orostachyscerebroside A | 1355694-62-0

• 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: orostachyscerebroside A
• CAS: 1355694-62-0
• 化学式: C₅₀H₉₁NO₁₀
• 分子量: 866.273
• InChiKey: MFHOFLFNMOCXFQ-OITXLTTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.56
• 重原子数：
  61.0
• 可旋转键数：
  40.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  189.17
• 氢给体数：
  8.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 orostachyscerebroside A 在 盐酸 作用下， 反应 18.0h， 生成
  参考文献：
  名称：

  Glycolipids from the aerial parts of Orostachys japonicus with fatty acid synthase inhibitory and cytotoxic activities

  摘要：

  Inhibition of fatty acid synthase (FAS) has been proposed as a new therapeutic target for the treatment of cancer. In our preliminary study, a MeOH extract of the aerial parts of Orostachys japonicus A. Berger (Crassulaceae) inhibited FAS activity (>95% inhibition at 62.5 mu g/mL). Through bioassay-guided fractionation, we isolated three cerebrosides (1-3), including one new compound (1), and seven glyceroglycolipids (4-10) from a FAS inhibitory hexane-soluble fraction of the MeOH extract of O. japonicus. On the basis of physicochemical and spectroscopic analyses including 10 and 20 NMR, HRFABMS, and ESIMS/MS, the structure of the new compound 1 was 1-O-(beta-D-glucopyranosyl)-(2S,3S,4R,6Z,10E)-2-[(2'R,6'Z,9'Z)-2-hydroxyeicosa-6',9'-dienoylamino)]-1,3,4-trihydroxytetracosa-6,10-diene, and it was named orostachyscerebroside A. Compounds 1-10 were tested for their in vitro FAS inhibitory activity, and compounds 1, 4, 5, 6, 7, and 8 inhibited the enzyme with micro-molar IC50 values both in the incorporation of [H-3] acetyl CoA (from 52.2 to 108.0 mu M) and in the oxidation of NADPH (from 19.5 to 30.3 mu M). Interestingly, compounds 1, 4, 5, 6, 7, and 8 with FAS inhibitory activity showed cytotoxic activity against HL-60 (human leukemia) and A549 (human lung adenocarcinoma) cancer cells, while none of them displayed cytotoxicity against MCF-7 (human breast adenocarcinoma) cells. This is the first report on the inhibition of FAS by glycolipids from O. japonicus and their cytotoxic activity and may provide a scientific basis for the folk remedy using the plant to treat cancer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2011.09.058