基于分子网络的石竹属植物中天蓝甙元新型 C-糖苷黄酮异构体的分离策略及其抗炎抗氧化活性评价。

Molecular networking-guided isolation strategy of a new C-glycosyl flavone rotamer from Stellaria alsine and evaluation of anti-inflammatory and antioxidant activities.

机构信息

College of Pharmacy and Research Institute of Life and Pharmaceutical Sciences, Sunchon National University, 255 Jungangno, Suncheon, 57922, Jeonnam, Korea.

Department of Natural Cosmetics Science, Graduate School, Sunchon National University, 255 Jungangno, Suncheon, 57922, Jeonnam, Korea.

出版信息

Metabolomics. 2023 Sep 5;19(9):79. doi: 10.1007/s11306-023-02042-6.

DOI:10.1007/s11306-023-02042-6

PMID:37670170

Abstract

INTRODUCTION

Stellaria alsine has traditionally been used as both a famine relief food and an alternative medicine in East Asia. Modern pharmacological studies have revealed that S. alsine has various biological effects such as anticancer, anti-hepatoma, anti-inflammatory, and antioxidative effects. However, the anti-inflammatory properties of chemical constituents derived from this plant have not been studied well.

OBJECTIVES

To identify potential therapeutic candidate for treating inflammatory diseases such as inflammatory bowel disease (IBD).

METHODS

The distribution of chemical compounds was investigated by Global Natural Product Social (GNPS)-based molecular networking (MN) analysis using UPLC-Orbitrap tandem mass spectrometry. The anti-inflammatory and antioxidative effects of S. alsine extracts and fractions were evaluated by measuring interleukin (IL)-8 and reactive oxygen species (ROS) productions.

RESULTS

The active EA layer of S. alsine showed the highest percentage of major compounds by feature-based molecular networking. The top candidate structures of EA fraction were rapidly annotated as flavone C- or O-glycosides via an advanced analysis tool, Network Annotation Propagation (NAP). With the GNPS molecular networking-guided isolation strategy, a new C-glycosyl flavone rotamer (1) was isolated. The structures of the major (1a) and minor (1b) rotational isomers were determined by extensive NMR analysis and MS/MS fragmentation. Finally, the anti-inflammatory activity of 1 was predicted by molecular docking simulations with IL-8 protein.

CONCLUSION

These results suggested that the compound 1 is a potential therapeutic candidate for inflammatory bowel disease (IBD).

摘要

简介

繁缕在东亚传统上被用作饥荒救济食品和替代药物。现代药理学研究表明，繁缕具有多种生物活性，如抗癌、抗肝癌、抗炎和抗氧化作用。然而，该植物化学物质的抗炎特性尚未得到很好的研究。

目的

寻找治疗炎症性疾病（如炎症性肠病[IBD]）的潜在治疗候选物。

方法

使用 UPLC-Orbitrap 串联质谱通过基于全球天然产物社会（GNPS）的分子网络（MN）分析研究化合物的分布。通过测量白细胞介素（IL）-8 和活性氧（ROS）的产生来评估繁缕提取物和馏分的抗炎和抗氧化作用。

结果

基于特征的分子网络分析显示，EA 层的 S. alsine 表现出最高比例的主要化合物。通过先进的分析工具网络注释传播（NAP），EA 馏分的顶级候选结构被快速注释为黄酮 C-或 O-糖苷。通过 GNPS 分子网络指导的分离策略，分离到一种新的 C-糖苷黄酮旋转异构体（1）。通过广泛的 NMR 分析和 MS/MS 碎片确定了主要（1a）和次要（1b）旋转异构体的结构。最后，通过与 IL-8 蛋白的分子对接模拟预测了 1 的抗炎活性。