Aaptanone, a novel zwitterionic metabolite of the aaptamine class with an oxygenated 1,6-naphthyridine core from the Vietnamese marine sponge Aaptos aaptos

A new zwitterionic compound, aaptanone, having a rare oxygenated 1,6-naphthyridine core, has been isolated from the Vietnamese marine sponge Aaptos aaptos, along with the known metabolites, aaptamine, isoaaptamine, and their hydrochloride salts. The structure of aaptanone was determined as 8-methoxy-1-methyl-5,6-dioxo-5,6-dihydro-4H-benzo[de]-1,6-naphthyridine-1-ium-9-olate from spectroscopic data, X-ray analysis, and by spectroscopic analysis of an N-methyl derivative.