DNA breaking activity and mutagenicity of soy sauce: characterization of the active components and identification of 4-hydroxy-5-methyl-3(2H)-furanone.

Soy sauce is a seasoning consumed widely in Southeast Asia. When supercoiled DNA was incubated with soy sauce at pH7.4 and 37 degrees C, extensive breaking of DNA single-strands was caused.

DNA strand breaks induced through active oxygen radicals by fragrant component 4-hydroxy-2-hydroxymethyl-5-methyl-3(2H)-furanone in Maillard reaction of hexose/amino acid.

The Maillard reaction of glucose/amino acid produces components that induce strand breakage of supercoiled DNA. This study was designed to elucidate the structure of the active components and the mechanisms of their DNA strand breakage. When an aqueous mixture of glucose/glycine heated under reflux for 4 hr was extracted with ethyl acetate, the extract showed mutagenicity to Salmonella typhimurium TA100 and strand-breaking activity for supercoiled DNA.