7',8'-dihydro-7'-(3'-methoxy-4',5'-dihydroxyphenyl)-8'-(hydroxymethyl)-6-methoxy-2H-pyrano[2,3-f]-7,8-benzodioxin-2-one

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 香豆素木脂素
• 英文名称: 7',8'-dihydro-7'-(3'-methoxy-4',5'-dihydroxyphenyl)-8'-(hydroxymethyl)-6-methoxy-2H-pyrano[2,3-f]-7,8-benzodioxin-2-one
• 英文别名: 2-(3,4-Dihydroxy-5-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one；2-(3,4-dihydroxy-5-methoxyphenyl)-3-(hydroxymethyl)-5-methoxy-2,3-dihydropyrano[3,2-h][1,4]benzodioxin-9-one
• 化学式: C₂₀H₁₈O₉
• 分子量: 402.358
• InChiKey: CGGQHUJEOUAHNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  124
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  谷胱甘肽 、 7',8'-dihydro-7'-(3'-methoxy-4',5'-dihydroxyphenyl)-8'-(hydroxymethyl)-6-methoxy-2H-pyrano[2,3-f]-7,8-benzodioxin-2-one 反应 2.0h， 生成
  参考文献：
  名称：

  Three lignans and one coumarinolignoid with quinone reductase activity from Eurycorymbus cavaleriei

  摘要：

  Four compounds. including one new lignan cavaol H (1), one new coumarinolignoid 5'-hydroxydeomiscosin B (4) and two known lignans (2-3) were isolated from the 95% ethanol extract of the twigs of Eurycorymbus cavaleriei. Their structures were established on the basis of various spectroscopic analyses including 1D-(H-1, C-13, and DEPT) and 2D-NMR (COSY, HMQC, and HMBC). The absolute stereochemistry of the two known lignans was firstly reported in this article by H-1 NMR studies on Mosher's ester derivatives. In the present study, quinone reductase induction activities of compounds 1-4 were assayed, compound 4 showed moderate quinone reductase induction with concentration to double the enzyme activity (CD) of 10.5 +/- 0.8 mu g/mL. Then we established LC-MS-MS analysis of glutathione (GSH) incubation with compound 4 to explain whether compound 4 induced quinone reductase through alkylating of the sulfhydryl groups of Keap1. Reconstructed selected ion chromatogram (SIC) of m/z 706 after compound 4 incubation with GSH was different from that with Tris-HCl buffer solution, which meant the quinone reductase induction activity of compound 4 attributed to alkylating the sulfhydryl groups of Keap1. (C) 2009 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2009.04.003