(2R,4S,5R,10R)-2-(β-D-glucopyranosyloxy)-8-oxo-eremophil-7(11)-ene | 917985-17-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2R,4S,5R,10R)-2-(β-D-glucopyranosyloxy)-8-oxo-eremophil-7(11)-ene
• 英文别名: alticoloside E
• CAS: 917985-17-2
• 化学式: C₂₁H₃₄O₇
• 分子量: 398.497
• InChiKey: YIUIOLNWUGPQSA-TVQNZXITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  28.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  116.45
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R,10R)-2-(β-D-glucopyranosyloxy)-8-oxo-eremophil-7(11)-ene 在 盐酸 、 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， 以 二氯甲烷 为溶剂， 反应 15.0h， 生成
  参考文献：
  名称：

  Medicinal Foodstuffs. XXXII. Novel Sesquiterpene Glycoside Sulfate, Fukinoside A, with Antiallergic Activity from Japanese Butterbur (Petasites japonicus)

  摘要：

  Novel sesquiterpene glycoside sulfate, fukinoside A, was isolated as the potassium salt from the aerial parts of Petasites japonicus. The absolute sterostructure of fukinoside A was elucidated on the basis of chemical and physicochemical evidence. In addition, fukinoside A was found to inhibit release of beta-hexosaminidase, as a marker of antigen-induced degranulation, in RBL-2H3 cells.

  DOI：

  10.3987/com-06-10858
• 作为产物：
  描述：

  fukinoside A potassium 在 1,4-二氧六环 、 吡啶 作用下， 反应 1.0h， 以84%的产率得到(2R,4S,5R,10R)-2-(β-D-glucopyranosyloxy)-8-oxo-eremophil-7(11)-ene
  参考文献：
  名称：

  Medicinal Foodstuffs. XXXII. Novel Sesquiterpene Glycoside Sulfate, Fukinoside A, with Antiallergic Activity from Japanese Butterbur (Petasites japonicus)

  摘要：

  Novel sesquiterpene glycoside sulfate, fukinoside A, was isolated as the potassium salt from the aerial parts of Petasites japonicus. The absolute sterostructure of fukinoside A was elucidated on the basis of chemical and physicochemical evidence. In addition, fukinoside A was found to inhibit release of beta-hexosaminidase, as a marker of antigen-induced degranulation, in RBL-2H3 cells.

  DOI：

  10.3987/com-06-10858

文献信息

• Structures of eremophilane-type sesquiterpene glucosides, alticolosides A–G, from the Far Eastern endemic Ligularia alticola Worosch
  作者：Alexandra S. Silchenko、Anatoly I. Kalinovsky、Ludmila P. Ponomarenko、Sergey A. Avilov、Pelageya V. Andryjaschenko、Pavel S. Dmitrenok、Peter G. Gorovoy、Natalia Yu. Kim、Valentin A. Stonik

  DOI：10.1016/j.phytochem.2014.11.003

  日期：2015.3

  Seven eremophilane-type sesquiterpene glucosides, alticolosides A-G, have been isolated from aerial parts of the endemic Far Eastern species Ligularia alticola Worosch. (Family Asteraceae) along with two known compounds, monoterpenoid glycoside (4S)-alpha-terpineol 8-O-beta-D-glucopyranoside and norditerpenoid glycoside 7(8)-dihydro-beta-ionone 3-O-beta-D-glucopyranoside. Alticoloside D was identified with the earlier known 8-O-(beta-D-glucopyranosyl)-2-oxo-eremophila-1(10),8,11-triene, but the stereostructure of the latter was revised on the basis of ROESY and CD data. All the glycosides are derivatives of new eremophilane-type aglycones, differing from known eremophilanes in details of planar and/or stereo structures except for the aglycone of alticoloside E. (C) 2014 Elsevier Ltd. All rights reserved.