kaempferol 3-O-β-D-xylopyranosyl-(1→2)-α-L-arabinofuranosyl-7-O-α-L-rhamnopyranoside | 1415248-05-3

• 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: kaempferol 3-O-β-D-xylopyranosyl-(1→2)-α-L-arabinofuranosyl-7-O-α-L-rhamnopyranoside
• 英文别名: 5-hydroxy-3-[(2S,3R,4S,5S)-4-hydroxy-5-(hydroxymethyl)-3-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxolan-2-yl]oxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• CAS: 1415248-05-3
• 化学式: C₃₁H₃₆O₁₈
• 分子量: 696.616
• InChiKey: FSKVWTWPEUJVNV-LNCVWQKISA-N

物化性质

• 沸点：
  1053.7±65.0 °C(Predicted)
• 密度：
  1.77±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  49
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  284
• 氢给体数：
  10
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  kaempferol 3-O-β-D-xylopyranosyl-(1→2)-α-L-arabinofuranosyl-7-O-α-L-rhamnopyranoside 在 盐酸 作用下， 以 水 为溶剂， 反应 4.0h， 生成 D-木糖 、 L-阿拉伯糖 、 L-鼠李糖
  参考文献：
  名称：

  Kaempferol glycosides from the twigs of Cinnamomum osmophloeum and their nitric oxide production inhibitory activities

  摘要：

  In the present study, ethanolic extract of twigs from Cinnamomum osmophloeum led to isolate nine kaempferol glycosides including two new kaempferol triglycosides that were characterized as kaempferol 3-O-beta-D-xylopyranosyl-(1 -> 2)-alpha-L-arabinofuranosyl-7-O-alpha-L-rhamnopyranoside (1) and kaempferol 3-O-beta-D-xylopyranosyl-(1 -> 2)-alpha-L-rhamnopyranosyl-7-O-alpha-L-rhamnopyranoside (2). The structures of these compounds were assigned by the application of 1D and 2D NMR spectroscopy and other techniques. Among these nine compounds, kaempferol 7-O-alpha-L-rhamnopyranoside (9) revealed inhibitory effect against LPS-induced production of nitric oxide in RAW 264.7 macrophages with an IC50 value of 41.2 mu M. It also slightly reduced PGE(2) accumulation by 26% at the concentration of 50 mu M. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.10.008

文献信息

• Kaempferol glycosides from the twigs of Cinnamomum osmophloeum and their nitric oxide production inhibitory activities
  作者：Huan-You Lin、Shang-Tzen Chang

  DOI：10.1016/j.carres.2012.10.008

  日期：2012.12

  In the present study, ethanolic extract of twigs from Cinnamomum osmophloeum led to isolate nine kaempferol glycosides including two new kaempferol triglycosides that were characterized as kaempferol 3-O-beta-D-xylopyranosyl-(1 -> 2)-alpha-L-arabinofuranosyl-7-O-alpha-L-rhamnopyranoside (1) and kaempferol 3-O-beta-D-xylopyranosyl-(1 -> 2)-alpha-L-rhamnopyranosyl-7-O-alpha-L-rhamnopyranoside (2). The structures of these compounds were assigned by the application of 1D and 2D NMR spectroscopy and other techniques. Among these nine compounds, kaempferol 7-O-alpha-L-rhamnopyranoside (9) revealed inhibitory effect against LPS-induced production of nitric oxide in RAW 264.7 macrophages with an IC50 value of 41.2 mu M. It also slightly reduced PGE(2) accumulation by 26% at the concentration of 50 mu M. (C) 2012 Elsevier Ltd. All rights reserved.