Free-radical depolymerization of glycosaminoglycan from sea cucumber Thelenata ananas by hydrogen peroxide and copper ions

Carbohydrate Polymers

Volumn 80, Issue 4, 2010, Pages 1116-1124

  Wu, Mingyi ^a   Xu, Shinmin ^a,c   Zhao, Jinhua ^b   Kang, Hui ^b   Ding, Hui ^a,c  

^a TIANJIN UNIVERSITY   (China)

^b Shenzhen Neptunus Bioengineering Holdings Co Ltd   (China)

^c National Engineering Research Center for Distillation Technology   (China)

Author keywords

Free radical depolymerization; Glycosaminoglycan; Kinetic; Sea cucumber

Indexed keywords

CHEMICAL COMPOSITIONS; CHONDROITIN SULFATES; COPPER IONS; GLYCOSAMINOGLYCAN; GLYCOSAMINOGLYCANS; MAIN CHAINS; NARROW MOLECULAR WEIGHT DISTRIBUTIONS; PSEUDO-FIRST ORDER KINETICS; REPRODUCIBILITIES; SEA CUCUMBER; SIDE-CHAIN; UNIMODAL DISTRIBUTION;

CHROMATOGRAPHIC ANALYSIS; FREE RADICAL REACTIONS; FREE RADICALS; HYDROGEN PEROXIDE; METAL IONS; MOLECULAR WEIGHT DISTRIBUTION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RESONANCE; SULFUR COMPOUNDS;

REACTION KINETICS;

ANANAS; ANANAS COMOSUS; HOLOTHUROIDEA;

EID: 77950367629     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2010.01.032     Document Type: Article

References (39)

