dehydromonacolin J

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: dehydromonacolin J
• 英文别名: (2R)-2-[2-[(1S,2S,6R,8S,8aR)-8-hydroxy-2,6-dimethyl-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]ethyl]-2,3-dihydropyran-6-one
• 化学式: C₁₉H₂₆O₃
• 分子量: 302.414
• InChiKey: LSAZKJJZGURZQL-JWCZRKTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 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：

  dehydromonacolin J 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以6 mg的产率得到dehydromonacolin N
  参考文献：
  名称：

  Cytotoxic Dehydromonacolins from Red Yeast Rice

  摘要：

  Two new dehydromonacolins (1 and 3), together with nine known monacolins (4-12), were isolated from red yeast rice. Compounds 4-6 were isolated from a natural resource for the first time. Their structures were elucidated by means of NMR and mass spectroscopic analyses. The structure of dehydromonacolin N (1) was further confirmed by its semisynthesis from monacolin K (lovastatin) (11). Dehydromonacolin J (2), an intermediate in the semisynthesis of 1, was obtained as a new dehydromonacolin. The structure of dehydromonacolin L (3) was also confirmed by an elimination reaction of monacolin L (12). Compound 1, possessing a C2 side chain, is unprecedented in the natural monacolin family and exhibited moderate cytotoxic activity against Hep G2, Caco-2, and MCF-7 cancer cell lines. Dehydromonacolin K (8) demonstrated the most potent cytotoxicity to all three of these cell lines. The structure activity relationship of natural and synthesized monacolins was discussed. This is the first report on the cytotoxic effects of dehydromonacolins.

  DOI：

  10.1021/jf203579f
• 作为产物：
  描述：

  洛伐他汀 在 甲基磺酰氯 、 三乙胺 、 lithium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成 dehydromonacolin J
  参考文献：
  名称：

  Cytotoxic Dehydromonacolins from Red Yeast Rice

  摘要：

  Two new dehydromonacolins (1 and 3), together with nine known monacolins (4-12), were isolated from red yeast rice. Compounds 4-6 were isolated from a natural resource for the first time. Their structures were elucidated by means of NMR and mass spectroscopic analyses. The structure of dehydromonacolin N (1) was further confirmed by its semisynthesis from monacolin K (lovastatin) (11). Dehydromonacolin J (2), an intermediate in the semisynthesis of 1, was obtained as a new dehydromonacolin. The structure of dehydromonacolin L (3) was also confirmed by an elimination reaction of monacolin L (12). Compound 1, possessing a C2 side chain, is unprecedented in the natural monacolin family and exhibited moderate cytotoxic activity against Hep G2, Caco-2, and MCF-7 cancer cell lines. Dehydromonacolin K (8) demonstrated the most potent cytotoxicity to all three of these cell lines. The structure activity relationship of natural and synthesized monacolins was discussed. This is the first report on the cytotoxic effects of dehydromonacolins.

  DOI：

  10.1021/jf203579f

文献信息

• [EN] METHODS FOR MAKING SIMVASTATIN AND INTERMEDIATES<br/>[FR] PROCEDES POUR FABRIQUER LA SIMVASTATINE ET LEURS INTERMEDIAIRES
  申请人：DIVERSA CORP

  公开号：WO2005040107A3

  公开（公告）日：2009-02-12
• Cytotoxic Dehydromonacolins from Red Yeast Rice
  作者：Lin Zhu、Lee-Fong Yau、Jing-Guang Lu、Guo-Yuan Zhu、Jing-Rong Wang、Quan-Bin Han、Wen-Luan Hsiao、Zhi-Hong Jiang

  DOI：10.1021/jf203579f

  日期：2012.2.1

  Two new dehydromonacolins (1 and 3), together with nine known monacolins (4-12), were isolated from red yeast rice. Compounds 4-6 were isolated from a natural resource for the first time. Their structures were elucidated by means of NMR and mass spectroscopic analyses. The structure of dehydromonacolin N (1) was further confirmed by its semisynthesis from monacolin K (lovastatin) (11). Dehydromonacolin J (2), an intermediate in the semisynthesis of 1, was obtained as a new dehydromonacolin. The structure of dehydromonacolin L (3) was also confirmed by an elimination reaction of monacolin L (12). Compound 1, possessing a C2 side chain, is unprecedented in the natural monacolin family and exhibited moderate cytotoxic activity against Hep G2, Caco-2, and MCF-7 cancer cell lines. Dehydromonacolin K (8) demonstrated the most potent cytotoxicity to all three of these cell lines. The structure activity relationship of natural and synthesized monacolins was discussed. This is the first report on the cytotoxic effects of dehydromonacolins.