Preparation of chitosan oligomers and characterization: Their antifungal activities and decay resistance

Holzforschung

Volumn 66, Issue 1, 2012, Pages 119-125

  Hussain, Ibrar ^a   Singh, Tripti ^a   Chittenden, Colleen ^a  

^a SCION   (New Zealand)

Author keywords

Chitosan oligomers; CP MAS 13C NMR; Nitrous acid deaminative depolymerization; Wood deteriorating fungi.

Indexed keywords

ANTI-FUNGAL ACTIVITY; ANTI-MICROBIAL ACTIVITY; CHITOSAN OLIGOMER; DECAY RESISTANCE; DEGREE OF DEACETYLATION; DEGREE OF POLYMERIZATION; LITERATURE DATA; MYCELIAL GROWTH; NITROUS ACID; NUTRIENT MEDIUM; PHYSICOCHEMICAL PROPERTY; PRINCIPAL FACTORS; SIGMA-ALDRICH; WOOD DETERIORATING FUNGI.;

ACETYLATION; BIOASSAY; DECAY (ORGANIC); FUNGI; INORGANIC ACIDS; MULTILAYERS; OLIGOMERS;

CHITOSAN;

BASIDIOMYCOTA; FUNGI;

EID: 84856133543     PISSN: 00183830     EISSN: 1437434X     Source Type: Journal    
DOI: 10.1515/HF.2011.130     Document Type: Article

References (34)

