Formation and Identification of Two Hydroxmethylfurfural–Glycine Adducts and Their Cytotoxicity and Absorption in Caco‑2 Cells

Our previous research showed that thioacetal and Schiff base formed between 5-hydroxymethylfurfural (HMF) and cysteine or lysine considerably decreased the cytotoxicity of HMF. In this study, two adol condensation adducts, named 2β-amino-3α-hydroxy-3-(5-(hydroxymethyl)­furan-2-yl)­propanoic acid (HGA) and 2α-amino-3β-hydroxy-3-(5-(hydroxymethyl)­furan-2-yl)­propanoic acid (HGB), were prepared from the reaction products of glycine and HMF, and their cytotoxicities were investigated in Caco-2 cells. Compared with HMF, HGA and HGB displayed lower cytotoxicities against Caco-2 cells with IC₅₀ values of 36.50 and 43.47 mM, respectively, versus 16.11 mM (HMF). In contrast to our findings in thioacetal and Schiff base products, HGA and HGB underwent a very high metabolism rate (99%) in Caco-2 cells. HGA and HGB may degrade to other products instead of HMF since no extracellular or intracellular HMF was detected.