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.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 4-Butyrolactone / analogs & derivatives*
  • 4-Butyrolactone / chemistry
  • 4-Butyrolactone / isolation & purification*
  • 4-Butyrolactone / pharmacology
  • Antioxidants / chemistry
  • Antioxidants / isolation & purification*
  • Antioxidants / pharmacology
  • Biphenyl Compounds
  • Furans / chemistry
  • Furans / isolation & purification*
  • Furans / pharmacology
  • Glucosides / chemistry
  • Glucosides / isolation & purification
  • Glucosides / pharmacology
  • Glycosides / chemistry
  • Glycosides / isolation & purification
  • Glycosides / pharmacology
  • Korea
  • Lignans / chemistry
  • Lignans / isolation & purification*
  • Lignans / pharmacology
  • Molecular Structure
  • Oleanolic Acid / analogs & derivatives*
  • Oleanolic Acid / chemistry
  • Oleanolic Acid / isolation & purification
  • Oleanolic Acid / pharmacology
  • Phenylpropionates / chemistry
  • Phenylpropionates / isolation & purification
  • Phenylpropionates / pharmacology
  • Picrates / pharmacology
  • Plant Bark / chemistry
  • Plants, Medicinal / chemistry*
  • Stereoisomerism
  • Styrax / chemistry*

Substances

  • Antioxidants
  • Biphenyl Compounds
  • Furans
  • Glucosides
  • Glycosides
  • Lignans
  • Phenylpropionates
  • Picrates
  • pinoresinol glycoside
  • styraxlignolide B
  • Oleanolic Acid
  • taraxerol
  • 1,1-diphenyl-2-picrylhydrazyl
  • syringin
  • 4-Butyrolactone