姜酮 | 61871-71-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 姜酮
• 中文别名: 姜辣二酮
• 英文名称: [6]-gingerdione
• 英文别名: <6>-gingerdione；gingerdione；1-(4-hydroxy-3-methoxyphenyl)decane-3,5-dione
• CAS: 61871-71-4
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: KMNVXQHNIWUUSE-UHFFFAOYSA-N

物化性质

• LogP：
  3.537 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 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：

  姜酮 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 生成 <6>-dehydrogingerdione
  参考文献：
  名称：

  Kato, Nobuharu; Hamada, Yasumasa; Shioiri, Takayuki, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 4, p. 1679 - 1682

  摘要：

  DOI：
• 作为产物：
  描述：

  姜酮 在 盐酸 、 六甲基二硅氮烷 、 lithium hexamethyldisilazane 、 苯酚 作用下， 以 苯 为溶剂， 反应 1.5h， 生成 姜酮
  参考文献：
  名称：

  通过区域选择性羟醛缩合合成（±）-[ n ] -姜油（姜的辛辣成分）和相关化合物：相对辛辣测定

  摘要：

  已发现在–78°C下用二异丙基氨基锂对三甲基甲硅烷基姜油酮（13）进行质子选择性（92：8，以取代基较少的烯酸酯为佳）：将阴离子与链烷烃和酰基咪唑缩合，以方便地合成（±）-[2]-[10]-和-[12]-姜醇（1）和[4]-，[6]-和[8]-姜二酮（9）。同样，3-甲氧基-4-三甲基甲硅烷基氧苄叉基丙酮（17）给出了（±）-[2]-[10]-脱氢姜油酚（8）和[4]-，[6]-和[8]-脱氢姜二酮（10）。 。

  DOI：

  10.1039/p19810000082

文献信息

• 6‐Gingerol and Semisynthetic 6‐Gingerdione Counteract Oxidative Stress Induced by ROS in Zebrafish
  作者：Tamilvelan Manjunathan、Ajay Guru、Jesu Arokiaraj、Pushparathinam Gopinath

  DOI：10.1002/cbdv.202100650

  日期：2021.12

  treated zebrafish larvae groups (96hpf) were exposed to compounds 1, 7 and 8, it increases the SOD (19, 19.1 and 18.7 U/mg protein), CAT (18.1, 16.5, and 15.8 μmol/mg levels and decreases the lipid peroxidation level (13, 15 and 18 nmol/mg protein), respectively. In vivo ROS levels and degree of cell death were studied using DCFDA and Acridine orange assays. Compounds 1, 7 and 8 decreases the ROS and cell

  6-姜酚 ( 1 ) 是生姜的主要成分之一，开发新的合成方法可以带来具有改进治疗特性的半合成类似物。为此，通过简单而稳健的萃取，然后进行柱纯化，优化了具有优异纯度的 6-姜酚的多克规模分离。然后首次通过选择性-OTBDMS保护、DMP氧化和脱保护反应序列从6-姜酚合成6-姜二酮, 7 。化合物1、7和8 （脱氢姜酮）在 DPPH、ABTS、超氧自由基清除测定和 H 2 O 2测定中在 10–50 μM 浓度下表现出优异的无细胞抗氧化特性。溶血研究表明，在浓度高达 50 μM 时，所有三种化合物均不会对人类红细胞表现出毒性。当 H 2 O 2处理的斑马鱼幼虫组（96hpf）暴露于化合物1 、 7和8时，SOD（19、19.1 和 18.7 U/mg 蛋白质）、CAT（18.1、16.5 和 15.8 μmol/mg 水平）增加使用DCFDA和吖啶橙测定法分别研究了体内ROS水平和细胞死亡程度
• 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。
• Activation of the Phase II Enzymes for Neuroprotection by Ginger Active Constituent 6-Dehydrogingerdione in PC12 Cells
  作者：Juan Yao、Chunpo Ge、Dongzhu Duan、Baoxin Zhang、Xuemei Cui、Shoujiao Peng、Yaping Liu、Jianguo Fang

  DOI：10.1021/jf405553v

  日期：2014.6.18

  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.
• MIDDLEDITCH, B. S.;JOHNSON, G. A.;GREGORY, R. R.;ALEJANDRO, M. A.;MARKAVE+, J. HIGH RESOLUT. CHROMATOGR., 12,(1989) N0, C. 677-679
  作者：MIDDLEDITCH, B. S.、JOHNSON, G. A.、GREGORY, R. R.、ALEJANDRO, M. A.、MARKAVE+

  DOI：——

  日期：——
• BIOAVAILABILITY ENHANCING COMPOUND
  申请人：Warnock W. Matthew

  公开号：US20120263808A1

  公开（公告）日：2012-10-18

  For enhancing bioavailability, a composition is administered comprising a Transient Receptor Potential cation channel subfamily V member 1 (TRPV1) agonist with a combined Scoville Heat Unit (SHU) milligram (mg) dose in the range of 280,000 to 400,000 SHU mg.