Structure elucidation and biomimetic synthesis of hostasinine A, a new benzylphenethylamine alkaloid from Hosta plantaginea

Hostasinine A (1), a benzylphenethylamine alkaloid with an unprecedented skeleton featuring a C-4-C-6 linkage and a nitrone moiety, was isolated from Hosta plantaginea. Its structure was established on the basis of spectroscopic data, and was further confirmed by single-crystal X-ray diffraction. The alkaloid was postulated biogenetically from haemanthidine via N-oxidation and aza-aldol-type condensation and was synthesized biomimetically. The inhibitory activities of 1 on acetylcholinesterase (AChE) and two tumor cell lines (K562 and A549) were also evaluated.