Synthesis, characterization, and antimicrobial activity of kojic acid grafted chitosan oligosaccharide

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 1, 2014, Pages 297-303

  Liu, Xiaoli ^a   Xia, Wenshui ^a   Jiang, Qixing ^a   Xu, Yanshun ^a   Yu, Peipei ^a  

^a JIANGNAN UNIVERSITY   (China)

Author keywords

antimicrobial activity; chitosan oligosaccharide; kojic acid

Indexed keywords

ANTI-BACTERIAL ACTIVITY; ANTI-BACTERIAL AGENTS; ANTI-MICROBIAL ACTIVITY; CHITOSAN OLIGOSACCHARIDE; DEGREE OF SUBSTITUTION; DIMETHYL SULFOXIDE (DMSO); KOJIC ACID; WATER-SOLUBLE CHITOSAN; STAPHYLOCOCCUS AUREUS;

ASPERGILLUS; BACTERIA; DIMETHYL SULFOXIDE; ESCHERICHIA COLI; OLIGOSACCHARIDES; ORGANIC SOLVENTS; ULTRAVIOLET VISIBLE SPECTROSCOPY; YEAST; ALKYLATION; CHITIN; FOURIER TRANSFORM INFRARED SPECTROSCOPY; MICROORGANISMS; SYNTHESIS (CHEMICAL);

CHITOSAN;

ANTIINFECTIVE AGENT; CHITOSAN; KOJIC ACID; OLIGOSACCHARIDE; PYRONE DERIVATIVE;

BACTERIUM; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; FUNGUS; MEDICINAL CHEMISTRY; SYNTHESIS;

ANTI-INFECTIVE AGENTS; BACTERIA; CHEMISTRY, PHARMACEUTICAL; CHITOSAN; FUNGI; MOLECULAR STRUCTURE; OLIGOSACCHARIDES; PYRONES;

ASPERGILLUS NIGER; ESCHERICHIA COLI; SACCHAROMYCES CEREVISIAE; STAPHYLOCOCCUS AUREUS;

EID: 84892167041     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf404026f     Document Type: Article

References (34)

