Polyamine derivatives from the bee pollen of Quercus mongolica with tyrosinase inhibitory activity

Bioorg Chem. 2018 Dec:81:127-133. doi: 10.1016/j.bioorg.2018.08.014. Epub 2018 Aug 10.

Abstract

Eighteen constituents, including nine new compounds, were isolated from the bee pollen of Quercus mongolica. The structures of the new compounds were established on the basis of combined spectroscopic analysis. Structurally, the nine new compounds are polyamine derivatives with phenolic moieties which were assigned as one putrescine derivative, mogolicine A (2), seven spermidine derivatives, mongolidines A-G (3-5, 8, 12, 14, 17) and one spermine derivative, mogoline A (18). Evaluation of the biological activity of isolated compounds revealed that the polyamine derivatives with coumaroyl and caffeoyl moieties showed tyrosinase inhibition with IC50 values of 19.5-85.8 μM; however, the addition of a methoxy group to phenolic derivatives reduced the inhibitory activity.

Keywords: Bee pollen; Polyamine; Putrescine; Quercus mongolica; Spermidine; Tyrosinase inhibition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Bees
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / pharmacology*
  • Molecular Structure
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Monophenol Monooxygenase / metabolism
  • Pollen / chemistry*
  • Polyamines / chemistry
  • Polyamines / isolation & purification
  • Polyamines / pharmacology*
  • Quercus / chemistry*
  • Structure-Activity Relationship

Substances

  • Enzyme Inhibitors
  • Polyamines
  • Monophenol Monooxygenase