Molecular modification of chlorogenic acid via radiolysis with inhibitory effects on NO production.

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Accounts of Chemical Research Pub Date : 2024-10-22 DOI:10.1093/bbb/zbae123

Gyeong Han Jeong, Hanui Lee, Kyung-Bon Lee, Byung Yeoup Chung, Hyoung-Woo Bai

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Abstract

The molecular modification of chlorogenic acid (1) through γ-irradiation resulted in the formation of five new products: chlorogenosins A (2), B (3), C (4), D (5), and E (6) along with known compounds rosmarinosin B (7), protocatechuic acid (8), and protocatechuic aldehyde (9). The structures of the new compounds were elucidated using spectroscopic methods, including one-dimensional and two-dimensional nuclear magnetic resonance, high-resolution electrospray ionization mass spectroscopy, and circular dichroism spectroscopy. The potential anti-inflammatory activities of all the isolated compounds were determined by evaluating their inhibitory effects on the nitric oxide (NO) production in lipopolysaccharide-induced RAW 264.7 macrophages. Notably, compounds 2 and 3, which contained two hydroxymethyl functionalities instead of the trans-olefinic moiety present in the original chlorogenic acid, exhibited stronger inhibitory effects on NO production than that of the original compound. These findings suggest that the predominant chemical changes induced in chlorogenic acid by γ-irradiation may enhance its anti-inflammatory properties.

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通过辐射分解对绿原酸进行分子修饰，从而抑制 NO 的产生。

通过γ-辐照对绿原酸（1）进行分子改造，形成了五种新产物：绿原酸 A（2）、B（3）、C（4）、D（5）和 E（6），以及已知化合物玫瑰苷 B（7）、原儿茶酸（8）和原儿茶醛（9）。利用光谱方法，包括一维和二维核磁共振、高分辨率电喷雾电离质谱和圆二色性光谱，阐明了新化合物的结构。通过评估这些化合物对脂多糖诱导的 RAW 264.7 巨噬细胞产生一氧化氮的抑制作用，确定了所有分离化合物的潜在抗炎活性。值得注意的是，化合物 2 和 3 含有两个羟甲基官能团，而不是原绿原酸中的反式烯烃基，它们对一氧化氮产生的抑制作用比原化合物更强。这些发现表明，γ-辐照诱导绿原酸发生的主要化学变化可能会增强其抗炎特性。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.