Chemical cross-linking gelatin with natural phenolic compounds as studied by high-resolution NMR spectroscopy

Biomacromolecules

Volumn 11, Issue 4, 2010, Pages 1125-1132

  Zhang, Xiaoqing ^a   Do, My Dieu ^a   Casey, Philip ^a   Sulistio, Adrian ^b   Qiao, Greg G ^b   Lundin, Leif ^a   Lillford, Peter ^a   Kosaraju, Shansha ^a  

^a CSIRO   (Australia)

^b UNIVERSITY OF MELBOURNE   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO GROUP; CAFFEIC ACIDS; CHEMICAL CROSS-LINKING; CONCENTRATION OF; CROSS-LINKED NETWORKS; GELATIN MATRIX; GELATIN SOLUTIONS; HIGH RESOLUTION; HIGH TEMPERATURE; MOLECULAR MOBILITY; MOLECULAR MODELS; NMR SPECTROSCOPY; NMR TECHNIQUES; PHENOLIC COMPOUNDS; REACTIVE SITE; TANNIC ACID;

ACIDS; GRAFTING (CHEMICAL); HYDROGELS; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHENOLS; SYNTHESIS (CHEMICAL);

CROSSLINKING;

CAFFEIC ACID; CARBON 13; GELATIN; NATURAL PRODUCT; PHENOL DERIVATIVE; TANNIN;

ARTICLE; CHEMICAL REACTION; CHEMISTRY; CONCENTRATION (PARAMETERS); COVALENT BOND; CROSS LINKING; CROSS REACTION; FILM; HIGH TEMPERATURE; HYDROGEL; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; PRIORITY JOURNAL; SOLID STATE; SOLUTION AND SOLUBILITY;

CAFFEIC ACIDS; CROSS-LINKING REAGENTS; GELATIN; HYDROGELS; MAGNETIC RESONANCE SPECTROSCOPY; MATERIALS TESTING; MODELS, MOLECULAR; MOLECULAR STRUCTURE; TANNINS;

EID: 77950813477     PISSN: 15257797     EISSN: 15264602     Source Type: Journal    
DOI: 10.1021/bm1001284     Document Type: Article

References (46)

