Dihydrogenistein (enol), TMS

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: Dihydrogenistein (enol), TMS
• 英文别名: trimethyl-[4-[4,5,7-tris(trimethylsilyloxy)-2H-chromen-3-yl]phenoxy]silane
• 化学式: C₂₇H₄₄O₅Si₄
• 分子量: 560.985
• InChiKey: LWULGJNSVIZUIP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.44
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  染料木素 在 葡萄糖 作用下， 以 aq. phosphate buffer 、 二甲基亚砜 、 甘油 为溶剂， 反应 3.08h， 生成 Dihydrogenistein (enol), TMS
  参考文献：
  名称：

  Biosynthesis of (−)-5-Hydroxy-equol and 5-Hydroxy-dehydroequol from Soy Isoflavone, Genistein Using Microbial Whole Cell Bioconversion

  摘要：

  Equols are isoflavandiols formed by reduction of soy isoflavones such as daidzein and genistein by gut microorganisms. These phytoestrogens are of interest for their various biological effects. We report biosynthesis from genistein to (-)-5-hydroxy-equol in recombinant E. coli expressing three reductases (daidzein reductase DZNR, dihidroclaidzein reductaier DHDR, tetrahydrodaidzein reductase THDR) and a racemase (dihydrodaidzein racemase, DDRC) originating from the Or, bacterium, Slackia isoflavoniconvertens. The biosynthesized 5-hydroxy4equol proved as an optically negative enantioiner,, none-theless it displayed an inverse Circular dichroism spectrum to (S)-equol. Compartmentalized expression of DZNR and DDRC in one E. coli strain and DHDR and THDR in another increased the yield, to 230 mg/L and the productivity to 38 mg/L/h. If the last reductase was Missing, the intermediate spontaneously dehydrated to 5-hydroxy-dehydroequol in up to 99 mg/L This novel isoflavene, previously not known to be synthesized in nature, was also detected in this biotransformation system:, Although (S)-equol favors binding to human estrogen receptor (hER) beta over,hER alpha, (-)-5-hydroxy-equol showed the opposite preference. This study provides elucidation of the biosynthetic route of (-)-5-hydroxy-equol and measurement of its potent antagonistic character as a phytoestrogen for the first time.

  DOI：

  10.1021/acschembio.7b00624