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Journal of Natural Medicines

, Volume 72, Issue 2, pp 381–389 | Cite as

Phenolic compounds from the leaves of Breynia officinalis and their tyrosinase and melanogenesis inhibitory activities

  • Ayano Sasaki
  • Yoshi Yamano
  • Sachiko Sugimoto
  • Hideaki OtsukaEmail author
  • Katsuyoshi MatsunamiEmail author
  • Takakazu Shinzato
Original Paper

Abstract

From the EtOAc-soluble fraction of a MeOH extract of the leaves of Breynia officinalis, five new compounds (15) along with 11 known compounds (616) were isolated. The structures of the new compounds were elucidated by spectroscopic methods and compounds 13 were found to be acylated hydroquinone apiofuranosylglucopyranosides, while compound 4 was an acylated hydroquinone glucopyranoside. Compound 5 was shown to be butyl p-coumarate and this seems to be its first isolation from a natural source. The tyrosinase inhibitory activity of all of the isolated compounds was assayed, and the activity was significant in p-coumarate derivatives. The most active compound, compound 3, also inhibited melanogenesis in an in vivo whole animal model, zebrafish.

Keywords

Breynia officinalis Euphorbiaceae Arbutin Tyrosinase inhibitory activity Zebrafish 

Notes

Acknowledgement

The authors are grateful for access to the superconducting NMR instrument (Brucker Avance III 600) at the Analytical Center of Molecular Medicine of the Hiroshima University Faculty of Medicine, and HR-ESI mass spectra were performed with LTQ Orbitrap XL spectrometer at the Analysis Center of Life Science of the Graduate School of Biomedical Sciences, Hiroshima University. This work was supported in part by Grants-in-Aid from the Ministry of Education, Culture, Sports, Science and Technology of Japan, and the Japan Society for the Promotion of Science (Nos. 22590006, 23590130, 25860078, 15H04651, and 17K08336). Thanks are also due to the Research Foundation for Pharmaceutical Sciences and the Takeda Science Foundation for the financial support. One of the authors (S.S.) thanks the Research Foundation for Pharmaceutical Sciences and the Cosmetology Research Foundation for the financial support.

Compliance with ethical standard

Conflict of interest

The authors declare no conflict of interest.

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Copyright information

© The Japanese Society of Pharmacognosy and Springer Japan KK 2017

Authors and Affiliations

  • Ayano Sasaki
    • 1
  • Yoshi Yamano
    • 1
  • Sachiko Sugimoto
    • 1
  • Hideaki Otsuka
    • 1
    • 2
    Email author
  • Katsuyoshi Matsunami
    • 1
    Email author
  • Takakazu Shinzato
    • 3
  1. 1.Department of Pharmacognosy, Graduate School of Biomedical and Health SciencesHiroshima UniversityHiroshimaJapan
  2. 2.Department of Natural Products Chemistry, Faculty of PharmacyYasuda Women′s UniversityHiroshimaJapan
  3. 3.Subtropical Field Science Center, Faculty of AgricultureUniversity of the RyukyusKunigami-GunJapan

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