(+)-afzelechin 5-O-β-D-glucopyranoside | 1395093-95-4

• 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: (+)-afzelechin 5-O-β-D-glucopyranoside
• 英文别名: (2S,3R,4S,5S,6R)-2-[[(2R,3S)-3,7-dihydroxy-2-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-5-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1395093-95-4
• 化学式: C₂₁H₂₄O₁₀
• 分子量: 436.416
• InChiKey: FKEOHZPUDDAEDB-FBEISHDNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (+)-afzelechin 5-O-β-D-glucopyranoside 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.0h， 生成 葡萄糖
  参考文献：
  名称：

  A new flavan-3-ol and the anti-inflammatory effect of flavonoids from the fruit peels ofWisteria floribunda

  摘要：

  A new flavan-3-ol, (+)-afzelechin 5-O-beta-D-glucopyranoside (2), together with 13 known flavonoids (1, 3-14), was isolated from the fruit peels of Wisteria floribunda. Their structures were assigned by detailed interpretation of NMR, MS, and CD spectroscopic data, as well as by comparing with published reports. The in vitro anti-inflammatory activity of the isolated compounds (1-14) was examined. Among them, compounds 3, 6, and 9 produced highest inhibitory effects on tumor necrosis factor alpha (TNF-alpha)-induced nuclear factor kappa-B activation in HepG2 cells with IC50 values of 14.1, 16.5, and 11.9 mu M, respectively. With the exception of compound 6, the compounds significantly inhibited the accumulation of pro-inflammatory inducible nitric oxide synthase and cyclooxygenase-2 proteins in TNF-alpha-stimulated HepG2 cells at a concentration as low as 0.1 mM.

  DOI：

  10.1080/10286020.2011.603306

文献信息

• A new flavan-3-ol and the anti-inflammatory effect of flavonoids from the fruit peels of<i>Wisteria floribunda</i>
  作者：Bui Huu Tai、Trinh Nam Trung、Nguyen Xuan Nhiem、Do Thi Ha、Chu Van Men、Vu Binh Duong、Hoang Van Luong、SeokBean Song、KiHwan Bae、Young Ho Kim

  DOI：10.1080/10286020.2011.603306

  日期：2011.10

  A new flavan-3-ol, (+)-afzelechin 5-O-beta-D-glucopyranoside (2), together with 13 known flavonoids (1, 3-14), was isolated from the fruit peels of Wisteria floribunda. Their structures were assigned by detailed interpretation of NMR, MS, and CD spectroscopic data, as well as by comparing with published reports. The in vitro anti-inflammatory activity of the isolated compounds (1-14) was examined. Among them, compounds 3, 6, and 9 produced highest inhibitory effects on tumor necrosis factor alpha (TNF-alpha)-induced nuclear factor kappa-B activation in HepG2 cells with IC50 values of 14.1, 16.5, and 11.9 mu M, respectively. With the exception of compound 6, the compounds significantly inhibited the accumulation of pro-inflammatory inducible nitric oxide synthase and cyclooxygenase-2 proteins in TNF-alpha-stimulated HepG2 cells at a concentration as low as 0.1 mM.