Regioselective synthesis of sulfated guar gum: comparative studies of structure and antioxidant activities.

ABSTRACT

We reported here a new synthesis of C-2 and C-3 sulfated guar gum (SRSGG) with low degree of substitution (DSS) of 0.58, employing triphenylchloromethane (TrCl) as a protected precursor. The yield and DSTr (calculated from the weight of triphenylmethanol) of triphenylmethylated GG (GGTr) was 165.6% and 0.71, respectively. In addition, low ratio (14) of chlorosulfuric acid to pyridine (14) was chosen in sulfation reaction since the protecting group was slightly sensitive to acid. Results of FT-IR and (13)C NMR spectroscopy indicated that C-2 and C-3 substitution was predominant but not fully sulfated in SRSGG. Size-exclusion chromatograph combined with multi-angle laser photometer (SEC-LLS) showed a decrease in molecular weight in the reaction. This might be due to the degradation in sulfation and deprotection process. Finally, we investigated the effect of structure features on the antioxidant activities in vitro. Vitro antioxidant experiments revealed that the regioselective sulfation at C-2 and C-3 and low molecular weight afforded strong antioxidant activities showing a much higher scavenging abilities of 1,1-diphenyl-2-picrylhydrazyl (DPPH) and hydroxyl radical than that by the known C-6-sulfated derivative. The antioxidant activities of sulfated polysaccharides were not a function of a single factor but a combination of molecular weight, DSS and substitution positions.