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Synthesis and characterization of hydroquinone fructoside using Leuconostoc mesenteroides levansucrase

  • Jin Kang
  • Young-Min Kim
  • Nahyun Kim
  • Du-Woon Kim
  • Seung-Hee Nam
  • Doman Kim
Biotechnological Products and Process Engineering

Abstract

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 1H and 13C 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-β-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 (IC50) of 1,1-diphenyl-2-picrylhydrazyl scavenging activity was 5.83 mM, showing higher antioxidant activity compared to β-arbutin (IC50 = 6.04 mM). The K i value of HQ-Fru (1.53 mM) against tyrosinase was smaller than that of β-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 β-arbutin (0.89% of HQ).

Keywords

Leuconostoc mesenteroides Levansucrase Hydroquinone Acceptor reaction Fructosylation 

Notes

Acknowledgments

This work was supported by 21C Frontier Microbial Genomics and the Applications Center Program. We thank the Korea Basic Science Institute Gwangju Branch for the NMR analysis.

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Copyright information

© Springer-Verlag 2009

Authors and Affiliations

  • Jin Kang
    • 1
  • Young-Min Kim
    • 1
  • Nahyun Kim
    • 2
  • Du-Woon Kim
    • 3
  • Seung-Hee Nam
    • 4
  • Doman Kim
    • 1
  1. 1.School of Biological Sciences and TechnologyChonnam National UniversityGwangjuRepublic of Korea
  2. 2.Korean Minjok Leadership AcademyHoengseongRepublic of Korea
  3. 3.Eco Marine Bio-CenterJeonnamRepublic of Korea
  4. 4.Jeonnam Agricultural Research & Extension ServicesJeonnamRepublic of Korea

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