New 2-(2-Phenylethyl)chromone derivatives from agarwood originating from Aquilaria sinensis

J Asian Nat Prod Res. 2022 Nov;24(11):1033-1040. doi: 10.1080/10286020.2021.2019222. Epub 2021 Dec 27.

Abstract

Two new dimeric 2-(2-phenylethyl)chromones, aquilasinenones L and M (1 and 2), and one new monomer analogue, 5S, 6 R, 7S, 8 R-tetrahydroxy-[2-(3-methoxy-4-hydroxyphenyl)ethyl]- 5,6,7,8-tetrahydrochromone (3), together with two known compounds, were isolated from the artificial agarwood originating from Aquilaria sinensis. Compound 1 was the first structure found with C8-O-C4"' linkage among 2-(2-phenylethyl)chromone dimers. Their structures were unambiguously elucidated based on 1 D and 2 D NMR spectroscopy, as well as by comparison with the literature. The absolute configuration was determined by ECD calculation. None of the compounds exhibited acetylcholinesterase inhibitory activity.

Keywords: 2-(2-phenylethyl)chromone; Agarwood; Aquilaria sinensis; ECD calculation.

MeSH terms

  • Acetylcholinesterase
  • Cholinesterase Inhibitors / chemistry
  • Cholinesterase Inhibitors / pharmacology
  • Chromones* / chemistry
  • Flavonoids / chemistry
  • Molecular Structure
  • Thymelaeaceae* / chemistry

Substances

  • Chromones
  • 2-(2-phenylethyl)chromone
  • Acetylcholinesterase
  • Cholinesterase Inhibitors
  • Flavonoids