styraxlignolide E

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素苷
• 英文名称: styraxlignolide E
• 英文别名: (3S,4S)-4-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]oxolan-2-one
• 化学式: C₂₆H₃₂O₁₁
• 分子量: 520.533
• InChiKey: AAGCATAPYOEULE-ZQJJHTFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  37
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  164
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  styraxlignolide E 在 Penicillium decumbens naringinase 作用下， 以 acetate buffer 为溶剂， 反应 5.0h， 以9 mg的产率得到外消旋马台树脂醇
  参考文献：
  名称：

  New Furofuran and Butyrolactone Lignans with Antioxidant Activity from the Stem Bark of Styrax japonica

  摘要：

  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"-methylene-dioxyphenyl)-8-oxo-3,7-dioxabicyclo [3.3.0]octane 4'-O-(beta-D-glucopyranoside) (1), (2S,3S)-2alpha-(3"-hydroxy-4"-methoxybenzyl)-3 -(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-O-(beta-D-glucopyranoside) (2), (2S,3S)2(alpha-(4"-hydroxy-3"-methoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-O-(fi-Dglucopyranoside) (3), (2S,3S)-2(alpha-(4"-hydroxy-3"-methoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4"-O-(beta-D-glucopyranoside) (4), and (2S,3S)-2alpha-(3",4"-dimethoxybenzyl)-3 -(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-beta4-D-glucopyranoside) (5) by spectroscopic means including 2D NMR. Compounds 1-8 were tested in vitro for antioxidant activity against 1,1-diphenyl-2-pierylhydrazyl (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 muM, respectively.

  DOI：

  10.1021/np040113m

文献信息

• New Furofuran and Butyrolactone Lignans with Antioxidant Activity from the Stem Bark of <i>Styrax </i><i>j</i><i>aponica</i>
  作者：Byung-Sun Min、Min-Kyun Na、Sei-Ryang Oh、Kyung-Seop Ahn、Gil-Saeng Jeong、Gao Li、Sang-Ku Lee、Hyouk Joung、Hyeong-Kyu Lee

  DOI：10.1021/np040113m

  日期：2004.12.1

  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"-methylene-dioxyphenyl)-8-oxo-3,7-dioxabicyclo [3.3.0]octane 4'-O-(beta-D-glucopyranoside) (1), (2S,3S)-2alpha-(3"-hydroxy-4"-methoxybenzyl)-3 -(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-O-(beta-D-glucopyranoside) (2), (2S,3S)2(alpha-(4"-hydroxy-3"-methoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-O-(fi-Dglucopyranoside) (3), (2S,3S)-2(alpha-(4"-hydroxy-3"-methoxybenzyl)-3beta-(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4"-O-(beta-D-glucopyranoside) (4), and (2S,3S)-2alpha-(3",4"-dimethoxybenzyl)-3 -(4'-hydroxy-3'-methoxybenzyl)-gamma-butyrolactone 4'-beta4-D-glucopyranoside) (5) by spectroscopic means including 2D NMR. Compounds 1-8 were tested in vitro for antioxidant activity against 1,1-diphenyl-2-pierylhydrazyl (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 muM, respectively.