Formation scheme and antioxidant activity of a novel Maillard pigment, pyrrolothiazolate, formed from cysteine and glucose
Kyoko Noda,Naoko Terasawa,Masatsune Murata
Food & Function Pub Date : 03/18/2016 00:00:00 , DOI:10.1039/C5FO01625H
Abstract

We recently identified 6-hydroxy-3[R],7a[S]-dimethyl-7-oxo-2,3-dihydropyrrolo[2,1-b]thiazole-3-calboxylic acid, a novel pyrrolothiazole derivative carrying a carboxy group and named pyrrolothiazolate, as a Mallard pigment formed from L-cysteine and D-glucose. Here we described the formation of its enantiomer, the plausible formation scheme of pyrrolothiazolate, and its antioxidant activity. When D-cysteine was used instead of L-cysteine in the reaction mixture, the enantiomer of pyrrolothiazolate was obtained. The carbon at position 1 of glucose was incorporated into two methyl groups of pyrrolothiazolate. The pigment was considered to be formed through 1-deoxyglucosone (1-DG). The dehydrated isomer of 1-DG would be condensed with the thiol and amino groups of cysteine. This condensate was dehydrated and cyclized to form pyrrolothiazolate. This compound was an antioxidant showing radical scavenging activity.

Graphical abstract: Formation scheme and antioxidant activity of a novel Maillard pigment, pyrrolothiazolate, formed from cysteine and glucose