Four new ginsenosides from red ginseng with inhibitory activity on melanogenesis in melanoma cells

Bioorg Med Chem Lett. 2015 Aug 15;25(16):3112-6. doi: 10.1016/j.bmcl.2015.06.017. Epub 2015 Jun 11.

Abstract

During a search for novel melanogenesis inhibitors originating from nature sources, four new ginsenosides, including three dammarane-type triterpenoid saponins, 20(S)-ginsenoside-Rf-1a (1), 20Z-ginsenoside-Rs4 (2), 23-O-methylginsenoside-Rg11 (3), and one oleanane-type saponin, ginsenoside-Ro-6'-O-butyl ester (4) were isolated from red ginseng (the steamed ginseng) to evaluate their protective effects against melanogenesis. Compounds 2 and 3 exhibited potent inhibitory effects against both melanin synthesis and tyrosinase activity in a dose-dependent manner in the α-MSH-stimulated B16 melanoma cells, and were more potent than the positive control arbutin, a well-known tyrosinase inhibitor. The results indicated that just the two carbon-20(22) double-bond-type ginsenosides showed strong inhibiting activity on melanogenesis through reducing tyrosinase activity. Thus, ginsenosides with such similar chemical structure in red ginseng may be potential natural products as tyrosinase inhibitors against malignant melanoma.

Keywords: Ginsenosides; Melanogenesis; Red ginseng; Tyrosinase inhibitor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Cell Line, Tumor
  • Ginsenosides / chemistry*
  • Ginsenosides / isolation & purification
  • Ginsenosides / pharmacology
  • Magnetic Resonance Spectroscopy
  • Melanins / biosynthesis
  • Melanoma, Experimental / metabolism
  • Melanoma, Experimental / pathology
  • Mice
  • Molecular Conformation
  • Panax / chemistry*
  • Panax / metabolism
  • Pigmentation / drug effects

Substances

  • Antineoplastic Agents, Phytogenic
  • Ginsenosides
  • Melanins