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

IF 1.4 4区 生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY
Gyeong Han Jeong, Hanui Lee, Kyung-Bon Lee, Byung Yeoup Chung, Hyoung-Woo Bai
{"title":"Molecular modification of chlorogenic acid via radiolysis with inhibitory effects on NO production.","authors":"Gyeong Han Jeong, Hanui Lee, Kyung-Bon Lee, Byung Yeoup Chung, Hyoung-Woo Bai","doi":"10.1093/bbb/zbae123","DOIUrl":null,"url":null,"abstract":"<p><p>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.</p>","PeriodicalId":9175,"journal":{"name":"Bioscience, Biotechnology, and Biochemistry","volume":null,"pages":null},"PeriodicalIF":1.4000,"publicationDate":"2024-10-22","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Bioscience, Biotechnology, and Biochemistry","FirstCategoryId":"5","ListUrlMain":"https://doi.org/10.1093/bbb/zbae123","RegionNum":4,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
引用次数: 0

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.

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。
求助全文
约1分钟内获得全文 求助全文
来源期刊
Bioscience, Biotechnology, and Biochemistry
Bioscience, Biotechnology, and Biochemistry 生物-生化与分子生物学
CiteScore
3.50
自引率
0.00%
发文量
183
审稿时长
1 months
期刊介绍: Bioscience, Biotechnology, and Biochemistry publishes high-quality papers providing chemical and biological analyses of vital phenomena exhibited by animals, plants, and microorganisms, the chemical structures and functions of their products, and related matters. The Journal plays a major role in communicating to a global audience outstanding basic and applied research in all fields subsumed by the Japan Society for Bioscience, Biotechnology, and Agrochemistry (JSBBA).
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信