luteolin 7-O-(2-apiosyl-6-malonyl)glucoside

• 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: luteolin 7-O-(2-apiosyl-6-malonyl)glucoside
• 英文别名: Luteolin 7-O-(2-apiosyl-6-malonyl)-glucoside；3-[[(2R,3S,4S,5R,6S)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-[2-(3,4-dihydroxyphenyl)-5-hydroxy-4-oxochromen-7-yl]oxy-3,4-dihydroxyoxan-2-yl]methoxy]-3-oxopropanoic acid
• 化学式: C₂₉H₃₀O₁₈
• 分子量: 666.546
• InChiKey: LPOQROCPKZWCGK-CQRLEKJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  47
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  289
• 氢给体数：
  9
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  luteolin 7-O-(2-apiosyl-6-malonyl)glucoside 在 sodium hydroxide 、 盐酸 作用下， 以 水 为溶剂， 反应 1.17h， 以0.3 g的产率得到木犀草苷
  参考文献：
  名称：

  Absorption and Metabolism of Luteolin in Rats and Humans in Relation to in Vitro Anti-inflammatory Effects

  摘要：

  Luteolin is a flavonoid present in plants in the form of aglycone or glucosides. In this study, luteolin glucosides (i.e., luteolin-7-O-beta-D-glucoside, luteolin-7-O-[2-(beta-D-apiosyl)-beta-D-glucoside], and luteolin-7-O-[2-(beta-D-apiosyl)-6-malonyl-beta-D-glucoside]) prepared from green pepper leaves as well as luteolin aglycone were orally administered to rats. Regardless of the administered luteolin form, luteolin glucuronides were mainly detected from plasma and organs. Subsequently, luteolin aglycone, the most absorbed form of luteolin in rats, was orally administered to humans. As a result, luteolin-3'-O-sulfate was mainly identified from plasma, suggesting that not only luteolin form but also animal species affect the absorption and metabolism of luteolin. When LPS-treated RAW264.7 cells were treated with luteolin glucuronides and luteolin sulfate (the characteristic metabolites identified from rats and humans, respectively), the different luteolin conjugates were metabolized in different ways, suggesting that such difference in metabolism results in their difference in anti-inflammatory effects.

  DOI：

  10.1021/acs.jafc.8b03273