Synthesis of ellagic acid glucoside using glucansucrase from Leuconostoc and characterization of this glucoside as a functional neuroprotective agent

Abstract

Ellagic acid glucoside was synthesized via transglucosylation using sucrose and glucansucrase derived from Leuconostoc mesenteroides B-512 FMCM. After such enzymatic synthesis, the product was purified by 50% ethyl acetate fraction and C18 column chromatography. Modification of ellagic acid glucoside was verified by LC-MS/MS at m/z 485.1 (M + Na)^- and m/z 531.1 (M + 3Na)^-. The yield of ellagic acid glucoside was 69% (3.47 mM) by response surface methodology using 150 mM sucrose, 300 mU/mL glucansucrase, and 5 mM ellagic acid. The synthesized ellagic acid glucoside showed improved water solubility, up to 58% higher brain nerve cell (SH-SY5Y) protective effect, threefold higher cortisol reducing effect, and fourfold stronger inhibitory effect on acetylcholinesterase (AChE) than ellagic acid. These results indicate that ellagic acid glucoside could be used as a neuroprotective agent.

Keywords: Brain protective effect; Ellagic acid; Glucansucrase; Leuconostoc mesenteroides; Transglucosylation.