Unusual Vilasinin-Class Limonoids from Trichilia rubescens

Eight vilasinin-class limonoids, including the unusually chlorinated rubescins K-M (1-3), the 2,3-epoxylated rubescin N (4), and rubescins O-R (5-8), were newly isolated from Trichilia rubescens. The structures of the isolated compounds were determined through spectroscopic and spectrometric analyses, as well as ECD calculations. The natural occurrence of chlorinated limonoids 1-3 was confirmed by chemical methods and HPLC analysis of a roughly fractionated portion of the plant extract. Eight selected limonoids, including previously known and new compounds, were evaluated for antiproliferative activity against five human tumor cell lines. All tested limonoids, except 8, exhibited significant potency, with IC₅₀ values of <10 μM; in particular, limonoid 14 strongly inhibited tumor cell growth, with IC₅₀ values of 0.54-2.06 μM against all tumor cell lines, including multi-drug-resistant cells.