Preparation, characterization, and biochemical activities of N -(2-Carboxyethyl)chitosan from squid pens

Journal of Agricultural and Food Chemistry

Volumn 63, Issue 9, 2015, Pages 2464-2471

  Huang, Jun ^a   Xie, Haihua ^a   Hu, Sheng ^b   Xie, Tian ^a   Gong, Jinyan ^a   Jiang, Chengjun ^a   Ge, Qing ^a   Wu, Yuanfeng ^a   Liu, Shiwang ^a   Cui, Yanli ^c   Mao, Jianwei ^a   Mei, Lehe ^b  

^a ZHEJIANG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b ZHEJIANG UNIVERSITY   (China)

^c ZHEJIANG UNIVERSITY   (China)

Author keywords

antioxidant; bile acid capacity; characterization; chitosan; N (2 carboxyethyl)chitosan; chitin

Indexed keywords

ACETYLATION; ALKALINITY; ANTIOXIDANTS; BODY FLUIDS; CHARACTERIZATION; CHITOSAN; MOLLUSCS; NUCLEAR MAGNETIC RESONANCE; OXYGEN; SHELLFISH; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

ANTIOXIDANT PROPERTIES; BILE ACID; BIOCHEMICAL ACTIVITY; BIOCHEMICAL PROPERTIES; DEGREES OF SUBSTITUTION; FOURIER TRANSFORM INFRA REDS; GOOD WATER-SOLUBILITY; NUCLEAR MAGNETIC RESONANCE(NMR);

CHITIN;

CEPHALOPODA;

ANTIOXIDANT; CHITOSAN; N-(2-CARBOXYETHYL)CHITOSAN;

ANALOGS AND DERIVATIVES; ANALYSIS; ANIMAL; CHEMISTRY; DECAPODIFORMES; INFRARED SPECTROSCOPY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SHELLFISH;

ANIMALS; ANTIOXIDANTS; CHITOSAN; DECAPODIFORMES; MAGNETIC RESONANCE SPECTROSCOPY; SHELLFISH; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 84924533790     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf505581n     Document Type: Article

References (47)

