The heparin-mimicking arabinogalactan sulfates from Anogeissus latifolia gum: Production, structures, and anti-herpes simplex virus activity

Int J Biol Macromol. 2021 Jul 31:183:1419-1426. doi: 10.1016/j.ijbiomac.2021.05.107. Epub 2021 May 20.

Abstract

Herpes simplex virus type 1(HSV-1) attaches to cell surface heparan sulfate aiming to enter into susceptible cells. In this work, we utilized a sulfur trioxide-pyridine in N,N-dimethylformamide (SO3·Pyr/DMF) based amalgamated extraction-sulfation procedure for producing arabinogalactan sulfates from Anogeissus latifolia gum. Chemical, chromatographic, spectroscopic and chemical data revealed that the derived polymers contained varying molecular masses (31-69 kDa) and degrees of sulfation (0.1-0.5), but similar saccharide compositions. The highly active polymer (HSV-1: IC50 and SI, respectively, of 127 μg/mL and 15.7) was a 69 kDa arabinogalactan holding sulfates at O-5 of arabinofuranosyl residues and showed no cytotoxicity as far as 2 mg/mL concentration. This chemically sulfated macromolecule acted by obstructing viral attachment and entry. Thus, SO3·Pyr/DMF is suitable for producing new molecules with varied structures and altered pharmacological activities from plant sources.

Keywords: Anogeissus latifolia gum; Anti-viral activity; Arabinogalactan sulfates; Integrated extraction-sulfation process.

MeSH terms

  • Antiviral Agents / chemistry*
  • Galactans / chemistry*
  • Heparin / chemistry*
  • Herpesvirus 1, Human / drug effects

Substances

  • Antiviral Agents
  • Galactans
  • Heparin
  • arabinogalactan