chrysoeriol-7-O-β-D-(3''-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: chrysoeriol-7-O-β-D-(3''-E-p-coumaroyl)-glucopyranoside
• 英文别名: chrysoeriol-7-β-D-(3''-E-p-coumaroyl)glucoside；[(2S,3R,4S,5R,6R)-3,5-dihydroxy-2-[5-hydroxy-2-(4-hydroxy-3-methoxyphenyl)-4-oxochromen-7-yl]oxy-6-(hydroxymethyl)oxan-4-yl] (E)-3-(4-hydroxyphenyl)prop-2-enoate
• 化学式: C₃₁H₂₈O₁₃
• 分子量: 608.556
• InChiKey: AZHOJNKUISNFQR-MCQBNALESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：

  chrysoeriol-7-O-β-D-(3''-E-p-coumaroyl)-glucopyranoside 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 48.0h， 生成 对羟基肉桂酸钠盐 、 柯伊利素-7-O-葡萄糖苷
  参考文献：
  名称：

  Flavonoids from phlomis lychnitys

  摘要：

  DOI：

  10.1016/s0031-9422(00)81598-8

文献信息

• Inhibition of Prostaglandin E2 and Leukotriene C4 in Mouse Peritoneal Macrophages and Thromboxane B2 Production in Human Platelets by Flavonoids from Stachys chrysantha and Stachys candida.
  作者：Helen SKALTSA、Paulina BERMEJO、Diamanto LAZARI、Ana Maria SILVAN、Alexios-Leandros SKALTSOUNIS、Aurora SANZ、Maria Jose ABAD

  DOI：10.1248/bpb.23.47

  日期：——

  Seven flavonoids of Stachys chrysantha and Stachys candida have been isolated. The structures of the compounds were elucidated by spectroscopic methods, particularly highfield NMR spectroscopy. The effects of the methanol extracts of these two endemic Greek Stachys sp. and their main flavonoids were examined on arachidonic acid (AA) metabolism in the cellular system (mouse peritoneal macrophages and human platelets). Their cytotoxicity on cells was also investigated. Most samples assayed did not exhibit any significant effect on prostaglandin E2 (PGE2)-release from calcium ionophore-stimulated mouse peritoneal macrophages. Only chrysoeriol-7-O-β-D-(3"-E-p-coumaroyl)-glucopyranoside, at the highest non-cytotoxic dose (50 μM), inhibited the release of PGE2, but this effect is not statistically significant. The release of leukotriene C4 (LTC4) by mouse peritoneal macrophages stimulated with calcium ionophore was inhibited by a crude extract of S. chrysantha, with an IC50 value of 34.3 μg/ml. Xanthomicrol (IC50=29.2 μM) and chrysoeriol-7-O-β-D-(3"-E-p-coumaroyl)-glucopyranoside (IC50=11.1 μM) also inhibited the release of LTC4, althouth it showed less potency than the reference compound nordihydroguaiaretic acid (NDGA) (IC50=2 μM). However, most samples assayed showed a significant effect on thromboxane B2 (TXB2)-release from calcium ionophore-stimulated human platelets, with inhibition percentages slightly lower than the reefrence drug ibuprofen (IC50=7 μM). The IC50 values are : crude extract of S. candida 23.3 μg/ml; crude extract of S. chrysantha 23.1 μg/ml; xanthomicrol 28.8 μM; calcycopterin 2.66 μM and chrysoeriol-7-O-β-D-(3"-E-p-coumaroyl)-glucopyranoside 8.8 μM. Our results indicate that the selective inhibition of TX-synthase enzyme may be the primary target of action of most of these samples, and one of the mechanisms through which thus exert their antiinflammatory effects.
• Flavonoids from phlomis lychnitys
  作者：F. Tomás、J.L. Nieto、F.A.T. Barberán、F. Ferreres

  DOI：10.1016/s0031-9422(00)81598-8

  日期：1986.4