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Polysaccharides of algae 68. Sulfated polysaccharides from the Kamchatka brown alga Laminaria bongardiana

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Abstract

Several fucoidan fractions were isolated from the biomass of the Kamchatka brown alga Laminaria bongardiana by hot water extraction followed by anion-exchange chromatography. Fucoidans were found to be composed of l-fucose, d-galactose, and sulfate as the major components, whereas d-xylose, d-mannose, d-glucuronic acid, and acetate were detected as the minor constituents. Highly sulfated fucoidan fractions F-2 and F-3 were solvolytically desulfated by heating in dimethyl sulfoxide in the presence of pyridine. The structures of native and desulfated polysaccharides were investigated by the methylation analysis and NMR spectroscopy. It was shown that F-2 contains fucan sulfate, the backbone of which is made of 1→3-linked α-l-fucopyranose residues with single α-l-Fucp branches at positions 2 and sulfate groups predominantly at positions 4. Sulfated fucoglucuronomannan, fucoglucuronan, and fucogalactan were detected in F-2 as concomitant polysaccharides. Fucan sulfate and sulfated fucogalactan were the major components of the fraction F-3. The anticoagulant properties of fucoidan fractions were assessed. It was demonstrated that the activity of the fraction F-3 is comparable with that of low-molecular-weight heparin (enoxaparin), whereas the activity of total fucoidan F and the fraction F-2 is ~2/3 and ~1/2, respectively, of the activity of F-3, which is in accordance with the lower sulfate content in these samples. Desulfated preparations F-2deS and F-3deS were completely devoid of anticoagulant activity.

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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

    M. I. Bilan, N. E. Ustyuzhanina, A. O. Chizhov, A. S. Shashkov, N. E. Nifantiev & A. I. Usov

  2. Kamchatka State Technical University (KamchatGTU), 35 ul. Klyuchevskaya, 683003, Petropavlovsk-Kamchatsky, Russian Federation

    N. G. Klochkova

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  1. M. I. Bilan
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  2. N. G. Klochkova
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  3. N. E. Ustyuzhanina
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  4. A. O. Chizhov
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  5. A. S. Shashkov
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  6. N. E. Nifantiev
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Correspondence to A. I. Usov.

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Dedicated to Academician of the Russian Academy of Sciences O. M. Nefedov on the occasion of his 85th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2729—2736, November, 2016.

For Part 67, see Ref. 1.

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Bilan, M.I., Klochkova, N.G., Ustyuzhanina, N.E. et al. Polysaccharides of algae 68. Sulfated polysaccharides from the Kamchatka brown alga Laminaria bongardiana . Russ Chem Bull 65, 2729–2736 (2016). https://doi.org/10.1007/s11172-016-1643-1

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  • DOI: https://doi.org/10.1007/s11172-016-1643-1

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