Biotechnology Letters

, 30:743 | Cite as

Inhibitory effects of arbutin-β-glycosides synthesized from enzymatic transglycosylation for melanogenesis

  • So-Young Jun
  • Kyung-Min Park
  • Ki-Won Choi
  • Min Kyung Jang
  • Hwan Yul Kang
  • Sang-Hyeon Lee
  • Kwan-Hwa Park
  • Jaeho Cha
Original Research Paper

Abstract

To develop a new skin whitening agent, arbutin-β-glycosides were synthesized and evaluated for their melanogenesis inhibitory activities. Three active compounds were synthesized via the transglycosylation reaction of Thermotoga neapolitana β-glucosidase and purified by recycling preparative HPLC. As compared with arbutin (IC50 = 6 mM), the IC50 values of these compounds were 8, 10, and 5 mM for β-d-glucopyranosyl-(1→6)-arbutin, β-d-glucopyranosyl-(1→4)-arbutin, and β-d-glucopyranosyl-(1→3)-arbutin, respectively. β-d-Glucosyl-(1→3)-arbutin also exerted the most profound inhibitory effects on melanin synthesis in B16F10 melanoma cells. Melanin synthesis was inhibited to a significant degree at 5 mM, at which concentration the melanin content was reduced to below 70% of that observed in the untreated cells. Consequently, β-d-glucopyranosyl-(1→3)-arbutin is a more effective depigmentation agent and is also less cytotoxic than the known melanogenesis inhibitor, arbutin.

Keywords

Arbutin Arbutin-β-glycosides Melanoma cell Transglycosylation Tyrosinase 

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Copyright information

© Springer Science+Business Media B.V. 2007

Authors and Affiliations

  • So-Young Jun
    • 1
  • Kyung-Min Park
    • 1
  • Ki-Won Choi
    • 1
  • Min Kyung Jang
    • 2
  • Hwan Yul Kang
    • 3
  • Sang-Hyeon Lee
    • 2
  • Kwan-Hwa Park
    • 4
  • Jaeho Cha
    • 1
  1. 1.Department of Biological Sciences, College of Natural SciencesPusan National UniversityBusanRepublic of Korea
  2. 2.Department of Bioscience and Biotechnology, College of EngineeringSilla UniversityBusanRepublic of Korea
  3. 3.Amaranth CosmeticsBusanRepublic of Korea
  4. 4.Department of Food Science and Biotechnology, School of Agricultural BiotechnologySeoul National UniversitySeoulRepublic of Korea

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