Diarylheptanoids with inhibitory effects on melanogenesis from the rhizomes of Curcuma comosa in B16 melanoma cells

Bioorg Med Chem Lett. 2013 Sep 15;23(18):5178-81. doi: 10.1016/j.bmcl.2013.07.010. Epub 2013 Jul 17.

Abstract

The methanolic extract from the dried rhizomes of Curcuma comosa cultivated in Thailand was found to inhibit melanogenesis in theophylline-stimulated murine B16 melanoma 4A5 cells. From the methanolic extract, three new diarylheptanoids, diarylcomosols I-III, were isolated together with 12 known diarylheptanoids. Their chemical structures were elucidated on the basis of chemical and physicochemical evidence. The diarylheptanoids inhibited melanogenesis, and several structural requirements of the active constituents for the inhibition were clarified. In particular, (3R)-1,7-bis(4-hydroxyphenyl)-(6E)-6-hepten-3-ol exhibited stronger inhibitory effect [IC50=0.36 μM] without inducing cytotoxicity. The biological effect was much stronger than that of a reference compound, arbutin [IC50=174 μM]. We conclude that diarylheptanoid analogs are promising therapeutic agents for the treatment of skin disorders.

Keywords: Curcuma comosa; Diarylcomosol; Diarylheptanoid; Melanogenesis inhibitor; Thai traditional medicine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Cell Proliferation / drug effects
  • Cell Survival / drug effects
  • Curcuma / chemistry*
  • Diarylheptanoids / chemistry
  • Diarylheptanoids / isolation & purification
  • Diarylheptanoids / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • Melanocytes / drug effects*
  • Melanocytes / metabolism
  • Melanoma, Experimental / drug therapy*
  • Melanoma, Experimental / pathology
  • Mice
  • Molecular Structure
  • Rhizome / chemistry*
  • Structure-Activity Relationship

Substances

  • Antineoplastic Agents
  • Diarylheptanoids