1. Angyal S.J. Complexes of metal cations with carbohydrates in solution. In: Tipson R.S., and Horton D. (Eds). Advances in carbohydrate chemistry and biochemistry Vol. 47 (1989), Academic Press, New York 1-43
2. Bertolini A.C., Mestres C., Colonna P., and Raffi J. Free radical formation in UV- and gamma-irradiated cassava starch. Carbohydrate Polymers 44 (2001) 269-271
3. Bianchini, P., & Mascellani, G. (1988). Novel oligosaccharides having pharmacological properties by depolymerisation of heparin. US patent 4791,195.
4. Casu B., and Gennaro U. A conductimetric method for the determination of sulphate and carboxyl groups in heparin and other mucopolysaccharides. Carbohydrate Research 39 (1975) 168-176
5. Casu B., Scovenna G., Cifonelli A.J., and Perlin A.S. Infrared spectra of glycosaminoglycans in deuterium oxide and deuterium chloride solution: Quantitative evaluation of uronic acid and acetamidodeoxyhexose moieties. Carbohydrate Research 63 (1978) 13-27
6. Chang K.L.B., Tai M.C., and Cheng F.H. Kinetics and products of the degradation of chitosan by hydrogen peroxide. Journal of Agricultural Food Chemistry 49 (2001) 4845-4851
7. Cheng Y., and Prud'homme R.K. Enzymatic degradation of guar and substituted guar galactomannans. Biomacromolecules 1 (2000) 782-788
8. Christensen B.E., Myhr M.H., and Smidsrød O. Degradation of double-stranded xanthan by hydrogen peroxide in the presence of ferrous ions: Comparison to acid hydrolysis. Carbohydrate Research 280 (1996) 85-99
9. Dubois M., Gilles K.A., Hamilton J.K., Rebers P.A., and Smith F. Colorimetric method for determination of sugars and related substances. Analytical Chemistry 28 (1956) 350-356
10. Hjerde T., Kristiansen T.S., Stokke B.T., Smidsrød O., and Christensen B.E. Conformation dependent depolymerisation kinetics of polysaccharides studied by viscosity measurements. Carbohydrate Polymers 24 (1994) 265-275
11. Hjerde T., Smidsrød O., Stokke B.T., and Christensen B.E. Acid hydrolysis of κ- and ι-carrageenan in the disordered and ordered conformations: Characterization of partially hydrolyzed samples and single-stranded oligomers released from the ordered structures. Macromolecules 31 (1998) 1842-1851
12. Hjerde T., Stokke B.T., Smidsrød O., and Christensen B.E. Free-radical degradation of triple-stranded scleroglucan by hydrogen peroxide and ferrous ions. Carbohydrate Polymers 37 (1998) 41-48
13. Karlsson A., and Singh S.K. Acid hydrolysis of sulphated polysaccharides. Desulphation and the effect on molecular mass. Carbohydrate Polymers 38 (1999) 7-15
14. Kosakai M., and Yosizawa Z. A partial modification of the carbazole method of bitter and muir for quantitation of hexuronic acids. Analytical Biochemistry 93 (1979) 295-298
15. Li J., and Lian E. Aggregation of human platelets by acidic mucopolysaccharide extracted from Stichopus japonicas Selenka. Journal of Thrombosis and Haemostasis 59 (1988) 435-439
16. Linhardt R.J., Loganathan D., Al-Hakim A., Wang H., Walenga J.M., Hoppensteadt D., et al. Oligosaccharide mapping of low molecular weight heparins: Structure and activity differences. Journal of Medicinal Chemistry 33 (1990) 1639-1645
17. Liu Z., and Perlin A.S. Evidence of a selective free radical degradation of heparin mediated by cupric ion. Carbohydrate Research 255 (1994) 183-191
18. Ma H., Zhou C., Zheng Y., Luo L., and Wang Z. Kinetics of ultrasonic degradation of polysaccharide from Porphyra yezoensis. Journal of Chemical Industry and Engineering (China) 58 (2007) 660-664
19. Mourão P.A.S., Pereira M.S., Pavão M.S.G., Mulloy B., Tollefsen D.M., Mowinckel M.C., et al. Structure and anticoagulant activity of a fucosylated chondroitin sulfate from echinoderm. Journal of Biological Chemistry 271 (1996) 23973-23984
20. Nardella A., Chaubet F., Boisson Vidal C., Blondin C., Durand P., and Jozefonvicz J. Anticoagulant low molecular weight fucans produced by radical process and ion exchange chromatography oh high molecular weight fucans extracted from the brown seaweed Ascophyllum nodosum. Carbohydrate Research 289 (1996) 201-208
21. Ofman D., Slim G.C., Watt D.K., and Yorke S.C. Free radical induced oxidative depolymerisation of chondroitin sulphate and dermatan sulphate. Carbohydrate Polymers 33 (1997) 47-56
22. Petit A.C., Noiret N., Sinquin C., Ratiskol J., Guézennec J., and Jouault S.C. Free-radical depolymerization with metallic catalysts of an exopolysaccharide produced by a bacterium isolated from a deep-sea hydrothermal vent polychaete annelid. Carbohydrate Polymers 64 (2006) 597-602
23. Portenlanger G., and Heusinger H. The influence of frequency on the mechanical and radical effects for the ultrasonic degradation of dextranes. Ultrasonics Sonochemistry 4 2 (1997) 127-130
24. Rota C., Liverani L., and Spelta F. Free radical generation during chemical depolymerization of heparin. Analytical Biochemistry 344 (2005) 193-203
25. Shatalov A.A., and Pereira H. Kinetics of polysaccharide degradation during ethanol-alkali delignification of giant reed - Part 2. Minor carbohydrates and uronic acids. Carbohydrate Polymers 61 (2005) 304-313
26. Singh S.K., Shen B.C., Chou S.T., and Fan L.T. Acid hydrolysis of κ-carrageenan in a batch reactor: Stochastic simulation of change of molecular weight distribution with time. Biotechnology Progress 10 (1994) 389-397
27. Suzuki N., Kitazato K., Takamatsu J., and Saito H. Antithrombotic and anticoagulant activity of depolymerized fragment of the glycosaminoglycan extracted from Stichopus japonicus Selenka. Journal of Thrombosis and Haemostasis 65 (1991) 369-373
28. Tsukamoto T., Hattori M., Sakabe M., and Haginaka J. Determination of the molecular mass of new L-fucose-containing glycosaminoglycan and its distribution by high-performance gel-permeation chromatography with laser light-scattering detection. Analytical Science 17 (2001) 555-558
29. Uchiyama H., Dobashi Y., Ohkouchi K., and Nagasawa K. Chemical change involved in the oxidative reductive depolymerization of hyaluronic acid. Journal of Biological Chemistry 265 (1990) 7753-7759
30. Vieira R.P., and Mourão P.A.S. Occurrence of a unique fucose-branched chondroitin sulfate in the body wall of a sea cucumber. Journal of Biological Chemistry 263 (1988) 18176-18183
31. Vieira R.P., Mulloy B., and Mourão P.A.S. Structure of a fucose-branched chondroitin sulfate from sea cucumber. Evidence for the presence of 3-O-sulfo-beta-d-glucuronosyl residues. Journal of Biological Chemistry 266 (1991) 13530-13536
32. Vismara E., Pierini M., Guglieri S., Liverani L., Mascellani G., and Torri G. Structural modification induced in heparin by a fenton-type depolymerization process. Seminars in Thrombosis and Hemostasis 33 (2007) 467-477
33. Volpi N. Dermatan sulfate from beef mucosa: Structure, physicochemical and biological properties of fractions prepared by chemical depolymerization and anion-exchange chromatography. Carbohydrate Research 255 (1994) 133-144
34. Volpi N., Mascellani G., and Bianchini P. Low molecular weight heparins (5 kDa) and oligoheparins (2 kDa) produced by gel permeation enrichment or radical process: Comparison of structures and physicochemical and biological properties. Analytical Biochemistry 200 (1992) 100-107
35. Yang Z., Li J.P., and Guan H.S. Preparation and characterization of oligomannuronates from alginate degraded by hydrogen peroxide. Carbohydrate Polymers 58 (2004) 115-121
36. Yoon J.S., Chin I.J., Kim M.N., and Kim C. Degradation of microbial polyesters: A theoretical prediction of molecular weight and polydispersity. Macromoleculars 29 (1996) 3303-3307
37. Yoshida K., Minami Y., Nemoto H., Numata K., and Yamanaka E. Structure of DHG, a depolymerized glycosaminoglycan from sea cucumber Stichopus japonicus. Tetrahedron Letters 33 (1992) 4959-4962
38. Zhang H., Mao W., Fang F., Li H., Sun H., Chen Y., et al. Chemical characteristics and anticoagulant activities of a sulfated polysaccharide and its fragments from Monostroma latissimum. Carbohydrate Polymers 71 (2008) 428-434
39. Zhao, J., Wu, M., Kang, H., Zeng, W., Liang, H., Li, Z., et al. (2009). Low molecular weight fractions and preparation of a fucosylated glycosaminoglycan from sea cucumber. CN patent 200910110114.0.