Guianolactones A and B, Two Rearranged Pentacyclic Limonoids from the Seeds of Carapa guianensis.

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.