The University of Danang - University of Technology and Education, Danang550000, Vietnam.
TPM Bioactives Division, The Product Makers Pty. Ltd., Melbourne 3173, Australia.
J Org Chem. 2023 Dec 15;88(24):17237-17248. doi: 10.1021/acs.joc.3c02093. Epub 2023 Nov 27.
Rosmarinic acid () is reported in separate studies to be either an inducer or reliever of oxidative stress, and this contradiction has not been resolved. In this study, we present a comprehensive examination of the radical scavenging activity of using density functional theory calculations in comparison with experimental data. In model physiological media, exhibited strong HO radical scavenging activity with overall rate constant values of 2.89 × 10 and 3.86 × 10 M s. is anticipated to exhibit excellent scavenging properties for HOO in an aqueous environment ( = 3.18 × 10 M s, ≈2446 times of Trolox) following the hydrogen transfer and single electron transfer pathways of the dianion state. The neutral form of the activity is equally noteworthy in a lipid environment ( = 3.16 × 10 M s) by the formal hydrogen transfer mechanism of the O6(7,15,16)-H bonds. Chelation with may prevent Cu(II) from reduction by the ascorbic acid anion (AA), hence blocking the OIL-1 pathway, suggesting that in an aqueous environment also serves as an OIL-1 antioxidant. The computational findings exhibit strong concurrence with the experimental observations, indicating that possesses a significant efficacy as a radical scavenger in physiological environments.
迷迭香酸 () 在不同的研究中被报道为氧化应激的诱导剂或缓解剂，这种矛盾尚未得到解决。在这项研究中，我们使用密度泛函理论计算对迷迭香酸的自由基清除活性进行了全面的检查，并与实验数据进行了比较。在模型生理介质中，迷迭香酸表现出很强的 HO 自由基清除活性，总速率常数值分别为 2.89×10 和 3.86×10 M s。预计迷迭香酸在水相环境中（ = 3.18×10 M s，约为 Trolox 的 2446 倍）通过二阴离子状态的氢转移和单电子转移途径表现出优异的 HOO 清除特性。通过 O6(7,15,16)-H 键的形式氢转移机制，中性形式在脂质环境中（ = 3.16×10 M s）的活性同样值得注意。与 螯合可能阻止 Cu(II)被抗坏血酸阴离子（AA）还原，从而阻断 OIL-1 途径，这表明迷迭香酸在水相环境中也作为 OIL-1 抗氧化剂。计算结果与实验观察结果具有很强的一致性，表明迷迭香酸在生理环境中作为自由基清除剂具有显著的功效。
