Regioselective sulfation of Artemisia sphaerocephala polysaccharide: Characterization of chemical structure

The biological activities of sulfated polysaccharides are related to the substitution positions of functional groups. In this study, regioselective sulfation of Artemisia sphaerocephala polysaccharides (S(RS)ASP) was prepared by using triphenylchloromethane (TrCI) as protecting precursor. FT-IR spectra and X-ray photoelectron spectroscopy (XPS) showed that-SO3- group (S6+, high binding energy of 168.7 eV) was widely present in sulfated polysaccharides. C-13 NMR spectroscopy showed that C-2 and C-3 substitution was occurred but not fully sulfation. Meanwhile, C-6 substituted signals near 65 ppm were not observed. The degree of substitution varied from 0.44 to 0.63 in S(RS)ASP which could be attributed to the low reactivity at secondary hydroxyl. Monosaccharide composition result showed a decrease in the ratio of mannose/glucose, indicating the change of chemical composition in sulfated polysaccharides. In size-exclusion chromatograph analysis, a decrease in molecular weight and broadening of molecular weight distribution of sulfated polysaccharides was also observed. It could be attributed to the hydrolysis of polysaccharide in the sulfated reaction. Crown Copyright (C) 2015 Published by Elsevier Ltd. All rights reserved.