Synthesis and characterization of hydroquinone glucoside using Leuconostoc mesenteroides dextransucrase

We synthesized a hydroquinone glucoside (HG) as a potential skin-whitening agent using Leuconostoc mesenteroides (B-1299CB BF563) dextransucrase with hydroquinone (HQ) as an acceptor and sucrose as a donor. The product was purified using butanol partitioning and silica gel column chromatography. The structure of the purified HG was determined by nuclear magnetic resonance and the ionic product was observed at m/z 295 (C12, H16, O7 Na)(+). HG was identified as 4-hydroxyphenyl-alpha-D-glucopyranoside. The optimum condition of HG synthesis, determined using a response surface methodology, was 450 mM HQ 215 mM sucrose, and 0.55 U/mL dextransucrase; the final HG produced was 544 mg/L The IC50 of diphenylpicryl-hydrazyl scavenging activity was 3.85 mM indicating a higher antioxidant activity compared to beta-arbutin (IC50 = 6.04 mM). HG-mediated inhibition of lipid peroxidation was 3.51% that of HQ (100%) and much higher than that of beta-arbutin (0.81% of HQ). In addition the IC50 value of nitrite-scavenging activity was 14.76 mM showing a superior scavenging activity to that of beta-arbutin IC50 = 27.09 mM). (c) 2009 Elsevier Inc. All rights reserved.