(4R,5R,6R,8R)-4-hydroxy-2-(hydroxymethyl)-8-methyl-9-oxo-11-oxatricyclo[6.2.1.0^1,5]undec-2-en-6-yl (2E)-2-methylbut-2-enoate | 1492981-23-3

• 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: (4R,5R,6R,8R)-4-hydroxy-2-(hydroxymethyl)-8-methyl-9-oxo-11-oxatricyclo[6.2.1.0^1,5]undec-2-en-6-yl (2E)-2-methylbut-2-enoate
• 英文别名: [(1R,4R,5R,6R,8R)-4-hydroxy-2-(hydroxymethyl)-8-methyl-9-oxo-11-oxatricyclo[6.2.1.01,5]undec-2-en-6-yl] (E)-2-methylbut-2-enoate
• CAS: 1492981-23-3
• 化学式: C₁₇H₂₂O₆
• 分子量: 322.358
• InChiKey: CTKLVKWVJNHUGO-PQXKERBESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (Z)-2-甲基-2-丁烯酸(3aR,4R,6R,10Z,11aR)-2,3,3a,4,5,6,7,11alpha-八氢-10-羟基甲基-6-甲基-3-亚甲基-2,7-二氧代-6,9-环氧环癸并[b]呋喃-4-基酯 在 Aspergillus terreus (soil fungi) 作用下， 以 二甲基亚砜 为溶剂， 反应 144.0h， 以1%的产率得到(4R,5R,6R,8R)-4-hydroxy-2-(hydroxymethyl)-8-methyl-9-oxo-11-oxatricyclo[6.2.1.0^1,5]undec-2-en-6-yl (2Z)-2-methylbut-2-enoate
  参考文献：
  名称：

  Unusual biotransformation products of the sesquiterpene lactone budlein A by Aspergillus species

  摘要：

  Biotransformation of chemicals by microorganisms can be effective in increasing chemical diversity. Some fungi have been described to be useful for the biotransformation of sesquiterpene lactones. Nevertheless, in most cases, only minor or simple transformations of functional groups have been observed. Budlein A is a sesquiterpene lactone found in high amounts in American sunflower-like species of the genus Viguiera (Asteraceae). It shows important biological effects like in vitro and in vivo anti-inflammatory activity, as well as cytotoxicity against cancer cell lines. With the aim to obtain potentially bioactive derivatives of budlein A and taking into account that obtaining semi-synthetic analogues is a very complex task, the capability of soil fungi to promote biotransformation was investigated. In this work, the biotransformation of budlein A by the soil fungi Aspergillus terreus and A. niger affording three unusual sesquiterpenoid derivatives with carbon skeletons is reported. The chemical structures of the compounds were elucidated by 1D and 2D NMR spectrometry and HR-ESI-MS. The stereochemistry and molecular conformation of one derivative was assessed by molecular modeling techniques. The fungal metabolites displayed a reduced cytotoxicity against HL-60 cells when compared to the original natural product. The results show the versatility of microbial-catalyzed biotransformations leading to unusual derivatives. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.09.022