CONSTITUENTS OF EUPOMATIA SPECIES .12. ISOLATION OF CONSTITUENTS OF THE TUBERS AND AERIAL PARTS OF EUPOMATIA-BENNETTII AND DETERMINATION OF THE STRUCTURES OF NEW ALKALOIDS FROM THE AERIAL PARTS OF E-BENNETTII AND MINOR ALKALOIDS OF E-LAURINA

Extraction of the aerial parts of Eupomatia bennettii F. Muell. yielded liriodenine, eupomatenoid-1, -3, -5 and -6, eupodienone-4 and -6, and the new compounds eupomatenoid-15 and -16, eupobennettin, eupomatilone-1, -2, -3, -4, -5 and -6, and four alkaloids imbiline-1, -2 and -3 and eupomatidine-1. From the tubers, eupomatenoid-1, -3, -4, -5 and -6, eupodienone-4 and -6 were isolated along with new products eupomatenoid-15, -16, -17 and -18, bennettinone and eupomatilone-3, -4, -6 and -7. Chemical and spectroscopic evidence is used to assign the structures of imbiline-1 (1), imbiline-2 (3), imbiline-3 (5) and eupomatidine-1 (6). The previously reported alkaloids from E. laurina R. Br., EL base-4 and EL base-5, were shown to be mixtures of imbiline-1, -2 and -3, and of eupomatidine-2 (10) and eupomatidine-3 (11), respectively. 3-Methoxyeupolauridine (15) was isolated from eupolauridine mother liquors.