Sulfated modification, characterization and antitumor activities of Radix hedysari polysaccharide

Int J Biol Macromol. 2012 Nov;51(4):471-6. doi: 10.1016/j.ijbiomac.2012.06.004. Epub 2012 Jun 15.

Abstract

Sulfated modification of a polysaccharide obtained from Radix hedysari (RHP) was studied. Four sulfated derivatives (RHPS) with variable degrees of substitution (DS) were obtained by the chlorosulfonic acid method with ionic liquids (ILs) as solvent and 4-dimethylaminopyridine (DMAP) as catalyst. The structures of RHPS were characterized by FT-IR spectra and ¹³C NMR spectra, and the results indicated that the sulfated groups were modified mainly at the C-6 position and C-2 position. Four kinds of RHPS showed different DS ranging from 0.63 to 1.45, and different weight-average molecular mass (Mw) ranging from 60.8 to 71.1 kDa with a little degradation. Compared with RHP, all of RHPS exhibited obvious antitumor activity on A549 cells and BGC-823 cells in vitro. However, they had no obvious influence on HEK293 cells, which indicated that they had low toxicity to normal cells. Flow cytometric studies indicated that the treatment of RHPS against A549 cells and BGC-823 cells could mediate the cell-cycle arrest in the G1 phase.

MeSH terms

  • 4-Aminopyridine / analogs & derivatives
  • 4-Aminopyridine / chemistry
  • Antineoplastic Agents / chemistry*
  • Antineoplastic Agents / pharmacology*
  • Apoptosis / drug effects
  • Catalysis
  • Cell Cycle Checkpoints / drug effects
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Fabaceae / chemistry*
  • HEK293 Cells
  • Humans
  • Imidazoles / chemistry
  • Kinetics
  • Molecular Weight
  • Plant Roots / chemistry*
  • Polymerization
  • Polysaccharides / chemistry*
  • Polysaccharides / pharmacology*
  • Solvents / chemistry
  • Structure-Activity Relationship
  • Sulfates / chemistry*

Substances

  • Antineoplastic Agents
  • Imidazoles
  • Polysaccharides
  • Solvents
  • Sulfates
  • 1-butyl-3-methylimidazolium chloride
  • 4-Aminopyridine
  • 4-dimethylaminopyridine