Antioxidant, antimicrobial properties of chitin, chitosan, and their derivatives

Chitin and Chitosan Derivatives: Advances in Drug Discovery and Developments

Volumn , Issue , 2013, Pages 201-212

  Ngo, Dai Nghiep ^a   Kim, Se Kwon ^b  

^a UNIVERSITY OF NATURAL SCIENCES   (Viet Nam)

^b Pukyong National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84902369404     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1201/b15636     Document Type: Chapter

References (68)

1. Akiyama, K., K. Kawazu, and A. Kobayashi. 1995. A novel method for chemo-enzymatic synthesis of elicitoractive chitosan oligomers and partially N-deacetylated chitin oligomers using N-acylated chitotrioses as substrates in a lysozyme-catalyzed transglycosylation reaction system. Carbohydrate Research 279:151-160.
2. Alves, N.M. and J.F. Manoa. 2008. Chitosan derivatives obtained by chemical modifications for biomedical and environmental applications. International Journal of Biological Macromolecules 43:401-414.
3. Chen, A.S., T. Taguchi, K. Sakai, K. Kikuchi, M.W. Wang, and I. Miwa. 2003. Antioxidant activities of chitobiose and chitotriose. Biological and Pharmaceutical Bulletin 26:1326-1330.
4. Chen, R.H. and M.T. Tsaih. 1998. Effect of temperature on the intrinsic viscosity and conformation of chitosans in dilute HCl solution. International Journal of Biological Macromolecules 23:135-141.
5. Chen, Y.M., Y.C. Chung, L.W. Wang, K.T. Chen, and S.Y. Li. 2002. Antibacterial properties of chitosan in waterborne pathogen. Journal of Environmental Science and Health 37:1979-1990.
6. Chung, Y.C., Y.P. Su, C.C. Chen, G. Jia, H.L. Wang, J.C. Wu, and J.G. Lin. 2004. Relationship between antibacterial activity of chitosan and surface characteristics of cell wall. Acta Pharmacologica Sinica 25:932-936.
7. Dzung, N.A., V.T.P. Khanh, P.Q. Anh, and P.T.A. Hong. 2007. Study on hydrolysis of chitosan by cellulase combined with gamma irradiation. Advances in Chitin Science. Antalya 10:96-100.
8. Einbu, A. and K.M. Vårum. 2007. Depolymerization and de-N-acetylation of chitin oligomers in hydrochloric acid. Biomacromolecules 8:309-314.
9. Einbu, A., H. Grasdalen, and K.M. Vårum. 2007. Kinetics of hydrolysis of chitin/chitosan oligomers in concentrated hydrochloric acid. Carbohydrate Research 342:1055-1062.
10. Feng, Y.W. and W.S. Xia. 2011. Preparation, characterization and antibacterial activity of water-soluble O-fumaryl-chitosan. Carbohydrate Polymers 83:1169-1173.
11. Guo, Z., R. Xing, S. Liu, Z. Zhong, X. Ji, L. Wang, and P. Li. 2007. Antifungal properties of Schiff bases of chitosan, N-substituted chitosan and quaternized chitosan. Carbohydrate Research 342:1329-1332.
12. Huang, R., Y. Du, and J. Yang. 2003. Preparation and anticoagulant activity of carboxybutyrylated hydroxyethyl chitosan sulfates. Carbohydrate Polymers 51:431-438.
13. Huang, R., N. Rajapakse, and S.K. Kim. 2006. Structural factors affecting radial scavenging activity of chitooligosaccharides (COS) and its derivatives. Carbohydrate Polymers 63:122-129.
14. Je, J.Y. and S.K. Kim. 2006a. Antimicrobial action of novel chitin derivative. Biochimica et Biophysica Acta 1760:104-109.
15. Je, J.Y. and S.K. Kim. 2006b. Reactive oxygen species scavenging activity of aminoderivatized chitosan with different degree of deacetylation. Bioorganic and Medicinal Chemistry 14:5989-5994.
