kaempferol 3-O-[6-(E)-feruloyl]-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside-7-O-β-D-glucopyranoside | 902120-18-7

• 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: kaempferol 3-O-[6-(E)-feruloyl]-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside-7-O-β-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6S)-6-[(2S,3R,4S,5S,6R)-4,5-Dihydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-3-yl]oxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate；[(2R,3S,4S,5R,6S)-6-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-3-yl]oxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl (E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate
• CAS: 902120-18-7
• 化学式: C₄₃H₄₈O₂₄
• 分子量: 948.84
• InChiKey: KQLBBTFFNWBFGO-VMBSDINDSA-N

物化性质

• 沸点：
  1252.9±65.0 °C(Predicted)
• 密度：
  1.75±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  67
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  380
• 氢给体数：
  13
• 氢受体数：
  24

反应信息

• 作为反应物：
  描述：

  kaempferol 3-O-[6-(E)-feruloyl]-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside-7-O-β-D-glucopyranoside 在 potassium hydroxide 作用下， 反应 24.0h， 以1 mg的产率得到山柰酚-3-O-槐二糖-7-O-葡萄糖苷
  参考文献：
  名称：

  Flavonoid Glycosides fromHosta longipes, Their Inhibition on NO Production, and Nerve Growth Factor Inductive Effects

  摘要：

  An extended phytochemical investigation of the leaves of Hosta longipes identified the new flavonoid glycoside, kaempferol-3-O-beta-D-glucopyranosyl-(1 -> 2)-[ 6'''-O-acetyl-beta-Dglucopyranoside]- 7-O-beta-D-glucopyranoside and five known flavonoid derivatives. The structures of two compounds were revealed by extensive NMR methods (H-1 and C-13 NMR, H-1-H-1 COSY, HMQC and HMBC) and chemical hydrolysis. NMR data of one of them are published for the first time. Bioactivities of six compounds revealed that five strongly inhibited the production of nitric oxide (NO) with IC50 values of 11.56-15.97 mu m in lipopolysaccharide (LPS)-stimulated BV-2 cells without cell toxicity. Two compounds showed moderate induction of secretion of nerve growth factor (NGF) in C6 glioma cells (124.70 +/- 7.71% and 117.02 +/- 3.60%, respectively).

  DOI：

  10.5935/0103-5053.20140060

文献信息

• Flavonoid Glycosides from<i>Hosta longipes</i>, Their Inhibition on NO Production, and Nerve Growth Factor Inductive Effects
  作者：Chung Sub Kim、Oh Wook Kwon、Sun Yeou Kim、Kang Ro Lee

  DOI：10.5935/0103-5053.20140060

  日期：——

  An extended phytochemical investigation of the leaves of Hosta longipes identified the new flavonoid glycoside, kaempferol-3-O-beta-D-glucopyranosyl-(1 -> 2)-[ 6'''-O-acetyl-beta-Dglucopyranoside]- 7-O-beta-D-glucopyranoside and five known flavonoid derivatives. The structures of two compounds were revealed by extensive NMR methods (H-1 and C-13 NMR, H-1-H-1 COSY, HMQC and HMBC) and chemical hydrolysis. NMR data of one of them are published for the first time. Bioactivities of six compounds revealed that five strongly inhibited the production of nitric oxide (NO) with IC50 values of 11.56-15.97 mu m in lipopolysaccharide (LPS)-stimulated BV-2 cells without cell toxicity. Two compounds showed moderate induction of secretion of nerve growth factor (NGF) in C6 glioma cells (124.70 +/- 7.71% and 117.02 +/- 3.60%, respectively).