1. Rinaudo, M. Chitin and chitosan: properties and applications Prog. Polym. Sci. 2006, 31, 603-632
2. Jeon, Y. J.; Kim, S. K. Production of chitooligosaccharides using an ultrafiltration membrane reactor and their antibacterial activity Carbohydr. Polym. 2000, 41, 133-141
3. Xia, W.; Liu, P.; Zhang, J.; Chen, J. Biological activities of chitosan and chitooligosaccharides Food Hydrocolloids 2011, 25, 170-179
4. Xu, J.; Zhao, X.; Han, X.; Du, Y. Antifungal activity of oligochitosan against Phytophthora capsici and other plant pathogenic fungi in vitro Pestic. Biochem. Physiol. 2007, 87, 220-228
5. Kendra, D. F.; Hadwiger, L. A. Characterization of the smallest chitosan oligomer that is maximally antifungal to Fusarium solani and elicits pisatin formation in Pisum sativum Exp. Mycol. 1984, 8, 276-281
6. Qin, C.; Zhou, B.; Zeng, L.; Zhang, Z.; Liu, Y.; Du, Y.; Xiao, L. The physicochemical properties and antitumor activity of cellulase-treated chitosan Food Chem. 2004, 84, 107-115
7. Jeon, Y. J.; Kamil, J. Y.; Shahidi, F. Chitosan as an edible invisible film for quality preservation of herring and Atlantic cod J. Agric. Food Chem. 2002, 50, 5167-5178
8. Kim, S.-K.; Rajapakse, N. Enzymatic production and biological activities of chitosan oligosaccharides (COS): a review Carbohydr. Polym. 2005, 62, 357-368
9. Can, Z.; Ya, D.; Yu, L.; Qi, P. Polymeric micelle systems of hydroxycamptothecin based on amphiphilic N -alkyl- N -trimethyl chitosan derivatives Colloids Surf. B: Biointerfaces 2007, 50, 192-199
10. Aytemir, M. D.; Ozcelik, B. Synthesis and biological activities of new Mannich bases of chlorokojic acid derivatives Med. Chem. Res. 2011, 20, 443-452
11. Aytemir, M. D.; Ozcelik, B. A study of cytotoxicity of novel chlorokojic acid derivatives with their antimicrobial and antiviral activities Eur. J. Med. Chem. 2010, 45, 4089-4095
12. Blumenthal, C. Z. Production of toxic metabolites in Aspergillus niger, Aspergillus oryzae, and Trichoderma reesei: justification of mycotoxin testing in food grade enzyme preparations derived from the three fungi Regul. Toxicol. Pharmacol. 2004, 39, 214-228
13. Higa, Y.; Kawabe, M.; Nabae, K.; Toda, Y.; Kitamoto, S.; Hara, T.; Tanaka, N.; Kariya, K.; Takahashi, M. Kojic acid-absence of tumor-initiating activity in rat liver, and of carcinogenic and photo-genotoxic potential in mouse skin J. Toxicol. Sci. 2007, 32, 143-159
14. Xiong, X.; Pirrung, M. C. Modular synthesis of candidate indole-based insulin mimics by Claisen rearrangement Org. Lett. 2008, 10, 1151-1154
15. Burdock, G. A.; Soni, M. G.; Carabin, I. G. Evaluation of health aspects of kojic acid in food Regul. Toxicol. Pharmacol. 2001, 33, 80-101
16. Khamaruddin, N. H.; Basri, M.; Lian, G.; Salleh, A. B.; Abdul-Rahman, R.; Ariff, A.; Mohamad, R.; Awang, R. Enzymatic synthesis and characterization of palm-based kojic acid ester J. Oil Palm Res. 2008, 20, 461-469
17. Lee, Y. S.; Park, J. H.; Kim, M. H.; Seo, S. H.; Kim, H. J. Synthesis of tyrosinase inhibitory kojic acid derivative Arch. Pharm. 2006, 339, 111-114
18. Marwaha, S. S.; Kaur, J.; Sodhi, G. S. Organomercury(II) complexes of kojic acid and maltol: synthesis, characterization, and biological studies J. Inorg. Biochem. 1994, 54, 67-74
19. Uher, M.; Hudecová, D.; Brtko, J.; Dobias, J.; Kováč, J.; Šturdík, E. Antifungal preparation. CS Patent 259592, 1989.
20. Cai, Q.; Gu, Z.; Chen, Y.; Han, W.; Fu, T.; Song, H.; Li, F. Degradation of chitosan by an electrochemical process Carbohydr. Polym. 2010, 79, 783-785
21. Sima, J.; Chochulová, B.; Veverka, M.; Makánová, J.; Hajselova, M.; Bradiaková, A. Efficiency of the photoreduction of iron (III) complexes with kojic acid derivatives Pol. J. Chem. 1993, 67, 1369-1374
22. 1H-NMR Carbohydr. Polym. 2005, 61, 155-161
23. 1H NMR method for the determination of the degree of deacetylation of chitosan J. Pharm. Biomed. Anal. 2003, 32, 1149-1158
24. Natalija, G.; Ricardas, M. Synthesis and study of water-soluble chitosan- O -poly(ethylene glycol) graft copolymers Eur. Polym. J. 2004, 40, 685-691
25. Hong, J. H.; Choi, Y. H. Physico-chemical properties of protein-bound polysaccharide from Agaricus blazei Murill prepared by ultrafiltration and spray drying process Int. J. Food Sci. Technol. 2007, 42, 1-8
26. Peniche, C.; Zaldivar, D.; Bulay, A.; Román, J. S. Study of the thermal degradation of poly(furfuryl methacrylate) by thermogravimetry Polym. Degrad. Stab. 1993, 40, 287-295
27. Qin, C.; Du, Y.; Xiao, L.; Li, Z.; Gao, X. Enzymic preparation of water-soluble chitosan and their antitumor activity Int. J. Biol. Macromol. 2002, 31, 111-117
28. Rhim, J. W.; Hong, S. I.; Park, H. M.; Ng, P. K. Preparation and characterization of chitosan-based nanocomposite films with antimicrobial activity J. Agric. Food Chem. 2006, 54, 5814-5822
29. Rosenberg, M.; Kopelman, I. J.; Talmon, Y. A scanning electron microscopy study of microencapsulation J. Food Sci. 1985, 50, 139-144
30. No, H. K.; Young Park, N.; Ho Lee, S.; Meyers, S. P. Antibacterial activity of chitosans and chitosan oligomers with different molecular weights Int. J. Food Microbiol. 2002, 74, 65-72
31. Chung, Y. C.; Su, Y. P.; Chen, C. C.; Jia, G. W.; Huey, W. Relationship between antibacterial activity of chitosan and surface characteristics of cell wall Acta Pharmacol. Sinica 2004, 25, 932-936
32. Wang, J.; Wang, H. Preparation of soluble p -aminobenzoyl chitosan ester by Schiff's base and antibacterial activity of the derivatives Int. J. Biol. Macromol. 2011, 48, 523-529
33. Xing, K.; Chen, X. G.; Kong, M.; Liu, C. S.; Cha, D. S.; Park, H. J. Effect of oleoyl-chitosan nanoparticles as a novel antibacterial dispersion system on viability, membrane permeability and cell morphology of Escherichia coli and Staphylococcus aureus Carbohydr. Polym. 2009, 76, 17-22
34. Mutlu, D. A.; Berrin, Ö. Original article, A study of cytotoxicity of novel chlorokojic acid derivatives with their antimicrobial and antiviral activities Eur. J. Med. Chem. 2010, 45, 4089-4095