[Chemical constituents from Turpiniae Folium]

Nineteen compounds were isolated from the Chinese medicinal material Turpiniae Folium by column chromatography on normal-phase silica gel, Sephadex LH-20, and MCI, and preparative high-performance liquid chromatography. Spectroscopic methods including nuclear magnetic resonance and high-resolution mass spectrometry were employed for the structure elucidation, by which the isolated compounds were identified as(4R,5S)-dihydroxy-6,7-megastigmadien-9-one(1), dehydrovomifoliol(2), loliolide(3), lupenone(4), β-amyrone(5), oleanolic acid(6), α-amyrone(7), friedelin(8),(20S)-3-oxo-20-hydroxytaraxastane(9), β-sitosterol(10),(13S,9Z,11E)-13-hydroxy-9,11-octadecadienoic acid methyl ester(11),(9E,11E)-13-oxo-9,11-octadecadienoic acid(12), vitamin E quinone(13), 3-furoic acid(14), 4-hydroxyisobenzofuran-1(3H)-one(15), eugenin(16), 4-hydroxybenzaldehyde(17), 4-hydroxyacetophenone(18), and vanillic acid(19). Among them, compound 1 was identified as a new megastigmane-type nor-sesquiterpenoid characterized by an allene moiety, and its absolute configuration was determined by quantum chemical calculation of the ECD spectrum. Additionally, compounds 2-5, 7-9, and 11-18 were isolated from the genus Turpinia for the first time. The antibacterial and anti-inflammatory activities of the compounds were evaluated by the double dilution method and the lipopolysaccharide(LPS)-induced inflammation model in mouse macrophage RAW264.7 cells, respectively. The results revealed the inhibitory effects of compounds 2 and 11-13 on nitric oxide production in LPS-induced RAW264.7 cells.