16. Jeon, Y.J. and S.K. Kim. 2000a. Production of chitooligosaccharides using an ultrafiltration membrane reactor and their antibacterial activity. Carbohydrate Polymers 41:133-141.
17. Jeon, Y.J. and S.K. Kim. 2000b. Continuous production of chitooligosaccharides using a dual reactor system. Process Biochemistry 35:623-632.
18. Jeon, Y.J. and S.K. Kim. 2001. Effect of antimicrobial activity of chitosan oligosaccharides N-conjugated with asparagines. Journal of Microbiology and Biotechnology 11:281-286.
19. Jeon, Y.J., P.J. Park, and S.K. Kim. 2001. Antimicrobial effect of chitooligosaccharides produced by bioreactor. Carbohydrate Polymers 44:71-76.
20. Kang, K.B., K.H. Lee, S.W. Chae, R. Zhang, M.S. Jung, Y.K. Lee, S.Y. Kim et al. 2005. Eckol isolated from Ecklonia cava attenuates oxidative stress induced cell damage in lung fibroblast cells. FEBS Letters 579:6295-6304.
21. Kim, K.W. and R.L. Thomas. 2007. Antioxidative activity of chitosans with varying molecular weights. Food Chemistry 101:308-313.
22. Kim, S.K. and P.J. Park 2001. Subacute toxicity of chitosan oligosaccharide in Sprague-Dawley rats. Arzneimittel Forschung Drug Research 51:769-774.
23. Kim, S.K., D.N. Ngo, and N. Rajapakse. 2006. Therapeutic prospectives of chitin, chitosan and their derivatives. Journal of Chitin and Chitosan 11:1-10.
24. Kurita, K. and M. Shimojoh. 2003. Nonnatural branched polysaccharides: Synthesis and properties of chitin and chitosan having disaccharide maltose branches. Biomacromolecules 4:1264-1268.
25. Li, X.F., X.Q. Feng, S. Yang, G.Q. Fu, T.P. Wang, and Z.X. Su. 2010. Chitosan kills Escherichia coli through damage to be of cell membrane mechanism. Carbohydrate Polymers 79:493-499.
26. Liu, J., H. Sun, F. Dong, Q. Xue, G. Wang, S. Qin, and Z. Guo. 2009. The influence of the cation of quaternized chitosans on antioxidant activity. Carbohydrate Polymers 78:439-443.
27. Mendis, E., M.M. Kim, N. Rajapakse, and S.K. Kim. 2008. Sulfated glucosamine inhibits oxidation of biomolecules in cells via a mechanism involving intracellular free radical scavenging. European Journal of Pharmacology 579:74-85.
28. Mi, F.L., Y.B. Wu, S.S. Shyu, J.Y. Schoung, Y.B. Huang, Y.H. Tsai, and J.Y. Hao. 2002. Control of wound infections using a bilayer chitosan wound dressing with sustainable antibiotic delivery. Journal of Biomedical Materials Research 59:438-449.
29. Mourya, V.K. and N.N. Inamdar. 2008. Chitosan modifications and applications: Opportunities galore. Reactive and Functional Polymers 68:1013-1051.
30. Muzzareli, R.A.A. 2002. The discovery of chitin, a 570 megayear old polymer. Chitosan in Pharmacy and Chemistry, Atec, Italy, 1-8.
31. Ngo, D.N., T.B.H. Nguyen, and B.L. Vong. 2012a. Antibacterial and antioxidant activity of N-aryl chitosan. Proceedings of the 9th Asia Pacific Chitin and Chitosan Symposium 2011 Nha Trang city, Vietnam, Agricultural Publishing House, Ho Chi Minh City, 208-212.
32. Ngo, D.H., D.N. Ngo, T.S. Vo, B.M. Ryu, Q.V. Ta, and S.K. Kim. 2012b. Protective effects of aminoethyl-chitooligosaccharides against oxidative stress and inflammation in murine microglial BV-2 cells. Carbohydrate Polymers 88:743-747.
33. Ngo, D.H., Z.J. Qian, D.N. Ngo, T.S. Vo, I. Wijessekara, and S.K. Kim. 2011a. Gallyl chitooligosaccharides inhibit intracellular free radical-mediated oxidation. Food Chemistry 128:974-981.
34. Ngo, D.H., Z.J. Qian, T.S. Vo, B.M. Ryu, D.N. Ngo, and S.K. Kim. 2011b. Antioxidant activity of gallate-chitooligosaccharides in mouse macrophage RAW 264.7 cells. Carbohydrate Polymers 84:1282-1288.
