loniphenyruviridoside B | 1338466-03-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: loniphenyruviridoside B
• 英文别名: (E)-3-[(3R,4aS,5R,6S)-5-ethenyl-1-oxo-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]-2-hydroxy-3-phenylprop-2-enoic acid
• CAS: 1338466-03-7
• 化学式: C₂₅H₂₈O₁₂
• 分子量: 520.49
• InChiKey: JANONPLUBJJWRY-LDRWPHMTSA-N

物化性质

• 沸点：
  814.1±65.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  192
• 氢给体数：
  6
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  甲醇 、 loniphenyruviridoside B 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 反应 0.33h， 以1.9 mg的产率得到methyl (E)-3-[(3R,4aS,5R,6S)-5-ethenyl-1-oxo-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,4a,5,6-tetrahydro-3H-pyrano[3,4-c]pyran-3-yl]-2-hydroxy-3-phenylprop-2-enoate
  参考文献：
  名称：

  Homosecoiridoids from the Flower Buds of Lonicera japonica

  摘要：

  Homosecoiridoids (1-15) were isolated from the flower buds of Lonicera japonica. Compounds 1-4, designated as loniphenyruviridosides A D, possess unprecedented skeletons featuring phenylpyruvic acid derived moieties coupled with an iridoid or a secoiridoid nucleus. Compounds 5-15 (lonijaposides D-N) are additional examples of the unusual pyridinium alkaloid-coupled secoiridoids (lonijaposides A C). The validity of the CD data to determine the configuration of the secoiridoid derivatives is discussed on the basis of detailed CD data analysis and semisynthesis of 2 and 3 with the co-occurring secologanic acid. The configuration of secologanic acid was determined by a single-crystal X-ray crystallographic analysis using anomalous scattering of Cu K alpha radiation. Biosynthetic pathways of the homosecoiridoids were postulated. Compounds 1-4 inhibited,STAT-3 activity of HELF cells, and lonijaposides F (7), H (9), I (10), and K (12) showed activity against the release of glucuronidase in rat polymorphonuclear leukocytes induced by platelet-activating factor.

  DOI：

  10.1021/np2004566
• 作为产物：
  描述：

  苯丙酮酸 、 7-hydroxysweroside 在 吡啶 作用下， 以 乙腈 为溶剂， 反应 96.0h， 以1.6 mg的产率得到loniphenyruviridoside C
  参考文献：
  名称：

  Homosecoiridoids from the Flower Buds of Lonicera japonica

  摘要：

  Homosecoiridoids (1-15) were isolated from the flower buds of Lonicera japonica. Compounds 1-4, designated as loniphenyruviridosides A D, possess unprecedented skeletons featuring phenylpyruvic acid derived moieties coupled with an iridoid or a secoiridoid nucleus. Compounds 5-15 (lonijaposides D-N) are additional examples of the unusual pyridinium alkaloid-coupled secoiridoids (lonijaposides A C). The validity of the CD data to determine the configuration of the secoiridoid derivatives is discussed on the basis of detailed CD data analysis and semisynthesis of 2 and 3 with the co-occurring secologanic acid. The configuration of secologanic acid was determined by a single-crystal X-ray crystallographic analysis using anomalous scattering of Cu K alpha radiation. Biosynthetic pathways of the homosecoiridoids were postulated. Compounds 1-4 inhibited,STAT-3 activity of HELF cells, and lonijaposides F (7), H (9), I (10), and K (12) showed activity against the release of glucuronidase in rat polymorphonuclear leukocytes induced by platelet-activating factor.

  DOI：

  10.1021/np2004566

文献信息

• Homosecoiridoids from the Flower Buds of <i>Lonicera japonica</i>
  作者：Yang Yu、Weixia Song、Chenggen Zhu、Sheng Lin、Feng Zhao、Xiuli Wu、Zhenggang Yue、Bo Liu、Sujuan Wang、Shaopeng Yuan、Qi Hou、Jiangong Shi

  DOI：10.1021/np2004566

  日期：2011.10.28

  Homosecoiridoids (1-15) were isolated from the flower buds of Lonicera japonica. Compounds 1-4, designated as loniphenyruviridosides A D, possess unprecedented skeletons featuring phenylpyruvic acid derived moieties coupled with an iridoid or a secoiridoid nucleus. Compounds 5-15 (lonijaposides D-N) are additional examples of the unusual pyridinium alkaloid-coupled secoiridoids (lonijaposides A C). The validity of the CD data to determine the configuration of the secoiridoid derivatives is discussed on the basis of detailed CD data analysis and semisynthesis of 2 and 3 with the co-occurring secologanic acid. The configuration of secologanic acid was determined by a single-crystal X-ray crystallographic analysis using anomalous scattering of Cu K alpha radiation. Biosynthetic pathways of the homosecoiridoids were postulated. Compounds 1-4 inhibited,STAT-3 activity of HELF cells, and lonijaposides F (7), H (9), I (10), and K (12) showed activity against the release of glucuronidase in rat polymorphonuclear leukocytes induced by platelet-activating factor.