Bioactive A-ring rearranged limonoids from the root barks of Walsura robusta

Publication date: Available online 1 March 2019Source: Acta Pharmaceutica Sinica BAuthor(s): Faliang An, Xiaobing Wang, Minghua Yang, Jun Luo, Lingyi KongAbstractScreening active natural products, rapid identification, and accurate isolation are of great important for modern natural lead compounds discovery1. We herely reported the isolation of seven new neotecleanin-type liminoids (1‒7), seven new limonoids with 5-oxatricyclo[5.4.0.11, 4]hendecane ring system (8‒14), and two new precursors (15‒16) together with four known limonoids (17‒20) from the root barks of Walsura robusta. Their structures, including their absolute configurations, were elucidated based on analyses of HR-ESI-MS, 1D/2D NMR, ECD spectrum calculations and single-crystal X-ray diffraction techniques. Compounds 2, 8, 9, 11, 13, 14, 18 showed significant anti-inflammatory activities in LPS-induced RAW 264.7 cell line, BV2 microglial cells, and Propionibacterium acnes-stimulated THP-1 human monocytic cells. Walrobsin M (11) exhibited anti-inflammatory activity with IC50 value of 7.96 ± 0.36 μmol/L, and down-regulated phosphorylation levels of ERK and p38 in a dose-dependent manner.Graphical abstractTwenty A/B spiro-type limonoids (1‒20) including seven new neotecleanin-type liminoids (1‒7), seven novel limonoids (8‒14) with 5-oxatricyclo[5.4.0.11, 4]hendecane ring system, and two key precursors (15‒16) were isolated from the root barks of Walsura robusta. Walrobsin M (11) significantly inhibi...

Source: Acta Pharmaceutica Sinica B - March 4, 2019 Category: Cancer & Oncology Source Type: research