A study on the photoisomerization of phenylpropanoids and the differences in their radical scavenging activity using in-situ NMR spectroscopy and on-line radical scavenging activity analysis

IF 2.3 3区农林科学 Q3 FOOD SCIENCE & TECHNOLOGY

Applied Biological Chemistry Pub Date : 2024-08-17 DOI:10.1186/s13765-024-00925-3

Sangah Park, Hojin Kim, Miyeon Bang, Byung-Hun Um, Jin Wook Cha

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Abstract

Phenylpropanoids are naturally occurring secondary metabolites that exhibit various biological activities such as ultra-violet (UV) light protection and reactive-oxygen species (ROS) scavenging. In this study, we utilized a light-emitting diode (LED) based in-situ UV irradiation nuclear magnetic resonance (NMR) technique to monitor the photoisomerization reactions of these phenylpropanoids under UV irradiation in real-time. Through this approach, we measured the photochemical reaction rates and photostationary state (PSS) ratios of these molecules and observed distinct reaction rate and PSS ratio information depending on the variation of substituent groups in each phenylpropanoid molecule. We also evaluated the radical scavenging activity (RSA) for each photochemical product through diphenyl-1-picrylhydrazyl radical (DPPH) assay and 2,2’-azino-bis(3-ethylbenzenthiazoline-6-sulphonic acid) (ABTS) assay. We found that the photoisomerization product of caffeic acid can increase both DPPH and ABTS radical scavenging activities, and confirmed the enhanced ABTS radical scavenging ability of caffeic acid cis-isomer based on the online high-pressure liquid chromatography (HPLC)-ABTS analysis and the PSS ratio information of each isomer.

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利用原位核磁共振光谱和在线自由基清除活性分析法研究苯丙类化合物的光异构化及其自由基清除活性的差异

苯丙烷是天然存在的次生代谢物，具有多种生物活性，如紫外线（UV）防护和清除活性氧（ROS）。在这项研究中，我们利用基于发光二极管（LED）的原位紫外线辐照核磁共振（NMR）技术，实时监测了这些苯丙类化合物在紫外线辐照下的光异构化反应。通过这种方法，我们测量了这些分子的光化学反应速率和光静止态（PSS）比率，并根据每个苯丙醇分子中取代基团的变化观察到了不同的反应速率和 PSS 比率信息。我们还通过二苯基-1-苦基肼自由基（DPPH）测定法和 2,2'-偶氮双（3-乙基苯并噻唑啉-6-磺酸）（ABTS）测定法评估了每种光化学产物的自由基清除活性（RSA）。根据在线高压液相色谱-ABTS分析和各异构体的PSS比值信息，证实了咖啡酸顺式异构体具有更强的ABTS自由基清除能力。

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来源期刊

Applied Biological Chemistry Chemistry-Organic Chemistry

CiteScore

5.40

自引率

6.20%

发文量

审稿时长

20 weeks

期刊介绍： Applied Biological Chemistry aims to promote the interchange and dissemination of scientific data among researchers in the field of agricultural and biological chemistry. The journal covers biochemistry and molecular biology, medical and biomaterial science, food science, and environmental science as applied to multidisciplinary agriculture.