Characteristic of alkylated chalcones from Angelica keiskei on influenza virus neuraminidase inhibition

Bioorg Med Chem Lett. 2011 Sep 15;21(18):5602-4. doi: 10.1016/j.bmcl.2011.06.130. Epub 2011 Jul 20.


As part of our ongoing effort to develop influenza virus neuraminidase (NA) inhibitors from various medicinal plants, we utilized bioassay-guided fractionation to isolated six alkylated chalcones (1-6) from Angelica keiskei. Xanthokeistal A (1) emerged as new compound containing the rare alkyl substitution, 6,6-dimethoxy-3-methylhex-2-enyl. When we tested the ability of these individual alkyl substituted chalcones to inhibit influenza virus NA hydrolysis, we found that 2-hydroxy-3-methyl-3-butenyl alkyl (HMB) substituted chalcone (3, IC(50)=12.3 μM) showed most potent inhibitory activity. The order of potency of substituted alkyl groups on for NA inhibition was HMB>6-hydroxyl-3,7-dimethyl-octa-2,7-dienyl>dimethylallyl>geranyl. All NA inhibitors screened were found to be reversible noncompetitive inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Angelica / chemistry*
  • Chalcones / chemistry
  • Chalcones / pharmacology*
  • Dose-Response Relationship, Drug
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Molecular Structure
  • Neuraminidase / antagonists & inhibitors*
  • Neuraminidase / metabolism
  • Orthomyxoviridae / enzymology*
  • Stereoisomerism
  • Structure-Activity Relationship


  • Chalcones
  • Enzyme Inhibitors
  • Neuraminidase