Novel Maillard Pigment, Furpenthiazinate, Having Furan and Cyclopentathiazine Rings Formed by Acid Hydrolysis of Protein in the Presence of Xylose or by Reaction between Cysteine and Furfural under Strongly Acidic Conditions.

Abstract

A novel Maillard pigment having partial structures of furan and cyclopentathiazine, named furpenthiazinate, was isolated and identified. Although this pigment was found in an acid hydrolysate of a Maillard reaction solution between soy protein and xylose, the same pigment was also formed by the Maillard reaction under strongly acidic conditions between soy protein and xylose and cysteine and furfural. The structure of its reduced form by NaBH4 was determined by MS, NMR, and X-ray analysis and identified as 7-(2-furanyl)-2,3,4,4a,5,6-hexahydrocyclopenta[ b][1,4]thiazin-4-ium-3-carboxylate, indicating that the chemical structure of furpenthiazinate is 7-(2-furanyl)-2,3,5,6-tetrahydrocyclopenta[ b][1,4]thiazine-3-carboxylic acid. Furpenthiazinate showed an absorption maximum at 400 nm and strong yellow color under acidic and neutral conditions. The color contribution of furpenthiazinate was estimated to be more than 60% in a reaction solution prepared from cysteine and furfural.