rhamnocitrin-3-O-β-D-(6''-O-E-p-coumaroyl)-glucopyranoside

• 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-β-D-(6''-O-E-p-coumaroyl)-glucopyranoside
• 英文别名: trans-tiliroside；[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[5-hydroxy-2-(4-hydroxyphenyl)-7-methoxy-4-oxochromen-3-yl]oxyoxan-2-yl]methyl (E)-3-(4-hydroxyphenyl)prop-2-enoate
• 化学式: C₃₁H₂₈O₁₃
• 分子量: 608.556
• InChiKey: FRZQTGONAKOMSV-GVHZWOLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  44
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  202
• 氢给体数：
  6
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 rhamnocitrin-3-O-β-D-(6''-O-E-p-coumaroyl)-glucopyranoside 在 吡啶 作用下， 反应 48.0h， 生成 (E)-3-(4-Acetoxy-phenyl)-acrylic acid (2R,3R,4S,5R,6S)-3,4,5-triacetoxy-6-[5-acetoxy-2-(4-acetoxy-phenyl)-7-methoxy-4-oxo-4H-chromen-3-yloxy]-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Biotransformation of the flavonoid tiliroside to 7-methylether tiliroside: bioactivity of this metabolite and of its acetylated derivative

  摘要：

  Incubation of kaempferol-3-O-beta-D-(6 ''-E-p-coumaroyl)-glucopyranoside (tiliroside) (1) with Aspergillus nidulans gives the 7-methyl ether of tiliroside (2) which is a new compound. Its structure is determined by spectroscopic methods. Cytotoxic studies of 2 and of its acetylated derivative 2a were carried out in vitro against fourteen human leukemic cell lines. Results clearly show that compound 2 is ineffective against all leukemic cell lines tested. On the contrary, compound 2a exhibited cytotoxic activity against four of the cell lines (HL60, DAUDI, HUT78 and MOLT3) and additionally, a dose- and time-dependent effect on DNA synthesis.

  DOI：

  10.1007/s000180050076
• 作为产物：
  描述：

  银锻苷 在 Aspergillus nidulans 作用下， 生成 rhamnocitrin-3-O-β-D-(6''-O-E-p-coumaroyl)-glucopyranoside
  参考文献：
  名称：

  Biotransformation of the flavonoid tiliroside to 7-methylether tiliroside: bioactivity of this metabolite and of its acetylated derivative

  摘要：

  Incubation of kaempferol-3-O-beta-D-(6 ''-E-p-coumaroyl)-glucopyranoside (tiliroside) (1) with Aspergillus nidulans gives the 7-methyl ether of tiliroside (2) which is a new compound. Its structure is determined by spectroscopic methods. Cytotoxic studies of 2 and of its acetylated derivative 2a were carried out in vitro against fourteen human leukemic cell lines. Results clearly show that compound 2 is ineffective against all leukemic cell lines tested. On the contrary, compound 2a exhibited cytotoxic activity against four of the cell lines (HL60, DAUDI, HUT78 and MOLT3) and additionally, a dose- and time-dependent effect on DNA synthesis.

  DOI：

  10.1007/s000180050076