1. Rinaudo, M. Chitin and chitosan: Properties and applications Prog. Polym. Sci. 2006, 31, 603-632
2. Muzzarelli, R. A. A. Carboxymethylated chitins and chitosans Carbohydr. Polym. 1988, 8, 1-21
3. Minke, R.; Blackwell, J. The structure of α-chitin J. Mol. Biol. 1978, 120, 167-181
4. Hajji, S.; Younes, I.; Ghorbel-Bellaaj, O.; Hajji, R.; Rinaudo, M.; Nasri, M.; Jellouli, K. Structural differences between chitin and chitosan extracted from three different marine sources Int. J. Biol. Macromol. 2014, 65, 298-306
5. Kurita, K.; Tomita, K.; Tada, T.; Ishii, S.; Nishimura, S. I.; Shimoda, K. Squid chitin as a potential alternative chitin source: Deacetylation behavior and characteristic properties J. Polym. Sci., Part A: Polym. Chem. 1993, 31, 485-491
6. Kurita, K.; Ishii, S.; Tomita, K.; Nishimura, S. I.; Shimoda, K. Reactivity characteristics of squid β-chitin as compared with those of shrimp chitin: High potentials of squid chitin as a starting material for facile chemical modifications J. Polym. Sci., Part A: Polym. Chem. 1994, 32, 1027-1032
7. Kurita, K. Controlled functionalization of the polysaccharide chitin Prog. Polym. Sci. 2001, 26, 1921-1971
8. Huang, J.; Zhao, D. K.; Hu, S.; Mao, J. W.; Mei, L. H. Biochemical activities of low molecular weight chitosans derived from squid pens Carbohydr. Polym. 2012, 87, 2231-2236
9. Jayakumar, R.; Chennazhi, K. P.; Muzzarelli, R. A. A.; Tamura, H.; Nair, S. V.; Selvamurugan, N. Chitosan conjugated DNA nanoparticles in gene therapy Carbohydr. Polym. 2010, 79, 1-8
10. Zhao, D. K.; Huang, J.; Hu, S.; Mao, J. W.; Mei, L. H. Biochemical activities of N,O-carboxymethyl chitosan from squid cartilage Carbohydr. Polym. 2011, 85, 832-837
11. Muzzarelli, R. A. A.; Morganti, P.; Morganti, G.; Palombo, P.; Palombo, M.; Biagini, G.; Mattioli Belmonte, M.; Giantomassi, F.; Orlandi, F.; Muzzarelli, C. Chitin nanofibrils/chitosan glycolate composites as wound medicaments Carbohydr. Polym. 2007, 70, 274-284
12. Muzzarelli, R. A. A. Chitins and chitosans for the repair of wounded skin, nerve, cartilage and bone Carbohydr. Polym. 2009, 76, 167-182
13. Kofuji, K.; Qian, C. J.; Nishimura, M.; Sugiyama, I.; Murata, Y.; Kawashima, S. Relationship between physicochemical characteristics and functional properties of chitosan Eur. Polym. J. 2005, 41, 2784-2791
14. Ong, S. Y.; Wu, J.; Moochhala, S. M.; Tan, M. H.; Lu, J. Development of a chitosan-based wound dressing with improved hemostatic and antimicrobial properties Biomaterials 2008, 29, 4323-4332
15. Shelma, R.; Sharma, C. P. Development of lauroyl sulfated chitosan for enhancing hemocompatibility of chitosan Colloid Surf. B-Biointerfaces 2011, 84, 561-570
16. Cheng, Z. H.; Huang, J.; Hu, S.; Jiang, C. J.; Ge, Q.; Lai, H. W.; Gong, J. Y.; Sun, P. L.; Mao, J. W.; Mei, L. H. Effects of hydroxypropyl degree on physiochemical activities of chitosan from squid pens Int. J. Biol. Macromol. 2014, 65, 246-251
17. Huang, J.; Cheng, Z. H.; Xie, H. H.; Gong, J. Y.; Lou, J.; Ge, Q.; Wang, Y. J.; Wu, Y. F.; Liu, S. W.; Sun, P. L.; Mao, J. W. Effect of quaternization degree on physiochemical and biological activities of chitosan from squid pens Int. J. Biol. Macromol. 2014, 70, 545-550
18. Wan, A. J.; Xu, Q.; Sun, Y.; Li, H. L. Antioxidant activity of high molecular weight chitosan and N,O-quaternized chitosans J. Agric. Food Chem. 2013, 61, 6921-6928
19. Ouchi, T.; Nishizawa, H.; Ohya, Y. Aggregation phenomenon of PEG-grafted chitosan in aqueous solution Polymer 1998, 39, 5171-5175
20. Jimtaisong, A.; Saewan, N. Utilization of carboxymethyl chitosan in cosmetics Int. J. Cosmet. Sci. 2014, 36, 12-21
21. Skorik, Y. A.; Gomes, C. A. R.; Vasconcelos, M. T. S. D.; Yatluk, Y. G. N -(2-Carboxyethyl)chitosans: Regioselective synthesis, characterisation and protolytic equilibria Carbohydr. Res. 2003, 338, 271-276
22. Kogan, G.; Skorik, Y. A.; Žitňanová, I.; Križková, L.; ɰuračková, Z.; Gomes, C. A. R.; Yatluk, Y. G.; Krajčovič, J. Antioxidant and antimutagenic activity of N -(2-carboxyethyl)chitosan Toxicol. Appl. Pharmacol. 2004, 201, 303-310
23. Lee, Y. M.; Shin, E. M.; Noh, S. T. Pervaporation separation of water-ethanol through modified chitosan membranes, II. Carboxymethyl, carboxyethyl, cyanoethyl, and amidoxime chitosan membranes Angew. Makromol. Chem. 1991, 192, 169-181
24. Sashiwa, H.; Yamamori, N.; Ichinose, Y.; Sunamoto, J.; Aiba, S. I. Chemical modification of chitosan 17a: Michael reaction of chitosan with acrylic acid in water Macromol. Biosci. 2003, 3, 231-233
25. Sashiwa, H.; Yamamori, N.; Ichinose, Y.; Sunamoto, J.; Aiba, S. Michael reaction of chitosan with various acryl reagents in water Biomacromolecules 2003, 4, 1250-1254
