1. New Furofuran and Butyrolactone Lignans with Antioxidant Activity from the Stem Bark of Styrax japonica
- Author
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Min, B.-S., Na, M.-K., Oh, S.-R., Ahn, K.-S., Jeong, G.-S., Li, G., Lee, S.-K., Joung, H., and Lee, H.-K.
- Abstract
A new furofuran lignan, styraxlignolide B (
1 ), and four new dibenzyl-γ-butyrolactone lignans, styraxlignolides C−F (2 −5 ), were isolated from the EtOAc-soluble fraction of stem bark of Styrax japonica. Known compounds, taraxerol (6 ), syringin (7 ), and (−)-pinoresinol glucoside (8 ), were also obtained. The structures of styraxligonolides B−F were determined as 2α-(4-hydroxy-3-methoxyphenyl)-6α-(3 ,4 -methylenedioxyphenyl)-8-oxo-3,7-dioxabicyclo[3.3.0]octane 4-O-(β-d -glucopyranoside) (1 ), (2S,3S)-2α-(3 -hydroxy-4 -methoxybenzyl)-3β-(4-hydroxy-3-methoxybenzyl)-γ-butyrolactone 4-O-(β-d -glucopyranoside) (2 ), (2S,3S)-2α-(4 -hydroxy-3 -methoxybenzyl)-3β-(4-hydroxy-3-methoxybenzyl)-γ-butyrolactone 4-O-(β-d -glucopyranoside) (3 ), (2S,3S)-2α-(4 -hydroxy-3 -methoxybenzyl)-3β-(4-hydroxy-3-methoxybenzyl)-γ-butyrolactone 4 -O-(β-d -glucopyranoside) (4 ), and (2S,3S)-2α-(3 ,4 -dimethoxybenzyl)-3β-(4-hydroxy-3-methoxybenzyl)-γ-butyrolactone 4-O-(β-d -glucopyranoside) (5 ) by spectroscopic means including 2D NMR. Compounds1 −8 were tested in vitro for antioxidant activity against 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals. Styraxlignolide C (2 ), styraxlignolide D (3 ), styraxlignolide E (4 ), and (−)-pinoresinol glucoside (8 ) exhibited weak radical-scavenging activity in the DPPH assay, with IC50 values of 380, 278, 194, and 260 μM, respectively.- Published
- 2004