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Preliminary structural characterization, anti-inflammatory and anticoagulant activities of chondroitin sulfates from marine fish cartilage

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Abstract

Chondroitin sulfates isolated from cartilage of five marine fish species: Atlantic salmon (Salmo salar), Greenland shark (Somniosus microcephalus), blackmouth catshark (Galeus melastomus), birdbeak dogfish (Deania calcea), and Arctic skate (Amblyraja hyperborea), were characterized in detail by 1H and 13C NMR spectroscopy. The complete signal assignments for carbohydrates were made and the relative contents of the key structural units were estimated by 2D homonuclear and heteronuclear NMR spectroscopy (COSY, TOCSY, NOESY, HSQC, and HMBC). The average length of the polysaccharide chain was evaluated from the integrated intensity ratio of the terminal and internal monosaccharide residues. The anti-inflammatory and anticoagulant activities of the specimens were studied. Chondroitin sulfates from salmon and Arctic skate exhibit considerable anti-inflammatory activity. All specimens manifest weak anticoagulant activity. The results of the present study indicate that chondroitin sulfates deserve more detailed investigation as potential anti-inflammatory agents.

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References

  1. D. R. Coombe, W. C. Kett, Cell. Mol. Life Sci., 2005, 62, 410.

    Article  CAS  Google Scholar 

  2. B. Lia, J. Suwanb, J. G. Martina, F. Zhangd, Zh. Zhanga, D. Hoppensteadte, M. Clarke, J. Fareede, R. J. Linhardt, Bio. Chem. Pharm., 2009, 78, 292.

    Article  Google Scholar 

  3. A. Cumashi, N. A. Ushakova, M. E. Preobrazhenskaya, A. D’Incecco, A. Piccoli, L. Totani, N. Tinari, G. E. Morozevich, A. E. Berman, M. I. Bilan, A. I. Usov, N. E. Ustyuzhanina, A. A. Grachev, C. J. Sanderson, M. Kelly, G. A. Rabinovich, S. Iacobelli, N. E. Nifantiev, Glycobiology, 2007, 17, 541.

    Article  CAS  Google Scholar 

  4. D. O. Croci, A. Cumashi, N. A. Ushakova, M. E. Preobrazhenskaya, A. Piccoli, L. Totani, N. E. Ustyuzhanina, M. I. Bilan, A. I. Usov, A. A. Grachev, G. E. Morozevich, A. E. Berman, C. J. Sanderson, M. Kelly, P. Di Gregorio, C. Rossi, N. Tinari, S. Iacobelli, G. A. Rabinovich, N. E. Nifantiev, PloS ONE, 2011, 6(2), e17283, doi:10.1371/journal.pone.0017283.

    Article  CAS  Google Scholar 

  5. L. Kjellen, U. Lindahl, Annu. Rev. Biochem., 1991, 60, 443.

    Article  CAS  Google Scholar 

  6. Chondroitin Sulfate: Structure, Role and Pharmacological Activity, Ed. N. Volpi, Academic Press, Amsterdam-Boston-Heidelberg-London-New York-Oxford-Paris-San Diego-San Francisco-Singapore-Sydney-Tokyo, 2006.

  7. J. M. Whitelock, R. V. Lozzo, Chem. Rev., 2005, 105, 2745.

    Article  CAS  Google Scholar 

  8. R. Lever, C. P. Page, Nature Reviews Drug Discovery, 2002, 1, 140.

    Article  CAS  Google Scholar 

  9. K. Sugahara, T. Mikami, T. Uyama, S. Mizuguchi, K. Nomura, H. Kitagawa, Curr. Opin. Struct. Biol., 2003, 13, 612.

    Article  CAS  Google Scholar 

  10. D. Bechard, T. Gentina, M. Delehedde, A. Scherpereel, M. Lyon, M. Aumercier, R. Vazeux, C. Richet, P. Degand, B. Jude, J. Biol. Chem., 2001, 276, 48341.

    CAS  Google Scholar 

  11. H. Kawashima, K. Atarashi, M. Hirose, J. Hirose, S. Yamada, K. Sugahara, M. Miyasaka, J. Biol. Chem., 2002, 277, 12921.

