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The preparation and antioxidant activity of glucosamine sulfate

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Abstract

Glucosamine sulfate was prepared from glucosamine hydrochloride that was produced by acidic hydrolysis of chitin by ion-exchange method. Optical rotation and elemental analysis characterized the degree of its purity. In addition, the antioxidant potency of chitosan derivative-glucosamine sulfate was investigated in various established in vitro systems, such as superoxide (O 2 )/hydroxyl (·OH) radicals scavenging, reducing power, iron ion chelating. The following results are obtained: first, glucosamine sulfate had pronounced scavenging effect on superoxide radical. For example the O 2 scavenging activity of glucosamine sulfate was 92.11% at 0.8 mg/mL. Second, the ·OH scavenging activity of glucosamine sulfate was also strong, and was about 50% at 3.2 mg/mL. Third, the reducing power of glucosamine sulfate was more pronounced. The reducing power of glucosamine sulfate was 0.643 at 0.75 mg/mL. However, its potency for ferrous ion chelating was weak. Furthermore, except for ferrous ion chelating potency, the scavenging rate of radical and reducing power of glucosamine sulfate were concentration-dependent and increased with their increasing concentrations, but its ferrous ion chelating potency decreased with the increasing concentration. The multiple antioxidant activities of glucosamine sulfate were evidents of reducing power and superoxide/hydroxyl radicals scavenging ability. These in vitro results suggest the possibility that glucosamine sulfate could be used effectively as an ingredient in health or functional food, to alleviate oxidative stress.

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References

  • Bucci, L. R. 1994. Chondroprotective agents. Glucosamine salts and chondroitin sulfates. Townsend Letter for Doctors 1: 52–54.

    Google Scholar 

  • Dahl, M. K., and T. Richardson, 1978. Photogeneration of superoxide anion in serum of bovine milk and in model systems containing riboflavin and amino Acids. J. Dairy Sci. 61: 400–407.

    Article  Google Scholar 

  • Decker, E. A. and B. Welch, 1990. Role of ferritin as a lipid oxidation catalyst in muscle food. J. Agric. Food Chem. 38: 674–677.

    Article  Google Scholar 

  • Foot, M. and M. Mulholland, 2005. Classification of chondroitin sulfate A, chondroitin sulfate C, glucosamine hydrochloride and glucosamine 6 sulfate using chemometric techniques. J. Pharmaceut. Biomed. Anal. 38(3): 397–407.

    Article  Google Scholar 

  • Gordon, M. H., 1990. The mechanism of antioxidant action in vitro. In B.J.F. Hudson (Ed.), Food antioxidants. London: Elsevier Applied Science. p. 1–18.

    Google Scholar 

  • Halliwell, B., J. M. C. Gutteridge and O. I. Aruoma, 1987. The deoxyribose method: a simple “test tube” assay for determination of rate constants for reactions of hydroxyl radicals. Anal. Biochem. 165: 215–219.

    Article  Google Scholar 

  • Mau, J. L., C. N. Chang, S. J. Huang and C. C. Chen, 2004. Antioxidant properties of methanolic extracts from Grifola frondosa, Morchella esculenta and Termitomyces albuminosus mycelia. Food Chem. 87: 111–118.

    Article  Google Scholar 

  • Meyer, A. S., and A. Isaksen, 1995. Application of enzymes as food antioxidants. Trends Food Sci. Technol. 6: 300–304.

    Article  Google Scholar 

  • Murad. Pharmaceutical composition and methods for improving wrinkles and other skin conditions. US Patent No. 5804594, 1988-09-08.

  • Müller-Faßbender, H., G. L. Bach, W. Haase, L. C. Rovati and I. Setnikar, 1994. Glucosamine sulfate compared to ibuptofen in osteoarthritis of the knee. Osteoarthritis Cartilage 2: 61–69.

    Article  Google Scholar 

  • Nishikimi, M., N. A. Rao and K. Yagi, 1972. The occurrence of superoxide anion in the reaction of reduced phenazine methosulphate and molecular oxygen. Biochem. Biophys. Res. Commun. 46: 849–864.

    Article  Google Scholar 

  • Noack, W., K. K. Förster, L. C. Rovatic and I. Setnikar, 1994. Glucosamine sulfates in osteoarthritis of the knee. Osteoarthritis Cartilage 2: 51–59.

