Gyeong Han Jeong, Hanui Lee, Kyung-Bon Lee, Byung Yeoup Chung, Hyoung-Woo Bai
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Molecular modification of chlorogenic acid via radiolysis with inhibitory effects on NO production.
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.
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.