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With the aim of discovering new cytotoxic prenylated stilbenes of the schweinfurthin series, Macaranga tanarius was selected for detailed phytochemical investigation among 21 Macaranga species examined by using a molecular networking approach. From an ethanol extract of the fruits, seven new prenylated stilbenes, schweinfurthins K–Q (7–13), were isolated, along with vedelianin (1), schwenfurthins E–G (2–4), mappain (5), and methyl-mappain (6). The structures of the new compounds were established by spectroscopic data analysis. The relative configurations of compounds 8, 12, and 13 were determined based on ROESY NMR spectroscopic analysis. The cytotoxic activities of compounds 1–13 were evaluated against the human glioblastoma (U87) and lung (A549) cancer cell lines.

Two bisindoline alkaloids, contortarine A, 16-epi-pleiomutinine and a reaction product of pleiomutinine, namely N4-chloromethyl-pleiomutinine, were isolated from the roots of Tabernaemontana contorta Stapf. together with five known compounds: pleiomutinine, 1-carbomethoxy-β-carboline, strictosidine lactam, pleiocarpamine, and pleiocarpine. The structures and relative configuration of these alkaloids were determined by extensive 1D and 2D NMR, and MS measurements. The absolute configuration of these compounds was determined by comparison of experimental and calculated ECD spectra. Among the isolated compounds, contortarine A, 1-carbomethoxy-β-carboline and strictosidine lactam presented cancer chemopreventive properties through either quinone reductase (QR) induction with CD values of 16.0 ± 2.5, 30.2 ± 6.1 and 23.1 ± 4.6 μM, respectively, while pleiomutinine and 16-epi-pleiomutinine displayed the inhibition of TNF-α induced NF-κB activity with IC50 at 11.7 ± 2.6 and 3.4 ± 1.1 μM, respectively.