P., Prieur C., Osmianski J., Moutounet M. Charge properties of some grape and wine polysaccharide and polyphenolic fractions. Am. J. Enol. Vitic. 47:1996;25-30
47. Ralet M.C., Dronnet V., Buchholt H.C., Thibault J.F. Enzymatically and chemically de-esterified lime pectins: characterization, polyelectrolyte behaviour and calcium binding properties. Carbohydr. Res. 336:2001;117-125
48. Hjerten S., Rosengren J., Pahlman S. Hydrophobic interaction chromatography. Synthesis and the use of some alkyl and aryl derivatives of agarose. J. Chromatogr. 101:1974;281-288
49. Randall H.M., Nakayama T.O.M. Temperature dependence of tannin adsorption by poly-N-vinyl pyrrolidone. Am. J. Enol. Vitic. 21:1970;162-167
50. Plumb G.S., De Pascual-Teresa S., Santos-Buelga C., Cheynier V., Williamson G. Antioxidant properties of catechins and proanthocyanidins: effect of polymerisation, galloylation and glycosylation. Free Radic. Res. 29:1998;351-358
51. 1H-NMR spectroscopy. Eur. J. Biochem. 219:1994;923-935
52. Spencer C.M., Cai Y., Martin R., Gaffney S.H., Goulding P.N., Magnaloto D., Lilley T.H., Haslam E. Polyphenol complexation - some thoughts and observations. Phytochemistry. 27:1988;2397-2409
53. Ricardo da Silva G.M., Cheynier V., Souquet J.M., Moutounet M., Cabanis J.C., Bourzeix M. Interaction of grape seed procyanidins with various proteins in relation to wine fining. J. Agric. Food Chem. 57:1991;111-125
54. De Freitas V., Mateus M. Structural features of procyanidin interactions with salivary proteins. J. Agric. Food Chem. 49:2001;940-945
55. Fletcher A.C., Porter L.J., Haslam E. Hindered rotation and helical structures in natural procyanidins. J. Chem. Soc., Chem. Commun. 1976;627-629
56. Le Bourvellec C., Le Quéré J.M., Sanoner P., Guyot S., Drilleau J.F. Inhibition of apple polyphenol oxidase activity by procyanidins and polyphenol oxidation products. J. Agric. Food Chem. 52:2004;122-130