1,4-di-O-β-D-gIucopyranosyloxy-2-methoxybenzene

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,4-di-O-β-D-gIucopyranosyloxy-2-methoxybenzene
• 英文别名: (2-methoxy-4-O-β-D-glucopyranosyl)phenol 1-O-β-D-glucopyranoside；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenoxy]oxane-3,4,5-triol
• 化学式: C₁₉H₂₈O₁₃
• 分子量: 464.424
• InChiKey: XYTIVPVWLLNVKO-SKYGPZSASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  208
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  1,4-di-O-β-D-gIucopyranosyloxy-2-methoxybenzene 在 β-glucosidase 作用下， 以 水 为溶剂， 反应 16.0h， 以3.5 mg的产率得到2-甲氧基对苯二酚
  参考文献：
  名称：

  Glycosides from the Stem Bark of Fraxinus sieboldiana

  摘要：

  A norditerpene glucopyranoside with a novel carbon skeleton (1), eight new aromatic glycosides (2-9), and 25 known glycosides have been isolated from a H2O-soluble portion of an ethanolic extract of the stem bark of Fraxinus sieboldiana. Their structures were determined by spectroscopic and chemical methods. Based on analysis of the NMR data of threo- and erythro-arylglycerols in different solvents, an application of Delta delta(C8-C7) values to distinguish threo-arylglycerol and erythro-arylglycerol isomers was proposed. In the in vitro assays, compound 5 displayed TNF-alpha secretion inhibitory activity with an IC50 value of 1.6 mu M, compound 6 showed antioxidative activity inhibiting Fe+2-cystine-induced rat liver microsomal lipid peroxidation with an IC50 value of 0.9 mu M, and plantasioside (10) showed selective activity against the human colon cancer cell line (HCT-8) with an IC50 value of 3.4 mu M.

  DOI：

  10.1021/np0700467

文献信息

• Glycosides from the Stem Bark of <i>Fraxinus </i><i>sieboldiana</i>
  作者：Sheng Lin、Sujuan Wang、Mingtao Liu、Maoluo Gan、Shuai Li、Yongchun Yang、Yinghong Wang、Wenyi He、Jiangong Shi

  DOI：10.1021/np0700467

  日期：2007.5.25

  A norditerpene glucopyranoside with a novel carbon skeleton (1), eight new aromatic glycosides (2-9), and 25 known glycosides have been isolated from a H2O-soluble portion of an ethanolic extract of the stem bark of Fraxinus sieboldiana. Their structures were determined by spectroscopic and chemical methods. Based on analysis of the NMR data of threo- and erythro-arylglycerols in different solvents, an application of Delta delta(C8-C7) values to distinguish threo-arylglycerol and erythro-arylglycerol isomers was proposed. In the in vitro assays, compound 5 displayed TNF-alpha secretion inhibitory activity with an IC50 value of 1.6 mu M, compound 6 showed antioxidative activity inhibiting Fe+2-cystine-induced rat liver microsomal lipid peroxidation with an IC50 value of 0.9 mu M, and plantasioside (10) showed selective activity against the human colon cancer cell line (HCT-8) with an IC50 value of 3.4 mu M.