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Mar Drugs
2022 Jun 06;206:. doi: 10.3390/md20060380.
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Fucose-Rich Sulfated Polysaccharides from Two Vietnamese Sea Cucumbers Bohadschia argus and Holothuria (Theelothuria) spinifera: Structures and Anticoagulant Activity.
Ustyuzhanina NE
,
Bilan MI
,
Dmitrenok AS
,
Tsvetkova EA
,
Nikogosova SP
,
Hang CTT
,
Thinh PD
,
Trung DT
,
Van TTT
,
Shashkov AS
,
Usov AI
,
Nifantiev NE
.
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Fucosylated chondroitin sulfates (FCSs) FCS-BA and FCS-HS, as well as fucan sulfates (FSs) FS-BA-AT and FS-HS-AT were isolated from the sea cucumbers Bohadschia argus and Holothuria (Theelothuria) spinifera, respectively. Purification of the polysaccharides was carried out by anion-exchange chromatography on DEAE-Sephacel column. Structural characterization of polysaccharides was performed in terms of monosaccharide and sulfate content, as well as using a series of non-destructive NMR spectroscopic methods. Both FCSs were shown to contain a chondroitin core [→3)-β-d-GalNAc-(1→4)-β-d-GlcA-(1→]n bearing sulfated fucosyl branches at O-3 of every GlcA residue in the chain. These fucosyl residues were different in pattern of sulfation: FCS-BA contained Fuc2S4S, Fuc3S4S and Fuc4S at a ratio of 1:8:2, while FCS-HS contained these residues at a ratio of 2:2:1. Polysaccharides differed also in content of GalNAc4S6S and GalNAc4S units, the ratios being 14:1 for FCS-BA and 4:1 for FCS-HS. Both FCSs demonstrated significant anticoagulant activity in clotting time assay and potentiated inhibition of thrombin, but not of factor Xa. FS-BA-AT was shown to be a regular linear polymer of 4-linked α-L-fucopyranose 3-sulfate, the structure being confirmed by NMR spectra of desulfated polysaccharide. In spite of considerable sulfate content, FS-BA-AT was practically devoid of anticoagulant activity. FS-HS-AT cannot be purified completely from contamination of some FCS. Its structure was tentatively represented as a mixture of chains identical with FS-BA-AT and other chains built up of randomly sulfated alternating 4- and 3-linked α-L-fucopyranose residues.
Figure 1. The 13C NMR spectra of fucosylated chondroitin sulfates FCS-BA and FCS-HS.
Figure 2. Fragments of 1H NMR spectra of fucosylated chondroitin sulfates FCS-BA and FCS-HS.
Figure 3. Repeating blocks of fucosylated chondroitin sulfates FCS-BA and FCS-HS. Unit A bears Fuc2S4S (D), whereas unit Aâ bears Fuc3S4S (E) or Fuc4S (F).
Figure 4. The 13C NMR spectra of sulfated fucans FS-BA and FS-HS.
Figure 5. The 1H NMR spectra of sulfated fucans FS-BA and FS-HS.
Figure 6. Repeating blocks of fucans FS-BA-AT and FS-HS-AT.
Figure 7. Anticoagulant activity of polysaccharides FCS-BA (blue), FCS-HS (red), FS-BA-AT (green) and enoxaparin (dotted line). (A) APTT assay, (B) Anti-IIa-activity in the presence of ATIII, (C) Anti-Xa-activity in the presence of ATIII. n = 4, p < 0.05.
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