Liriodendronine,an oxoaporphine pigment from discolored sapwood of Liriodendron tulipifera

A new violet oxoaporphine alkaloid. liriodendronine, has been isolated from the discolored sapwood of Liniodendron tulipifera and its structure determined by spectroscopic methods and by conversion into a corunnine-type compound, 2-O,N-dimethylliriodendronine. UV studies demonstrated that the compound exists primarily as a quinone-methide in a neutral medium, a dianion in base, an isoquinolinium ion in weak acid, and as an antiaromatic conjugate acid in conc H₂SO₄.