Structure-Activity Relationship of Xanthones as Inhibitors of Xanthine Oxidase

Molecules. 2018 Feb 9;23(2):365. doi: 10.3390/molecules23020365.

Abstract

Polygala plants contain a large number of xanthones with good physiological activities. In our previous work, 18 xanthones were isolated from Polygala crotalarioides. Extented study of the chemical composition of the other species Polygala sibirica led to the separation of two new xanthones-3-hydroxy-1,2,6,7,8-pentamethoxy xanthone (A) and 6-O-β-d-glucopyranosyl-1,7-dimethoxy xanthone (C)-together with 14 known xanthones. Among them, some xanthones have a certain xanthine oxidase (XO) inhibitory activity. Furthemore, 14 xanthones as XO inhibitors were selected to develop three-dimensional quantitative structure-activity relationship (3D-QSAR) using comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) models. The CoMFA model predicted a q² value of 0.613 and an r² value of 0.997. The best CoMSIA model predicted a q² value of 0.608 and an r² value of 0.997 based on a combination of steric, electrostatic, and hydrophobic effects. The analysis of the contour maps from each model provided insight into the structural requirements for the development of more active XO inhibitors.

Keywords: 3D-QSAR; gout; xanthine oxidase inhibitors; xanthone.

MeSH terms

  • Humans
  • Molecular Docking Simulation
  • Molecular Structure
  • Plant Extracts / chemistry*
  • Plant Extracts / isolation & purification
  • Protein Binding
  • Static Electricity
  • Tracheophyta / chemistry*
  • Xanthine Oxidase / antagonists & inhibitors*
  • Xanthones / chemistry*

Substances

  • Plant Extracts
  • Xanthones
  • Xanthine Oxidase