shikometabolin A

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: shikometabolin A
• 化学式: C₃₂H₂₈O₉
• 分子量: 556.569
• InChiKey: FOBNXANLUWKAKZ-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.21
• 重原子数：
  41.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  172.59
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  紫草素 以 二甲基亚砜 为溶剂， 反应 72.0h， 以0.35%的产率得到metaboshikonin II
  参考文献：
  名称：

  Biotransformation of shikonin by human intestinal bacteria

  摘要：

  The bacterial transformation of shikonin (1) in culture media has been investigated using human intestinal bacteria. Of 24 anaerobes tested, Bacteroides fragilis subsp. thetaotus showed an ability to transform 1 extensively to ten metabolites, five monomers; anhydroalkannin (2), deoxyshikonin (3), cycloshikonin (4), metaboshikonin I (5) and II (6), and five dimers; shikometabolins A (7), B (8), C (9), D (10) and E (11), after anaerobic incubation for 3 days. The structures of these metabolites were determined mainly by 2D-NMR including the INADEQUATE experiment.

  DOI：

  10.1016/s0040-4020(01)81108-x

文献信息

• Shikometabolins A, B, C and D, novel dimeric naphthoquinone metabolites obtained from shikonin by human intestinal bacteria
  作者：Meselhy R. Meselhy、Shigetoshi Kadota、Koji Tsubono、Akihiko Kusai、Masao Hattori、Tsuneo Namba

  DOI：10.1016/s0040-4039(00)75844-8

  日期：1994.1

  Shikometabolins A (2), B (3), C (4) and D (5), four novel naphthoquinone dimers, have been isolated after anaerobic incubation of shikonin (1) with Bacteroides fragillis subsp. thetaotus, and their structures have been determined by means of 2-D NMR spectroscopy including INADEQUATE experiments.
• Biotransformation of shikonin by human intestinal bacteria
  作者：Meselhy R. Meselhy、Shigetoshi Kadota、Koji Tsubono、Masao Hattori、Tsuneo Namba

  DOI：10.1016/s0040-4020(01)81108-x

  日期：1994.3

  The bacterial transformation of shikonin (1) in culture media has been investigated using human intestinal bacteria. Of 24 anaerobes tested, Bacteroides fragilis subsp. thetaotus showed an ability to transform 1 extensively to ten metabolites, five monomers; anhydroalkannin (2), deoxyshikonin (3), cycloshikonin (4), metaboshikonin I (5) and II (6), and five dimers; shikometabolins A (7), B (8), C (9), D (10) and E (11), after anaerobic incubation for 3 days. The structures of these metabolites were determined mainly by 2D-NMR including the INADEQUATE experiment.