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Inhibition of neuraminidase activity by polyphenol compounds isolated from the roots of Glycyrrhiza uralensis.
Bioorg Med Chem Lett. 2010 Feb 01; 20(3):971-4.BM

Abstract

We isolated 18 polyphenols with neuraminidase inhibitory activity from methanol extracts of the roots of Glycyrrhiza uralensis. These polyphenols consisted of four chalcones (1-4), nine flavonoids (5-13), four coumarins (14-17), and one phenylbenzofuran (18). When we tested the effects of these individual compounds and analogs thereof on neuraminidase activation, we found that isoliquiritigenin (1, IC(50)=9.0 microM) and glycyrol (14, IC(50)=3.1 microM) had strong inhibitory activity. Structure-activity analysis showed that the furan rings of the polyphenols were essential for neuraminidase inhibitory activity, and that this activity was enhanced by the apioside group on the chalcone and flavanone backbone. In addition, the presence of a five-membered ring between C-4 and C-2' in coumestan was critical for neuraminidase inhibition. All neuraminidase inhibitors screened were found to be reversible noncompetitive inhibitors.

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Authors+Show Affiliations

Ryu YB
Bioindustry Technology Research Center and AI Control Material Research Center, Korea Research Institute of Bioscience and Biotechnology, Jeongeup 580-185, Republic of Korea.
Kim JH
No affiliation info available
Park SJ
No affiliation info available
Chang JS
No affiliation info available
Rho MC
No affiliation info available
Bae KH
No affiliation info available
Park KH
No affiliation info available
Lee WS
No affiliation info available

MeSH

Enzyme ActivationFlavonoidsGlycyrrhiza uralensisNeuraminidasePhenolsPlant ExtractsPlant RootsPolyphenolsStructure-Activity Relationship

Pub Type(s)

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

Language

eng

PubMed ID

20064716

Citation

Ryu, Young Bae, et al. "Inhibition of Neuraminidase Activity By Polyphenol Compounds Isolated From the Roots of Glycyrrhiza Uralensis." Bioorganic & Medicinal Chemistry Letters, vol. 20, no. 3, 2010, pp. 971-4.
Ryu YB, Kim JH, Park SJ, et al. Inhibition of neuraminidase activity by polyphenol compounds isolated from the roots of Glycyrrhiza uralensis. Bioorg Med Chem Lett. 2010;20(3):971-4.
Ryu, Y. B., Kim, J. H., Park, S. J., Chang, J. S., Rho, M. C., Bae, K. H., Park, K. H., & Lee, W. S. (2010). Inhibition of neuraminidase activity by polyphenol compounds isolated from the roots of Glycyrrhiza uralensis. Bioorganic & Medicinal Chemistry Letters, 20(3), 971-4. https://doi.org/10.1016/j.bmcl.2009.12.106
Ryu YB, et al. Inhibition of Neuraminidase Activity By Polyphenol Compounds Isolated From the Roots of Glycyrrhiza Uralensis. Bioorg Med Chem Lett. 2010 Feb 1;20(3):971-4. PubMed PMID: 20064716.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Inhibition of neuraminidase activity by polyphenol compounds isolated from the roots of Glycyrrhiza uralensis. AU - Ryu,Young Bae, AU - Kim,Jang Hoon, AU - Park,Su-Jin, AU - Chang,Jong Sun, AU - Rho,Mun-Chual, AU - Bae,Ki-Hwan, AU - Park,Ki Hun, AU - Lee,Woo Song, Y1 - 2010/01/04/ PY - 2009/10/13/received PY - 2009/12/02/revised PY - 2009/12/14/accepted PY - 2010/1/13/entrez PY - 2010/1/13/pubmed PY - 2010/9/21/medline SP - 971 EP - 4 JF - Bioorganic & medicinal chemistry letters JO - Bioorg Med Chem Lett VL - 20 IS - 3 N2 - We isolated 18 polyphenols with neuraminidase inhibitory activity from methanol extracts of the roots of Glycyrrhiza uralensis. These polyphenols consisted of four chalcones (1-4), nine flavonoids (5-13), four coumarins (14-17), and one phenylbenzofuran (18). When we tested the effects of these individual compounds and analogs thereof on neuraminidase activation, we found that isoliquiritigenin (1, IC(50)=9.0 microM) and glycyrol (14, IC(50)=3.1 microM) had strong inhibitory activity. Structure-activity analysis showed that the furan rings of the polyphenols were essential for neuraminidase inhibitory activity, and that this activity was enhanced by the apioside group on the chalcone and flavanone backbone. In addition, the presence of a five-membered ring between C-4 and C-2' in coumestan was critical for neuraminidase inhibition. All neuraminidase inhibitors screened were found to be reversible noncompetitive inhibitors. SN - 1464-3405 UR - https://www.unboundmedicine.com/medline/citation/20064716/Inhibition_of_neuraminidase_activity_by_polyphenol_compounds_isolated_from_the_roots_of_Glycyrrhiza_uralensis_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0960-894X(09)01829-0 DB - PRIME DP - Unbound Medicine ER -