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

  • Kosei Yamauchi
  • Misaki Natsume
  • Kaho Yamaguchi
  • Irmanida Batubara
  • Tohru MitsunagaEmail author
Original Research
  • 16 Downloads

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.

Keywords

Zingiber officinale var rubrum Vanilloid compounds Melanogenesis B16 melanoma 

Notes

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.

Compliance with ethical standards

Conflict of interest

The authors declare that they have no conflicts of interest.

Supplementary material

44_2019_2380_MOESM1_ESM.docx (5.4 mb)
Supplementary Information

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Kosei Yamauchi
    • 1
  • Misaki Natsume
    • 1
  • Kaho Yamaguchi
    • 1
  • Irmanida Batubara
    • 2
  • Tohru Mitsunaga
    • 1
    Email author
  1. 1.Graduate School of Natural Science and TechnologyGifu UniversityGifuJapan
  2. 2.Faculty of Mathematics and Natural Sciences, Tropical Biopharmaca Research Center, Department of ChemisrtyBogor Agriculture UniversityBogorIndonesia

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