7-O-β-glucopyranosyl matteucinol | 101395-11-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 7-O-β-glucopyranosyl matteucinol
• 英文别名: matterucinol 7-O-β-glucopyranoside；mattucinol-7-O-β-D-glucopyranoside；matteucinol 7-O-β-D-glucoside；matteucinol-7-O-β-D-glucopyranoside；(2S)-5-hydroxy-2-(4-methoxyphenyl)-6,8-dimethyl-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3-dihydrochromen-4-one
• CAS: 101395-11-3
• 化学式: C₂₄H₂₈O₁₀
• 分子量: 476.48
• InChiKey: HPXOUFFMSLZOLE-WUQIJIJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  3-羟基-3-甲基-5-氧代-5-[[(2R,3S,4S,5R,6S)-3,4,5-三羟基-6-[(2S)-5-羟基-2-(4-甲氧基苯基)-6,8-二甲基-4-氧代色满-7-基]氧基四氢吡喃-2-基]甲氧基]戊酸 在 重氮甲烷 作用下， 以 甲醇 为溶剂， 以2 mg的产率得到methyl matteuorienate A
  参考文献：
  名称：

  Five New C-Methyl Flavonoids, the Potent Aldose Reductase Inhibitors from Matteuccia orientalis TREV.

  摘要：

  Five new compounds, matteuorien, matteuorienin, and matteuorienate A (7), B (8), and C (9) were isolated together with five known compounds from the MeOH extract of the rhizome of Matteuccia orientalis TREV. The structures of these compounds were determined by the use of spectroscopic methods including two dimensional (2D)-NMR experiments and chemical methods, except for the configuration at the C-3‴ of matteuorienate A (7), B (8), and C (9). Among them, matteuorienate A, B, and C showed very strong aldose reductase inhibitory activity. A structure-activity relationship study showed that a carboxyl group played an important part in aldose reductase inhibitory activity in these three compounds.

  DOI：

  10.1248/cpb.43.1558