A Lignoid Glycoside and Dimeric Phenylpropanoids from Daphne oleoides

Abstract

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 CHCl 3 -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-(b-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-(b-d-glucopyranoside) (4) and ()-medioresinol (5).

Two Pairs of Enantiomeric Neolignans from Lobelia Chinensis

“…Compounds 3-7 were respectively identified as (+)pinoresinol (3), (+)-medioresinol (4), (-)-syringaresinol (5), (+)-epipinoresinol (6), and (-)-episyringaresinol ( 7) by comparison of their spectroscopic data with those reported in the literatures [13][14][15][16][17][18][19][20]. To our knowledge, all the above compounds were isolated from the title plant for the first time.…”