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Ultra-high-performance liquid chromatography supports a new reaction mechanism between free radicals and ferulic acid with antimicrobial and antioxidant activities
Industrial Crops and Products ( IF 5.9 ) Pub Date : 2020-06-27 , DOI: 10.1016/j.indcrop.2020.112701
Sharise B.R. Berton , Márcia R.P. Cabral , Guilherme A.M. de Jesus , Maria H. Sarragiotto , Eduardo J. Pilau , Alessandro F. Martins , Elton G. Bonafé , Makoto Matsushita

The chemical reaction involving phenolic antioxidants from plant´ extracts have not been adequately studied. In this study, we investigate a quick, accurate, and innovative strategy to elucidate the ferulic acid reaction employing a conclusive analytical tool (ultra-high-performance liquid chromatography coupled with electrospray ionization quadrupole time-of-flight tandem mass spectrometry, UHPLC-ESI-Q-TOF-MS/MS) used in pharmaceutical, cosmetic, food, and biomedical applications. The ferulic acid- DPPH (2,2-diphenyl-1-picrylhydrazyl) reaction presented three chromatographic peaks with retention times at 5.95, 8.69, and 9.04 min. The peak at 385.0928 mass/charge (m/z) is assigned to the ferulic acid-ferulic acid dimer, while the m/z 586.1193 signal indicates the adduct presence. This statement is confirmed by the fragmentation step, which supports characteristics peaks ascribed to the original DPPH at m/z 195.9986 and m/z 225.9972. The peak m/z 778.1605 is attributed to the formation of a new compound (called radimerSB) that has never identified before. According to the reaction mechanism, the ferulic acid may provide antioxidant activity mainly by hydrogen-atom transfer reaction. Furthermore, we compare the antimicrobial action of ferulic acid and Trolox. We show that against ferulic acid prevents the crop growth of Staphylococcus aureus (S. aureus) and Escherichia coli (E. coli). The ferulic acid biological activities can be useful to develop new bio-based materials for technological applications (e.g., medical purposes). It is essential to understand the reaction mechanism between DPPH and antioxidants. The DPPH can quantify the concentration of antioxidants in plant extracts. The biological activities (antimicrobial, cytotoxicity, and others) of these extracts depend on the type and concentration of antioxidants and their reaction products.



中文翻译:

超高效液相色谱支持自由基和阿魏酸之间具有抗菌和抗氧化活性的新反应机理

尚未充分研究涉及植物提取物中的酚类抗氧化剂的化学反应。在这项研究中,我们研究了一种快速,准确和创新的方法,以使用结论性分析工具(超高效液相色谱与电喷雾电离四极杆飞行时间串联质谱,UHPLC-ESI结合使用)阐明阿魏酸反应-Q-TOF-MS / MS)用于制药,化妆品,食品和生物医学应用。阿魏酸-dPPH 2,2-二苯基-1-吡啶并肼基)反应出现三个色谱峰,保留时间分别为5.95、8.69和9.04分钟。在385.0928质量/电荷(m / z)处的峰归属于阿魏酸-阿魏酸二聚体,而m / z 586.1193信号指示加合物的存在。片段化步骤证实了这一说法,该步骤支持归因于原始特征峰的特征峰dPPHm / z 195.9986和m / z 225.9972。m / z 778.1605峰归因于从未发现的新化合物(称为radimerSB)的形成。根据反应机理,阿魏酸可以主要通过氢原子转移反应提供抗氧化活性。此外,我们比较了阿魏酸和Trolox的抗菌作用。我们表明,针对阿魏酸会阻止金黄色葡萄球菌S. aureus)和大肠杆菌(E. coli)的作物生长。阿魏酸的生物活性对于开发用于技术应用(例如医学目的)的新型生物基材料可能有用。了解两者之间的反应机理至关重要dPPH和抗氧化剂。的dPPH可以量化植物提取物中抗氧化剂的浓度。这些提取物的生物学活性(抗微生物,细胞毒性等)取决于抗氧化剂及其反应产物的类型和浓度。

更新日期:2020-06-27
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