Skip to main content
Log in

Polysaccharides of algae: 60. Fucoidan from the pacific brown alga Analipus japonicus (Harv.) winne (Ectocarpales, Scytosiphonaceae)

  • Structural Studies
  • Published:
Russian Journal of Bioorganic Chemistry Aims and scope Submit manuscript

Abstract

A fucoidan containing L-fucose, sulfate, and O-acetyl groups at a molar ratio 3:2:1, as well as minor amounts of xylose, galactose, and uronic acids was isolated from the brown alga Analipus japonicus collected in the Sea of Japan. The structures of the native polysaccharide and the products of its desulfation and deacetylation were studied by the methods of methylation, periodate oxidation, and NMR spectroscopy. It was shown that a polysaccharide molecule mainly consists of a linear carbohydrate chain of (1→3)-linked α-L-fucopyranose residues, which bears numerous branches in the form of single α-L-fucopyranose residues (three branches at position 4 and one branch at position 2 per each ten residues of the main chain). Sulfate groups occupy positions 2 and (to a lesser extent) 4, most of the terminal nonreducing fucose residues being sulfated twice. The acetyl groups are located predominantly at positions 4. The structural role of minor monosaccharides was not established.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Bilan, M.I., Grachev, A.A., Shashkov, A.S., Nifantiev, N.E., and Usov, A.I., Carbohydr. Res., 2006, vol. 341, pp. 238–245.

    Article  PubMed  CAS  Google Scholar 

  2. Nagumo, T. and Nishino, T., Fucan Sulfates and Their Anticoagulant Activities in Polysaccharides in Medicinal Applications, Dumitriu, S., Ed., New York: Marcel Dekker, Inc., 1996, pp. 545–574.

    Google Scholar 

  3. Mourão, P.A.S., Curr. Pharm. Design, 2004, vol. 10, pp. 967–981.

    Article  Google Scholar 

  4. Berteau, O. and Mulloy, B., Glycobiology, 2003, vol. 13, p. 29R–40R.

    Article  PubMed  CAS  Google Scholar 

  5. Bilan, M.I., Grachev, A.A., Ustuzhanina, N.E., Shashkov, A.S., Nifantiev, N.E., and Usov, A.I., Carbohydr. Res., 2002, vol. 337, pp. 719–730.

    Article  PubMed  CAS  Google Scholar 

  6. Duarte, M.E.R., Cardoso, M.A., Noseda, M.D., and Cerezo, A.S., Carbohydr. Res., 2001, vol. 333, pp. 281–293.

    Article  PubMed  CAS  Google Scholar 

  7. Ponce, N.M.A., Pujol, C.A., Damonte, E.B., Flores, M.L., and Stortz, C.A., Carbohydr. Res., 2003, vol. 338, pp. 153–165.

    Article  PubMed  CAS  Google Scholar 

  8. Sakai, T., Kimura, H., Kojima, K., Shimanaka, K., Ikai, K., and Kato, I., Mar. Biotechnol., 2003, vol. 5, pp. 70–78.

    Article  PubMed  CAS  Google Scholar 

  9. Silva, T.M.A., Alves, L.G., de Queiroz, K.C.S., Santos, M.G.L., Marques, C.T., Chavante, S.F., Rocha, H.A.O., and Leite, E.L., Brazilian J. Med. Biol. Res., 2005, vol. 38, pp. 523–533.

    CAS  Google Scholar 

  10. Rocha, H.A.O., Moraes, F.A., Trindade, E.S., Franco, C.R.C., Torquato, R.J.S., Veiga, S.S., Valente, A.P., Mourão, P.A.S., Leite, E.L., Nader, H.B., and Dietrich, C.P., J. Biol. Chem., 2005, vol. 280, pp. 41 278–41 288.

    Article  CAS  Google Scholar 

  11. Khatuntseva, E.A., Ustuzhanina, N.E., Zatonskii, G.V., Shashkov, A.S., Usov, A.I., and Nifant’ev, N.E., J. Carbohydr. Chem, 2000, vol. 19, pp. 1151–1173.

    Article  CAS  Google Scholar 

  12. Gerbst, A.G., Ustuzhanina, N.E., Grachev, A.A., Khatuntseva, E.A., Tsvetkov, D.E., Shashkov, A.S., Usov, A.I., Preobrazhenskaya, M.E., Ushakova, N.A., and Nifantiev, N.E., J. Carbohydr. Chem, 2003, vol. 22, pp. 109–122.

    Article  CAS  Google Scholar 

  13. Gerbst, A.G., Grashev, A.A., Ustuzhanina, N.E., Khatuntseva, E.A., Tsvetkov, D.E., Usov, A.I., Shashkov, A.S., Preobrazhenskaya, M.E., Ushakova, N.A., and Nifantiev, N.E., Bioorg. Khim., 2004, vol. 30, pp. 156–167; Rus. J. Bioorg. Chem., 2004, vol. 30, pp. 137–147.

