Thymol, benzofuranoid, and phenylpropanoid derivatives: anti-inflammatory constituents from Eupatorium cannabinum.

Five new compounds, 9-O-angeloyl-8,10-dehydrothymol (1), 9-(3-methylbutanoyl)-8,10-dehydrothymol (2), eupatobenzofuran (3), 2-hydroxy-2,6-dimethylbenzofuran-3(2H)-one (4), and 1-(2-hydroxy-4-methylphenyl)propan-1,2-dione (5), have been isolated from the aerial part of Eupatorium cannabinum subsp. asiaticum, together with 16 known compounds (6-21). Compounds 6-8, 11, 13, and 15 exhibited inhibition (IC50 values≤18.4 μM) of superoxide anion generation by human neutrophils in response to formyl-L-methionyl-L-leucyl-L-phenylalanine/cytochalasin B (fMLP/CB). Compounds 2, 3, 10, 13, and 15 inhibited fMLP/CB-induced elastase release with IC50 values≤18.3 μM.