paeoniflorigenone

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: paeoniflorigenone
• 英文别名: [(1R,3S,6S,8R,10R)-8-hydroxy-3-methyl-5-oxo-2,9-dioxatricyclo[4.3.1.03,8]decan-10-yl]methyl benzoate
• 化学式: C₁₇H₁₈O₆
• 分子量: 318.326
• InChiKey: BANPEMKDTXIFRE-DSCSFJNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (+)-paeoniflorigenone-1-O-β-D-glucopyranoside 在 snailase LJ₀₄₂₇B₂₀₁₁Z 、 水 作用下， 反应 12.0h， 以3.5 mg的产率得到paeoniflorigenone
  参考文献：
  名称：

  Structures and Biological Evaluation of Monoterpenoid Glycosides from the Roots of Paeonia lactiflora

  摘要：

  Fractionation of an aqueous extract of the air-dried roots of a traditional Chinese medicinal plant, Paeonia lactiflora, yielded the new monoterpenoid glycosides 1-10. Their structures were assigned via spectroscopic techniques, and the absolute configurations of 1, 4-6, and 8 were verified via chemical methods, specific rotation, and electronic circular dichroism data. Compounds 1-4 are rare compared to the reported cage-like paeoniflorin derivatives; that is, they comprised two monoterpenoidal moieties. In the in vitro assay, compounds 5, 8, and 9 showed weak inhibitions against lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages, with IC50 values of 64.8, 60.1, and 97.5 mu M, respectively.

  DOI：

  10.1021/acs.jnatprod.8b00087

文献信息

• Structures and Biological Evaluation of Monoterpenoid Glycosides from the Roots of <i>Paeonia lactiflora</i>
  作者：Rui Li、Jing-Fang Zhang、Yu-Zhuo Wu、Yan-Cheng Li、Gui-Yang Xia、Ling-Yan Wang、Bo-Lin Qiu、Min Ma、Sheng Lin

  DOI：10.1021/acs.jnatprod.8b00087

  日期：2018.5.25

  Fractionation of an aqueous extract of the air-dried roots of a traditional Chinese medicinal plant, Paeonia lactiflora, yielded the new monoterpenoid glycosides 1-10. Their structures were assigned via spectroscopic techniques, and the absolute configurations of 1, 4-6, and 8 were verified via chemical methods, specific rotation, and electronic circular dichroism data. Compounds 1-4 are rare compared to the reported cage-like paeoniflorin derivatives; that is, they comprised two monoterpenoidal moieties. In the in vitro assay, compounds 5, 8, and 9 showed weak inhibitions against lipopolysaccharide-induced nitric oxide production in RAW264.7 macrophages, with IC50 values of 64.8, 60.1, and 97.5 mu M, respectively.