2S,4S,5R,7R,8R,11R-2-hydroxyeremophil-1(10)-en-12,8-olide | 1425376-83-5

• 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: 2S,4S,5R,7R,8R,11R-2-hydroxyeremophil-1(10)-en-12,8-olide
• 英文别名: sibiriolide C；Racemosalactone E；(3R,3aR,4aR,5S,7S,9aR)-7-hydroxy-3,4a,5-trimethyl-3,3a,4,5,6,7,9,9a-octahydrobenzo[f][1]benzofuran-2-one
• CAS: 1425376-83-5
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: XZQRUWPDGTZJEB-ROTUKVCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-α-甲氧基-α-(三氟甲基)苯乙酸 、 2S,4S,5R,7R,8R,11R-2-hydroxyeremophil-1(10)-en-12,8-olide 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以3.5 mg的产率得到2S,7R,8R,11R-2-hydroxyeremophil-1(10)-en-12,8-olide-2-O-(S)-MTPA ester
  参考文献：
  名称：

  Sesquiterpene lactones from the aerial parts of Xanthium sibiricum and their cytotoxic effects on human cancer cell lines

  摘要：

  The EtOH extract of the aerial parts of Xanthium sibiricum afforded six sesquiterpene lactones (STLs), including two new eremophilanolides. The structures of the new compounds were established on the basis of spectroscopic methods and the modified Mosher's method to be the C-11 epimers of 2S,4S,5R,7R,8R-2-hydroxy-eremophil-1(10)-en-12,8-olide [11R: 1 (sibiriolide C); 11S: 2 (sibiriolide D)]. The isolated compounds were evaluated for their in vitro cytotoxicities against five human cancer cell lines (Huh-7 hepatocarcinoma, KB nasopharynx carcinoma, Jurkat T cell lymphoblast, BGC-823 and KE-97 gastric carcinoma) using the CellTiter-Glo (TM) luminescent cell viability assay method. Compounds 4-6, each possessing an a-methylene-g-lactone moiety, were found to have noteworthy cytotoxic effects with IC50 values ranging from 1.1 to 18.0 mu M. (C) 2012 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.phytol.2012.07.008