6-methoxyquercetin 3-galactoside | 35399-34-9

• 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: 6-methoxyquercetin 3-galactoside
• 英文别名: patuletin 3-O-β-D-galactopyranoside；Patuletin-3-galactosid；Patuletin 3-O-beta-D-galactoside；2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-methoxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
• CAS: 35399-34-9
• 化学式: C₂₂H₂₂O₁₃
• 分子量: 494.409
• InChiKey: AFBZFRQNKMLRPU-UFJVGALSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  216
• 氢给体数：
  8
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  6-methoxyquercetin 3-galactoside 在 盐酸 、 水 作用下， 生成 口服葡萄糖
  参考文献：
  名称：

  Anti-inflammatory Potential of Flavonoids from the Aerial Parts of Corispermum marschallii

  摘要：

  The isolation of phenolics from aerial parts of Corispermum marschallii yielded a total of 13 compounds including nine previously undescribed patuletin and spinacetin glycosides. These were identified as patuletin 3-O-beta-D-galactopyranosyl-7-O-beta-D-glucopyranoside (1), spinacetin 3-O-beta-D-galactopyranosyl-7-O-beta-D-glucopyranoside (2), patuletin 3-O-(6 ''-O-beta-D-glucopyranosyl) -beta-D-galactopyranoside (3), patuletin 3-O-(6 ''-O-alpha-L-arabinopyranosyl)-beta-D-galactopyranoside (4), patuletin 3-O-(2 ''-O-(5 '''-O-alpha-L-arabinopyranosyl)-beta-D-apiofuranosyl)-beta-D-galactopyranoside (5), patuletin 3-O-(2 ''-O-beta-D-apiofuranosyl)-beta-D-galactopyranoside (6), spinacetin 3-O-beta-D-galactopyranoside (7), patuletin 3-O-beta-D-galacto pyranosyl-7-O-(6 '''-O-feruloyl)-beta-D-glucopyranoside (8), and spinacetin 3-O-beta-D-galactopyranosyl-7-O-(6 '''-O-feruloyl)-beta-D-glucopyranoside (9). Structure elucidation was based on UV-visible, multistage MS, and 1D and 2D NMR spectroscopy and chemical derivatization, which allowed the identification on the glycosides with two different hexose moieties occurring at different positions of the aglycones. Most of the compounds tested inhibited the production of pro-inflammatory factors such as ROS, IL-8, and TNF-alpha in stimulated neutrophils.

  DOI：

  10.1021/acs.jnatprod.8b00152

文献信息

• Anti-inflammatory Potential of Flavonoids from the Aerial Parts of <i>Corispermum marschallii</i>
  作者：Karolina Pawłowska、Monika E. Czerwińska、Marcin Wilczek、Jakub Strawa、Michał Tomczyk、Sebastian Granica

  DOI：10.1021/acs.jnatprod.8b00152

  日期：2018.8.24

  The isolation of phenolics from aerial parts of Corispermum marschallii yielded a total of 13 compounds including nine previously undescribed patuletin and spinacetin glycosides. These were identified as patuletin 3-O-beta-D-galactopyranosyl-7-O-beta-D-glucopyranoside (1), spinacetin 3-O-beta-D-galactopyranosyl-7-O-beta-D-glucopyranoside (2), patuletin 3-O-(6 ''-O-beta-D-glucopyranosyl) -beta-D-galactopyranoside (3), patuletin 3-O-(6 ''-O-alpha-L-arabinopyranosyl)-beta-D-galactopyranoside (4), patuletin 3-O-(2 ''-O-(5 '''-O-alpha-L-arabinopyranosyl)-beta-D-apiofuranosyl)-beta-D-galactopyranoside (5), patuletin 3-O-(2 ''-O-beta-D-apiofuranosyl)-beta-D-galactopyranoside (6), spinacetin 3-O-beta-D-galactopyranoside (7), patuletin 3-O-beta-D-galacto pyranosyl-7-O-(6 '''-O-feruloyl)-beta-D-glucopyranoside (8), and spinacetin 3-O-beta-D-galactopyranosyl-7-O-(6 '''-O-feruloyl)-beta-D-glucopyranoside (9). Structure elucidation was based on UV-visible, multistage MS, and 1D and 2D NMR spectroscopy and chemical derivatization, which allowed the identification on the glycosides with two different hexose moieties occurring at different positions of the aglycones. Most of the compounds tested inhibited the production of pro-inflammatory factors such as ROS, IL-8, and TNF-alpha in stimulated neutrophils.