Synthesis and functional characterization of caffeic acid glucoside using leuconostoc mesenteroides dextransucrase

Abstract

Caffeic acid was modified via. transglucosylation using sucrose and dextransucrase-from Leuconostoc mesenteroides B-512FMCM. Following enzymatic modification, a caffeic acid glucoside was isolated by butanol separation, silica gel chromatography, and preparative HPLC. The synthesized caffeic acid glucoside had a molecular mass-to-charge ratio of 365 m/z, and its structure was identified as caffeic acid-3-O-alpha-D-glucopyranoside. The production of this caffeic acid-3-O-alpha-D-glucopyranoside at a concentration of 153 mM was optimized using 325 mM caffeic acid, 355 mM sucrose, and 650 mU mL(-1) dextransucrase in the synthesis reaction: In comparison with the caffeic acid, the caffeic acid-3-O-alpha-D-glucopyranoside displayed 3-fold higher water solubility, 1.66-fold higher antilipid peroxidation effect, 15% stronger inhibitiOn of colon cancer cell growth, and 11.5-fold higher browning resistance. These results indicate that this caffeic acid-3-O-alpha-D-glucopyranoside may be a suitable functional component of food and pharmaceutical products.