Synthesis and characterization of hydroquinone fructoside using Leuconostoc mesenteroides levansucrase.
Hydroquinone (HQ) functions as a skin-whitening agent, but it has the potential to cause dermatitis. We synthesized a HQ fructoside (HQ-Fru) as a potential skin-whitening agent by reacting levansucrase from Leuconostoc mesenteroides with HQ as an acceptor and sucrose as a fructofuranose donor. The product was purified using 1-butanol partition and silica-gel column chromatography. The structure of the purified HQ-Fru was determined by (1)H and (13)C nuclear magnetic resonance, and the molecular ion of the product was observed at m/z 295 (C12 H16 O7 Na)(+). The HQ-Fru was identified as 4-hydroxyphenyl-beta-D: -fructofuranoside. The optimum condition for HQ-Fru synthesis was determined using a response surface method (RSM), and the final optimum condition was 350 mM HQ, 115 mM sucrose, and 0.70 U/ml levansucrase, and the final HQ-Fru produced was 1.09 g/l. HQ-Fru showed anti-oxidation activities and inhibition against tyrosinase. The median inhibition concentration (IC(50)) of 1,1-diphenyl-2-picrylhydrazyl scavenging activity was 5.83 mM, showing higher antioxidant activity compared to beta-arbutin (IC(50) = 6.04 mM). The K ( i ) value of HQ-Fru (1.53 mM) against tyrosinase was smaller than that of beta-arbutin (K ( i ) = 2.8 mM), indicating that it was 1.8-times better as an inhibitor. The inhibition of lipid peroxidation by HQ-Fru was 105.3% that of HQ (100%) and 118.9 times higher than that of beta-arbutin (0.89% of HQ).
Kang
Jin
J
Chonnam National University, Gwangju, Republic of Korea.
Kim
Young-Min
YM
Kim
Nahyun
N
Kim
Du-Woon
DW
Nam
Seung-Hee
SH
Kim
Doman
D
D000975:Antioxidants / Q000378:metabolism / Q000494:pharmacology; D001426:Bacterial Proteins / Q000378:metabolism*; D004791:Enzyme Inhibitors / Q000378:metabolism / Q000494:pharmacology; D005632:Fructose / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000378:metabolism* / Q000494:pharmacology; D006602:Hexosyltransferases / Q000378:metabolism*; D006873:Hydroquinones / Q000302:isolation & purification / Q000378:metabolism* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D007934:Leuconostoc / Q000201:enzymology*; D009682:Magnetic Resonance Spectroscopy; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors; D013395:Sucrose / Q000378:metabolism
D000975:Antioxidants; D001426:Bacterial Proteins; D004791:Enzyme Inhibitors; D006873:Hydroquinones; D005632:Fructose; D013395:Sucrose; D014442:Monophenol Monooxygenase; D006602:Hexosyltransferases; C021513:levansucrase; C031927:hydroquinone