Melanogenesis inhibitors from Coix lacryma-jobi seeds in B16-F10 melanoma cells

Nat Prod Res. 2017 Dec;31(23):2712-2718. doi: 10.1080/14786419.2017.1292270. Epub 2017 Feb 16.

Abstract

An adenine derivative, 9-β-D-glucopyranosyl adenine, reported for the first time from a natural source, in addition to nine known compounds were isolated from the seeds of Coix lacryma-jobi. Their structures were elucidated based on extensive spectroscopic and chemical studies. The isolated compounds and the ethanol extract have been assayed for melanin inhibition using B16-F10 melanoma cell line. The results of our study suggested the potential use of Coix lacryma-jobi seeds as a skin whitening agent and reveal the seeds to be a rich source of important phytochemicals with melanogenesis inhibitory activity. Among the isolated compounds, coixol (2) and 2-O-β-glucopyranosyl-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (8) exhibited potent melanogenesis inhibitory activity with no obvious melanocytotoxicity. The rest of the compounds showed weak to moderate activity.

Keywords: 9-β-D-glucopyranosyl adenine; Coix lacryma-jobi; Poaceae; adlay; coixol; melanogenesis.

MeSH terms

  • Animals
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Benzoxazines / pharmacology
  • Benzoxazoles / analysis
  • Benzoxazoles / pharmacology
  • Cell Line, Tumor
  • Coix / chemistry*
  • Drug Evaluation, Preclinical / methods
  • Melanins / antagonists & inhibitors*
  • Melanins / metabolism
  • Melanoma, Experimental / drug therapy
  • Melanoma, Experimental / metabolism*
  • Melanoma, Experimental / pathology
  • Mice
  • Molecular Structure
  • Plant Extracts / chemistry
  • Plant Extracts / pharmacology
  • Seeds* / chemistry

Substances

  • Antineoplastic Agents, Phytogenic
  • Benzoxazines
  • Benzoxazoles
  • Melanins
  • Plant Extracts
  • 6-methoxybenzoxazolinone