Some experiments with picrotoxinin and tutin

Abstract

Many non-nitrogenous bitter principles (amaroids) have been isolated from plants, although few have yet been adequately examined from the point of view of their chemical structure. Perhaps the best known amaroid of established structure is santonin C15H18O3, the active constituent of the wormseed of Artemisia cina and maritime: The presence of a lactone grouping is a characteristic of many of these substances, and this is true of picrotoxin and tutin, both of which like santonin are oxygenated C15 compounds. Picrotoxin is extracted from the fruits of anamirta cocculus, a menispermaceous plant idigenous to the East Indies, and has been used as a fish poison for a long time. The bitter principle was first isolated by a French apothecary, P. Boullay, Bl. Pharm. 1812, 4, 367 Who named it picrotoxin. He believed it to be an alkaloid, but it has been shown to contain only C, H and O. It is now generally believed that picrotoxin is a molecular compound Sielisch, Annalen, 1912, 391 of two dilactones, picrotoxinin and picrotin. Picrotoxinin C15H16O6m.p. 209° is the physiologically active constituent whereas picrotin is physiologically inactive.