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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.

p-Coumaric acid (4-hydroxycinnamic acid) is a phenolic acid that has low toxicity in mice (LD50 = 2850 mg kg(-1) body weight), serves as a precursor of other phenolic compounds, and exists either in free or conjugated form in plants. Conjugates of p-coumaric acid have been extensively studied in recent years due to their bioactivities. In this review, the occurrence, bioavailability and bioaccessibility of p-coumaric acid and its conjugates with mono-, oligo- and polysaccharides, alkyl alcohols, organic acids, amine and lignin are discussed. Their biological activities, including antioxidant, anti-cancer, antimicrobial, antivirus, anti-inflammatory, antiplatelet aggregation, anxiolytic, antipyretic, analgesic, and anti-arthritis activities, and their mitigatory effects against diabetes, obesity, hyperlipaemia and gout are compared. Cumulative evidence from multiple studies indicates that conjugation of p-coumaric acid greatly strengthens its biological activities; however, the high biological activity but low absorption of its conjugates remains a puzzle. © 2015 Society of Chemical Industry.

Inhibition of acrylamide formation in food has been extensively reported, but some mitigation methods result in a concomitant increase in hydroxymethylfurfural (HMF), a food contaminant mainly produced through Maillard reaction. Mitigation strategies to reduce HMF are not yet available. This study showed that cysteine alone or in combination with glycine could simultaneously and significantly reduce the content of acrylamide and HMF in asparagine/glucose model as well as in biscuits. Mixing 0.36 g/100 g of cysteine and 0.2 g/100 g (w/w) of glycine into the dough reduced 97.8% and 93.2% of acrylamide and HMF, respectively, in biscuits. Cysteine reduced HMF content possibly by reacting with formed HMF through Michael adduction and Maillard reaction.

Ferulic acid is a natural compound that possesses multiple physiological and pharmaceutical functions. The chemical, physical, and pharmaceutical properties of this phenolic acid can be improved by derivatives with other active compounds. This sentence (Hence, such improvements can widen the applications of ferulic acid in the food, cosmetic, and pharmaceutical industries.) has been deleted. This article reviewed the identification, preparation, and biological activities of feruloyl derivatives of carbohydrates, glycerol and glycerides, amide, fatty alcohol, myo-inositol, and nitric oxide. It also briefly discussed other derivatives. Researchers are encouraged to carry out toxicological, pharmacokinetic, and clinical investigation of potent active feruloyl derivatives and to develop other derivatives. Review Article Pei et al.; ARRB, 5(6): 512-528, 2015; Article no.ARRB.2015.054 513

p-Coumaric acid (4-hydroxycinnamic acid) is a phenolic acid that has low toxicity in mice (LD50 = 2850 mg kg(-1) body weight), serves as a precursor of other phenolic compounds, and exists either in free or conjugated form in plants. Conjugates of p-coumaric acid have been extensively studied in recent years due to their bioactivities. In this review, the occurrence, bioavailability and bioaccessibility of p-coumaric acid and its conjugates with mono-, oligo- and polysaccharides, alkyl alcohols, organic acids, amine and lignin are discussed. Their biological activities, including antioxidant, anti-cancer, antimicrobial, antivirus, anti-inflammatory, antiplatelet aggregation, anxiolytic, antipyretic, analgesic, and anti-arthritis activities, and their mitigatory effects against diabetes, obesity, hyperlipaemia and gout are compared. Cumulative evidence from multiple studies indicates that conjugation of p-coumaric acid greatly strengthens its biological activities; however, the high biological activity but low absorption of its conjugates remains a puzzle. © 2015 Society of Chemical Industry.

Chlorogenic acid (CGA) is a phenolic acid that ubiquitously exists in fruits. This work aims to investigate whether and how CGA influences HMF formation during heating fructose alone, or with an amino acid. The results showed that that CGA increased 5-hydroxymethylfurfural (HMF) formation. At pH 5.5 and 7.0, the addition of 5.0 μmol/ml CGA increased HMF formation by 49.4% and 25.2%, respectively when heating fructose alone, and by 9.0% and 16.7%, respectively when heating fructose with aspartic acid. CGA significantly increased HMF formation by promoting 3-deoxosone formation, and its conversion to HMF by inhibiting HMF elimination, especially in the Maillard reaction system. A comparison of the catalytic capacity of CGA with its six analogous compounds showed that both its di-hydroxyphenyl and carboxyl groups function in increasing HMF formation.