Carapanolides C-I from the seeds of andiroba (Carapa guianensis, Meliaceae).

Five new mexicanolide-type limonoids, carapanolides C-G (1-5), together with two new phragmalin-type limonoids, carapanolides H-I (6, 7), were isolated from the oil of Carapa guianasis AUBLET (Meliaceae) seeds. Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D NMR spectra and FABMS. Carapanolides C (1), E (3), and I (7) exhibited moderate activity in the P388 (IC50 17.9 μM in 1, 15.8 μM in 3) and L1210 cell lines (IC50 13.3 μM in 1, 18.1 μM in 3, 16.9 μM in 7). On the other hand, Carapanolide D (2) exhibited a strong inhibitory effect in the HL-60 cell line (IC50 11.0 μM), Carapanolides F (4) showed inhibitory activity in the L1210 cell line (IC50 15.9 μM), and the cytotoxic activity of Carapanolides I (7) was moderate in all cell lines.