glomeraside F | 1401233-66-6

• 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: glomeraside F
• 英文别名: (1R,3R,16R,17S,18S,19R)-17,18,19-trihydroxy-3-undecyl-2,14,20-trioxabicyclo[14.3.1]icosan-13-one
• CAS: 1401233-66-6
• 化学式: C₂₈H₅₂O₇
• 分子量: 500.717
• InChiKey: BMXOGZXPEJQXNB-PUMRMUNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  glomeraside F 、 乙酸酐 在 吡啶 作用下， 生成
  参考文献：
  名称：

  Cyclic glycolipids from glandular trichome exudates of Cerastium glomeratum

  摘要：

  Fourteen cyclic glycolipids, named glomerasides A-N, have been isolated from the glandular trichome exudate of Cerastium glomeratum (Caryophyllaceae). Their structures were determined by spectroscopic analysis of the glycolipids, as well as by application of the Ohrui-Akasaka method to the fatty acid methyl esters derived from the glycolipids and GCMS studies of trimethylsilyl ether derivatives of the methyl esters. The various glomerasides have a glycosidic linkage between the anomeric hydroxy group of the glucose and the C-11, C-10 or C-9 positions of the docosanoyl moiety. They also contained an ester linkage between the C-6 hydroxy group of the glucose ring and the carboxyl group of the oxygenated fatty acid to form their macrocyclic structures. The glucose moiety was optionally acetylated and/or malony-lated at the C-2 or C-3 hydroxy groups. Among these compounds, the 1,6'-cyclic ester of 11(R)-(2-O-acetyl-beta-D-glucopyranosyloxy)docosanoic acid (glomeraside D) was the most abundant (25%). (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2012.07.001

文献信息

• Cyclic glycolipids from glandular trichome exudates of Cerastium glomeratum
  作者：Teigo Asai、Yuki Nakamura、Yui Hirayama、Kiyoshi Ohyama、Yoshinori Fujimoto

  DOI：10.1016/j.phytochem.2012.07.001

  日期：2012.10

  Fourteen cyclic glycolipids, named glomerasides A-N, have been isolated from the glandular trichome exudate of Cerastium glomeratum (Caryophyllaceae). Their structures were determined by spectroscopic analysis of the glycolipids, as well as by application of the Ohrui-Akasaka method to the fatty acid methyl esters derived from the glycolipids and GCMS studies of trimethylsilyl ether derivatives of the methyl esters. The various glomerasides have a glycosidic linkage between the anomeric hydroxy group of the glucose and the C-11, C-10 or C-9 positions of the docosanoyl moiety. They also contained an ester linkage between the C-6 hydroxy group of the glucose ring and the carboxyl group of the oxygenated fatty acid to form their macrocyclic structures. The glucose moiety was optionally acetylated and/or malony-lated at the C-2 or C-3 hydroxy groups. Among these compounds, the 1,6'-cyclic ester of 11(R)-(2-O-acetyl-beta-D-glucopyranosyloxy)docosanoic acid (glomeraside D) was the most abundant (25%). (C) 2012 Elsevier Ltd. All rights reserved.