Sesquiterpenoids and Lactone Derivatives from Ligularia dentata

Seven new compounds were isolated from the roots of Ligularia dentata, including five bisabolane‐type sesquiterpenoids (bisabolane=1‐(1,5‐dimethylhexyl)‐4‐methylcyclohexane), namely (8β,10α)‐8‐(angeloyloxy)‐5,10‐epoxybisabola‐1,3,5,7(14)‐tetraene‐2,4,11‐triol (1), (8β,10α)‐8‐(angeloyloxy)‐5,10‐epoxythiazolo[5,4‐a]bisabola‐1,3,5,7(14)‐tetraene‐4,11‐diol (2), (1α,2α,3β,5α,6β)‐1,5,8‐tris(angeloyloxy)‐10,11‐epoxy‐2,3‐dihydroxybisabol‐7(14)‐en‐4‐one (3), (1α,2α,3β,5α,6β)‐2,5,8‐tris(angeloyloxy)‐10,11‐epoxy‐1,3‐dihydroxybisabol‐7(14)‐en‐4‐one (4), and (1α,2β,3β,5α,6β)‐1,8‐bis(angeloyloxy)‐2,3‐epoxy‐5,10‐dihydroxy‐11‐methoxybisabol‐7(14)‐en‐4‐one (5) (angeloyloxy=[(2Z)‐2‐methyl‐1‐oxobut‐2‐enyl]oxy), and two lactone derivatives, (2α,3β,5α)‐2‐(acetyloxy)‐9‐methoxy‐5‐(methoxycarbonyl)‐2,3‐dimethylheptano‐5‐lactone (6), and (2β,4β)‐2‐ethyl‐5‐hydroxy‐5‐(methoxycarbonyl)‐4,5‐dimethylpentano‐4‐lactone (7) (α/β denote relative configurations), together with (2E,4R,5S)‐2‐ethylidene‐5‐(methoxycarbonyl)‐4‐methylhexano‐5‐lactone (8), a known synthetic compound. Compound 2 is the first sesquiterpenoid derivative containing the uncommon benzothiazole moiety. The structures of 1–8 were established by spectroscopic methods, especially 2D‐NMR and MS analyses.