1-dehydro-6-gingerdione

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1-dehydro-6-gingerdione
• 英文别名: dehydro-[6]-gingerdione；6-dehydrogingerdione；1-(4-Hydroxy-3-methoxyphenyl)dec-1-ene-3,5-dione；1-(4-hydroxy-3-methoxyphenyl)dec-1-ene-3,5-dione
• 化学式: C₁₇H₂₂O₄
• 分子量: 290.359
• InChiKey: JUKHKHMSQCQHEN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-dehydro-6-gingerdione 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以70%的产率得到姜酮
  参考文献：
  名称：

  Activation of the Phase II Enzymes for Neuroprotection by Ginger Active Constituent 6-Dehydrogingerdione in PC12 Cells

  摘要：

  The cellular endogenous antioxidant system plays pivotal roles in counteracting or retarding the pathogenesis of many neurodegenerative diseases. Molecules with the ability to enhance the antioxidant defense thus are promising candidates for neuroprotective drugs. 6-Dehydrogingerdione (6-DG), one of the major components of dietary ginger, has received increasing attention due to its multiple pharmacological activities. However, how this pleiotropic molecule works on the neuronal system has not been studied. This paper reports that 6-DG efficiently scavenges various free radicals in vitro and displays remarkable cytoprotection against oxidative stress-induced neuronal cell damage in the neuron-like rat pheochromocytoma cell line, PC12 cells. Pretreatment of PC12 cells with 6-DG significantly up-regulates a panel of phase II genes as well as the corresponding gene products, such as glutathione, heme oxygenase, Nad(p)h: quinone oxidoreductase, and thioredoxin reductase. Mechanistic study indicates that activation of the Keap1-Nrf2-ARE pathway is the molecular basis for the cytoprotection of 6-DG. This is the first revelation of this novel mechanism of 6-DG as an Nrf2 activator against oxidative injury, providing the potential therapeutic use of 6-DG as neuroprotective agent.

  DOI：

  10.1021/jf405553v
• 作为产物：
  描述：

  正己酸乙酯 在 boron trioxide 、 异丁胺 、 sodium hydride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 1-dehydro-6-gingerdione
  参考文献：
  名称：

  Activation of the Phase II Enzymes for Neuroprotection by Ginger Active Constituent 6-Dehydrogingerdione in PC12 Cells

  摘要：

  The cellular endogenous antioxidant system plays pivotal roles in counteracting or retarding the pathogenesis of many neurodegenerative diseases. Molecules with the ability to enhance the antioxidant defense thus are promising candidates for neuroprotective drugs. 6-Dehydrogingerdione (6-DG), one of the major components of dietary ginger, has received increasing attention due to its multiple pharmacological activities. However, how this pleiotropic molecule works on the neuronal system has not been studied. This paper reports that 6-DG efficiently scavenges various free radicals in vitro and displays remarkable cytoprotection against oxidative stress-induced neuronal cell damage in the neuron-like rat pheochromocytoma cell line, PC12 cells. Pretreatment of PC12 cells with 6-DG significantly up-regulates a panel of phase II genes as well as the corresponding gene products, such as glutathione, heme oxygenase, Nad(p)h: quinone oxidoreductase, and thioredoxin reductase. Mechanistic study indicates that activation of the Keap1-Nrf2-ARE pathway is the molecular basis for the cytoprotection of 6-DG. This is the first revelation of this novel mechanism of 6-DG as an Nrf2 activator against oxidative injury, providing the potential therapeutic use of 6-DG as neuroprotective agent.

  DOI：

  10.1021/jf405553v

文献信息

• 6-Gingerol-derived semisynthetic analogs mitigate oxidative stress, and reverse acrylamide induced neurotoxicity in zebrafish
  作者：Tamilvelan Manjunathan、Ajay Guru、B. Haridevamuthu、Rambabu Dandela、Jesu Arokiaraj、Pushparathinam Gopinath

  DOI：10.1039/d3nj01004j

  日期：——

  A semisynthetic strategy has been developed for the synthesis of novel 6-gingerol based analogs using simple and robust chemistries. These newer analogs were able to quench ROS and RNS in vitro, and retrieve the oxidative stress induced by acrylamide in zebrafish larvae. They are also capable of restoring the locomotion behavior in zebrafish.

  已经开发出一种半合成策略，用于使用简单而稳健的化学合成新型 6-姜酚基类似物。这些较新的类似物能够在体外淬灭 ROS 和 RNS ，并恢复斑马鱼幼虫中丙烯酰胺诱导的氧化应激。它们还能够恢复斑马鱼的运动行为。
• New Strategies to Improve the Efficiency of Curcumin‐Based Iridium Complexes for OLED Devices
  作者：Valeria Lino、Carmela Tania Prontera、Maria Grazia Maglione、Carmela Borriello、Paolo Tassini、Paola Manini

  DOI：10.1002/ejoc.202400288

  日期：2024.8.5

  OLED devices fabricated by using of a series of iridium(III) complexes featuring natural or nature-inspired β-diketone ligands. This revealed that both luminance, efficiency and power efficiency were strongly influenced by the tendency of the complexes to fo.rm aggregates by π-stacking interactions.

  通过追求结构-性能关系的方法，我们对使用一系列具有天然或自然启发的β-二酮配体的铱(III)配合物制造的OLED器件的性能进行了比较研究。这表明，复合物通过 π 堆积相互作用形成聚集体的趋势强烈影响亮度、效率和功率效率。