Formation of hydroxyfuranone and hydroxypyranone derivatives with DNA-breaking activity in the Maillard reaction of glucose and albumin under physiological conditions.

Formation of DNA breaking hydroxyfuranone and hydroxypyranone derivatives in the Maillard reaction of glucose and bovine serum albumin (BSA) under physiological conditions was investigated. A mixture of glucose and BSA was incubated at 37 degrees C in water or in 1 M phosphate buffer (pH 7.4). The ethyl acetate/2-propanol extract of the reaction mixtures showed significant DNA breaking activity against supercoiled DNA especially in the presence of Fe(III) ion. Gas chromatography/mass spectrometry analysis of the mixture revealed the formation of DNA breaking hydroxyfuranones (HMF and DMHF) and hydroxypyranone (DDMP).