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- Title
Molecular networking-guided isolation strategy of a new C-glycosyl flavone rotamer from Stellaria alsine and evaluation of anti-inflammatory and antioxidant activities.
- Authors
Kim, Chang-Kwon; Yu, Soojung; Lee, Mina
- 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).
- Subjects
EAST Asia; INFLAMMATORY bowel diseases; ANTI-inflammatory agents; CHEMICAL properties; FOOD relief; MOLECULES; FLAVONES
- Publication
Metabolomics, 2023, Vol 19, Issue 9, p1
- ISSN
1573-3882
- Publication type
Article
- DOI
10.1007/s11306-023-02042-6