kaempferol-3,7-di-O-β-D-glucopyranoside decacetate | 131627-87-7

• 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-3,7-di-O-β-D-glucopyranoside decacetate
• 英文别名: Paeonoside Decaacetate；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-[5-acetyloxy-2-(4-acetyloxyphenyl)-4-oxo-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxychromen-7-yl]oxyoxan-2-yl]methyl acetate
• CAS: 131627-87-7
• 化学式: C₄₇H₅₀O₂₆
• 分子量: 1030.9
• InChiKey: NLVNWKWBXDAKIC-GHNQEIAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  73
• 可旋转键数：
  27
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  326
• 氢给体数：
  0
• 氢受体数：
  26

反应信息

• 作为产物：
  描述：

  山柰酚-3,7-二-O-葡萄糖苷 、 乙酸酐 在 吡啶 作用下， 生成 kaempferol-3,7-di-O-β-D-glucopyranoside decacetate
  参考文献：
  名称：

  Evolvosides C–E, flavonol-4-O-triglycosides from Evolvulus alsinoides and their anti-stress activity

  摘要：

  Phytochemical investigation of the n-butanol fraction of Evolvulus alsinoides (Linn.) led to the isolation of three new phenolic glycosides, evolvosides C, D and E (1-3) along with six known compounds (4-9). The structures of the compounds were elucidated on the basis of spectroscopic analysis, viz. 1D and 2D NMR experiments, chemical study, and comparison with literature data. Evolvoside C (1) was characterized as kaempferol 4'-O-beta-D-glucopyranosyl-(1 -> 2)-alpha-L-rhamnopyranosyl-(1 -> 6)-beta-D-glucopyranoside, whereas evolvosides D and E (2-3) were found to be mono and di-O-methyl derivatives of 1. The new compounds (1-3) represent rare triglycoside derivatives of flavonol at C-4'. The isolated compounds (1-6) were screened for acute stress-induced biochemical changes in male Sprague-Dawley rats at a dose of 40 mg/kg body weight. Compounds 1 and 2 displayed anti-stress effects by normalizing hyperglycemia, plasma corticosterone, plasma creatine kinase, and adrenal hypertrophy. Compounds 3 and 6 were also found to be effective in normalizing most of these stress parameters, whereas compounds 4 and 5 were ineffective in normalizing most of these effects. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.040