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Chem Biodivers. 2013 Feb;10(2):167-76. doi: 10.1002/cbdv.201200251.

Melanogenesis-inhibitory activity of aromatic glycosides from the stem bark of Acer buergerianum.

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1
College of Science and Technology, Nihon University, 1-8-14 Kanda Surugadai, Tokyo 101-8308, Japan. akihisa.toshihiro@nihon-u.ac.jp

Abstract

A new benzyl glucoside, 3-O-demethylnikoenoside (1), along with eleven known compounds, including seven aromatic glycosides, 2-8, three lignans, 9-11, and one cyclitol, 12, were isolated from the BuOH-soluble fraction of a MeOH extract of Acer buergerianum stem bark. The structures of the new compound were elucidated on the basis of extensive spectroscopic analyses and comparison with literature. Upon evaluation of compounds 1-12 on melanogenesis in B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH), three compounds, i.e., hovetrichoside B (8), pinoresinol 4-O-β-D-glucopyranoside (9), and pinoresinol 4-O-β-D-apiofuranosyl-(1→2)-β-D-glucopyranoside (10), have been found to exhibit inhibitory effects with 41-49% melanin content compared to the control at 100 μM and low cytotoxicity to the cells (81-92% cell viability at 100 μM). Western blot analysis showed that compound 8 reduced the protein levels of MITF (=microphtalmia-associated transcription factor) and tyrosinase, in a concentration-dependent manner, suggesting that 8 inhibits melanogenesis in α-MSH-stimulated B16 melanoma cells by, at least in part, inhibiting the expression of MITF, followed by decreasing the expression of tyrosinase. On the other hand, upon Western blotting, compound 9 was found to reduce the protein levels of tyrosinase and TRP-2, while it increased MITF and TRP-1 (=tyrosine-related protein 1), in a concentration-dependent manner, indicating that 9 inhibits melanogenesis in α-MSH-stimulated B16 melanoma cells by, at least in part, inhibiting the expression of tyrosinase and TRP-2.

PMID:
23418164
DOI:
10.1002/cbdv.201200251
[Indexed for MEDLINE]
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