Modification of Chitosan for the Generation of Functional Derivatives
Source abstract
Abstract
Today, chitosan (CS) is probably considered as a biofunctional polysaccharide with the most notable growth and potential for applications in various fields. The progress in chitin chemistry and the need to replace additives and non-natural polymers with functional natural-based polymers have opened many new opportunities for CS and its derivatives. Thanks to the specific reactive groups of CS and easy chemical modifications, a wide range of physico-chemical and biological properties can be obtained from this ubiquitous polysaccharide that is composed of β-(1,4)-2-acetamido-2-deoxy-d-glucose repeating units. This review is presented to share insights into multiple native/modified CSs and chitooligosaccharides (COS) associated with their functional properties. An overview will be given on bioadhesive applications, antimicrobial activities, adsorption, and chelation in the wine industry, as well as developments in medical fields or biodegradability.
Source: crossref · Quality: baseline
Research context
OpenAlex topics: Nanocomposite Films for Food Packaging · Polysaccharides and Plant Cell Walls · Studies on Chitinases and Chitosanases
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
CNRS, SIGMA Clermont, Institut Pascal, Université Clermont Auvergne, F-63000 Clermont-Ferrand, France
ENSCBP Bordeaux INP-Unité de Recherche œnologie, ISVV, 210 chemin de Leysotte, CS 50008, CEDEX 33882 Villenave d’Ormon, France
BIOLAFFORT, 11 rue Aristide Bergès, 33270 Floirac, France
ADERA-MICROFLORA, Unité de Recherche œnologie, ISVV, 210 chemin de Leysotte, CS 50008, CEDEX 33882 Villenave d’Ormon, France
UMR1083 Sciences pour l’œnologie, équipe BIO, INRA SupAgro, UM1, 2 place Viala, F-34060 CEDEX F-34060 Montpellier, France
Funding
Agence Nationale de la Recherche
References (100+)
Show source-provided references
1. Chitosan as an adhesive10.1016/j.eurpolymj.2014.09.008 ↗
2. Biomedical applications of chitin and chitosan-based nanomaterials—A short review10.1016/j.carbpol.2010.04.074 ↗
3. Chitin and chitosan polymers: Chemistry, solubility and fiber formation10.1016/j.progpolymsci.2009.04.001 ↗
4. Bioactivity of chitosan and its derivatives
5. Effects of different artificial dermal scaffolds on vascularization and scar formation of wounds in pigs with full-thickness burn
6. Extraction, chemical modification and characterization of chitin and chitosan10.1016/j.ijbiomac.2018.08.139 ↗
7. Strong adhesion and cohesion of chitosan in aqueous solutions10.1021/la403124u ↗
8. Chitosan-based gastroretentive floating drug delivery technology: An updated review10.1517/17425247.2012.673581 ↗
9. Chitosan-based hydrogels: From preparation to biomedical applications10.1016/j.carbpol.2018.05.033 ↗
10. Influence of chitosan concentration on mechanical and barrier properties of corn starch/chitosan films10.1016/j.ijbiomac.2017.02.008 ↗
11. Dimassi, S., Tabary, N., Chai, F., Branchemain, N., and Martel, B. (2018). Sulfonated and sulfated chitosan derivatives for biomedical applications: A review. Carbohydr. Polym., 382–396.10.1016/j.carbpol.2018.09.011 ↗
12. Carboxymethyl chitosan: Properties and biomedical applications10.1016/j.ijbiomac.2018.09.131 ↗
13. Carboxymethyl chitosan as a matrix material for platinum, gold, and silver nanoparticles10.1021/bm800835e ↗
14. Preparation, characterization and antibacterial activity of chitosan and phosphorylated chitosan from cuttlebone of Sepia kobiensis (Hoyle, 1885)10.1016/j.btre.2015.10.007 ↗
15. Sur la nature des champignons
16. A review of chitin and chitosan applications10.1016/S1381-5148(00)00038-9 ↗
17. Crini, G., Badot, P.M., and Guibal, E. (2009). Chitine et Chitosane. Du biopolymère à l’application, Presses Universitaires de Franche Comté.
