Chalcones Isolated from Angelica keiskei and Their Inhibition of IL-6 Produdion in TNF-α-stimulated MG-63 Cell

Six chalcone compounds, 2',4',4-trihydroxy-3'[2-hydroxy-7-methyl-3-methylene-6-octaenyl]chalcone (1), 2',4',4-trihydroxy-3'-geranylchalcone (2), 2',4',4-trihydroxy-3'-[6-hydroxy-3,7-dimethyl-2,7-octadienyl]chalcone (3), 2',4-dihydroxy-4'-methoxy-3'-[2-hydroperoxy-3-methyl-3-butenyl]chalcone (4), 2',4-dihydroxy-4'-methoxy-3'-geranylchalcone (5), and 2',4-dihydroxy-4'-methoxy-3'[3-methyl-3-butenyl]chalcone (6) were isolated from the leaves of Angelica keiskei K (Umbelliferae). The structure of each isolated compound was determined using spectroscopic methods. Among the isolates, compounds 1-3 appeared to have potent inhibitory activity of IL-6 production in TNF-alpha-stimulated MG-63 cell, while compounds 4-6 did not. The distinct structural difference between compounds 1-3 and 4-6 was the presence of C-4 hydroxyl group in the chalcone moiety. Our results imply that the inhibitory activity of IL-6 production in TNF alpha-stimulated MG-63 cell may be affected by the presence of C-4' hydroxyl group in the chalcone moiety.