2β-hydroxyfukinone | 35945-75-6

• 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: 2β-hydroxyfukinone
• 英文别名: 2-hydroxyfukinone；(4aR,5S,7R,8aR)-7-hydroxy-4a,5-dimethyl-3-propan-2-ylidene-4,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one
• CAS: 35945-75-6
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: YIVBFYZTSPNDJU-FUTJPDQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 2β-hydroxyfukinone 以 氘代吡啶 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Structures of eremophilane-type sesquiterpene glucosides, alticolosides A–G, from the Far Eastern endemic Ligularia alticola Worosch

  摘要：

  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.

  DOI：

  10.1016/j.phytochem.2014.11.003
• 作为产物：
  描述：

  (2R,4S,5R,10R)-2-(β-D-glucopyranosyloxy)-8-oxo-eremophil-7(11)-ene 在 盐酸 作用下， 反应 3.0h， 以84%的产率得到2β-hydroxyfukinone
  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

• THE STRUCTURES OF EREMOFUKINONE, 9-ACETOXYFUKINANOLIDE AND S-JAPONIN FROM<i>PETASITES JAPONICUS</i>MAXIM
  作者：Keizo Naya、Masao Kawai、Masami Naito、Tsuneo Kasai

  DOI：10.1246/cl.1972.241

  日期：1972.3.5

  This paper deals with the structural determination of three new sesquiterpenes, eremofukinone (I), 9-acetoxyfukinanolide (II) and S-japonin (III), which were isolated from Petasites japonicus Maxim.

  本文讨论了从Petasites japonicus Maxim中分离出的三种新的倍半萜类化合物（eremofukinone (I)、9-acetoxyfukinanolide (II)和S-japonin (III)）的结构测定。
• Medicinal Foodstuffs. XXXII. Novel Sesquiterpene Glycoside Sulfate, Fukinoside A, with Antiallergic Activity from Japanese Butterbur (Petasites japonicus)
  作者：Masayuki Yoshikawa、Toshio Morikawa、Junji Tanaka、Hiroshi Shimoda

  DOI：10.3987/com-06-10858

  日期：——

  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.
• 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.