Bioassay and NMR-HSQC-Guided Isolation and Identification of Phthalide Dimers with Anti-Inflammatory Activity from the Rhizomes of Angelica sinensis

被引:1
作者
Wen, Hongyan [1 ]
Li, Sheng [1 ]
Wei, Yinling [1 ]
Sun, Yong [2 ]
Fu, Lijun [2 ]
Zhang, Xiumin [2 ]
Zhang, Yu [1 ]
机构
[1] Chinese Acad Sci, Kunming Inst Bot, State Key Lab Phytochemistry & Nat Med, Kunming 650201, Peoples R China
[2] Beijing Acad Food Sci, Beijing, Peoples R China
基金
国家重点研发计划;
关键词
Angelica sinensis; bioactivity and HSQC-guided; phthalic dimers; angesilides A-I; anti-inflammatoryactivity;
D O I
10.1021/acs.jafc.4c11704
中图分类号
S [农业科学];
学科分类号
09 ;
摘要
Under the guidance of a bioactivity-guided approach and HSQC characteristic signals, nine pairs of phthalic dimers, angesilides A-I (1-9), with complex polycyclic skeletons featuring bridged, fused, and spiro ring systems were discovered from the rhizomes of Angelica sinensis. Their structures and absolute configurations were established by comprehensive spectroscopic methods, X-ray diffraction analysis, and chiral separation. Plausible biosynthetic pathway for 1-9 was proposed. Moreover, the anti-inflammatory activities of all isolates were evaluated in lipopolysaccharide (LPS) stimulated mouse leukemia cells of monocyte macrophages (RAW = 264.7). Among them, compound 9 showed a remarkable inhibitory activity with IC50 values of 425 nM and could significantly decrease IL-1 beta and IL-6 transcription levels. Interestingly, (+)-9 has superior NO inhibitory activity compared to that of (-)-9, which was verified by further molecular docking analysis. The findings provide new insights into A. sinensis as a functional food or for the development of new anti-inflammatory drug candidates.
引用
收藏
页码:4630 / 4641
页数:12
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