Inhibition of neuraminidase activity by polyphenol compounds isolated from the roots of Glycyrrhiza uralensis.
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.
Ryu
Young Bae
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
Jang Hoon
JH
Park
Su-Jin
SJ
Chang
Jong Sun
JS
Rho
Mun-Chual
MC
Bae
Ki-Hwan
KH
Park
Ki Hun
KH
Lee
Woo Song
WS
D004789:Enzyme Activation / Q000187:drug effects / Q000502:physiology; D005419:Flavonoids / Q000302:isolation & purification / Q000494:pharmacology*; D029882:Glycyrrhiza uralensis; D009439:Neuraminidase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D010636:Phenols / Q000302:isolation & purification / Q000494:pharmacology*; D010936:Plant Extracts / Q000302:isolation & purification / Q000494:pharmacology*; D018517:Plant Roots; D059808:Polyphenols; D013329:Structure-Activity Relationship
D005419:Flavonoids; D010636:Phenols; D010936:Plant Extracts; D059808:Polyphenols; D009439:Neuraminidase