Chemically sulfated arabinoxylans from Plantago ovata seed husk: Synthesis, characterization and antiviral activity

Abstract

Limited options for the treatments of diseases triggered through viral infections revealed the quest for novel antiviral drugs. Polysaccharide sulfates owing to their unique mode of action are prominent antiviral drug candidates. Herein, the arabinoxylan of Plantago ovata seed husk was simultaneously extracted and chemically sulfated using sulphur trioxide-pyridine reagent in N,N-dimethylformamide solvent (SO3⋅Py/DMF). Thus, three arabinoxylan sulfates (IS1201–IS1203) holding variable degrees of sulfation (DS: 0.1–0.9), molar masses (18.4–31.3 kDa) and glycosyl makeup (Ara: Xyl::10–19:81–90; molar ratio) were produced and then characterized. According to the results, these polymers displayed anti-herpes simplex virus type 1 activity and their potency depends upon DS. The utmost effective compound (IS1203, IC50: 2.9 μg mL−1) was a 18.4 kDa arabinoxylan possessing sulfate groups at O-3 and O-2,3 positions of xylopyranosyl (Xylp), and O-5 of arabinofuranosyl (Araf) residues. Besides, this polymer showed no cytotoxicity at concentration up to 1000 μg mL−1. Given that polysaccharide sulfates have antiviral activities, synthesis of new molecules possessing diverse structures will be a useful addition to the arsenal of antivirals.