On the hydroperoxyl radical scavenging activity of estrogens in lipid and aqueous media: A theoretical study

IF 1.9 4区 化学 Q2 CHEMISTRY, ORGANIC
María F. Hernández-Hernández, Eduardo A. Tejeda-Medina, César Espinoza, Manuel E. Medina
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Abstract

Despite the evidence on the antioxidant capability of estrogens, little is known about their reaction mechanism involved. According to the above, this work was carried out on the hydroperoxyl radical scavenging activity of three estrogens—estriol (EST), estradiol (ESD), and estrone (ESO)—in lipid and aqueous media by theoretical methodologies employing the DFT. In lipid and aqueous media, hydrogen transfer was the main reaction mechanism on the hydroperoxyl radical scavenging of EST, ESD, and ESO. The reaction rate constants calculated in lipid media were 1.08 × 106, 8.39 × 104, and 6.43 × 104 M−1 s−1 for the EST, ESD, and ESO, respectively. The reaction rate constants calculated in aqueous media were 3.00 × 106, 3.58 × 106, and 1.05 × 108 M−1 s−1 on the hydroperoxyl radical scavenging activity of EST, ESD, and ESO, respectively. The results also showed that the EST, ESD, and ESO estrogens could scavenge high reactivity radicals through the SET mechanism in aqueous media. In lipid media, estrogens are moderate antioxidants, whereas in aqueous media, these are good antioxidants. These theoretical results support the intrinsic antioxidant activity of EST, ESD, and ESO estrogens in lipid and aqueous media.

Abstract Image

脂质和水介质中雌激素清除羟基自由基活性的理论研究
尽管有证据表明雌激素具有抗氧化能力,但对其反应机制知之甚少。基于此,本研究采用DFT理论方法对三种雌激素雌三醇(EST)、雌二醇(ESD)和雌酮(ESO)在脂质和水介质中的羟基自由基清除活性进行了研究。在脂质和水介质中,氢转移是EST、ESD和ESO清除羟基自由基的主要反应机制。在脂质介质中EST、ESD和ESO的反应速率常数分别为1.08 × 106、8.39 × 104和6.43 × 104 M−1 s−1。在水溶液中,EST、ESD和ESO对羟基自由基清除能力的反应速率常数分别为3.00 × 106、3.58 × 106和1.05 × 108 M−1 s−1。结果还表明,EST、ESD和ESO雌激素可通过SET机制清除水中的高反应性自由基。在脂质介质中,雌激素是中等抗氧化剂,而在水介质中,雌激素是良好的抗氧化剂。这些理论结果支持了EST、ESD和ESO雌激素在脂质和水介质中的内在抗氧化活性。
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来源期刊
CiteScore
3.60
自引率
11.10%
发文量
161
审稿时长
2.3 months
期刊介绍: The Journal of Physical Organic Chemistry is the foremost international journal devoted to the relationship between molecular structure and chemical reactivity in organic systems. It publishes Research Articles, Reviews and Mini Reviews based on research striving to understand the principles governing chemical structures in relation to activity and transformation with physical and mathematical rigor, using results derived from experimental and computational methods. Physical Organic Chemistry is a central and fundamental field with multiple applications in fields such as molecular recognition, supramolecular chemistry, catalysis, photochemistry, biological and material sciences, nanotechnology and surface science.
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