    Article  CAS  Google Scholar 

  12. D. A. Morgenstern, R. A. Asher, J. W. Fawcett, Prog. Brain. Res., 2002, 137, 313.

    Article  CAS  Google Scholar 

  13. A. Oohira, F. Matsui, Y. Tokita, S. Yamauchi, S. Aono, Arch. Biochem. Biophys., 2000, 374, 24.

    Article  CAS  Google Scholar 

  14. F. D. Menozzi, K. Pethe, P. Bifani, F. Soncin, M. J. Brennan, C. Locht, Mol. Microbiol., 2002, 43, 1379.

    Article  CAS  Google Scholar 

  15. R. N. Achur, M. Valiyaveettil, D. C. Gowda, J. Biol. Chem., 2002, 278, 11705.

    Article  Google Scholar 

  16. K. Sugahara, S. Yamada, Trends Glycosci. Glycotechnol., 2000, 12, 321.

    Article  CAS  Google Scholar 

  17. M. Takai, H. Kono, US Patent Application 20.030.162.744, 2003.

  18. M. I. Bilan, A. A. Grachev, N. E. Ustuzhanina, A. S. Shashkov, N. E. Nifantiev, A. I. Usov, Carbohydr. Res., 2002, 337, 719.

    Article  CAS  Google Scholar 

  19. L. O. Anderson, T. W. Barrowcliffe, E. Holmer, E. A. Johnson, G. E. Sims, Thromb. Res., 1976, 9, 575.

    Article  Google Scholar 

  20. M. E. Preobrazhenskaya, A. E. Berman, V. I. Mikhailov, N. A. Ushakova, A. V. Mazurov, A. V. Semenov, A. I. Usov, N. E. Nifantiev, N. V. Bovin, Biochem. Mol. Bio. Intl., 1997, 43, 443.

    CAS  Google Scholar 

  21. N. A. Ushakova, M. E. Preobrazhenskaya, N. E. Nifant’ev, A. I. Usov, T. V. Pochechueva, O. E. Galanina, N. V. Bovin, Vopr. Med. Khim. [Probl. Med. Chem.], 1999, 45, 375 (in Russian).

    CAS  Google Scholar 

  22. A. Mucci, L. Schenetti, N. Volpi, Carbohydr. Polym., 2000, 41, 37.

    Article  CAS  Google Scholar 

  23. F. Maccari, F. Ferrarini, N. Volpi, Carbohydr. Res., 2010, 345, 1575.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    V. B. Krylov, A. A. Grachev, N. E. Ustyuzhanina, A. S. Shashkov & N. E. Nifantiev

  2. V. N. Orekhovich Institute of Biomedical Chemistry, Russian Academy of Medical Sciences, 10 ul. Pogodinskaya, 119121, Moscow, Russian Federation

    N. A. Ushakova, M. E. Preobrazhenskaya & N. I. Kozlova

  3. Murmansk State Technical University, 13 ul. Sportivnaya, 183010, Murmansk, Russian Federation

    M. N. Portsel & I. N. Konovalova

  4. N. M. Knipovich Polar Research Institute of Marine Fisheries and Oceanography, 6 ul. Knipovicha, 183000, Murmansk, Russian Federation

    V. Yu. Novikov

  5. RI-B-NT Research Institute of Bioinformatics and Nanotechnology, Schauenburgerstrasse 116, D-24118, Kiel, Germany

    H. -Ch. Siebert

  6. Institute for Biochemistry and Endocrinology, Veterinary Faculty, Justus Liebig University, Frankfurter Strasse 100, D-35392, Giessen, Germany

    H. -Ch. Siebert

Authors
  1. V. B. Krylov
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  2. A. A. Grachev
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  3. N. E. Ustyuzhanina
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  4. N. A. Ushakova
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  5. M. E. Preobrazhenskaya
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  6. N. I. Kozlova
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  7. M. N. Portsel
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  8. I. N. Konovalova
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  9. V. Yu. Novikov
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  10. H. -Ch. Siebert
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  11. A. S. Shashkov
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  12. N. E. Nifantiev
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Corresponding author

Correspondence to N. E. Nifantiev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 731–738, April, 2011.

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Krylov, V.B., Grachev, A.A., Ustyuzhanina, N.E. et al. Preliminary structural characterization, anti-inflammatory and anticoagulant activities of chondroitin sulfates from marine fish cartilage. Russ Chem Bull 60, 746–753 (2011). https://doi.org/10.1007/s11172-011-0115-x

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  • DOI: https://doi.org/10.1007/s11172-011-0115-x

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