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新型表儿茶素低聚物对一氧化氮生成的抑制作用。

Inhibitory Effects of New Epicatechin Oligomers on Nitric Oxide Production.

机构信息

Research Division for Biotechnology, Advanced Radiation Technology Institute (ARTI), Korea Atomic Energy Research Institute (KAERI), Jeongeup 56212, Republic of Korea.

Center for Companion Animal New Drug Development, Korea Institute of Toxicology (KIT), Jeongeup 56212, Republic of Korea.

出版信息

Int J Mol Sci. 2024 Oct 14;25(20):11022. doi: 10.3390/ijms252011022.

DOI:10.3390/ijms252011022
PMID:39456804
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11507282/
Abstract

The primary aim of this research was to identify the structural characteristics of three newly derived procyanidins from cold plasma-treated (-)-epicatechin, known for their anti-inflammatory properties. The newly generated compounds were isolated through column chromatography, and their chemical structures were elucidated through spectroscopic data analyses, including both one-dimensional and two-dimensional nuclear magnetic resonance (NMR) and mass spectrometry (MS) techniques. Furthermore, their absolute configurations were determined via circular dichroism (CD) spectroscopy. The inhibitory activity of the isolated compounds on nitric oxide (NO) production and expression levels of inducible NO synthase (iNOS) in lipopolysaccharide (LPS)-induced RAW 264.7 macrophages was evaluated. Three new procyanidins-methylenetrisepicatechin (), isomethylenetrisepicatechin (), and methylenebisepicatechin ()-along with two reported dimeric flavan-3-ols ( and ), were identified from plasma-treated (-)-epicatechin (). The unique oligomerized products and linked by methylene bridges significantly suppressed both NO production and iNOS expression, demonstrating higher anti-inflammatory activities in LPS-stimulated RAW 264.7 cells compared with the parent compound. The newly oligomerized procyanidins have potential applications in the treatment of inflammatory diseases owing to their significant anti-inflammatory properties.

摘要

本研究的主要目的是鉴定三种新型原花青素的结构特征，这些原花青素源自经冷等离子体处理的（-）-表儿茶素，具有抗炎特性。通过柱层析分离新生成的化合物，并通过包括一维和二维核磁共振（NMR）和质谱（MS）技术在内的光谱数据分析来阐明其化学结构。此外，通过圆二色性（CD）光谱确定其绝对构型。评估了分离得到的化合物对脂多糖（LPS）诱导的 RAW 264.7 巨噬细胞中一氧化氮（NO）产生和诱导型一氧化氮合酶（iNOS）表达水平的抑制活性。从等离子体处理的（-）-表儿茶素（）中鉴定出三种新型原花青素-亚甲基三没食子酸酯（）、异亚甲基三没食子酸酯（）和亚甲基双没食子酸酯（）以及两种报道的二聚黄烷-3-醇（和）。通过亚甲基桥连接的独特齐聚产物和显著抑制了 NO 的产生和 iNOS 的表达，与母体化合物相比，在 LPS 刺激的 RAW 264.7 细胞中表现出更高的抗炎活性。由于其显著的抗炎特性，新的齐聚原花青素具有在炎症性疾病治疗中的应用潜力。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/837e/11507282/d8fbe54bb2cc/ijms-25-11022-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/837e/11507282/03200a937b28/ijms-25-11022-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/837e/11507282/3a4d3c42d572/ijms-25-11022-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/837e/11507282/e4af5fec3855/ijms-25-11022-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/837e/11507282/86ee45b4adcf/ijms-25-11022-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/837e/11507282/d8fbe54bb2cc/ijms-25-11022-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/837e/11507282/03200a937b28/ijms-25-11022-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/837e/11507282/3a4d3c42d572/ijms-25-11022-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/837e/11507282/e4af5fec3855/ijms-25-11022-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/837e/11507282/86ee45b4adcf/ijms-25-11022-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/837e/11507282/d8fbe54bb2cc/ijms-25-11022-g005.jpg

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本文引用的文献

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