Anti-respiratory syncytial virus and anti-herpes simplex virus activity of chemically engineered sulfated fucans from Cystoseira indica

Seaweed polysaccharides, particularly sulfated ones, exhibited potent antiviral activity against a wide variety of enveloped viruses, such as herpes simplex virus and respiratory viruses. Different mechanisms of action were suggested, which may range from preventing infection to intracellular antiviral activity, at different stages of the viral cycle. Herein, we generated two chemically engineered sulfated fucans (C303 and C304) from Cystoseira indica by an amalgamated extraction-sulfation procedure using chlorosulfonic acid-pyridine/N,N-dimethylformamide and sulfur trioxide-pyridine/N,N-dimethylformamide reagents, respectively. These compounds exhibited activity against HSV-1 and RSV with 50 % inhibitory concentration values in the range of 0.75–2.5 μg/mL and low cytotoxicity at concentrations up to 500 μg/mL. The antiviral activities of chemically sulfated fucans (C303 and C304) were higher than the water (C301) and CaCl2 extracted (C302) polysaccharides. Compound C303 had a (1,3)-linked fucan backbone and was branched. Sulfates were present at positions C-2, C-4, and C-2,4 of Fucp, and C-6 of Galp residues of this polymer. Compound C304 had a comparable structure but with more sulfates at C-4 of Fucp residue. Both C303 and C304 were potent antiviral candidates, acting in a dose-dependent manner on the adsorption and other intracellular stages of HSV-1 and RSV replication, in vitro. [Display omitted] •Using ClSO3H.Py/DMF and SO3.Py/DMF reagents two sulfated polysaccharides were generated from C. indica.•These polymers that have a (1,3)-linked fucan backbone possesses novel structural features.•Sulfate was present at positions C-2, C-4 and C-2,4 of Fucp and C-6 of Galp residues in these fucans with 19 % sulfate.•In vitro, both sulfated fucans inhibited the replication of RSV and HSV-1.•The mode of action involves virucidal effect, inhibition of viral entrance, and additional subsequent effects.