Structural characteristics of flavanones and flavones from Cudrania tricuspidata for neuraminidase inhibition.
The structural characteristics of flavonoids (1-3 and 6-8) from the root of Cudrania tricuspidata required for neuraminidase inhibition were studied and compared with commercially available flavonoids (4, 5, and 9-12). Alkylated flavanones (1-3) display better inhibition than the corresponding parent compound 4. Importantly, flavanone 1 bearing a C-8 hydrated prenyl group showed extremely high inhibition with IC(50) of 380 nM. On the other hand, the parent flavone 5 was more effective than alkylated analogues (6-8). Isolated inhibitors (1-3 and 6-8) showed noncompetitive inhibition in kinetic studies. The binding affinity of flavanones (1-4) for neuraminidase in in silico docking experiments correlated well with their IC(50) values and noncompetitive inhibition mode.
Ryu
Young Bae
YB
Bioindustry Technology and AI Control Biomaterial Research Center, KRIBB, Jeongeup, Republic of Korea.
Curtis-Long
Marcus J
MJ
Lee
Ji Won
JW
Ryu
Hyung Won
HW
Kim
Jun Young
JY
Lee
Woo Song
WS
Park
Ki Hun
KH
D000998:Antiviral Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D001665:Binding Sites; D003198:Computer Simulation; D004791:Enzyme Inhibitors / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D044950:Flavanones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D047309:Flavones / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D031624:Maclura / Q000737:chemistry*; D009439:Neuraminidase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D018517:Plant Roots / Q000737:chemistry; D013329:Structure-Activity Relationship
D000998:Antiviral Agents; D004791:Enzyme Inhibitors; D044950:Flavanones; D047309:Flavones; D009439:Neuraminidase