Structure and Antiviral Activity of the Galactofucan Sulfates Extracted from Undaria Pinnatifida (Phaeophyta)

Abstract

The galactofucan sulfate extract (GFS) obtained from the brown seaweed Undaria pinnatifida by extraction with dilute acid is a potent inhibitor of the herpes viruses HSV-1, HSV-2 and HCMV, with IC50 values determined in vitro of 1.1, 0.2 and 0.5 μgmL−1, respectively. Fractionation of GFS by anion exchange chromatography gave three fractions which differed in their uronic acid and sulfate contents and in their antiviral activity, as well as in having somewhat reduced molecular weights compared to GFS. The low uronic acid/high sulfate fraction (F2M), obtained in 63% yield, had similar molar proportions of galactopyranosyl and fucopyranosyl residues, little associated protein and was equipotent with GFS (IC50 values of 1.1, 0.1 and 0.5 μgmL−1, respectively). The high uronic acid/low sulfate fraction (F1M), obtained in 18% yield, had a much lower proportion of galactopyranosyl residues and was less active (IC50 values of 4.6, 1.0 and 4.0 μgmL−1, respectively). The minor low uronic acid/high sulfate fraction (F4M) had a significant amount of associated protein and was also less active (IC50 = 3.1, 1.0 and 2.0 μgmL−1, respectively). The structure of the major fraction (F2M) was shown to be complex by glycosyl linkage analysis before and after solvolytic desulfation, with many component sugar residues being identified, although 3-linked fucopyranosyl 2,4-disulfate residues were a prominent feature.

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Correspondence to R. H. Furneaux.

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Hemmingson, J.A., Falshaw, R., Furneaux, R.H. et al. Structure and Antiviral Activity of the Galactofucan Sulfates Extracted from Undaria Pinnatifida (Phaeophyta). J Appl Phycol 18, 185 (2006). https://doi.org/10.1007/s10811-006-9096-9

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Keywords

  • Anti-herpes
  • Brown alga
  • Galactofucans
  • Structure