1. Veis, A. The Macromolecules Chemistry of Gelatin New York; Academic Press: London, 1964.
2. Hastings, G. W.; Ducheyne, P. Macromolecular Biomaterials; CRC Press: Boca Raton, FL, 1984.
3. Esposito, E.; Cortesi, R.; Nastruzzi, C. Gelatin microspheres: influence of preparation parameters and thermal treatment on chemico-physical and biopharmaceutical properties Biomaterials 1995, 20, 2009 - 2020
4. Arvanitoyannis, I.; Psomiadou, E.; Nakayama, A.; Biba, S.; Yamamoto, N. Edible films made from gelatin, soluble starch and polyols Food Chem. 1997, 60, 593 - 604
5. Sobral, P. J. A.; Menegalli, F. C.; Hubinger, M. D.; Roques, M. A. Mechanical, water vapor barrier and thermal properties of gelatin based ediable films Food Hydrocolloids 2001, 15, 423 - 432
6. Yakimets, I.; Wellner, N.; Smith, A. C.; Wilson, R. H.; Farhat, I.; Mitchell, J. Mechanical properties with respect to water content of gelatin films in glassy state Polymer 2005, 46, 12577 - 12585
7. Chiellini, E.; Cinelli, P.; Corti, A.; Kenawy, E. R. Composite films based on waste gelatin: thermal-mechnical properties and biodegradation testing Polym. Degrad. Stab. 2001, 73, 549 - 555
8. Gerrard, J. A. Protein-protein crosslinking in food: methods, consequences, applications Trends Food Sci. Technol. 2002, 13, 389 - 397
9. Bigi, A.; Cojazzi, G.; Panzavolta, S.; Rubini, K.; Roveri, N. Mechanical and thermal properties of gelatin films at different degrees of glutaraldehyde crosslinking Biomaterials 2001, 22, 763 - 768
10. Gerrard, J. A.; Brown, P. K.; Faye, S. E. Maillard crosslinking of food proteins I: the reaction of glutaraldehyde, formaldehyde and glyceraldehyde with ribonuclease Food Chem. 2002, 79, 343 - 349
11. Gerrard, J. A.; Brown, P. K.; Faye, S. E. Maillard crosslinking of food proteins II: the reactions of glutaraldehyde, formaldehyde and glyceraldehyde with wheat proteins in vitro and in situ Food Chem. 2003, 80, 35 - 43
12. Martucci, J. F.; Ruseckaite, R. A.; Vazquez, A. Creep of glutaraldehyde-crosslinked gelatin films Mater. Sci. Eng., A 2006, 435-436, 681 - 686
13. Olde, D.; Dijkstra, P. J.; van Luyn, M. J. A.; van Wachem, P. B.; Nieuwenhuis, P.; Feijen, J. Glutaraldehyde as a crosslinking agent for collagen-based biomaterilas J. Mater. Sci.: Mater. Med. 1995, 6, 460 - 472
14. Kuijpers, A. J.; Engbers, G. H. M.; De Smedt, S. C.; Meyvis, T. K. L.; Demeester, J.; Krijgsveld, J.; Zaat, S. A. J.; Dankert, J. Characterization of the netword structure of carbodiimide cross-linked gelatin gels Macromolecules 1999, 32, 3325 - 3333
15. Sung, H. W.; Huang, D. M.; Chang, W. H.; Huang, R. N.; Hsu, J. C. Evalution of gelatin hydrogel crosslinked with various crosslinking agents as bioadhesives: in vitro study J. Biomed. Mater. Res. 1999, 46, 520 - 530
16. van Wachem, P. B.; Zeeman, R.; Dijkstra, P. J.; Feijen, J.; Hendricks, M.; Cahalan, P. T.; can Luyn, M. J. A. Characterization and biocompatibility of epoxy-crosslinked dermal sheep collagens J. Biomed. Mater. Res. 1999, 47, 270 - 277
17. Kolodziejska, I.; Piotrowska, B. The water vapour permeability, mechanical properties and solubility of fish gelatin-chitosan films modified with transglutaminase or 1-ethyl-3(3-dimethylaminopropyl) carbodiimide (EDC) and plasticied with glycerol Food Chem. 2007, 103, 295 - 300
18. Boanini, E.; Rubini, K.; Panzavolta, S.; Bigi, A. Chemico-physical characterization of gelatin films modified with oxidized alginate Acta Biomater. 2010, 6, 383 - 388
19. Spanos, G.; Wrolsted, R. E. Phenolics of apple, pear, and white grape juices and their changes with processing and storage. A review J. Agric. Food Chem. 1992, 40, 1478 - 1487
20. Matheis, G.; Whitaker, J. R. Modification of proteins by polyphenol oxidase and peroxidase and their products J. Food Biochem. 1984, 8, 137 - 162
21. Asquith, T. N.; Butler, L. G. Interactions of condensed tannins with selected proteins Phytochemistry 1986, 25, 1591 - 1593
22. Wu, J.; Chiu, S.-C.; Pearce, E. M.; Kwei, T. K. Effect of phenolic compounds on gelatin behavior of gelatin gels J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 224 - 231
