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Original Article

Antioxidant activity of oligochitosan Maillard reaction products using oligochitosan as the amino or carbonyl groups donors

, , , , , , & show all
Pages 1964-1971 | Received 25 Dec 2017, Accepted 23 Jun 2018, Published online: 30 Aug 2018

References

  • Eaton, P.; Fernandes, J. C.; Pereira, E.; Pintado, M. E.; Xavier, M. F. Atomic Force Microscopy Study of the Antibacterial Effects of Chitosans on Escherichia coli and Staphylococcus aureus. Ultramicroscopy. 2008, 108, 1128–1134. DOI: 10.1016/j.ultramic.2008.04.015.
  • Kim, S. K.; Rajapakse, N. Enzymatic Production and Biological Activities of Chitosan Oligosaccharides (COS): A Review. Carbohydr. Polym. 2005, 62, 357–368. DOI: 10.1016/j.carbpol.2005.08.012.
  • Huang, R.; Mendis, E.; Kim, S. K. Improvement of ACE Inhibitory Activity of Chitooligosaccharides (COS) by Carboxyl Modification. Bioorgan Med. Chem. 2005, 13, 3649–3655. DOI: 10.1016/j.bmc.2005.03.034.
  • Kjell, M. V.; Mette, H. O.; Olav, S. Water-Solubility of Partially N-Acetylated Chitosans as a Function of pH: Effect of Chemical Composition and Depolymerisation. Carbohydr. Polym. 1994, 25, 65–70. DOI: 10.1016/0144-8617(94)90140-6.
  • Je, J. Y.; Park, P. J.; Kim, S. K. Free Radical Scavenging Properties of Hetero-Chitooligosaccharides Using an ESR Spectroscopy. Food Chem. Toxicol. 2004, 42, 381–387. DOI: 10.1016/j.fct.2003.10.001.
  • Chae, S. Y.; Son, S.; Lee, M.; Jang, M. K.; Nah, J. W. Deoxycholic Acid-Conjugated Chitosan Oligosaccharide Nanoparticles for Efficient Gene Carrier. J. Control Release. 2005, 109, 330–344. DOI: 10.1016/j.jconrel.2005.09.040.
  • Fernandes, J. C.; Eaton, P.; Nascimento, H.; Belo, L.; Rocha, S.; Vitorino, R.; Amado, F.; Gomes, J.; Santos-Silva, A.; Pintado, M. E.; et al. Effects of Chitooligosaccharides on Human Red Blood Cell Morphology and Membrane Protein Structure. Biomacromolecules. 2008, 9, 3346–3352. DOI: 10.1021/bm800622f.
  • Ngo, D. H.; Qian, Z. J.; Vo, T. S.; Ryu, B. M.; Ngo, D. N.; Kim, S. K. Antioxidant Activity of Gallate-Chitooligosaccharides in Mouse Macrophage RAW264.7 Cells. Carbohydr. Polym. 2011, 84, 1282–1288. DOI: 10.1016/j.carbpol.2011.01.022.
  • Lu, X.; Guo, H.; Zhang, Y. Protective Effects of Sulfated Chitooligosaccharides against Hydrogen Peroxide-Induced Damage in MIN6 Cells. Int. J. Biol. Macromol. 2012, 50, 50–58. DOI: 10.1016/j.ijbiomac.2011.09.020.
  • Hodge, J. E. Dehydrated Foods. Chemistry of Browning Reactions in Model Systems. J. Agr. Food Chem. 1953, 1, 625–651. DOI: 10.1021/jf60015a004.
  • Chang, H. L.; Chen, Y. C.; Tan, F. J. Antioxidative Properties of a Chitosan–Glucose Maillard Reaction Product and Its Effect on Pork Qualities during Refrigerated Storage. Food Chem. 2011, 124, 589–595. DOI: 10.1016/j.foodchem.2010.06.080.
  • Li, S. L.; Lin, J.; Chen, X. M. Effect of Chitosan Molecular Weight on the Functional Properties of Chitosan-Maltose Maillard Reaction Products and Their Application to Fresh-Cut Typha latifolia L. Carbohydr. Polym. 2014, 102, 682–690. DOI: 10.1016/j.carbpol.2013.10.102.
  • Wu, S.; Hu, J.; Wei, L.; Du, Y.; Shi, X.; Zhang, L. Antioxidant and Antimicrobial Activity of Maillard Reaction Products from Xylan with Chitosan/Chitooligomer/Glucosamine Hydrochloride/Taurine Model Systems. Food Chem. 2014, 148, 196–203. DOI: 10.1016/j.foodchem.2013.10.044.
  • Sun, T.; Qin, Y. Y.; Xu, H. L.; Xie, J.; Hu, D. M.; Xue, B.; Hua, X. Y. Antibacterial Activities and Preservative Effect of Chitosan Oligosaccharide Maillard Reaction Products on Penaeus vannamei. Int. J. Biol. Macromol. 2017, 105, 764–768. DOI: 10.1016/j.ijbiomac.2017.07.100.
  • Jung, W. K.; Park, P. J.; Ahn, C. B.; Je, J. Y. Preparation and Antioxidant Potential of Maillard Reaction Products from (MRPs) Chitooligomer. Food Chem. 2014, 145, 173–178. DOI: 10.1016/j.foodchem.2013.08.042.
  • Sun, T.; Chen, C. H.; Zhu, Y.; Xie, J. Antioxidant Activity Assessment of Chitosan Oligosaccharide Derivatives from Maillard Reaction with Glucose. Food Sci. 2011, 32, 14–18.