    Article  Google Scholar 

  • Pin-Der-Duh, X., 1998. Antioxidant activity of burdock (Arctium lappa Linne): its scavenging effect on free-radical and active oxygen. J. Am. Oil Chem. Soc. 75: 455–461.

    Article  Google Scholar 

  • Pin-Der-Duh, X., X. Pin-Chan-Du and X. Gow-Chin-Yen, 1999. Action of methanolic extract of mung hulls as inhibitors of lipid peroxidation and non-lipid oxidative damage. Food Chem. Toxicol. 37: 1 055–1 061.

    Google Scholar 

  • Reginster J. Y., R. Deroisy, L. C. Rovati, R. L. Lee, E. Lejeane, O. Bruyere, G. Giacovelli, Y. Henrotin, J. E. Daore and C. Gossett, 2001. Long-term effects of glucosamine sulphate on osteoarthritis progression: a randomized, placebo-controlled clinical trial. Lancet. 357: 251–256.

    Article  Google Scholar 

  • Rovati, L. C., 1992. Clinical research in osteoarthritis: design and results of short-term and long-term trials with disease-modifying drugs. Int. J. Tiss. Reac. 14(5): 243–251.

    Google Scholar 

  • Rovati, L. C., 1997. The clinical profile of glucosamine sulfate as a selective symptom modifying drug in osteoarthritis: current data and perspectives. Osteoarthritis Cartilage. 5(Suppl. A): 72.

    Google Scholar 

  • Setnikar, I., 1986. Pharmacokinetics of glucosamine in the dog and man. Forsch & Drug Res. 36(1): 729–733.

    Google Scholar 

  • Setnikar, I., R. Cereda, M. A. Pacini and L., Revel 1991. Antireactive properties of glucosamine sulfate. Arzneimittelforschung 41: 157–161.

    Google Scholar 

  • Shikhman, A. R., N. Alaaeddine and M. K. Lotz, 1999. N-acetlyglucosamine prevents IL-1 mediated activation of chondrocytes. Arthritis Rheum. 42(Suppl.): S381.

    Google Scholar 

  • Smith, C., B. Halliwell and O. I. Aruoma, 1992. Protection by albumin against the pro-oxidant actions of phenolic dietary components. Food Chem. Toxicol. 30: 483–489.

    Article  Google Scholar 

  • Tapadinhas, M. J., 1982. Oral glucosamine sulfate in the management of arthrosis: report on a milti-center open investigation in Portugal. Pharmatherapeutica 3(3): 157–168.

    Google Scholar 

  • Weisman, Bernaed, Boca Raton. Natural composition for treating bone or joint inflammation. US Patent No. 5929050, 1999-03-30.

  • Xing, R. E., H. H. Yu, S. Liu, W. W. Zhang, Q. B. Zhang, Z. E. Li and P. C. Li, 2005. Antioxidant activity of differently regioselective chitosan sulfates in vitro. Bioorgan. Med. Chem. 13: 1 387–1 392.

    Google Scholar 

  • Xing, R. E., S. Liu, Z. Y. Guo, H. H. Yu, P. B. Wang, P. C. Li, Z. E. Li and P. C. Li, 2005. Relevance of molecular weight of chitosan and its derivatives and their antioxidant activities in vitro. Bioorgan. Med. Chem. 13: 1 573–1 577.

    Google Scholar 

  • Yen, G. C. and H. Y. Chen, 1995. Antioxidant activity of various tea extracts in relation to their antimutagenicity. J. Agric. Food Chem. 43: 27–32.

    Article  Google Scholar 

  • Yin, X. Q., Q. Lin and Q. Zhang, 2002. O 2 Scavenging activity of chitosan and its metal complexes. Chin. J. Appl. Chem. 19(4): 325–328. (in Chinese)

    Google Scholar 

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Correspondence to Ronge Xing  (邢荣娥) or Pengcheng Li  (李鹏程).

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Supported by the Talent Program of Chinese Academy of Sciences (Dongbei Zhi Chun) and Award Foundation of Scientific Research for Excellent Young and Middle-Age Scientist of Shandong Province (No. 2007BS07002)

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Xing, R., Liu, S., Wang, L. et al. The preparation and antioxidant activity of glucosamine sulfate. Chin. J. Ocean. Limnol. 27, 283–287 (2009). https://doi.org/10.1007/s00343-009-9135-x

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  • DOI: https://doi.org/10.1007/s00343-009-9135-x

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