A lignoid glycoside and dimeric phenylpropanoids from Daphne oleoides

Three new natural products, a lignoid glycoside 1 and two dimeric phenylpropanoids 2 and 3, along with two known lignans 4 and 5, were isolated from the BuOH- and CHCl₃-soluble fractions of the whole plant of Daphne oleoides (Thymelaeaceae). The structures of the new compounds were established by spectroscopic techniques, including 2D NMR. as 4-(β-D-glucopyranosyloxy)-9′-hydroxy-3.3′,4′ -trimethoxy-7′.9-epoxylignan (1), (1R,2S,5R,6R)-6-(3-ethyl-4-hydroxy-5-methoxyphenyl)-2-(4-hydroxy-3,5- dimethoxyphenyl)-3,7-dioxabicyclo-[3.3.0] octane (2) and (1R,2S,5R,6S)-2,6-bis(3-ethyl-4-hydroxy-5-methoxyphenyl)-3.7- dioxabicyclo[3.3.0]octane (3). The other lignans were identified as (+)-pinoresinol O-(β-D-glucopyranoside) (4) and (+)-medioresinol (5).