Structure-activity relationship for vanilloid compounds from extract of Zingiber officinale var rubrum rhizomes: effect on extracellular melanogenesis inhibitory activity

Abstract

The components in the methanol extract of Zingiber officinale var rubrum (red ginger) were isolated by a series of column chromatography and identified by Nuclear Magnetic Resonance (NMR) and Matrix-assisted laser desorption/ionization-time of flight mass spectrometry (MALDI-TOFMS). Thirteen components, including eleven vanilloid compounds, were isolated from the extract. All the isolated components reduced extracellular melanin contents. Structure-activity relationship studies suggested that elongation of the carbon chain of shogaol and gingerol increased the extracellular melanogenesis inhibitory activity, and that the carbonyl and hydroxyl groups on the carbon chain in gingerol played an important role in this effect. In order to reveal the importance of the vanillyl group for the melanogenesis inhibitory activity, 6-gingerol (1) and 6-shogaol (5), which were the main compounds in the extract, were glucosylated and their effects were evaluated. The glucosylated 6-shogaol resulted in improved melanogenesis inhibitory activity, while the glucosylated 6-gingerol had no such effect. These results indicated different mechanisms for the melanogenesis inhibitory activity of the two vanilloid compounds.

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Acknowledgements

This work was supported by a Grant-in-Aid for Early-Career Scientists Research Activity from Japan Society for the Promotion of Science (JSPS) KAKENHI Grant Number JP18K14499.

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Correspondence to Tohru Mitsunaga.

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Yamauchi, K., Natsume, M., Yamaguchi, K. et al. Structure-activity relationship for vanilloid compounds from extract of Zingiber officinale var rubrum rhizomes: effect on extracellular melanogenesis inhibitory activity. Med Chem Res 28, 1402–1412 (2019). https://doi.org/10.1007/s00044-019-02380-y

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Keywords

  • Zingiber officinale var rubrum
  • Vanilloid compounds
  • Melanogenesis
  • B16 melanoma