35. Ngo, D.N., M.M. Kim, and S.K. Kim. 2007. Effects of chitin oligosaccharides on production of reactive oxygen species and matrix metalloproteinases in live cells. In: Dans: Senel, S., Varum, K. M., Murat, S. M., Atilla, H. A., (eds.) Advances in Chitin Science. Ankara. Vol. X, 355-359.
36. Ngo, D.N., M.M. Kim, and S.K. Kim. 2008a. Chitin oligosaccharides inhibit oxidative stress in live cells. Carbohydrate Polymers 74:228-234.
37. Ngo, D.N., M.M. Kim, and S.K. Kim. 2012c. Protective effects of aminoethyl-chitooligosaccharides against oxidative stress in RAW 264.7 cells. International Journal of Biological Macromolecules 50:624-631.
38. Ngo, D.N., M.M. Kim, Z.J. Qian, W.K. Jung, S.H. Lee, and S.K. Kim. 2010. Free radical scavenging activities of low molecular weight chitin oligosaccharides lead to antioxidant effect in live cells. Journal of Food Biochemistry 34, S1:161-177.
39. Ngo, D.N., S.H. Lee, M.M. Kim, and S.K. Kim. 2009. Production of chitin oligosaccharides with different molecular weights and their antioxidant effect in RAW 264.7 cells. Journal of Functional Foods 1:188-198.
40. Ngo, D.N., Z.J. Qian, J.Y. Je, M.M. Kim, and S.K. Kim. 2008b. Aminoethyl chitooligosaccharides inhibit the activity of angiotensin converting enzyme. Process Biochemistry 43:119-123.
41. No, H.K., N.Y. Park, S.H. Lee, and S.P. Mayers. 2002. Antibacterial activity of chitosans and chitosan oligomers with different molecular weights. International Journal of Food Microbiology 74:65-72.
42. Park, P.J., J.Y. Je, and S.K. Kim. 2004a. Antimicrobial activity of hetero-chitosans and their oligosaccharide with different molecular weights. Journal of Microbiology and Biotechnology 14:317-323.
43. Park, P.J., J.Y. Je, and S.K. Kim. 2004b. Free radical scavenging activities of differently deacetylated chitosans using an ESR spectrometer. Carbohydrate Polymers 55:17-22.
44. Park, P.J., H.K. Lee, and S.K. Kim. 2004c. Preparation of heterochitooligosaccharides and their antimicrobial activity on Vibrio parahaemolyticus. Journal of Microbiology and Biotechnology 14:41-47.
45. Pasanphan, W. and S. Chirachanchai. 2008. Conjugation of gallic acid onto chitosan: An approach for green and water-based antioxidant. Carbohydrate Polymers 72:169-177.
46. Paul, W. and C.P. Sharma. 2004. Chitosan and alginate wound dressings: A short review. Trends in Biomaterials and Artificial Organs 18:18-23.
47. Rafael, O.P., T. Mirelle, C.C.G. Teresa, L.D.B. Vanildo, C.T. João, J.T. Marcio, and A.O.T. Vera. 2013. Synthesis, characterization and antifungal activity of quaternary derivatives of chitosan on Aspergillus flavus. Microbiological Research 168:50-55.
48. Rajapakse, N., M.M. Kim, E. Mendis, and S.K. Kim. 2007. Inhibition of free radical-mediated oxidation of cellular biomolecules by carboxylated chitooligosaccharides. Bioorganic and Medicinal Chemistry 15:997-1003.
49. Roller, S. and N. Covill. 1999. The antifungal properties of chitosan in laboratory media and apple juice. International Journal of Food Microbiology 47:67-77.
50. Sajomsang, W., P. Gonil, and S. Tantayanon. 2009. Antibacterial activity of quaternary ammonium chitosan containing mono or disaccharide moieties: Preparation and characterization. International Journal of Biological Macromolecules 44:419-427.
