11-hydroxydemethyleneberberine

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: 11-hydroxydemethyleneberberine
• 英文别名: 9,10-Dimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-2,3,11-triol；9,10-dimethoxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-7-ium-2,3,11-triol
• 化学式: C₁₉H₁₈NO₅
• 分子量: 340.356
• InChiKey: DHMKLQYEEAWPPI-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  83
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  小檗碱 在 水 、 咪康唑 作用下， 以 aq. phosphate buffer 为溶剂， 反应 11.0h， 生成 11-hydroxydemethyleneberberine
  参考文献：
  名称：

  11-Hydroxylation of Protoberberine by the Novel Berberine-Utilizing Aerobic Bacterium Sphingobium sp. Strain BD3100

  摘要：

  Protoberberine alkaloids, including berberine, palmatine, and berberrubine, are produced by medicinal plants and are known to have various pharmacological effects. We isolated two berberine-utilizing bacteria, Sphingobium sp. strain BD3100 and Rhodococcus sp. strain BD7100, from soil collected at a natural medicine factory. BD3100 had the unique ability to utilize berberine or palmatine as the sole carbon and energy source. BD3100 produced demethyleneberberine in berberine-supplemented medium. In a resting-cell incubation with berberine, BD3100 produced 11-hydroxyberberine; the structure of 11-hydroxyberberine was determined by detailed analysis of NMR and MS spectroscopic data. alpha-Naphthoflavone, miconazole, and ketoconazole, which are known inhibitors of cytochrome P450, interfered with BD3100 metabolism of berberine in resting cells. Inhibition by miconazole led to the production of a new compound, 11-hydroxydemethyleneberberine. In a resting-cell incubation with palmatine, BD3100 generated 11-hydroxypalmatine. This work represents the first report of the isolation and characterization of novel berberine-utilizing aerobic bacteria for the production of 11-hydroxylation derivatives of berberine and palmatine.

  DOI：

  10.1021/acs.jnatprod.5b00408

文献信息

• 11-Hydroxylation of Protoberberine by the Novel Berberine-Utilizing Aerobic Bacterium <i>Sphingobium</i> sp. Strain BD3100
  作者：Hisashi Takeda、Kazuki Ishikawa、Daigo Wakana、Masao Fukuda、Fumihiko Sato、Tomoo Hosoe

  DOI：10.1021/acs.jnatprod.5b00408

  日期：2015.12.24

  Protoberberine alkaloids, including berberine, palmatine, and berberrubine, are produced by medicinal plants and are known to have various pharmacological effects. We isolated two berberine-utilizing bacteria, Sphingobium sp. strain BD3100 and Rhodococcus sp. strain BD7100, from soil collected at a natural medicine factory. BD3100 had the unique ability to utilize berberine or palmatine as the sole carbon and energy source. BD3100 produced demethyleneberberine in berberine-supplemented medium. In a resting-cell incubation with berberine, BD3100 produced 11-hydroxyberberine; the structure of 11-hydroxyberberine was determined by detailed analysis of NMR and MS spectroscopic data. alpha-Naphthoflavone, miconazole, and ketoconazole, which are known inhibitors of cytochrome P450, interfered with BD3100 metabolism of berberine in resting cells. Inhibition by miconazole led to the production of a new compound, 11-hydroxydemethyleneberberine. In a resting-cell incubation with palmatine, BD3100 generated 11-hydroxypalmatine. This work represents the first report of the isolation and characterization of novel berberine-utilizing aerobic bacteria for the production of 11-hydroxylation derivatives of berberine and palmatine.