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5-(Hydroxymethyl)-2-furfural (HMF), an active furfural, widely exists in various food products and has potential safety risks. It can be eliminated by occurring aldol condensation with α-unsubstituted ketones in the presence of catalysts. However, the elimination process between HMF and ketones from food is rarely studied. In this study, the adduct formation between HMF and zingerone (ZGR) catalyzed by proline was investigated. It revealed that the adduct formation led to 99.75% of HMF being trapped under the optimized reaction condition. Moreover, the in vitro digestion stability of HMF-ZGR adduct (HMZ) and its cytotoxicity against Caco-2 cells were evaluated. The results indicated that more than 75% of HMZ was remained after a three-stage simulated digestion. Following 24 and 48 h of incubation, HMZ exhibited cytotoxicity against Caco-2 cells with IC50 values of 41.47 ± 5.33 and 25.39 ± 3.12 mM, respectively, versus 35.39 ± 4.03 and 19.17 ± 2.10 mM by HMF.

To improve the quality and safety of brown fermented milk (BFM), the formation and alterations of potentially harmful Maillard reaction products (MRPs), including 3-deoxyglucosone (3-DG), methylglyoxal (MGO), 5-(hydroxymethyl)-2-furfural (HMF), acrylamide and flavour components were investigated during the browning, fermentation and commercial storage. MRPs were shown to be produced mainly during the browning stage. The levels of different substances varied during the fermentation and commercial storage stage. The proportion and type of carboxylic acids in the flavour components significantly increased during the fermentation stage. Browning index of milk during the browning stage was shown to be positively associated with the 3-DG (Pearson’s r = 0.9632), MGO (Pearson’s r = 0.9915), HMF (Pearson’s r = 0.9772), and acrylamide (Pearson’s r = 0.7910) levels and the total percentage of the flavour components from four different categories (Pearson’s r = 0.7407). Changes in physicochemical properties of BFM during production not only contribute to predict the formation of potentially unhealthy MRPs, but also Lactobacillus species used for the fermentation should be carefully selected to improve the quality of this product.

A major product formed during the Maillard reaction is 5-(hydroxymethyl)-2-furfural (HMF), which is present in various foods and beverages such as honey and fruit juice. HMF was shown to be a hepatocarcinogen in female mice using long-term bioassays. Although HMF is not a mutagen in conventional in vitro mutation assays, 5-sulfoxymethylfurfural (SMF), a reactive metabolite of HMF produced following sulfotransferase conjugation, does show mutagenicity. Thus, HMF-induced hepatocarcinogenesis likely involves genotoxic mechanisms. To clarify the mechanisms underlying HMF-induced hepatocarcinogenesis, female B6C3F1 gpt delta mice were given HMF at carcinogenic doses (188 or 375 mg/kg b.w.) by gavage for 5 days per week for 4 weeks. This treatment produced no significant differences in mutant frequencies (MFs) of gpt and red/gam (Spi-) genes among the groups. These results suggest that genotoxicity does not contribute to HMF-induced hepatocarcinogenesis. Parameters related to cell proliferation, such as proliferation cell nuclear antigen-labeling index and Cyclin D1 and E1 mRNA expression, exhibited no significant changes in the livers of HMF-treated groups. In view of the lack of carcinogenicity in rats, HMF may be considered to be a weak carcinogen. These results help us to understand the underlying mechanisms of action of HMF carcinogenesis. [ABSTRACT FROM AUTHOR]

Abstract: α-Dicarbonyl compounds, namely glyoxal (GO), methylglyoxal (MGO) and 3-deoxyglucosone (3-DOG), as well as 5-(hydroxymethyl)-2-furfural (5-HMF) were found and measured in carbonated soft drinks (CSD). It was realized that high fructose corn syrup (HFCS) in regular CSDs was the major source of α-dicarbonyl compounds in beverages after comparison of levels in regular and diet CSDs. In two most commonly used HFCS formulas, 42% and 55% HFCS, the highest level of dicarbonyl found was 3-DOG, followed by MGO, and then GO. The stability of dicarbonyls in CSDs containing HFCS and (−)-epigallocatechin gallate (EGCG) which were incubated at 35 and 45°C was investigated. It was found that EGCG decreased from 1mg/mL to 0.5 and 0.3mg/mL for 35 and 45°C, respectively, in 16 days storage. Moreover, the reactions of EGCG with MGO, 3-DOG and 5-HMF were observed from the comparison of storage CSDs with and without EGCG under acidic conditions. [Copyright &y& Elsevier]

Abstract: 5-(Hydroxymethyl)-2-furfural (HMF), a pyrolysate of carbohydrate isolated from instant coffee (Coffea arabica L.), selectively inhibits the activities of mammalian DNA polymerase λ (pol λ) and terminal deoxynucleotidyltransferase (TdT) which are family X pols, in vitro. The compound influenced neither the activities of replicative DNA polymerases such as α, δ, and ε, nor even the activity of pol β which is from the same family and thought to have a very similar three-dimensional structure to the pol β-like region of pol λ. Since parts of HMF such as furan, furfuryl alcohol, and 2-furaldehyde did not influence the activities of any enzymes tested, the substituted form of furan with a hyroxymethyl group and a formyl group might be important for the inhibition of pol λ and TdT. The inhibitory effect of HMF on intact pol λ (i.e., residues 1–575), a truncated pol λ lacking the N-terminal BRCA1 C-terminus domain (133–575, del-1 pol λ) and another truncated pol λ lacking the N-terminal proline-rich region (245–575, del-2 pol λ) was dose-dependent, and 50% inhibition was observed at a concentration of 26.1, 10.3, and 4.6μM, respectively. The IC50 value of HMF for TdT was the same as that for del-2 pol λ (5.5μM). The HMF-induced inhibition of both pol λ and TdT activities was competitive with respect to both the DNA template-primer and the dNTP substrate. On the basis of these results, HMF was suggested to bind to the pol β-like region of pol λ and TdT. [Copyright &y& Elsevier]

To improve the quality and safety of brown fermented milk (BFM), the formation and alterations of potentially harmful Maillard reaction products (MRPs), including 3-deoxyglucosone (3-DG), methylglyoxal (MGO), 5-(hydroxymethyl)-2-furfural (HMF), acrylamide and flavour components were investigated during the browning, fermentation and commercial storage. MRPs were shown to be produced mainly during the browning stage. The levels of different substances varied during the fermentation and commercial storage stage. The proportion and type of carboxylic acids in the flavour components significantly increased during the fermentation stage. Browning index of milk during the browning stage was shown to be positively associated with the 3-DG (Pearson's r = 0.9632), MGO (Pearson's r = 0.9915), HMF (Pearson's r = 0.9772), and acrylamide (Pearson's r = 0.7910) levels and the total percentage of the flavour components from four different categories (Pearson's r = 0.7407). Changes in physicochemical properties of BFM during production not only contribute to predict the formation of potentially unhealthy MRPs, but also Lactobacillus species used for the fermentation should be carefully selected to improve the quality of this product. [ABSTRACT FROM AUTHOR]