51. Sajomsang, W., U. Ruktanonchai, P. Gonil, V. Mayen, and P. Opanasopit. 2009a. Methylated N-aryl chitosan derivative/DNA complex nanoparticles for gene delivery: Synthesis and structure-activity relationships. Carbohydrate Polymers 78:743-752.
52. Sajomsang, W., S. Tantayanon, V. Tangpasuthadol, and W.H. Daly. 2009b. Quaternization of N-aryl chitosan derivatives: Synthesis, characterization and antibacterial activity. Carbohydrate Research 344:2502-2511.
53. Sajomsang, W., S. Tantayanon, V. Tangpasuthadol, M. Thatteb, and W.H. Daly. 2008. Synthesis and characterization of N-aryl chitosan derivatives. International Journal of Biological Macromolecules 43:79-87.
54. Samain, E., S. Drouillard, A. Heyraud, H. Driguez, and R.A. Geremia. 1997. Gram-scale synthesis of recombinant chitooligosaccharides in Escherichia coli. Carbohydrate Research 302:35-42.
55. Sashiwa, H. and S.I. Aiba. 2004. Chemically modified chitin and chitosan as biomaterials. Progress in Polymer Science 29:887-908.
56. Shao, J., Y. Yang, and Q. Zhong. 2003. Studies on preparation of oligoglucosamine by oxidative degradation under microwave irradiation. Polymer Degradation and Stability 82:395-398.
57. Somjit, K., Y. Ruttanapornwareesakul, K. Hara, and Y. Nozaki. 2005. The cryoprotectant effect of shrimp chitin and shrimp chitin hydrolysate on denaturation and unfrozen water of lizardfish Surimi during frozen storage. Food Research International 38:345-355.
58. Sun, T., D. Zhou, F. Mao, and Y. Zhu. 2007. Preparation of low-molecular-weight carboxymethyl chitosan and their superoxide anion scavenging activity. European Polymer Journal 43:652-656.
59. Tikhonov, V. E., E.A. Stepnova, V.G. Babak, I.A. Yamskov, P.G. Javier, H.B. Jansson, V.L. Luis et al. 2006. Bactericidal and antifungal activities of a low molecular weight chitosan and its N-/2(3)-(dodec-2-enyl) succinoyl/-derivatives. Carbohydrate Polymers 64:66-72.
60. Tsai, G.J. and S.P. Hwang. 2004. In vitro and in vivo antibacterial activity of shrimp chitosan against some intestinal bacteria. Fisheries Science 70:675-681.
61. Tsai, G.J., W.H. Su, H.C. Chen, and C.L. Pan. 2002. Antimicrobial activity of shrimp chitin and chitosan from different treatments and applications of fish preservation. Fisheries Science 68:170-177.
62. Vong, B.L. and D.N. Ngo. 2010. Synthesis and antifungal activity of N-aryl chitosan derivatives. The Science and Technology, Vietnam. 48:108-113.
63. Xia, W., P. Liu, J. Zhang, and J. Chen. 2011. Biological activities of chitosan and chitooligosaccharides. Food Hydrocolloids 25:170-179.
64. Xing, R., S. Liu, H. Yu, Z. Guo, P. Wang, C. Li, Z. Li, and P. Li. 2005a. Salt-assisted acid hydrolysis of chitosan to oligomers under microwave irradiation. Carbohydrate Research 340:2150-2153.
65. Xing, R., S. Liu, Z. Guo, H. Yu, P. Wang, C. Li, Z. Li, and P. Li. 2005b. Relevance of molecular weight of chitosan and its derivatives and their antioxidant activities in vitro. Bioorganic and Medicinal Chemistry 13:1573-1577.
66. Yang, T.C., C.C. Chou, and C.F. Li. 2005. Antibacterial activity of N-alkylated disaccharide chitosan derivatives. International Journal of Food Microbiology 97:237-245.
67. Yoon, N.Y., D.N. Ngo, and S.K. Kim. 2009. Acetylcholinesterase inhibitory activity of novel chitooligosaccharide derivatives. Carbohydrate Polymers 78:869-872.
68. Zhou, X., Y. Hu, Y. Tian, and X. Hu. 2009. Effect of N-trimethyl chitosan enhancing the dissolution properties of the lipophilic drug cyclosporin A. Carbohydrate Polymers 76:285-290.