18. Chitin and chitosan preparation from marine sources. Structure, properties and applications10.3390/md13031133 ↗
19. Can fungi compete with marine sources for chitosan production?10.1016/j.ijbiomac.2017.01.112 ↗
20. The cellular basis of chitin synthesis in fungi and insects: Common principles and differences10.1016/j.ejcb.2011.04.014 ↗
21. Application of Spectroscopic Methods for Structural Analysis of Chitin and Chitosan10.3390/md8051567 ↗
22. Chitin Deacetylases: Properties and Applications10.3390/md8010024 ↗
23. Versali, M.F., Clerisse, F., Bruyere, J.M., and Gautier, S. (2003). Cell Wall Derivatives from Biomass and Preparation Thereof. (7556946 B2), U.S. Patent.
24. A method for direct preparation of chitosan with low molecular weight from fungi10.1016/S0939-6411(03)00189-9 ↗
25. Valorisation des résidus industriels de pêches pour la transformation de chitosane par technique hydrothermo-chimique
26. Molecular weight and degree of acetylation of high-intensity ultrasonicated chitosan10.1016/j.foodhyd.2004.11.002 ↗
27. Wu, T. (2017). Sonochemical and Hydrophobic Modification of Chitin and Chitosan. [Ph.D. Thesis, Univ Tennessee]. Available online: https://trace.tennessee.edu/utk_graddiss/286/.
28. Extraction and characterization of chitin and chitosan from marine sources in Arabian Gulf10.1016/j.carbpol.2009.01.032 ↗
29. Physicochemical, functional, antioxidant and antibacterial properties of chitosan extracted from shrimp wastes by microwave technique10.1016/j.aoas.2013.01.006 ↗
30. Ultrasound-assisted conversion of alpha-chitin into chitosan10.1016/j.apacoust.2015.10.002 ↗
31. Eco-friendly extraction and characterization of chitin and chitosan from the shrimp shell waste via microwave irradiation10.1016/j.psep.2016.09.020 ↗
32. Chitin deacetylases: New, versatile tools in biotechnology10.1016/S0167-7799(00)01462-1 ↗
33. Chitin Extraction from Crustacean Shells Using Biological Methods—A Review
34. (2019, January 10). Chitosan Market by Source, Global Opportunity Analysis and Industry Forecast, 2014–2022. Available online: https://www.alliedmarketresearch.com/chitosan-market.
35. Bellich, B., D’Agostino, I., Semeraro, S., Gamini, A., and Cesàro, A. (2016). The Good, the Bad and the Ugly of Chitosans. Mar. Drugs, 14.10.3390/md14050099 ↗
36. Quaternized N-substituted carboxymethyl chitosan derivatives as antimicrobial agents10.1016/j.ijbiomac.2013.05.022 ↗
37. Luan, F., Wei, L., Zhang, J., Tan, W., Chen, Y., Don, F., Li, Q., and Guo, Z. (2018). Preparation and Characterization of Quaternized Chitosan Derivatives and Assessment of Their Antioxidant Activity. Molecules, 23.10.3390/molecules23030516 ↗
38. Hydrophobic derivatives of chitosan: Characterization and rheological behaviour10.1016/0141-8130(96)01095-1 ↗
39. Specific interactions in modified chitosan systems10.1021/bm0580025 ↗
40. The aggregative behavior of hydrophobically modified chitosans with high substitution degree in aqueous solution10.1016/j.carbpol.2008.01.009 ↗
41. Synthesis of novel quaternary chitosan derivatives via N-chloroacyl-6-Otriphenylmethylchitosans
42. Chitosan-modifications and applications: Opportunities galore10.1016/j.reactfunctpolym.2008.03.002 ↗
43. Characterization of chemical and solid-state structures of acylated chitosans10.1016/S0032-3861(99)00270-0 ↗
44. Novel N-unsaturated fatty acyl and N-trimethylacetyl derivatives of chitosan10.1016/0144-8617(95)00012-V ↗
45. Novel N-saturated-fatty-acyl derivatives of chitosan soluble in water and in aqueous acid and alkaline solutions10.1016/S0144-8617(01)00243-0 ↗
46. Oxychitin-chitosan microcapsules for pharmaceutical use
