Gastroprotective 2-(2-phenylethyl)chromone-sesquiterpene hybrids from the resinous wood of Aquilaria sinensis (Lour.) Gilg

Bioorg Chem. 2023 Apr:133:106396. doi: 10.1016/j.bioorg.2023.106396. Epub 2023 Jan 30.

Abstract

Six previously unprecedented 2-(2-phenylethyl)chromone-sesquiterpene hybrids, aquisinenins A-F (1 - 6), were isolated from the resinous wood of Aquilaria sinensis by a LC-MS-guided fractionation procedure. Their structures were determined by extensive spectroscopic analysis (1D and 2D NMR, UV, IR, and HRMS) and experimental and computed ECD data. Compounds 1 - 6 were rare dimeric 2-(2-phenylethyl)chromone-sesquiterpene derivatives featuring 5,6,7,8-tetrahydro-2-(2-phenylethyl)chromone hybridized with different sesquiterpene (eudesmane/guaiane type) moieties via ester bond. Furthermore, all the isolated compounds were evaluated for their protective effects on taurocholic acid (TCA)-induced GES-1 cell injury. The most effective aquisinenin F (6) was used to elucidate the involved mechanism on protection against TCA-induced gastric mucosal damage. Our results indicated that 6 protected against gastric mucosal cell insult by downregulation of the ER stress triggered by TCA.

Keywords: 2-(2-Phenylethyl)chromone-sesquiterpene hybrid; Aquilaria sinensis; Aquisinenin; Chinese agarwood; Gastric mucosal protection.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromones
  • Flavonoids / chemistry
  • Molecular Structure
  • Resins, Plant
  • Sesquiterpenes*
  • Thymelaeaceae* / chemistry
  • Wood / chemistry

Substances

  • Chromones
  • 2-(2-phenylethyl)chromone
  • Flavonoids
  • Sesquiterpenes
  • Resins, Plant