Preparation and characterization of water-soluble chitosan produced by Maillard reaction

Fisheries Science

Volumn 72, Issue 5, 2006, Pages 1096-1103

  Chung, Ying Chien ^a   Tsai, Cheng Fang ^b   Li, Chin Fung ^c  

^a CHINA INSTITUTE OF TECHNOLOGY   (Taiwan)

^b ASIA UNIVERSITY   (Taiwan)

^c NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

Chitosan; Maillard reaction; Rheological property; Solubility

Indexed keywords

EID: 33749001969     PISSN: 09199268     EISSN: 14442906     Source Type: Journal    
DOI: 10.1111/j.1444-2906.2006.01261.x     Document Type: Article

References (40)

1. Nishimura Y, Kim HS, Ilota N, Arima H, Bom HS, Kim YH, Watanabe Y, Yukawa M, Ozawa T. Radioprotective effect of chitosan in sub-lethally X-ray irradiated mice. J. Radiat. Res. 2003; 44: 53-58.
2. Chung YC, Kuo CL, Chen CC. Preparation and important functional properties of water-soluble chitosan produced through Maillard reaction. Bioresource Technol. 2005; 96: 1473-1482.
3. Xie W, Xu P, Liu Q. Antioxidant activity of water-soluble chitosan derivatives. Bioorg. Med. Chem. Lett. 2001; 11: 1699-1701.
4. Sugimoto M, Morimoto M, Sashiwa H, Shigemasa Y. Preparation and characterization of water-soluble chitin and chitosan derivatives. Carbohydr. Polym. 1998; 36: 49-59.
5. Holme KR, Perlin AS. Chitosan N-sulfate. A water-soluble polyelectrolyte. Carbohydr. Res. 1997; 302: 7-12.
6. Muzzarelli RAA, Ilari P. Solubility and structure of N- carboxymethylchitosan. Int. J. Biol. Macromol. 1994; 6: 177-180.
7. Delben F, Muzzarelli RAA, Terbojevich M. Thermodynamic study of the protonation and interaction with metal cations of three chitosan derivatives. Carbohydr. Polym. 1989; 11: 205-210.
8. Muzzarelli RAA. Modified chitosan carrying sulfonic acid groups. Carbohydr. Polym. 1992; 5: 461-475.
9. Muzzarelli RAA, Ilari P, Tomasetti M. Preparation and characteristic properties of 5-methylpyrrolidinone chitosan. Carbohydr. Polym. 1993; 20: 99-106.
10. Dung PI, Milas M, Rinaudo M, Desbrieres J. Water soluble derivatives obtained by controlled chemical modifications of chitosan. Carbohydr. Polym. 1994; 24: 209-215.
11. Jia Z, Shen D, Xu W. Synthesis and antibacterial activities of quaternary ammonium salt of chitosan. Carbohydr. Res. 2001; 333: 1-6.
12. Ilyina AV, Tikhonov VE, Albulov AI, Variamov VP. Enzymic preparation of acid-free-water-soluble chitosan. Process Biochem. 2000; 35: 563-568.
13. Kubota N, Tatsumoto N, Sano T, Taori K. A simple preparation of half N-acetylated chitosan highly soluble in water and aqueous organic solvents. Carbohydr. Res. 2000; 324: 268-274.
14. 2- radicals with carboxymethylated chitin derivatives. Biomacromolecules 2004; 5: 458-462.
15. Dutta U, Dain JA. Capillary electrophoretic analysis of advanced glycation endproducts formed from the reaction of reducing sugars with the amino group of glucosamine. Anal. Biochem. 2005; 343: 237-243.
16. Tessier FJ, Monnier VM, Sayre LM, Kornfield JA. Triosidines: novel Maillard reaction products and cross-links from the reaction of triose sugars with lysine and arginine residues. Biochem. J. 2003; 369: 705-719.
17. Kato A, Minaki K, Kobayashi K. Improvement of emulsifying properties of egg white protein by the attachment of polysaccharide through Maillard reaction in a dry state. J. Agric. Food Chem. 1993; 41: 540-543.
18. Nakamura S, Kato A, Kobayashi K. Enhanced antioxidative effect of ovalbumin due to covalent binding of polysaccharides. J. Agric. Food Chem. 1992; 40: 2033-2037.
19. Saeki H. Preparation of neoglycoprotein from carp myofibrillar protein by Maillard reaction with glucose: biochemical properties and emulsifying properties. J. Agric. Food Chem. 1997; 45: 680-684.