47. TEMPO-mediated oxidation of chitin, regenerated chitin and N-acetylated chitosan10.1016/j.carbpol.2004.08.011 ↗
48. Conversion of crystal structure of the chitin to facilitate preparation of a 6-carboxychitin10.1016/j.carbpol.2006.02.036 ↗
49. TEMPO-Mediated Oxidation of Polysaccharides: An Ongoing Story10.1016/j.carbpol.2017.02.028 ↗
50. 6-Oxychitins, novel hyaluronan-like regiospecifically carboxylated chitins10.1016/S0144-8617(99)00027-2 ↗
51. Miconazole-loaded 6-oxychitin-chitosan microcapsules10.1016/S0144-8617(02)00257-6 ↗
52. Water-soluble chitosan derivatives and pH-responsive hydrogels by selective C-6 oxidation mediated by TEMPO-laccase redox system10.1016/j.carbpol.2018.01.050 ↗
53. The Influence of citric acid crosslinked PVA/chitosan membrane hydrophilicity on the transport of creatinine and urea10.22146/ijc.21286 ↗
54. Characterization of the interaction between chitosan and inorganic sodium phosphates by means of rheological and optical microscopy studies10.1016/j.carbpol.2012.08.037 ↗
55. Monolith enzymatic microreactor at the frontier of glycomic toward a new route for the production of bioactive oligosaccharides10.1016/j.molcatb.2009.04.016 ↗
56. Fragmentation of Chitosan by Acids10.1155/2013/508540 ↗
57. Preparation of Chitooligosaccharides with Degree of Polymerization Higher than 6 by Acid or Enzymatic Degradation of Chitosan10.1016/j.bej.2005.04.025 ↗
58. Kinetics and Products of the Degradation of Chitosan by Hydrogen Peroxide10.1021/jf001469g ↗
59. Free Radical Degradation of Chitosan with Potassium Persulfate10.1016/S0141-3910(01)00205-1 ↗
60. Preparation of Chitosan Oligomers by Irradiation10.1016/S0141-3910(02)00226-4 ↗
61. Effect of Molecular Weight Reduction by Gamma Irradiation on Chitosan Film Properties10.1016/j.msec.2015.05.009 ↗
62. Effect of Time/Temperature Treatment Parameters on Depolymerization of Chitosan10.1002/app.11628 ↗
63. Degradation of Chitin and Chitosan by a Recombinant Chitinase Derived from a Virulent Aeromonas hydrophila Isolated from Diseased Channel Catfish10.4236/aim.2015.59064 ↗
64. An Aspergillus chitosanase with potential for large-scale preparation of chitosan oligosaccharides10.1042/BA20000063 ↗
65. Gohi, B., Zeng, H.Y., and Pan, A. (2016). Optimization and Characterization of Chitosan Enzymolysis by Pepsin. Bioengineering, 3.10.3390/bioengineering3030017 ↗
66. Preparation and Characterisation of Low Molecular Weight Chitosan and Chito-Oligomers by a Commercial Enzyme10.1016/j.polymdegradstab.2004.09.008 ↗
67. Antibacterial Activity of a Chitooligosaccharide Mixture Prepared by Cellulase Digestion of Shrimp Chitosan and Its Application to Milk Preservation10.4315/0362-028X-63.6.747 ↗
68. Depolymerization of Chitosan Using a High-Pressure Homogenizer
69. Depolymerization of chitosan-metal complexes via a solution plasma technique10.1016/j.carbpol.2013.11.025 ↗
70. Ibrahim, K., El-Eswed, B., Abu-Sbeih, K., Arafat, T., Al Omari, M., Darras, F., and Badwan, A. (2016). Preparation of Chito-Oligomers by Hydrolysis of Chitosan in the Presence of Zeolite as Adsorbent. Mar. Drugs, 14.10.3390/md14080043 ↗
71. Electrochemical depolymerization of chitosans using the IrO2 electrode with interlayers as anode10.4028/www.scientific.net/MSF.847.281 ↗
72. Chitosan, chitin-glucan and chitin effects on minerals (iron, lead, cadmium) and organic (Ochratoxin A) contaminants in wines10.1007/s00217-007-0577-0 ↗
73. Water-solubility of partially N-acetylated chitosans as a function of pH: Effect of chemical composition and depolymerisation10.1016/0144-8617(94)90140-6 ↗
