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Chemical Compound Review

alpha-Arbutin     (2R,3S,4S,5R,6R)-2- (hydroxymethyl)-6-(4...

Synonyms: PubChem16460, CHEMBL226495, SureCN435261, AC1L4KBI, AK-77730, ...
 
 
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Disease relevance of alpha-Arbutin

 

High impact information on alpha-Arbutin

  • A new synthesis of alpha-arbutin via Lewis acid catalyzed selective glycosylation of tetra-O-benzyl-alpha-D-glucopyranosyl trichloroacetimidate with hydroquinone [4].
  • Both alpha-Ab-alpha-G1 and alpha-Ab-alpha-G2 exhibited competitive-type inhibition on human tyrosinase as alpha-arbutin does [5].
  • We studied the inhibitory effects of 4-hydroxyphenyl alpha-glucopyranoside (alpha-arbutin) on melanogenesis in cultured human melanoma cells, HMV-II, and in a three-dimensional cultured human skin model. alpha-Arbutin showed no inhibitory effect on HMV-II cell growth at a concentration below 1.0 mM [2].
  • Treatment of the human skin model with 250 microg of alpha-arbutin did not inhibit cell viability, while melanin synthesis was reduced to 40% of that in the control [2].

References

  1. Modulating effects of a novel skin-lightening agent, alpha-lipoic acid derivative, on melanin production by the formation of DOPA conjugate products. Tsuji-Naito, K., Hatani, T., Okada, T., Tehara, T. Bioorg. Med. Chem. (2007) [Pubmed]
  2. Inhibitory effects of alpha-arbutin on melanin synthesis in cultured human melanoma cells and a three-dimensional human skin model. Sugimoto, K., Nishimura, T., Nomura, K., Sugimoto, K., Kuriki, T. Biol. Pharm. Bull. (2004) [Pubmed]
  3. Enzymatic synthesis of alpha-arbutin by alpha-anomer-selective glucosylation of hydroquinone using lyophilized cells of Xanthomonas campestris WU-9701. Kurosu, J., Sato, T., Yoshida, K., Tsugane, T., Shimura, S., Kirimura, K., Kino, K., Usami, S. J. Biosci. Bioeng. (2002) [Pubmed]
  4. A new synthesis of alpha-arbutin via Lewis acid catalyzed selective glycosylation of tetra-O-benzyl-alpha-D-glucopyranosyl trichloroacetimidate with hydroquinone. Wang, Z.X., Shi, X.X., Chen, G.R., Ren, Z.H., Luo, L., Yan, J. Carbohydr. Res. (2006) [Pubmed]
  5. Syntheses of alpha-arbutin-alpha-glycosides and their inhibitory effects on human tyrosinase. Sugimoto, K., Nomura, K., Nishimura, T., Kiso, T., Sugimoto, K., Kuriki, T. J. Biosci. Bioeng. (2005) [Pubmed]
 
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