New furofuran and butyrolactone lignans with antioxidant activity from the stem bark of Styrax japonica

  • J Nat Prod. 2004 Dec;67(12):1980-4. doi: 10.1021/np040113m.
Byung-Sun Min  1 ,  Min-Kyun Na ,  Sei-Ryang Oh ,  Kyung-Seop Ahn ,  Gil-Saeng Jeong ,  Gao Li ,  Sang-Ku Lee ,  Hyouk Joung ,  Hyeong-Kyu Lee
Affiliations
  • 1. Laboratory of Immunomodulator, Korea Research Institute of Bioscience and Biotechnology, 52 Eoeun-dong, Yuseong, Daejeon 305-333, Korea.
PMID: 15620237 DOI: 10.1021/np040113m
Abstract

A new furofuran lignan, styraxlignolide B (1), and four new dibenzyl-gamma-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 2alpha-(4'-hydroxy-3'-methoxyphenyl)-6alpha-(3' ',4' '-methylenedioxyphenyl)-8-oxo-3,7-dioxabicyclo[3.3.0]octane 4'-O-(beta-D-glucopyranoside) (1), (2S,3S)-2alpha-(3' '-hydroxy-4' '-methoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-O-(beta-D-glucopyranoside) (2), (2S,3S)-2alpha-(4' '-hydroxy-3' '-methoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-O-(beta-D-glucopyranoside) (3), (2S,3S)-2alpha-(4' '-hydroxy-3' '-methoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4' '-O-(beta-D-glucopyranoside) (4), and (2S,3S)-2alpha-(3' ',4' '-dimethoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-O-(beta-D-glucopyranoside) (5) by spectroscopic means including 2D NMR. Compounds 1-8 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 microM, respectively.

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