Rhusflavanone and mesuaferrone B: tyrosinase and elastase inhibitory biflavonoids extracted from the stamens of Mesua ferrea L

Nat Prod Res. 2021 Mar;35(6):1024-1028. doi: 10.1080/14786419.2019.1613395. Epub 2019 May 28.

Abstract

Chemical isolation and bioactivity studies were conducted on the stamens of Mesua ferrea L., which are being used in a traditional skincare formulation in Myanmar. Rhusflavanone and mesuaferrone B were obtained as the main biflavonoids together with lupeol, five common flavonoids, and five phenolic compounds. After being identified by NMR and other spectroscopic analyses, these compounds were evaluated for their 1,1-diphenyl-2-picrylhydrazyl (DPPH)-radical scavenging, human leukocyte elastase inhibitory, and mushroom tyrosinase inhibitory activities. The two biflavonoids exhibited strong inhibitory activities against elastase and tyrosinase, but low DPPH-radical scavenging activities. The contents of rhusflavanone and mesuaferrone B in the stamens were 0.35 ± 0.04% and 0.55 ± 0.06%, respectively. Moreover, lupeol was considered to be a cosmetically important component of the stamens because of its high content and strong elastase inhibitory activity. Rhusflavanone was reported to be isolated from M. ferrea for the first time.

Keywords: Mesua; elastase; lupeol; melanin; mesuaferrone; rhusflavanone; tyrosinase.

MeSH terms

  • Agaricales / enzymology
  • Benzopyrans / chemistry
  • Benzopyrans / isolation & purification*
  • Benzopyrans / pharmacology*
  • Biflavonoids / chemistry
  • Biflavonoids / isolation & purification*
  • Biflavonoids / pharmacology*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Flowers / chemistry*
  • Humans
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Monophenol Monooxygenase / metabolism
  • Pancreatic Elastase / antagonists & inhibitors*
  • Pancreatic Elastase / metabolism

Substances

  • Benzopyrans
  • Biflavonoids
  • Enzyme Inhibitors
  • mesuaferrone b
  • Monophenol Monooxygenase
  • Pancreatic Elastase