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

J Nat Med. 2018 Mar;72(2):381-389. doi: 10.1007/s11418-017-1148-8. Epub 2017 Dec 20.

Abstract

From the EtOAc-soluble fraction of a MeOH extract of the leaves of Breynia officinalis, five new compounds (1-5) along with 11 known compounds (6-16) were isolated. The structures of the new compounds were elucidated by spectroscopic methods and compounds 1-3 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: Arbutin; Breynia officinalis; Euphorbiaceae; Tyrosinase inhibitory activity; Zebrafish.

MeSH terms

  • Animals
  • Hydroxybenzoates / chemistry*
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Monophenol Monooxygenase / pharmacology
  • Plant Leaves / chemistry*
  • Zebrafish

Substances

  • Hydroxybenzoates
  • Monophenol Monooxygenase
  • phenolic acid