26. Sashiwa, H.; Shigemasa, Y.; Roy, R. Novel N-alkylation of chitosan via Michael type reaction Chem. Lett. 2000, 8, 862-863
27. Willett, W. C. Diet and health: What should we eat? Science 1994, 264, 532-537
28. Castagnino, E.; Francesca Ottaviani, M.; Cangiotti, M.; Morelli, M.; Casettari, L.; Muzzarelli, R. A. A. Radical scavenging activity of 5-methylpyrrolidinone chitosan and dibutyryl chitin Carbohydr. Polym. 2008, 74, 640-647
29. Muzzarelli, R. A. A.; Boudrant, J.; Meyer, D.; Manno, N.; DeMarchis, M.; Paoletti, M. G. Current views on fungal chitin/chitosan, human chitinases, food preservation, glucans, pectins and inulin: A tribute to Henri Braconnot, precursor of the carbohydrate polymers science, on the chitin bicentennial Carbohydr. Polym. 2012, 87, 995-1012
30. Jiang, X.; Chen, L.; Zhong, W. A new linear potentiometric titration method for the determination of deacetylation degree of chitosan Carbohydr. Polym. 2003, 54, 457-463
31. Ding, F. Y.; Shi, X. W.; Li, X. X.; Cai, J.; Duan, B.; Du, Y. M. Homogeneous synthesis and characterization of quaternized chitin in NaOH/urea aqueous solution Carbohydr. Polym. 2012, 87, 422-426
32. Muzzarelli, R. A. A.; Orlandini, F.; Pacetti, D.; Boselli, E.; Frega, N. G.; Tosi, G.; Muzzarelli, C. Chitosan taurocholate capacity to bind lipids and to undergo enzymatic hydrolysis: An in vitro model Carbohydr. Polym. 2006, 66, 363-371
33. Prouillac, C.; Vicendo, P.; Garrigues, J. C.; Poteau, R.; Rima, G. Evaluation of new thiadiazoles and benzothiazoles as potential radioprotectors: Free radical scavenging activity in vitro and theoretical studies (QSAR, DFT) Free Radical Biol. Med. 2009, 46, 1139-1148
34. Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. Antioxidant activity applying an improved ABTS radical cation decolorization assay Free Radical Biol. Med. 1999, 26, 1231-1237
35. Yuan, H. M.; Zhang, W. W.; Li, X. G.; Lü, X. X.; Li, N.; Gao, X. L.; Song, J. M. Preparation and in vitro antioxidant activity of κ-carrageenan oligosaccharides and their oversulfated, acetylated, and phosphorylated derivatives Carbohydr. Res. 2005, 340, 685-692
36. Huang, J.; Chen, W. W.; Hu, S.; Gong, J. Y.; Lai, H. W.; Liu, P.; Mei, L. H.; Mao, J. W. Biochemical activities of 6-carboxy-β-chitin derived from squid pens Carbohydr. Polym. 2013, 91, 191-197
37. Cai, Z. S.; Song, Z. Q.; Yang, C. S.; Shang, S. B.; Yin, Y. B. Synthesis, characterization and antibacterial activity of quaternized N, O -(2-carboxyethyl) chitosan Polym. Bull. 2009, 62, 445-456
38. Kong, X. P. Simultaneous determination of degree of deacetylation, degree of substitution and distribution fraction of -COONa in carboxymethyl chitosan by potentiometric titration Carbohydr. Polym. 2012, 88, 336-341
39. Xiao, B.; Wan, Y.; Wang, X. Y.; Zha, Q. C.; Liu, H. M.; Qiu, Z. Y.; Zhang, S. M. Synthesis and characterization of N -(2-hydroxy)propyl-3-trimethyl ammonium chitosan chloride for potential application in gene delivery Colloid Surf. B-Biointerfaces 2012, 91, 168-174
40. Pestov, A. V.; Kodess, M. I.; Matochkina, E. G.; Yatluk, Y. G. Selective mono-N-2-carboxyethylation of chitosan in the presence of magnesium halides Carbohydr. Polym. 2011, 86, 783-788
41. Zhou, Y. S.; Yang, H. J.; Liu, X.; Mao, J.; Gu, S. J.; Xu, W. L. Electrospinning of carboxyethyl chitosan/poly(vinyl alcohol)/silk fibroin nanoparticles for wound dressings Int. J. Biol. Macromol. 2013, 53, 88-92
42. Daggy, B. P.; OConnell, N. C.; Jerdack, G. R.; Stinson, B. A.; Setchell, K. D. Additive hypocholesterolemic effect of psyllium and cholestyramine in the hamster: Influence on fecal sterol and bile acid profiles J. Lipid Res. 1997, 38, 491-502
43. Wang, Y. J.; Yu, Y. Z.; Mao, J. W. Carboxymethylated β-glucan derived from Poria cocos with biological activities J. Agric. Food Chem. 2009, 57, 10913-10915
44. Xie, M. H.; Hu, B.; Wang, Y.; Zeng, X. X. Grafting of gallic acid onto chitosan enhances antioxidant activities and alters rheological properties of the copolymer J. Agric. Food Chem. 2014, 62, 9128-9136
45. Sun, T.; Yao, Q.; Zhou, D. X.; Mao, F. Antioxidant activity of N -carboxymethyl chitosan oligosaccharides Bioorg. Med. Chem. Lett. 2008, 18, 5774-5776
46. Xing, R. E.; Liu, S.; Guo, Z. Y.; Yu, H. H.; Wang, P. B.; Li, C. P.; Li, Z. E.; Li, P. C. Relevance of molecular weight of chitosan and its derivatives and their antioxidant activities in vitro Bioorg. Med. Chem. 2005, 13, 1573-1577
47. Duh, P. D.; Tu, Y. Y.; Yen, G. C. Antioxidant activity of water extract of Harng Jyur (Chrysanthemum morifolium Ramat) LWT - Food Sci. Technol. 1999, 32, 269-277