    PubMed  CAS  Google Scholar 

  14. Usov, A.I., Smirnova, G.P., Bilan, M.I., and Shashkov, A.S., Bioorg. Khim., 1998, vol. 24, pp. 437–445; Rus. J. Bioorg. Chem., 1998, vol. 24, pp. 382–389.

    CAS  Google Scholar 

  15. Chizhov, A.O., Dell, A., Morris, H.R., Haslam, S.M., McDowell, R.A., Shashkov, A.S., Nifant’ev, N.E., Khatuntseva, E.A., and Usov, A.I., Carbohydr. Res., 1999, vol. 320, pp. 108–119.

    Article  PubMed  CAS  Google Scholar 

  16. Bilan, M.I., Grachev, A.A., Ustuzhanina, N.E., Shashkov, A.S., Nifantiev, N.E., and Usov, A.I., Carbohydr. Res., 2004, vol. 339, pp. 511–517.

    Article  PubMed  CAS  Google Scholar 

  17. Usov, A.I., Kosheleva, E.A., and Yakovlev, A.P., Bioorg. Khim., 1985, vol. 11, pp. 830–836.

    CAS  Google Scholar 

  18. Rees, D.A., Polysaccharide Conformations, in MTP Intern. Review of Science: vol. 7, Carbohydrates, Aspinall, G.O., Ed., London: Butterworth, 1973, pp. 251–283.

    Google Scholar 

  19. Patankar, M.S., Oehninger, S., Barnett, T., Williams, R.L., and Clark, G.F., J. Biol. Chem., 1993, vol. 268, pp. 21770–21776.

    PubMed  CAS  Google Scholar 

  20. Petruš L., Gray, D.G., and BeMiller, J.N., Carbohydr. Res., 1995, vol. 268, pp. 319–323.

    Article  Google Scholar 

  21. Lipkind, G.M., Shashkov, A.S., Nifantiev, N.E., and Kochetkov, N.K., Carbohydr. Res., 1992, vol. 237, pp. 11–22.

    Article  PubMed  CAS  Google Scholar 

  22. Nagaoka, M., Shibata, H., Kimura-Takagi, I., Hashimoto, S., Kimura, K., Makino, T., Aiyama, R., Ueyama, S., and Yokokura, T., Glycoconjugate J., 1999, vol. 16, pp. 19–26.

    Article  CAS  Google Scholar 

  23. Sloneker, J.H., Gas-liquid Chromatography of Alditol Acetates in Methods in Carbohydrate Chemistry, Whistler, R.L. and BeMiller, J.N., Eds., N.Y., Academic, 1972, vol. 6, pp. 20–24.

  24. Dodgson, K.S. and Price, R.G., Biochem. J., 1962, vol. 84, pp. 106–110.

    PubMed  CAS  Google Scholar 

  25. Usov, A.I., Bilan, M.I., and Klochkova, N.G., Bot. Mar., 1995, vol. 38, pp. 43–51.

    Article  CAS  Google Scholar 

  26. Hestrin, S., J. Biol. Chem., 1949, vol. 180, pp. 249–261.

    CAS  PubMed  Google Scholar 

  27. Gerwig, G.J., Kamerling, J.P., and Vliegenthart, J.F.G., Carbohydr. Res., 1978, vol. 62, pp. 349–357.

    Article  CAS  Google Scholar 

  28. Dubois, M., Gilles, K.A., Hamilton, J.K., Rebers, P.A., and Smith, F., Anal. Chem., 1956, vol. 28, pp. 350–356.

    Article  CAS  Google Scholar 

  29. Ciukanu, I. and Kerek, F., Carbohydr. Res., 1984, vol. 131, pp. 209–217.

    Article  Google Scholar 

  30. Bjorndal, H., Hellerquist, C.G., Lindberg, B., and Svensson, S., Angew. Chem., Int. Ed. Engl., 1970, vol. 9, pp. 610–619.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. I. Usov.

Additional information

Original Russian Text © M.I. Bilan, A.N. Zakharova, A.A. Grachev, A.S. Shashkov, N.E. Nifantiev, A.I. Usov, 2007, published in Bioorganicheskaya Khimiya, 2007, Vol. 33, No. 1, pp. 44–53.

For communication 59, see [1].

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bilan, M.I., Zakharova, A.N., Grachev, A.A. et al. Polysaccharides of algae: 60. Fucoidan from the pacific brown alga Analipus japonicus (Harv.) winne (Ectocarpales, Scytosiphonaceae). Russ J Bioorg Chem 33, 38–46 (2007). https://doi.org/10.1134/S1068162007010049

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162007010049

Key words

Navigation