Toxic principles of hippomane mancinella. II. Structure of Hippomanin A

Abstract

Hippomanin A is a pale yellow crystalline toxic principle isolated from the water-soluble portion of the ethanolic extract of Hippomane mancinella. Acid hydrolysis gave glucose, gallic acid and ellagic acid, thus showing that it belonged to the class of "crystalline tannins" and was isomeric with corilagin. The presence of free anomeric hydroxyl was shown by methylation and by reduction with sodium borohydride. Mass spectral and chemical evidence showed that the structure was 2-galloyl-4,6-hexahydroxydiphenoyl-D-glucose.