Possible adducts formed between hydroxymethylfurfural and selected amino acids, and their release in simulated gastric model

Summary This work aimed to investigate the reactivity of hydroxymethylfurfural (HMF) with selected amino acids, to identify the produced adducts and to clarify whether or not the adducts release HMF after their digestion under gastric conditions. Results showed that cysteine, glycine and lysine can deplete the added HMF, and their reactivity increased with increasing pH and temperature. Cysteine (25 μmol mL−1) depleted 91.0% of the added HMF (315.3 μg mL−1) at 40 °C in 15 min, lysine did not eliminate HMF until 80 °C, and glycine started to eliminate HMF at 100 °C. Four adducts for cysteine, three adducts for lysine and only one adduct for glycine were identified through HPLC–MS–MS after they reacted with HMF. The adducts formed from the reaction mixture of cysteine, lysine and glycine with HMF only released 1.7%, 2.6% and 10.5% of eliminated HMF, respectively, after their digestion in simulated gastric conditions.