(2'R,3'R,6'R)-7-(2',3'-dihydroxy-6',7'-epoxy-3',7'-dimethyloctyloxy)-6,8-dimethoxycoumarin | 1388627-68-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: (2'R,3'R,6'R)-7-(2',3'-dihydroxy-6',7'-epoxy-3',7'-dimethyloctyloxy)-6,8-dimethoxycoumarin
• 英文别名: altissimacoumarin E；7-[(2R,3R)-5-[(2R)-3,3-dimethyloxiran-2-yl]-2,3-dihydroxy-3-methylpentoxy]-6,8-dimethoxychromen-2-one
• CAS: 1388627-68-6
• 化学式: C₂₁H₂₈O₈
• 分子量: 408.449
• InChiKey: BANQKNDBYSHYOO-VTJXTGGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2'R,3'R,6'R)-7-(2',3'-dihydroxy-6',7'-epoxy-3',7'-dimethyloctyloxy)-6,8-dimethoxycoumarin 、 甲氧基-三氟甲基苯 在 吡啶 作用下， 反应 3.0h， 以0.7 mg的产率得到[(2R,3R)-1-(6,8-dimethoxy-2-oxochromen-7-yl)oxy-5-[(2R)-3,3-dimethyloxiran-2-yl]-3-hydroxy-3-methylpentan-2-yl] (2R)-3,3,3-trifluoro-2-methoxy-2-phenylpropanoate
  参考文献：
  名称：

  Terpenylated Coumarins As SIRT1 Activators Isolated from Ailanthus altissima

  摘要：

  Four new terpenylated coumarins (1-4) were isolated from the stem bark of Ailanthus altissima by bioactivity-guided fractionation using an in vitro SIRT1 deacetylation assay. Their structures were identified as (2'R,3'R)-7-(2',3'-dihydroxy-3',7'-dimethylocta-6'-enyloxy)-6,8-dimethoxycoumarin (1), 6,8-dimethoxy-7-(3',7'-dimethylocta-2',6'-dienyloxy)coumarin (2), (2'R,3'R,6'R)-7-(2',3'-dihydroxy-6',7'-epoxy-3',7'-dimethyloctaoxy)-6,8-dimethoxycoumarin (3), and (2'R,3'R,4'S,5'S)-6,8-dimethoxy-7-(3',7'-dimethyl-4',5'-epoxy-2'-hydroxyocta-6'-enyloxy)coumarin (4). Compounds 1-4 strongly enhanced SIRT1 activity in an in vitro SIRT1-NAD/NADH assay and an in vivo SIRT1-p53 luciferase assay. These compounds also increased the NAD-to-NADH ratio in HEK293 cells. The present results suggest that terpenylated coumarins from A. altissima have a direct stimulatory effect on SIRT1 deacetylation activity and may serve as lead molecules for the treatment of some age related disorders.

  DOI：

  10.1021/np300258u