  • Toei, K.; Sawada, M. A Turbidimetric Method for Colloid Titrations. Anal. Chim. Acta. 1976, 83, 59–65. DOI: 10.1016/S0003-2670(01)84736-X.
  • Sun, T.; Zhu, Y.; Xie, J.; Yin, X. Antioxidant Activity of N-Acyl Chitosan Oligosaccharide with Same Substituting Degree. Bioorgan Med. Chem. 2011, 21, 798–800. DOI: 10.1016/j.bmcl.2010.11.097.
  • Yamaguchi, T.; Takamura, H.; Matoba, T.; Terao, J. HPLC Method for Evaluation of the Free Radical-Scavenging Activity of Foods by Using 1, 1-Diphenyl-2-Picrylhydrazyl. Biosci. Biotech. Bioch. 1998, 62, 1201–1204. DOI: 10.1271/bbb.62.1201.
  • Yen, G. C.; Chen, H. Y. Antioxidant Activity of Various Tea Extracts in Relation to Their Antimutagenicity. J. Agric. Food Chem. 1995, 43, 27–32. DOI: 10.1021/jf00049a007.
  • Zheng, Z.; Luo, Y.; Yao, L.; Lu, J.; Bu, G. Effects of Maillard Reaction Conditions on the Functional Properties of WPI Chitosan Oligosaccharide Conjugates. J. Food Sci. Technol. 2014, 51, 3794–3802. DOI: 10.1007/s13197-013-0946-6.
  • Chang, X. H.; Chen, D. R.; Jiao, X. L. Chitosan-Based Aerogels with High Adsorption Performance. J. Phys. Chem. B. 2008, 112, 7721–7725. DOI: 10.1021/jp8011359.
  • Umemura, K.; Kawai, S. Modification of Chitosan by the Maillard Reaction Using Cellulose Model Compounds. Carbohydr. Polym. 2007, 68, 242–248. DOI: 10.1016/j.carbpol.2006.12.014.
  • Fridovich, I. The Biology of Oxygen Radicals. Science 1978, 201, 875–880.
  • Banerjee, A.; Dasgupta, N.; De, B. In Vitro Study of Antioxidant Activity of Syzygium Cumini Fruit. Food Chem. 2005, 90, 727–733. DOI: 10.1016/j.foodchem.2004.04.033.
  • Singh, N.; Rajini, P. S. Free Radical Scavenging Activity of an Aqueous Extract of Potato Peel. Food Chem. 2004, 85, 611–616. DOI: 10.1016/j.foodchem.2003.07.003.
  • Feng, T.; Du, Y.; Li, J.; Hu, Y.; Kennedy, J. F. Enhancement of Antioxidant Activity of Chitosan by Irradiation. Carbohydr. Polym. 2008, 73, 126–132. DOI: 10.1016/j.carbpol.2007.11.003.
  • Yen, M. T.; Yang, J. H.; Mau, J. L. Antioxidant Properties of Chitosan from Crab Shells. Carbohydr. Polym. 2008, 74, 840–844. DOI: 10.1016/j.carbpol.2008.05.003.
  • Chien, P. J.; Sheu, F.; Huang, W. T.; Su, M. S. Effect of Molecular Weight of Chitosans on Their Antioxidative Activities in Apple Juice. Food Chem. 2007, 102, 1192–1198. DOI: 10.1016/j.foodchem.2006.07.007.
  • Xing, R.; Liu, S.; Guo, Z.; Yu, H.; Zhong, Z.; Ji, X.; Li, P. Relevance of Molecular Weight of Chitosan-N-2-Hydroxypropyl Trimethyl Ammonium Chloride and Their Antioxidant Activities. Eur. J. Med. Chem. 2008, 43, 336–340. DOI: 10.1016/j.ejmech.2007.03.025.
  • Ying, G. Q.; Xiong, W. Y.; Wang, H.; Sun, Y.; Liu, H. Z. Preparation, Water Solubility and Antioxidant Activity of Branched-Chain Chitosan Derivatives. Carbohydr. Polym. 2011, 83, 1787–1796. DOI: 10.1016/j.carbpol.2010.10.037.
  • Silván, J. M.; Van, L. J.; Olano, A.; Del, Castillo, M. D. Corrigendum to “Analysis and Biological Properties of Amino Acid Derivates Formed by Maillard Reaction in Foods”. J. Pharm. Biomed. Anal. 2007, 43, 1543–1551. DOI: 10.1016/j.jpba.2006.11.001.
  • Farvin, K. H. S.; Jacobsen, C. Phenolic Compounds and Antioxidant Activities of Selected Species of Seaweeds from Danish Coast. Food Chem. 2013, 138, 1670–1681. DOI: 10.1016/j.foodchem.2012.10.078.
  • Duh, P. D.; Du, P. C.; Yen, G. C. Action of Methanolic Extract of Mung Bean Hulls as Inhibitors of Lipid Peroxidation and Non-Lipid Oxidative Damage. Food Chem. Toxicol. 1999, 37, 1055–1061. DOI: 10.1016/S0278-6915(99)00096-4.
  • Ercan, B.; Köksal, E. Evaluation of Reducing Power and Radical Scavenging Activities of Water and Ethanol Extracts from Sumac (Rhus coriaria L.). Food Res. Int. 2010, 44, 2217–2221. DOI: 10.1016/j.foodres.2010.11.001.
  • Jarmila, V.; Vavríková, E. Chitosan Derivatives with Antimicrobial, Antitumour and Antioxidant Activities – A Review. Curr. Pharm. Design. 2011, 17, 3596–3607. DOI: 10.2174/138161211798194468.