Synthesis and characterization of ampelopsin glucosides using dextransucrase from Leuconostoc mesenteroides B-1299CB4: Glucosylation enhancing physicochemical properties

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 (C21H22O13·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 70 mM ampelopsin, 150 mM sucrose, and 1 U/mL dextransucrase, which resulted in an AMPLS-G1 yield of 34 g/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 Ki value of 40.16 μM. This value was smaller than that of AMPLS (Ki = 62.56 μM) and much smaller than that of β-arbutin (Ki = 514.84 μM), a commercial active ingredient of whitening cosmetics. These results indicate the potential of AMPLS and AMPLS-G1 as superior ingredients for functional cosmetics.

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► We synthesized novel ampelopsin-glucoside (AMPLS-G1) with dextransucrase.
► The AMPLS-G1 displayed 89-fold increased water solubility compared to AMPLS.
► The AMPLS-G1 showed 14.5-fold browning resistance than AMPLS.
► The AMPLS-G1 showed competitive inhibition against tyrosinase.
► This Ki value was 12.8-fold smaller than that of β-arbutin.