23. Chatterjee, S.; Chowdhury, R.; Bhattacharya, P. A mathematical analysis of the effect of pH and protein concentration on adsorption of proteins on immobilised tannin Biochem. Eng. J. 2000, 5, 77 - 82
24. Rawel, H. M.; Kroll, J.; Hohl, U. C. Model studies on reactions of plant phenols with whey proteins Nahrung/Food 2001, 2, 72 - 81
25. Strauss, G.; Gibson, S. M. Plant phenolics as cross-linkers of gelatin gels and gelatin-based coacervates for use as food ingredients Food Hydrocolloids 2004, 18, 81 - 89
26. Xing, F.; Cheng, G.; Yi, K.; Ma, L. Nanoencapsulation of capsaicin by complex coacervation of gelatin, acacia and tannins J. Appl. Polym. Sci. 2005, 96, 2225 - 2229
27. Cao, N.; Fu, Y.; He, J. Mechnical properties of gelatin films crosslinked, respectively, by ferulic acid and tannin acid Food Hydrocolloids 2007, 21, 575 - 584
28. Spencer, M. C.; Cai, Y.; Martin, R.; Gaffney, S. H.; Goulding, P. N.; Magnolato, D.; Lilley, T. H.; Haslam, E. Polyphenol complexation: some thoughts and observations Phytochemistry 1988, 27, 2397 - 2409
29. Siebert, K. J. Effects of protein-polyphenol interactions on beverage haze, stabilization, and analysis J. Agric. Food. Chem. 1999, 47, 353 - 362
30. Charlton, A. J.; Baxter, N. J.; Khan, M. L.; Moir, A. J. G.; Haslam, E.; Davies, A. P.; Williamson, M. P. Polyphenol/peptide binding and precipitation J. Agric. Food Chem. 2002, 50, 1593 - 1601
31. Singh, H. Modification of food proteins by covalent crosslinking Trends Food Sci. Technol. 1991, 2, 196 - 200
32. Robbins, R. J. Phenolic acids in food: an overview of analytical methodology J. Agric. Food Chem. 2003, 51, 2866 - 2887
33. Bittner, S. When quinones meet amino acids: chemical, physical and biological consequences Amino Acids 2005, 30, 205 - 224
34. McBrierty, V.; Packer, K. Nuclear Magnetic Resonance in Solid Polymers; Cambridge University Press: Cambridge, U.K., 1993.
35. 13C NMR spectroscopy Prog. Polym. Sci. 1985, 11, 221 - 282
36. Mendieta-Taboada, O.; Sobral, P. J. d. A.; Carvalho, R. A.; Habitante, A. M. Thermomechanical properties of biodegradable films based on blends of gelatin and poly(vinyl alcohol) Food Hydrocolloids 2008, 22, 1485 - 1492
37. Pati, S.; Losito, I.; Palmisano, F.; Zambonin, P. G. Characterization of caffeic acid enzymatic oxidation by-products by liquid chromatography coupled to electrospray ionization tandem mass spectrometry J. Chromatogr., A 2006, 1102, 184 - 192
38. Amiot, M. J.; Tacchini, M.; Aubert, S.; Nicolas, J. Phenolic composition and browning susceptibility of various apple cultivars at maturity J. Food Sci. 1992, 57, 958 - 962
39. Tazaki, H.; Taguchi, D.; Hayashida, T.; Nabeta, K. Stable isotope labelling on oxidative coupling of caffeic acid via o -quinone Biosci., Biotechnol., Biochem. 2001, 65, 2613 - 2621
40. Zhang, X.; Hoobin, P.; Burgar, I.; Do, M. The pH effect on the mechanical performance and phase mobility of thermally processed wheat gluten-based natural polymer materials Biomacromolecules 2006, 7, 3466 - 3473
41. Zhang, X.; Hoobin, P.; Burgar, I.; Do, M. Chemical modification of wheat protein-based natural polymers: cross-linking effect on mechanical properties and phase structures J. Agric. Food Chem. 2006, 54, 9858 - 9865
42. Zhang, X.; Do, M.; Bilyk, A. Chemical modification of wheat protein-based natural polymers: formation of polymer networks with alkoxysilanes to modify molecular motions and enhance the material performance Biomacromolecules 2007, 8, 1881 - 1889
43. Zhang, X.; Do, M. Plasticization and crosslinking effects of acetone -formaldehyde and tannin resins on wheat protein-based natural polymers Carbohydr. Res. 2009, 344, 1180 - 1189
44. Zhang, X.; Burgar, I.; Do, M.; Lourbakos, E. Intermolecular interactions and phase structures of plasticized wheat proteins materials Biomacromolecules 2005, 6, 1661 - 1671
45. Zhang, X.; Do, M.; Hoobin, P.; Burgar, I. The phase composition and molecular motions of plasticized wheat gluten-based biodegradable polymer materials studied by solid-state NMR spectroscopy Polymer 2006, 47, 5888
46. 13C NMR spectroscopy Macromolecules 1992, 25, 2336 - 2340