title: Characteristic of alkylated chalcones from Angelica keiskei on influenza virus neuraminidase inhibition.
abstract: 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.
authors.affiliation: Eco-Friendly Biomaterial Research Center, Korea Research Institute of Bioscience and Biotechnology, KRIBB, Jeongeup 580-185, Republic of Korea.
authors.forename: Ji-Young
authors.initials: JY
authors.lastname: Park
authors.forename: Hyung Jae
authors.initials: HJ
authors.lastname: Jeong
authors.forename: Young Min
authors.initials: YM
authors.lastname: Kim
authors.forename: Su-Jin
authors.initials: SJ
authors.lastname: Park
authors.forename: Mun-Chual
authors.initials: MC
authors.lastname: Rho
authors.forename: Ki Hun
authors.initials: KH
authors.lastname: Park
authors.forename: Young Bae
authors.initials: YB
authors.lastname: Ryu
authors.forename: Woo Song
authors.initials: WS
authors.lastname: Lee
mesh_terms: D029969:Angelica / Q000737:chemistry*; D047188:Chalcones / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D009439:Neuraminidase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D009975:Orthomyxoviridae / Q000201:enzymology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D047188:Chalcones; D004791:Enzyme Inhibitors; D009439:Neuraminidase