Inhibition Mechanism of L-Cysteine on Maillard Reaction by Trapping 5-Hydroxymethylfurfural

Abstract

The Maillard reaction (MR) can affect the color, flavor, organoleptic properties, and nutritional value of food. Sometimes, MR is undesirable due to lowering the nutrient utilization, producing harmful neo-formed compounds, etc. In this case, it is necessary to control MR. Some chemical substances, such as phenolic acid, vitamins, aminoguanidine, and thiols extracted from garlic or onion, can effectively prevent MR. In this study, L-cysteine (L-cys) was found to inhibit MR after screening 10 sulfhydryl compounds by comparing their ability to mitigate browning. The inhibition mechanism was speculated to be related to the removal of 5-hydroxymethylfurfural (HMF), a key mid-product of MR. The reaction product of HMF and L-cys was identified and named as 1-dicysteinethioacetal–5-hydroxymethylfurfural (DCH) according to the mass spectrum and nuclear magnetic resonance spectrum of the main product. Furthermore, DCH was detected in the glutamic–fructose mixture after L-cys was added. In addition, the production of DCH also increased with the addition of L-cys. It also was worth noting that DCH showed no cell toxicity to RAW 264.7 cells. Moreover, the in vitro assays indicated that DCH had anti-inflammatory and antioxidant activities. In conclusion, L-cys inhibits MR by converting HMF into another adduct DCH with higher safety and health benefits. L-cys has the potential to be applied as an inhibitor to prevent MR during food processing and storage.