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Characteristic of alkylated chalcones from Angelica keiskei on influenza virus neuraminidase inhibition.
Bioorg Med Chem Lett. 2011 Sep 15; 21(18):5602-4.BM

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.

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Authors+Show Affiliations

Park JY
Eco-Friendly Biomaterial Research Center, Korea Research Institute of Bioscience and Biotechnology, KRIBB, Jeongeup 580-185, Republic of Korea.
Jeong HJ
No affiliation info available
Kim YM
No affiliation info available
Park SJ
No affiliation info available
Rho MC
No affiliation info available
Park KH
No affiliation info available
Ryu YB
No affiliation info available
Lee WS
No affiliation info available

MeSH

AngelicaChalconesDose-Response Relationship, DrugEnzyme InhibitorsMolecular StructureNeuraminidaseOrthomyxoviridaeStereoisomerismStructure-Activity Relationship

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21824777

Citation

Park, Ji-Young, et al. "Characteristic of Alkylated Chalcones From Angelica Keiskei On Influenza Virus Neuraminidase Inhibition." Bioorganic & Medicinal Chemistry Letters, vol. 21, no. 18, 2011, pp. 5602-4.
Park JY, Jeong HJ, Kim YM, et al. Characteristic of alkylated chalcones from Angelica keiskei on influenza virus neuraminidase inhibition. Bioorg Med Chem Lett. 2011;21(18):5602-4.
Park, J. Y., Jeong, H. J., Kim, Y. M., Park, S. J., Rho, M. C., Park, K. H., Ryu, Y. B., & Lee, W. S. (2011). Characteristic of alkylated chalcones from Angelica keiskei on influenza virus neuraminidase inhibition. Bioorganic & Medicinal Chemistry Letters, 21(18), 5602-4. https://doi.org/10.1016/j.bmcl.2011.06.130
Park JY, et al. Characteristic of Alkylated Chalcones From Angelica Keiskei On Influenza Virus Neuraminidase Inhibition. Bioorg Med Chem Lett. 2011 Sep 15;21(18):5602-4. PubMed PMID: 21824777.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Characteristic of alkylated chalcones from Angelica keiskei on influenza virus neuraminidase inhibition. AU - Park,Ji-Young, AU - Jeong,Hyung Jae, AU - Kim,Young Min, AU - Park,Su-Jin, AU - Rho,Mun-Chual, AU - Park,Ki Hun, AU - Ryu,Young Bae, AU - Lee,Woo Song, Y1 - 2011/07/20/ PY - 2011/03/30/received PY - 2011/06/02/revised PY - 2011/06/14/accepted PY - 2011/8/10/entrez PY - 2011/8/10/pubmed PY - 2011/12/20/medline SP - 5602 EP - 4 JF - Bioorganic & medicinal chemistry letters JO - Bioorg Med Chem Lett VL - 21 IS - 18 N2 - 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. SN - 1464-3405 UR - https://www.unboundmedicine.com/medline/citation/21824777/Characteristic_of_alkylated_chalcones_from_Angelica_keiskei_on_influenza_virus_neuraminidase_inhibition_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0960-894X(11)00939-5 DB - PRIME DP - Unbound Medicine ER -