6'''-(3-hydroxy-3-methylglutaroyl)-2''-O-β-D-galactopyranosyl orientin

• 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'''-(3-hydroxy-3-methylglutaroyl)-2''-O-β-D-galactopyranosyl orientin
• 英文别名: (3S)-5-[[(2R,3R,4S,5R,6S)-6-[(2S,3R,4S,5S,6R)-2-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-8-yl]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-3-hydroxy-3-methyl-5-oxopentanoic acid
• 化学式: C₃₃H₃₈O₂₀
• 分子量: 754.653
• InChiKey: MBUUXGSFPUWZGK-UQPJEDJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  53
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  340
• 氢给体数：
  12
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  6'''-(3-hydroxy-3-methylglutaroyl)-2''-O-β-D-galactopyranosyl orientin 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 orientin-2''-O-galactopyranoside 、 荭草苷
  参考文献：
  名称：

  FlavoneC-glycosides from the flowers ofTrollius chinensisand their anti-complementary activity

  摘要：

  Phytochemical investigation of ethanol extract from the flowers of Trollius chinensis Bunge resulted in the isolation of two new flavone C-glycosides (12), along with 10 known compounds (312). The structures of the new compounds were established as 6?-(3-hydroxy-3-methylglutaroyl)-2-O--d-galactopyranosyl orientin (1) and 6?-(3-hydroxy-3-methylglutaroyl)-2-O--d-galactopyranosyl vitexin (2) on the basis of various spectroscopic analysis (including different 1D and 2D NMR spectroscopies, high-resolution electrospray ionization mass spectrometry) and chemical evidences. Bioassay showed that eight flavonoids inhibited complement activation on the classic pathway in vitro, with their IC50 values ranging from 0.88 to 4.02mM, which may contribute to the applications of the herb in treatment of acute respiratory distress syndrome, etc.

  DOI：

  10.1080/10286020.2012.760545

文献信息

• Flavone<i>C</i>-glycosides from the flowers of<i>Trollius chinensis</i>and their anti-complementary activity
  作者：Jiang-Yun Liu、Sheng-Yin Li、Jian-Yong Feng、Yan Sun、Jin-Na Cai、Xiao-Fei Sun、Shi-Lin Yang

  DOI：10.1080/10286020.2012.760545

  日期：2013.4

  Phytochemical investigation of ethanol extract from the flowers of Trollius chinensis Bunge resulted in the isolation of two new flavone C-glycosides (12), along with 10 known compounds (312). The structures of the new compounds were established as 6?-(3-hydroxy-3-methylglutaroyl)-2-O--d-galactopyranosyl orientin (1) and 6?-(3-hydroxy-3-methylglutaroyl)-2-O--d-galactopyranosyl vitexin (2) on the basis of various spectroscopic analysis (including different 1D and 2D NMR spectroscopies, high-resolution electrospray ionization mass spectrometry) and chemical evidences. Bioassay showed that eight flavonoids inhibited complement activation on the classic pathway in vitro, with their IC50 values ranging from 0.88 to 4.02mM, which may contribute to the applications of the herb in treatment of acute respiratory distress syndrome, etc.