74. The use of chitosan as alternative to bentonite for wine fining: Effects on heat-stability, proteins, organic acids, colour, and volatile compounds in an aromatic white wine10.1016/j.foodchem.2018.05.005 ↗
75. Data on changes in red wine phenolic compounds and headspace aroma compounds after treatment of red wines with chitosans with different structures10.1016/j.dib.2018.02.029 ↗
76. Effect of fungal chitosan preparation on Brettanomyces bruxellensis, a wine contaminant10.1111/jam.12682 ↗
77. Effectiveness of chitosan preparations against Brettanomyces bruxellensis grown in culture media and red wines
78. Molecular Diagnosis of Brettanomyces bruxellensis’ Sulfur Dioxide Sensitivity Through Genotype Specific Method10.3389/fmicb.2018.01260 ↗
79. Evaluation of different factors affecting antimicrobial properties of chitosan10.1016/j.ijbiomac.2016.01.022 ↗
80. Evaluating the impact of a fungal-origin chitosan preparation on Brettanomyces bruxellensis in the context of wine aging10.4081/ws.2014.4574 ↗
81. Evaluation of antibacterial efficiency of chitosan and chitosan nanoparticles on cariogenic streptococci: An in vitro study
82. The fungicidal effect of chitosan on fungi of varying cell wall composition10.1016/S0147-5975(79)80054-7 ↗
83. Influence of acetylation degree and molecular weight of homogeneous chitosans on antibacterial and antifungal activities10.1016/j.ijfoodmicro.2014.04.029 ↗
84. Antibacterial activity of chemically defined chitosans: Influence of molecular weight, degree of acetylation and test organism10.1016/j.ijfoodmicro.2011.04.023 ↗
85. Inhibition of Bacillus cereus spore outgrowth and multiplication by chitosan10.1016/j.ijfoodmicro.2011.06.013 ↗
86. Chitosan and its antimicrobial potential—A critical literature survey10.1111/j.1751-7915.2008.00080.x ↗
87. Evaluation and insights into chitosan antimicrobial activity against anaerobic oral pathogens10.1016/j.anaerobe.2012.04.009 ↗
88. Antibacterial activity and mechanism of action of chitosan solutions against apricot fruit rot pathogen Burkholderia seminalis10.1016/j.carres.2011.04.042 ↗
89. Gallic acid-grafted-chitosan inhibits foodborne pathogens by a membrane damage mechanism10.1021/jf401254g ↗
90. Effectiveness of chitosan against wine-related microorganisms10.1007/s10482-014-0362-6 ↗
91. The Antimicrobial Action of Chitosan Against the Wine Spoilage Yeast Brettanomyces/Dekkera10.1166/jcc.2013.1037 ↗
92. Integration of lysozyme into chitosan nanoparticles for improving antibacterial activity10.1016/j.carbpol.2016.08.076 ↗
93. Effect of chitosan, and bacteriocin—Producing Carnobacterium maltaromaticum on survival of Escherichia coli and Salmonella Typhimurium on beef10.1016/j.ijfoodmicro.2018.10.003 ↗
94. The use of chitoologosaccharides in beer brewing for protection against beer spoilage bacteria and its influence on beer performance10.1007/s10529-015-2013-z ↗
95. Chitosan inactivates spoilage yeasts but enhances survival of Escherichia coli O157:H7 in apple juice10.1111/j.1365-2672.2004.02527.x ↗
96. Lysozyme immobilized on chitosan beads: Kinetic characterization and antimicrobial activity in white wines10.1016/j.foodcont.2015.11.015 ↗
97. Synthesis and in vitro antifungal efficacy of oleoyl-chitosan nanoparticles against plant pathogenic fungi10.1016/j.ijbiomac.2015.09.074 ↗
98. The antifungal properties of chitosan in laboratory media and apple juice10.1016/S0168-1605(99)00006-9 ↗
99. Chitosans as new tools against biofilms formation on the surface of silicone urinary catheters10.1016/j.ijbiomac.2018.07.088 ↗
100. Selective antimicrobial action of chitosan against spoilage yeasts in mixed culture fermentations10.1007/s10295-004-0112-2 ↗