quercetin 5,3'-di-O-β-D-glucopyranoside | 1021297-98-2

• 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: quercetin 5,3'-di-O-β-D-glucopyranoside
• CAS: 1021297-98-2
• 化学式: C₂₇H₃₀O₁₇
• 分子量: 626.525
• InChiKey: MIWYDNODAWFFTD-UINLEYECSA-N

物化性质

• 沸点：
  1038.1±65.0 °C(Predicted)
• 密度：
  1.814±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.07
• 重原子数：
  44.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  289.66
• 氢给体数：
  11.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  quercetin 5,3'-di-O-β-D-glucopyranoside 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 0.08h， 生成 isoquercitrin
  参考文献：
  名称：

  Regioselective formation of quercetin 5-O-glucoside from orally administered quercetin in the silkworm, Bombyx mori

  摘要：

  The cocoons of some races of the silkworm, Bombyx mori, have been shown to contain 5-O-glucosylated flavonoids, which do not occur naturally in the leaves of their host plant, mulberry (Morus alba). Thus, dietary flavonoids could be biotransformed in this insect. In this study, we found that after feeding silkworms a diet rich in the flavonol quercetin, quercetin 5-O-glucoside was the predominant metabolite in the midgut tissue, while quercetin 5,4'-di-O-glucoside was the major constituent in the hemolymph and silk glands. UDP-glucosyltransferase (UGT) in the midgut could transfer glucose to each of the hydroxyl groups of quercetin, with a preference for formation of 5-O-glucoside, while quercetin 5,4'-di-O-glucoside was predominantly produced if the enzyme extracts of either the fat body or silk glands were incubated with quercetin 5-O-glucoside and UDP-glucose. These results suggest that dietary quercetin was glucosylated at the 5-OP position in the midgut as the first-pass metabolite of quercetin after oral absorption, then glucosylated at the 4'-O position in the fat body or silk glands. The 5-O-glucosylated flavonoids retained biological activity in the insect, since the total free radical scavenging capacity of several tissues increased after oral administration of quercetin. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2007.11.009