L-ergothioneine disulfide | 33605-54-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: L-ergothioneine disulfide
• CAS: 33605-54-8
• 化学式: C₁₈H₂₈N₆O₄S₂
• 分子量: 456.59
• InChiKey: VTVISAVQEMOKMM-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.33
• 重原子数：
  30.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  137.62
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  麦角硫因 在 甲酸 、 copper(II) sulfate 作用下， 反应 0.5h， 生成 L-ergothioneine disulfide
  参考文献：
  名称：

  Dietary Sources and Antioxidant Effects of Ergothioneine

  摘要：

  Ergothioneine is a native membrane-impermeable thiol compound that is specifically accumulated in cells via the organic cation transporter OCTN1. In humans, OCTN1 and ergothioneine have been implicated in the etiopathogenesis of autoimmune disorders. However, available evidence about dietary sources and the functional role of ergothioneine in human physiology is scarce. Here, we analyzed the ergothioneine content in common foods using liquid chromatography tandem-mass spectrometry. Additionally, we assessed the protective potency of ergothioneine against various oxidative stressors in OCTN1-expressing cells in comparison with the main intracellular thiol antioxidant glutathione by evaluating cell viability with the MTT reduction assay. Only some food contained ergothioneine with highest concentrations detected in specialty mushrooms, kidney, liver, black and red beans, and oat bran. Ergothioneine exhibited cell protection only against copper(II)-induced toxicity but was far less potent than glutathione, indicting that ergothioneine is not involved in the intracellular antioxidant thiol defense system.

  DOI：

  10.1021/jf071328f