1. Akiyama, K., Kawazu, K., Kobayashi, A. (1995) A novel method for chemo-enzymatic synthesis of elicitor-active chitosan oligomers and partially N-deacetylated chitin oligomers using N-acylated chitotrioses as substrates in a lysozyme-catalyzed transglycosylation reaction system. Carbohyd. Res. 279:151-160. (Pubitemid 26019369)
2. Allan, G.G., Peyron, M. (1995) Molecular weight manipulation of chitosan II: Prediction and control of extent of depolymerization by nitrous acid. Carbohyd. Res. 277:273-282.
3. Bahrke, S., Einarsson, J.M., Gislason, J., Haebel, S., Letzel, M.C., Peter-Katalinić, J., Peter, M.G. (2002) Sequence analysis of chitooligosaccharides by matrix-assisted laser desorption ionization postsource decay mass spectrometry. Biomacromolecules 3:696-704.
4. Boyd, J., Porteous, R., Soffe, N., Delepierre, M. (1985) 1H- and 13C-N.M.R. assignments and conformational analysis of some monosaccharide and oligosaccharide substrate-analogues of lysozyme. Carbohyd. Res. 139:35-46.
5. Cabrera, J.C., Van Cutsem, P. (2005) Preparation of chitooligosaccharides with degree of polymerization higher than 6 by acid or enzymatic degradation of chitosan. Biochem. Eng. J. 25:165-172. (Pubitemid 41116430)
6. Coma, V., Martial-Gros, A., Garreau, S., Copinet, A., Salin, F., Deschamps, A. (2006) Edible antimicrobial films based on chitosan matrix. J. Food Sci. 67:1162-1169. (Pubitemid 34577458)
7. de Britto, D., Forato, L.A., Assis, O.B.G. (2008) Determination of the average degree of quaternization of N,N,N-trimethylchitosan by solid state 13C NMR. Carbohydr. Polym. 74:86-91.
8. Defaye, J., Gadelle, A., Pedersen, C. (1994) A convenient access to β-(1→4)-linked 2-amino-2-deoxy-D-glucopyranosyl fluoride oligosaccharides and β-(1→4)-linked 2-amino-2-deoxy-Dglucopyranosyl oligosaccharides by fluorolysis and fluorohydrolysis of chitosan. Carbohyd. Res. 261:267-277. (Pubitemid 24257649)
9. Domard, A., Cartier, N. (1989) Glucosamine oligomers: 1. Preparation and characterization. Int. J. Biol. Macromol. 11:297-302. (Pubitemid 19249454)
10. Du, Y., Zhao, Y., Dai, S., Yang, B. (2009) Preparation of watersoluble chitosan from shrimp shell and its antibacterial activity. Innovat. Food Sci. Emerg. Tech. 10:103-107.
11. Eikenes, M., Fongen, M., Roed, L., Stenstrøm, Y. (2005) Determination of chitosan in wood and water samples by acidic hydrolysis and liquid chromatography with online fluorescence derivatization. Carbohyd. Polym. 61:29-38. (Pubitemid 40774010)
12. Jeon, Y.J., Shahidi, F., Kim, S.K. (2000) Preparation of chitin and chitosan oligomers and their applications in physiological functional foods. Food Rev. Int. 16:159-176.
13. Jeon, Y.J., Park, P.J., Kim, S.K. (2001) Antimicrobial effect of chitooligosaccharides produced by bioreactor. Carbohyd. Polym. 44:71-76.
14. Kean, T., Thanou, M. (2010) Biodegradation, biodistribution and toxicity of chitosan. Adv. Drug Deliver. Rev. 62:3-11.
15. Kendra, D.F., Hadwiger, L.A. (1984) Characterization of the smallest chitosan oligomer that is maximally antifungal to Fusarium solani and elicits pisatin formation in Pisum sativum. Exp. Mycol. 8:276-281. (Pubitemid 14012217)
16. Laflamme, P., Benhamou, N., Bussières, G., Dessureault, M. (1999) Differential effect of chitosan on root rot fungal pathogens in forest nurseries. Can. J. Bot. 77:1460-1468. (Pubitemid 30144084)
17. Laka, M., Chernyavskaya, S. (2009) Effect of salts on the formation and properties of microcrystalline cellulose and chitosan gels. Holzforschung 63:665-669.
18. Lee, J., Furukawa, I., Sakuno, T. (1993) Preservative effectiveness against Tyromyces palustris in wood after pre-treatment with chitosan and impregnation with chromated copper arsenate. Jpn. J. Wood Chem. Soc. 39:103-108.
19. Nordtveit, R.J., Vårum, K.M., Smidsrød, O. (1994) Degradation of fully water-soluble, partially N-acetylated chitosans with lysozyme. Carbohyd. Polym. 23:253-260.
20. Ratajska, M., Struszczyk, M.H., Boryniec, S., Peter, M.G., Loth, F. (1997) The degree of deacetylation of chitosan: Optimization of the IR method. Polimery/Polymers 42:572-575. (Pubitemid 127634726)
21. SAS Institute Inc. SAS/STAT user's guide, Release 6.03 Edition. SAS Institute Inc., Cary, NC, USA, 1989.
22. Singh, S., Gallagher, R., Derrick, P.J., Crout, D.H.G. (1995) Glycosidase- catalysed oligosaccharide synthesis: Preparation of the N-acetylchitooligosaccharides penta-N-acetylchitopentaose and hexa-N-acetylchitohexaose using the Î2-N-acetylhexosaminidase of Aspergillus oryzae. Tetrahedron:Asymmetry 6:2803-2810.
23. Singh, T., Vesentini, D., Singh, A.P., Daniel, G. (2008) Effect of chitosan on physiological, morphological and ultrastructural characteristics of wood degrading fungi. Int. Biodeter. Biodegrad. 62:116-124.
24. Tamura, H., Sawada, M., Nagahama, H., Higuchi, T., Tokura, S. (2006) Influence of amide content on the crystal structure of chitin. Holzforschung 60:480-484. (Pubitemid 44253260)
25. Tømmeraas, K., Strand, S.P., Tian, W., Kenne, L., Vårum, K.M. (2001a) Preparation and characterisation of fluorescent chitosans using 9-anthraldehyde as fluorophore. Carbohyd. Res. 336:291-296. (Pubitemid 33139762)
26. Tømmeraas, K., Vårum, K.M., Christensen, B.E., Smidsrød, O. (2001b) Preparation and characterisation of oligosaccharides produced by nitrous acid depolymerisation of chitosans. Carbohyd. Res. 333:137-144. (Pubitemid 32595625)
27. Torr, K.M., Chittenden, C., Franich, R.A., Kreber, B. (2005) Advances in understanding bioactivity of chitosan and chitosan oligomers against selected wood-inhabiting fungi. Holzforschung 59:559-567. (Pubitemid 41225287)
28. Torr, K.M., Singh, A.P., Franich, R.A. (2006) Improving stiffness of lignocellulosics through cell wall modification with chitosanmelamine co-polymers. N. Z. J. For. Sci. 36:87-98. (Pubitemid 44203921)
29. Trombotto, S., Ladavière, C., Delolme, F., Domard, A. (2008) Chemical preparation and structural characterization of a homogeneous series of chitin/chitosan oligomers. Biomacromolecules 9:1731-1738.
30. Uchida, Y., Izume, M., Ohtakara, A. (1989) Preparation of chitosan oligomers with purified chitosanase and its application. In: Chitin and Chitosan. Eds. Skjak-Braek, G., Anthonsen, T., Sandford, P. Elsevier, London, pp. 373-382.
31. Usui, T., Matsui, H., Isobe, K. (1990) Enzymic synthesis of useful chito-oligosaccharides utilizing transglycosylation by chitinolytic enzymes in a buffer containing ammonium sulfate. Carbohyd. Res. 203:65-77.
32. Yoon, J.H. (2005) Enzymatic synthesis of chitooligosaccharides in organic cosolvents. Enzyme Microb. Technol. 37:663-668. (Pubitemid 41306254)
33. Zawadzki, J., Kaczmarek, H. (2010) Thermal treatment of chitosan in various conditions. Carbohyd. Polym. 80:395-401.
34. Zhang, H., Du, Y., Yu, X., Mitsutomi, M., Aiba, S.I. (1999) Preparation of chitooligosaccharides from chitosan by a complex enzyme. Carbohyd. Res. 320:257-260. (Pubitemid 29488509)