Nakijiquinones J-R, Sesquiterpenoid Quinones with an Amine Residue from Okinawan Marine Sponges

Nine new sesquiterpenoid quinones, nakijiquinones J-R (1 -9), have been isolated from three collections of Okinawan marine sponges of the family Spongiidae, and the structures and configurations were elucidated from the spectroscopic data and chemical correlations. Nakijiquinones J-L (1-3), M and N (4 and 5, respectively), 0 (6), 11 and Q (7 and 8, respectively), and R (9) are new sesquiterpenoid quinones possessing (S)-2-methylbutylamine, isopentylamine, isobutylamine, phenethylamine, and taurine residues, respectively, attached to each quinone ring.