Structurally Diverse Matrine‐Based Alkaloids with Anti‐inflammatory Effects from Sophora alopecuroides. Issue 12 (24th October 2021)

• Record Type: Journal Article
• Authors: Luo, Ding; Chen, Neng‐Hua; Wang, Wen‐Zhi; Zhang, Ji‐Hui; Li, Can‐Jie; Zhuo, Xue‐Fang; Tu, Zhen‐Chao; Wu, Zhong‐Nan; Fan, Chun‐Lin; Zhang, Hai‐Peng; Li, Yao‐Lan; Wang, Guo‐Cai; Zhang, Yu‐Bo
• Is Part Of: Chinese journal of chemistry. Volume 39:Issue 12(2021)
• Page Start: 3339
• Page End: 3346
• Publication Date: 2021-10-24
• Subjects: Sophora alopecuroides -- Alkaloids -- Structure elucidation -- Anti‐inflammatory activity -- Biological activitiy -- Configuration determination; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/cjoc.202100526
• Languages: English
• ISSNs: 1001-604X

Abstract

Main observation and conclusion: A phytochemical investigation on the seeds of Sophora alopecuroides led to obtaining fourteen structurally diverse matrine‐based alkaloids (1 —14 ), including eight new ones (1, 6, 8 —12, 14 ). Notably, alopecuroide F (1 ) represents the first dimeric matrine‐type skeleton assembled via unprecedent C‐13–C‐12' connection. The new structures were determined through extensive spectroscopic data (UV, OR, HRESIMS, 1D, and 2D NMR), ECD calculations, and three instances, verified by X‐ray crystallography. Biologically, all alkaloids were evaluated for cytotoxicity against four human cancer cell lines (HepG2, A549, THP‐1, and MCF‐7) and anti‐inflammatory activities for two pro‐inflammatory cytokines (TNF‐ α and IL‐6). Alopecuroide F (1 ) can inhibit TNF‐α and IL‐6 productions in a dose‐dependent manner, with IC50 values of 35.6 ± 0.5 and 41.7 ± 0.8 μmol/L, respectively. Abstract :