2-methyl-L-erythritol-1-O-(6-O-trans-sinapoyl)-β-D-glucopyranoside

• 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: 2-methyl-L-erythritol-1-O-(6-O-trans-sinapoyl)-β-D-glucopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-[(2R,3S)-2,3,4-trihydroxy-2-methylbutoxy]oxan-2-yl]methyl (E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate
• 化学式: C₂₂H₃₂O₁₃
• 分子量: 504.488
• InChiKey: BPDKEJSAHDRLIA-FYZWRTOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  205
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2-methyl-L-erythritol-1-O-(6-O-trans-sinapoyl)-β-D-glucopyranoside 在 盐酸 、 水 作用下， 反应 2.0h， 生成 葡萄糖
  参考文献：
  名称：

  2-Methyl-l-erythritol glycosides from Gardenia jasminoides

  摘要：

  Two new glycosides, 2-methyl-L-erythritol-4-O-(6-O-trans-sinapoyl)-beta-D-glucopyranoside (1) and 2-methyl-L-erythritol-1-O-(6-O-trans-sinapoyl)-beta-D-glucopyranoside (2), along with two known triterpenoids (3-4), four quinic add derivatives (5-8) and one flavonoid (9) were isolated from the fruit of Gardenia jasminoides. Their structures were elucidated through MS and 2D NMR experiments (HMQC and HMBC). Inhibitory effects of the isolated compounds on nitric oxide production in lipopolysaccharide-activated macrophages were evaluated. Though 2-methyl-D-erythritol and its glycosides have been reported in a few references, this is the first report about 2-methyl-L-erythritol glycosides. Based on this finding, we propose that 2-methyl-L-erythritol might be a new intermediate in the non-mevalonate biosynthesis of terpenoids. (c) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2013.05.018