Tetranortriterpenoids from Cipadessa baccifera

Five new mexicanolide-type tetranortriterpenoids, tigloylseneganolide A (1), 2'R-methylbutanoylproceranolide (2), 2'S-methylbutanoylproceranolide (3), 2'R-cipadesin A (4), and 2'R-cipadesin (6), as well as the known 2'S-epimers of 4 and 6 (5 and 7), together with six other known limonoids, were isolated from the seeds of Cipadessa baccifera. The structures of these compounds were elucidated on the basis of spectroscopic analyses and chemical methods. 1H NMR-based conformational analysis was applied to establish the absolute configuration of the sterically hindered 2-methylbutanoyl in three epimeric pairs (2-7). A general rule for the determination of the absolute configurations of 2R- and 2S-methylbutanoyl groups at C-3 of a limonoid in a mixture is proposed.