kaempferol 4′-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside | 1169835-58-8

• 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 4′-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside
• 英文别名: kaempferol-4'-O-α-L-rhamnopyranosyl-(1->6)-β-D-glucopyranoside；evolvoside B；Kaempferol 4'-rutinoside；3,5,7-trihydroxy-2-[4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxyphenyl]chromen-4-one
• CAS: 1169835-58-8
• 化学式: C₂₇H₃₀O₁₅
• 分子量: 594.526
• InChiKey: NTBNRFPZTCXMTF-QETNVOEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  245
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  kaempferol 4′-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside 、 乙酸酐 在 吡啶 作用下， 生成 kaempferol 4′-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside nonusacetate
  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