20. Lin CW, Lin JC. Characterization and blood coagulation evaluation of the water-soluble chitooligosaccharides prepared by facile fractionation method. Biomacromolecules 2003; 4: 1691-1697.
21. Usui M, Tamura H, Nakamura K, Ogawa T, Muroshita M, Azakami H, Kanuma S, Kato A. Enhanced bactericidal action and masking of allergen structure of soy protein by attachment of chitosan through Maillard-type protein-polysaccharide conjugation. Nahrung 2004; 48: 69-72.
22. Toei K, Kohara T. A conductometric method for colloid titrations. Anal. Chim. Acta 1976; 83: 59-65.
23. Yalpani M, Hall LD. Some chemical and analytical aspects of polysaccharide modification. 3. Formation of branched-chain, soluble chitosan derives. Macromolecules 1984; 17: 272-281.
24. Yang TC, Chou CC, Li CF. Preparation, water solubility and rheological property of the N-alkylated mono or disaccharide chitosan derivatives. Food Res. Int. 2002; 35: 707-713.
25. Sannan T, Kurita K, Iwakura Y. Studies on chitin, 2: effect of deacetylation on solubility. Makromol. Chem. 1976; 177: 3589-3600.
26. Kato Y, Matsuki T, Kato N, Nakamura R. Maillard reaction of disaccharides with protein: suppressive effect of nonreducing end pyranoside groups on browning and protein. J. Agric. Food Chem. 1989; 37: 1077-1081.
27. Chen RH, Lin WC, Lin JH. Effects of pH, ionic strength, and type of anion on the rheological properties of chitosan solutions. Acta Polym. 1994; 45: 41-46.
28. Holdsworth SD. Rheological models used for the prediction of the flow properties of food products. Trans. Inst. Chem. Eng. Part C 1993; 71: 139-179.
29. Cabodevila O, Hill SE, Armstrong HJ, Sousa DI, Mitchell JR. Gelatin enhancement of soy protein isolate using the Maillard reaction and high temperature. J. Food Sci. 1994; 59: 872-878.
30. Kogan G, Skorik YA, Zitnanova I, Krizkova L, Durackova Z, Gomes CAR, Yatluk YG, Krajcovic J. Antioxidant and antimutagenic activity of N-(2-carboxyethyl) chitosan. Toxicol. Appl. Pharmacol. 2004; 201: 303-310.
31. Nishimura SI, Kohgo O, Kurita K, Kuzuhara H. Chemospecific manipulations of a rapid polysaccharide: syntheses of novel chitosan derivatives with excellent solubility in common organic solvents by regioselective chemical modifications. Macromolecules 1991; 24: 4745-4748.
32. Heras A, Rodriguez NM, Ramos VM, Agullo E. N-methylene phosphonic chitosan: a novel soluble derivative. Carbohydr. Polym. 2001; 44: 1-8.
33. Trung TS, Thein-Han WW, Qui NT, Ng CH, Stevens WF. Functional characteristics of shrimp chitosan and its membranes as affected by the degree of deacetylation. Bioresource Technol. 2006; 97: 659-663.
34. Filar LJ, Wirick MG. Bulk and solution properties of chitosan. In: Muzzarelli RAA, Pariser ER (eds). Chitin and Chitosan. MIT Sea grant Program, Cambridge, MA. 1978; 169-181.
35. Wang W, Xu D. Viscosity and flow properties of concentrated solutions of chitosan with different degrees of deacetylation. Int. J. Biol. Macromol. 1994; 16: 149-152.
36. Nishi N, Ebina A, Nishimura S, Tsutsumi A, Hasegawa O, Tokura S. High phosphorylated derivatives of chitin, partially deacetylated chitin and chitosan as new functional polymers: preparation and characterization. Int. J. Biol. Macromol. 1986; 8: 311-317.
37. Flory PJ. Principles of Polymer Chemistry. Cornell University Press, Ithaca, NY. 1953.
38. Rodriguez-Sanchez D, Kienzle-Sterzer CA, Rha C. Intrinsic viscosity of chitosan solution as affected by ionic strength. In: Hirano S, Tokura S (eds). Chitin and Chitosan. Japanese Society of Chitin and Chitosan, Sapporo. 1982; 30-33.
39. Bohdanecky M, Kovar J. Viscosity of Polymer Solutions. Elsevier, New York. 1982.
40. Lapasin R, Pricl S. Rheology of Industrial Polysaccharides: Theory and Applications. Blackie Academic and Professional/Chapman and Hall, Glasgow. 1995.