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

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

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Eco-Friendly Biomaterial Research Center, Korea Research Institute of Bioscience and Biotechnology, KRIBB, Jeongeup 580-185, Republic of Korea.


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.

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