Constituents of Eupomatia Species. XII. 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

Abstract

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.