rhamnocitrin-3-O-{(3S)-hydroxy-3-methyl-5-[(S)-1-phenylethylamino]glutaryl-(1->6)}-[α-L-rhamnopyranosyl-(1->2)]-β-D-galactopyranoside | 1386974-96-4

• 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: rhamnocitrin-3-O-{(3S)-hydroxy-3-methyl-5-[(S)-1-phenylethylamino]glutaryl-(1->6)}-[α-L-rhamnopyranosyl-(1->2)]-β-D-galactopyranoside
• 英文别名: [(2R,3R,4S,5R,6S)-3,4-dihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxochromen-3-yl]oxy-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]methyl (3S)-3-hydroxy-3-methyl-5-oxo-5-[[(1S)-1-phenylethyl]amino]pentanoate
• CAS: 1386974-96-4
• 化学式: C₄₂H₄₉NO₁₈
• 分子量: 855.847
• InChiKey: GKXNDWRIAIACER-LAVJJDRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  61
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  290
• 氢给体数：
  9
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  rhamnocitrin-3-O-{(3S)-hydroxy-3-methyl-5-[(S)-1-phenylethylamino]glutaryl-(1->6)}-[α-L-rhamnopyranosyl-(1->2)]-β-D-galactopyranoside 在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 (3R)-1-[(S)-1-phenylethyl]mevalonamide
  参考文献：
  名称：

  3-Hydroxy-3-Methylglutaryl Flavonol Glycosides from Oxytropis falcata

  摘要：

  Five new 3-hydroxy-3-methylglutaryl (HMG) flavonol 3-O-glycosides, named oxytroflavosides A-E (1-5), and two new rhamnocitrin 3-O-glycosides, oxytroflavosides F and G (6 and 7) were isolated from the n-BuOH-soluble fraction of an EtOH extract of Oxytropis falcata together with seven known kaempferol glycosides (8-14), of which six were isolated from the genus Oxytropis for the first time. The structures of these compounds were elucidated by spectroscopic techniques and chemical methods. The absolute configuration of HMG in compounds 1-5 was determined to be S through spectroscopic analysis of the mevalonamide obtained by amidation and reduction of the HMG moiety. Compounds 1-10 were evaluated for anti-inflammatory activities using lipopolysaccharide-induced RAW 264.7 cells, but none of them showed inhibitory effects on NO production.

  DOI：

  10.1021/np300292f
• 作为产物：
  描述：

  (S)-(-)- α-甲基苄胺 、 氧氟草苷A 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 以41 mg的产率得到rhamnocitrin-3-O-{(3S)-hydroxy-3-methyl-5-[(S)-1-phenylethylamino]glutaryl-(1->6)}-[α-L-rhamnopyranosyl-(1->2)]-β-D-galactopyranoside
  参考文献：
  名称：

  3-Hydroxy-3-Methylglutaryl Flavonol Glycosides from Oxytropis falcata

  摘要：

  Five new 3-hydroxy-3-methylglutaryl (HMG) flavonol 3-O-glycosides, named oxytroflavosides A-E (1-5), and two new rhamnocitrin 3-O-glycosides, oxytroflavosides F and G (6 and 7) were isolated from the n-BuOH-soluble fraction of an EtOH extract of Oxytropis falcata together with seven known kaempferol glycosides (8-14), of which six were isolated from the genus Oxytropis for the first time. The structures of these compounds were elucidated by spectroscopic techniques and chemical methods. The absolute configuration of HMG in compounds 1-5 was determined to be S through spectroscopic analysis of the mevalonamide obtained by amidation and reduction of the HMG moiety. Compounds 1-10 were evaluated for anti-inflammatory activities using lipopolysaccharide-induced RAW 264.7 cells, but none of them showed inhibitory effects on NO production.

  DOI：

  10.1021/np300292f