Identification of six new lupane-type triterpenoids from Acanthopanax koreanum leaves and their tyrosinase inhibitory activities

Bioorg Med Chem Lett. 2016 Feb 1;26(3):1061-1067. doi: 10.1016/j.bmcl.2015.12.020. Epub 2015 Dec 8.

Abstract

Chemical investigation of Acanthopanax koreanum leaves resulted in the isolation of 13 compounds (1-13), including six new (20,29)-dehydrolupane-type triterpenoids: 3α,11α,30-trihydroxylup-20(29)-en-23,28-dioic acid (1), 3α,11α,30-trihydroxylup-20(29)-en-28-oic acid (2), 3α,11α,30-trihydroxylup-23-al-20(29)-en-28-oic acid (3), 3α, 11α-dihydroxy-20-oxo-30-norlupane-23,28-dioic acid (5), (20S)-3α-hydroxy-30 oxolupane-23,28-dioic acid (8), (20S)-3β,7β,29-trihydroxy-lupane-23-al-28-oic acid (10), and one novel compound isolated for the first time, named 3α,20α,29-trihydroxylupane-23,28-dioic acid (9), together with six known compounds (4, 6, 7, and 11-13). Chemical structures of the isolated compounds were evaluated by analyzing and comparing spectroscopic data with those reported in the literature. These compounds were also evaluated for their tyrosinase inhibitory effects. Among them, compounds 3, 7, 9, and 12 showed significant inhibitory effects, with inhibitory concentrations of 50% (IC50) values ranging from 8.61 to 63.5 μM.

Keywords: Acanthopanax koreanum; Araliaceae; Lupane-type triterpenoids; Tyrosinase inhibitory activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Eleutherococcus / chemistry*
  • Eleutherococcus / metabolism
  • Enzyme Inhibitors / chemistry*
  • Enzyme Inhibitors / isolation & purification
  • Enzyme Inhibitors / metabolism
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Molecular Conformation
  • Monophenol Monooxygenase / antagonists & inhibitors*
  • Monophenol Monooxygenase / metabolism
  • Plant Extracts / chemistry*
  • Plant Leaves / chemistry
  • Plant Leaves / metabolism
  • Protein Binding
  • Triterpenes / chemistry*
  • Triterpenes / isolation & purification
  • Triterpenes / metabolism

Substances

  • Enzyme Inhibitors
  • Plant Extracts
  • Triterpenes
  • lupane
  • Monophenol Monooxygenase