Glycosidic inhibitors of melanogenesis from leaves of Momordica charantia

Chem Biodivers. 2012 Jul;9(7):1221-30. doi: 10.1002/cbdv.201100350.

Abstract

Eight glycosidic compounds, 1-8, including two new compounds, (4ξ)-α-terpineol 8-O-[α-L-arabinopyranosyl-(1→6)-β-D-glucopyranoside] (5) and myrtenol 10-O-[β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside] (7), were isolated from the BuOH-soluble fraction of a MeOH extract of Momordica charantia leaves. The structures of the new compounds were elucidated on the basis of extensive spectroscopic analyses and comparison with literature. Upon evaluation of compounds 1-8 on the melanogenesis in B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH), these compounds were found to exhibit inhibitory activities with 7.1-27.0% and 23.6-46.4% reduction of melanin content at 30 μM and 100 μM, respectively, with no or almost no toxicity to the cells (80.0-103.5% of cell viability at 100 μM). Western blot analysis showed that compound 7 reduced the protein levels of MITF, tyrosinase, TRP-1, and TRP-2 mostly in a concentration-dependent manner, suggesting that this compound inhibits melanogenesis on the α-MSH-stimulated B16 melanoma cells by, at least in part, inhibiting the expression of MITF, followed by decreasing the expression of tyrosinase, TRP-1, and TRP-2.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Cell Survival / drug effects
  • Glycosides / chemistry
  • Glycosides / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Melanins / antagonists & inhibitors*
  • Melanins / metabolism
  • Mice
  • Momordica charantia / chemistry*
  • Plant Leaves / chemistry*

Substances

  • Antineoplastic Agents
  • Glycosides
  • Melanins