Four new guaiane sesquiterpenoids from agarwood of Aquilaria filaria

Fitoterapia. 2019 Jun:135:79-84. doi: 10.1016/j.fitote.2019.04.007. Epub 2019 Apr 14.

Abstract

Six 8,12-epoxyguaiane sesquiterpenes (1-6), together with two known 2-(2-phenylethyl)chromone derivatives (7-8) were isolated from agarwood originating from Aquilaria filaria. Their structures were established by spectroscopic methods including IR, HRESIMS, 1D, and 2D NMR, and comparison with the published data. The absolute configuration of compound 1 was unambiguously determined by quantum chemical calculation of the electronic circular dichroism (ECD) spectrum. All compounds were tested for their α-glucosidase inhibitory activity and cytotoxicity. Compound 5 showed significant α-glucosidase inhibitory activity with IC50 value of 253.2 ± 9.7 μM (Acarbose, 743. 4 ± 3.3 μM). Compounds 2-4 displayed weak cytotoxicity against K562 tumor cell lines.

Keywords: 2-(2-phenylethyl)chromone; Agarwood; Aquilaria filaria; Cytotoxicity; Sesquiterpenoid; α-Glucosidase inhibitory activity.

MeSH terms

  • Cell Survival / drug effects
  • Glycoside Hydrolase Inhibitors / chemistry
  • Glycoside Hydrolase Inhibitors / isolation & purification
  • Glycoside Hydrolase Inhibitors / pharmacology*
  • Humans
  • K562 Cells
  • Molecular Structure
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification
  • Sesquiterpenes / pharmacology*
  • Sesquiterpenes, Guaiane / chemistry
  • Sesquiterpenes, Guaiane / isolation & purification
  • Sesquiterpenes, Guaiane / pharmacology*
  • Thymelaeaceae / chemistry*
  • Wood / chemistry

Substances

  • Glycoside Hydrolase Inhibitors
  • Sesquiterpenes
  • Sesquiterpenes, Guaiane
  • guaiane