从Piceatannol到电生成的超氧化物中协同的双质子合电子转移在N,N-Dimethylformamide中
Tatsushi Nakayama1, Bunji Uno2
1Gifu Pharmaceutical University, 1-25-4 Daigaku-nishi, Gifu 501-1196, Japan.
ACS omega
|June 17, 2024
概括
皮塞坦诺尔通过一个涉及其甲基醇组的两质子合电子转移机制有效地清除超氧化基离子 (O2•-). 这使得piceatannol与catechol和trans-resveratrol相比,是一种优越的抗氧化剂.
科学领域:
- 电化学 电化学 电化学
- 化学动力学 化学动力学
- 计算化学计算化学
- 抗氧化剂研究 抗氧化剂研究
背景情况:
- 超氧化基离子 (O2•-) 是一种参与氧化应激的活性氧物种.
- 多因其抗氧化特性而闻名,但它们的反应机制需要详细的研究.
- 一种stilbenoid的piceatannol具有独特的catechol部分,这可能会影响其抗氧化能力.
研究的目的:
- 研究piceatannol与电化学生成的超氧化基离子 (O2•-) 的反应性.
- 阐明了电子转移机制,涉及到O2被piceatannol清理.
- 为了比较piceatannol的O2•-清除功效与类似的化合物,如甲基醇和转白醇.
主要方法:
- 循环电压测量用于研究氧化还原行为.
- 在现场控制的电解电位电子自旋共振 (ESR) 用于激素检测.
- 密度函数理论 (DFT) 计算用于机械洞察力.
- 在N,N-二甲基形式胺中进行电化学测量.
主要成果:
- 皮塞坦诺尔通过质子合电子转移与O2发生反应.
- 皮塞坦诺的甲基醇部分对于O2清理至关重要.
- 确定了一种协调的两质子合电子转移 (2PCET) 机制.
- 皮塞坦诺显示出比甲基醇和转白醇更高的O2清除活性.
- 皮塞阿坦诺的斯蒂尔本部分可以提高2PCET速率.
结论:
- 皮塞坦诺尔是一种有效的超氧化基离子的清除剂.
- 通过甲基醇部分的2PCET机制解释了其强大的抗氧化活性.
- 与甲基醇和转白醇相比,Piceatannol表现出优越的O2清理能力.
相关概念视频
¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)
1.0K
When proton-coupled carbon-13 spectra are simplified by a broadband proton decoupling technique, structural information about the coupled protons is lost. Distortionless enhancement by polarization transfer (DEPT) is a technique that provides information on the number of hydrogens attached to each carbon in a molecule. While the DEPT experiment utilizes complex pulse sequences, the pulse delay and flip angle are specifically manipulated. The resulting signals have different phases depending on...
1.0K
Aldehydes and Ketones with Amines: Imine Formation Mechanism
5.4K
Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...
5.4K
Nuclear Overhauser Enhancement (NOE)
665
Irradiation of a spin-active nucleus causes an increase or decrease in the signal intensity of neighboring nuclei that are not necessarily chemically bonded or involved in J-coupling. This phenomenon, called the Nuclear Overhauser Enhancement (NOE), results from through-space interactions between the nuclear spins. The NOE effect decreases with increasing internuclear distance and is generally not observed beyond 4 angstroms. In NOE, dipole-dipole interactions between neighboring...
665
Photochemical Electrocyclic Reactions: Stereochemistry
1.8K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
Selection Rules: Photochemical Activation
1.8K
Oxidation and Reduction of Organic Molecules
6.4K
Energy production within a cell involves many coordinated chemical pathways. Most of these pathways are combinations of oxidation and reduction reactions, which occur at the same time. An oxidation reaction strips an electron from an atom in a compound, and the addition of this electron to another compound is a reduction reaction. Because oxidation and reduction usually occur together, these pairs of reactions are called redox reactions.
The removal of an electron from a molecule, results in a...
The removal of an electron from a molecule, results in a...
6.4K
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
1.7K
Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
1.7K


