2"-O-acetyl-4"-O-p-hydroxybenzoyl-p-hydroxyphenyl-α-L-rhamnopyranosyl-(1→6)-O-β-D-glucopyranoside | 1604837-66-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2"-O-acetyl-4"-O-p-hydroxybenzoyl-p-hydroxyphenyl-α-L-rhamnopyranosyl-(1→6)-O-β-D-glucopyranoside
• 英文别名: euphorbinoside；[(2S,3R,4R,5R,6R)-5-acetyloxy-4-hydroxy-2-methyl-6-[[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(4-hydroxyphenoxy)oxan-2-yl]methoxy]oxan-3-yl] 4-hydroxybenzoate
• CAS: 1604837-66-2
• 化学式: C₂₇H₃₂O₁₄
• 分子量: 580.543
• InChiKey: YGUBZNGDFCPKFN-KWCXJFABSA-N

物化性质

• 沸点：
  854.9±65.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  211
• 氢给体数：
  6
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  2"-O-acetyl-4"-O-p-hydroxybenzoyl-p-hydroxyphenyl-α-L-rhamnopyranosyl-(1→6)-O-β-D-glucopyranoside 在 盐酸 、 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.0h， 生成 D-葡萄糖 、 L-rhamnopyranose
  参考文献：
  名称：

  Anti-inflammatory components of Euphorbia humifusa Willd.

  摘要：

  Two new compounds, euphorbinoside (1) and dehydropicrorhiza acid methyl diester (2), along with 24 known compounds (3-26) were isolated from Euphorbia humifusa Willd. The effects of these compounds on soluble epoxide hydrolase (sEH) inhibitory activity were evaluated. Flavonoid compounds (10-21) exhibited high sEH inhibitory activity. Among them, compounds 12, 13, and 19 greatly inhibited sEH enzymatic activity, with IC50 values as low as 18.05 +/- 1.17, 18.64 +/- 1.83, and 17.23 +/- 0.84 mu M, respectively. In addition, the effects of these compounds on lipopolysaccharide (LPS)-induced nitric oxide (NO) and tumor necrosis factor alpha (TNF-alpha) production by RAW 264.7 cells were investigated. Compounds 3-6, 8, 18, 20-23, and 25-26 inhibited the production of both NO and TNF-alpha, with IC50 values ranging from 11.1 +/- 0.9 to 45.3 +/- 1.6 mu M and 14.4 +/- 0.5 to 44.5 +/- 1.2 mu M, respectively. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.014

文献信息

• Anti-inflammatory components of Euphorbia humifusa Willd.
  作者：Bui Thi Thuy Luyen、Bui Huu Tai、Nguyen Phuong Thao、Kim Ji Eun、Ji Yun Cha、Ming Jie Xin、Young Mi Lee、Young Ho Kim

  DOI：10.1016/j.bmcl.2014.03.014

  日期：2014.4

  Two new compounds, euphorbinoside (1) and dehydropicrorhiza acid methyl diester (2), along with 24 known compounds (3-26) were isolated from Euphorbia humifusa Willd. The effects of these compounds on soluble epoxide hydrolase (sEH) inhibitory activity were evaluated. Flavonoid compounds (10-21) exhibited high sEH inhibitory activity. Among them, compounds 12, 13, and 19 greatly inhibited sEH enzymatic activity, with IC50 values as low as 18.05 +/- 1.17, 18.64 +/- 1.83, and 17.23 +/- 0.84 mu M, respectively. In addition, the effects of these compounds on lipopolysaccharide (LPS)-induced nitric oxide (NO) and tumor necrosis factor alpha (TNF-alpha) production by RAW 264.7 cells were investigated. Compounds 3-6, 8, 18, 20-23, and 25-26 inhibited the production of both NO and TNF-alpha, with IC50 values ranging from 11.1 +/- 0.9 to 45.3 +/- 1.6 mu M and 14.4 +/- 0.5 to 44.5 +/- 1.2 mu M, respectively. (c) 2014 Elsevier Ltd. All rights reserved.