3-(3-hydroxy-4,4-dimethyl-3,4-dihydro-2H-[1,4]dioxepino[2,3-g]benzofuran-6-yl)propanoic acid | 1428263-45-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-(3-hydroxy-4,4-dimethyl-3,4-dihydro-2H-[1,4]dioxepino[2,3-g]benzofuran-6-yl)propanoic acid
• CAS: 1428263-45-9
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: KGODBZJNNBNMFP-UHFFFAOYSA-N

物化性质

• 沸点：
  486.3±45.0 °C(Predicted)
• 密度：
  1.318±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.36
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  89.13
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  欧前胡素 在 Penicillium janthinellum AS 、 liquid potato medium 作用下， 以 丙酮 为溶剂， 反应 120.0h， 以1%的产率得到3-(7-(2,3-dihydroxy-3-methylbutoxy)-6-hydroxybenzofuran-5-yl)propanoic acid
  参考文献：
  名称：

  Biotransformation of imperatorin by Penicillium janthinellum. Anti-osteoporosis activities of its metabolites

  摘要：

  Imperatorin (IMP) is a major constituent of many herbal medicines and possesses anti-osteoporosis activity. The present research work aimed to study the biotransformation processes of IMP and evaluated the anti-osteoporosis activity of the transformed metabolites. Among 18 strains of filamentous fungi screened, Penicillium janthinellum AS 3.510 exhibited good capability to metabolise IMP to the new derivatives. Ten transformed products were isolated and purified, and their structures were identified accurately based on spectroscopic data. Eight metabolites (2-8 and 10) were novel and previously unreported. The major biotransformation reactions involved hydroxylation of the prenyloxy side-chain and the lactone ring-opening reaction of furocoumarin skeleton. In addition, anti-osteoporosis activities of all products (1-10) were evaluated using MC3T3-E1 cells. The results showed that products 5 and 8 had the best bioactivities in increasing MC3T3-E1 cell growth. These products could be used in future therapeutic regimens for treating osteoporosis. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.foodchem.2012.11.138