Abstract:Two new mexicanolide-type limonoids, carapanolides T-U (1-2), and three new phragmalin-type limonoids, carapanolides V-X (3-5), were isolated from the seeds of Carapa guianensis (andiroba). Their structures were determined on the basis of 1D-and 2D-NMR spectroscopy.

Two new phragmalin-type limonoids, Carapanosins A and B (1 and 2), and a new gedunin-type limonoid, Carapansin C (3), together with five known limonoids (4–8) were isolated from the oil of Carapa guianensis AUBLET (Meliaceae) seeds, a traditional medicine in Brazil and Latin American countries. Their structures were elucidated on the basis of spectroscopic analyses using 1D and 2D NMR techniques and HRFABMS. Compounds 1–8 were evaluated for their effects on the production of NO in LPS-activated mouse peritoneal macrophages. The NO inhibitory assay suggested that Compounds 3, 6, and 8 may be valuable as potential inhibitors of macrophage activation.

Two novel rearranged limonoids, guianolactones A (1) and B (2), were isolated from Carapa guianensis Aubl. (Meliaceae) seeds. The structures of 1 and 2 with their absolute configurations were elucidated in detailed examinations using single-crystal X-ray diffraction analyses and 2D NMR spectra. Guianolactone A (1) has a novel 5/6/6/6/6 pentacyclic core including two δ-lactone and a tetrahydropyran ring, while guianolactone B (2) is a novel limonoid with a 6/6/5/6/6 pentacyclic core featuring a δ-lactone and a tetrahydrofuran ring.

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