New Flavones, a 2-(2-Phenylethyl)-4H-chromen-4-one Derivative, and Anti-Inflammatory Constituents from the Stem Barks of Aquilaria sinensis

Molecules. 2015 Nov 24;20(11):20912-25. doi: 10.3390/molecules201119736.

Abstract

In the current study, two new flavones, 4'-O-geranyltricin (1) and 3'-O-geranylpolloin (2), and a new 2-(2-phenylethyl)-4H-chromen-4-one derivative, 7-hydroxyl-6-methoxy-2-(2-phenylethyl)chromone (3), have been isolated from the stem barks of A. sinensis, together with 21 known compounds 4-24. The structures of new compounds 1-3 were determined through spectroscopic and MS analyses. Compounds 2, 3, 5, 6, and 8-10 exhibited inhibition (IC50≤12.51 μM) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 3, 6, 8, 10, and 19 inhibited fMLP/CB-induced elastase release with IC50 values≤15.25 μM. This investigation reveals bioactive isolates (especially 2, 3, 5, 6, 8, 9, 10, and 19) could be further developed as potential candidates for the treatment or prevention of various inflammatory diseases.

Keywords: 2-(2-phenylethyl)-4H-chromen-4-one; Aquilaria sinensis; Thymelaeaceae; anti-inflammatory activity; flavone; structure elucidation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / isolation & purification
  • Anti-Inflammatory Agents / pharmacology*
  • Flavones / chemistry*
  • Flavones / isolation & purification
  • Flavones / pharmacology*
  • Humans
  • Leukocyte Elastase / antagonists & inhibitors
  • Molecular Structure
  • Neutrophils / drug effects
  • Neutrophils / metabolism
  • Plant Bark / chemistry*
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology
  • Tracheophyta / chemistry*

Substances

  • Anti-Inflammatory Agents
  • Flavones
  • Plant Extracts
  • Leukocyte Elastase