Synthesis and characterization of ampelopsinglucosides using dextransucrase from Leuconostoc mesenteroides B-1299CB4: Glucosylation enhancing physicochemical properties = Leuconostoc 유래 덱스트란수크라제에 의한 앤펠롭신 배당체 합성과 생리적 물성 증가

Abstract

Novel ampelopsin glucosides (AMPLS-Gs) were enzymatically synthesized and purified using a Sephadex LH-20 column. Each structure of the purified AMPLS-Gs was determined by nuclear magnetic resonance, and the ionic product of AMPLS-G1 was observed at m/z 505 (C 21H 22O 13·Na) + using matrix-assisted laser desorption ionization time-of-flight mass spectrometry. AMPLS-G1 was identified as ampelopsin-4'-O-α-d-glucopyranoside. The optimum condition for AMPLS-G1, determined using response surface methodology, was 70mM ampelopsin, 150mM sucrose, and 1U/mL dextransucrase, which resulted in an AMPLS-G1 yield of 34g/L. The purified AMPLS-G1 displayed 89-fold increased water solubility and 14.5-fold browning resistance compared to those of AMPLS and competitive inhibition against tyrosinase with a K i value of 40.16μM. This value was smaller than that of AMPLS (K i=62.56μM) and much smaller than that of β-arbutin (K i=514.84μM), a commercial active ingredient of whitening cosmetics. These results indicate the potential of AMPLS and AMPLS-G1 as superior ingredients for functional cosmetics.