(7S,8R)-3,5,5′-trimethoxy-4′,7-epoxy-8,3′-neolignan-4,9,9′-triol 4-O-β-D-xylopyranoside | 1428904-02-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: (7S,8R)-3,5,5′-trimethoxy-4′,7-epoxy-8,3′-neolignan-4,9,9′-triol 4-O-β-D-xylopyranoside
• 英文别名: (2S,3R,4S,5R)-2-[4-[(2S,3R)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2,6-dimethoxyphenoxy]oxane-3,4,5-triol
• CAS: 1428904-02-2
• 化学式: C₂₆H₃₄O₁₁
• 分子量: 522.549
• InChiKey: TVGBJLCLEOPFGT-DTYUEUJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  37
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  157
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (7S,8R)-3,5,5′-trimethoxy-4′,7-epoxy-8,3′-neolignan-4,9,9′-triol 4-O-β-D-xylopyranoside 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 D-木糖
  参考文献：
  名称：

  Antioxidant Lignans and Chromone Glycosides from Eurya japonica

  摘要：

  Four new 8,8',7,2'-lignans, (+)-ovafolinin B-9'-O-beta-D-glucopyranoside (1), (-)-ovafolinin B-9'-O-beta-D-glucopyranoside (2), (+)-ovafolinin E-9'-O-beta-D-glucopyranoside (3), and (-)-ovafolinin E-9'-0-13-o-glucopyranoside (4), two neolignans, eusiderin N (5) and (7S,8R)-3,5,5'-trimethoxy4',7-epoxy-8,3'-neolignan-9,9'-diol-4-O-beta-D-xylopyranoside (6), and two new chromone glycosides, 5,7-dihydroxy-4Hchromen-4-one-3-O-beta-D-glucopyranoside (7) and 5,7-dihydroicy-4H-chromen-4-one-3-0-fl-o-xylopyranoside (8), together with 25 known compounds, were isolated from the stems of Eurya japonica. Structural elucidation of compounds 1-8 was established by spectroscopic methods, especially 2D NMR techniques, electronic circular dichroism data, and comparison with reported data. The isolates were evaluated for antioxidant and anti-NO production activities. Compounds 1, 2, 12-20, and 29 (ED50 23.40 mu M for 1) demonstrated potent antioxidant activity compared to the positive control a-tocopherol (ED50 27.21 yM). On the other hand, compounds 1, 2, 7-9, 12-20, and 32 showed only weak anti-NO production activity when compared to the positive control quercetin.

  DOI：

  10.1021/np3007638

文献信息

• Antioxidant Lignans and Chromone Glycosides from <i>Eurya japonica</i>
  作者：Li-Ming Yang Kuo、Li-Jie Zhang、Hung-Tse Huang、Zhi-Hu Lin、Chia-Ching Liaw、Hui-Ling Cheng、Kuo-Hsiung Lee、Susan L. Morris-Natschke、Yao-Haur Kuo、Hsiu-O Ho

  DOI：10.1021/np3007638

  日期：2013.4.26

  Four new 8,8',7,2'-lignans, (+)-ovafolinin B-9'-O-beta-D-glucopyranoside (1), (-)-ovafolinin B-9'-O-beta-D-glucopyranoside (2), (+)-ovafolinin E-9'-O-beta-D-glucopyranoside (3), and (-)-ovafolinin E-9'-0-13-o-glucopyranoside (4), two neolignans, eusiderin N (5) and (7S,8R)-3,5,5'-trimethoxy4',7-epoxy-8,3'-neolignan-9,9'-diol-4-O-beta-D-xylopyranoside (6), and two new chromone glycosides, 5,7-dihydroxy-4Hchromen-4-one-3-O-beta-D-glucopyranoside (7) and 5,7-dihydroicy-4H-chromen-4-one-3-0-fl-o-xylopyranoside (8), together with 25 known compounds, were isolated from the stems of Eurya japonica. Structural elucidation of compounds 1-8 was established by spectroscopic methods, especially 2D NMR techniques, electronic circular dichroism data, and comparison with reported data. The isolates were evaluated for antioxidant and anti-NO production activities. Compounds 1, 2, 12-20, and 29 (ED50 23.40 mu M for 1) demonstrated potent antioxidant activity compared to the positive control a-tocopherol (ED50 27.21 yM). On the other hand, compounds 1, 2, 7-9, 12-20, and 32 showed only weak anti-NO production activity when compared to the positive control quercetin.