Liriogerphines A-D(1-4, respectively), an unprece-dented class of hybrids of germacranolide-type sesquiterpenoids andaporphine-type alkaloids, were isolated from the rare medicinal plantLiriodendron chinense. Their structures were elucidated by compre-hensive spectroscopic analyses combined with electronic circulardichroism calculations and X-ray crystallographic data. Biosyntheti-cally, an aza-Michael addition reaction is proposed to be involved inthe assemblies of this class of hybrids. Compound4exhibitedcytotoxicity against leukemia cells via inducing apoptosis andinhibiting Bcl-2 expression.