PMID: 8598830Feb 29, 1996Paper

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

Mutation Research
K HiramotoK Kikugawa

Abstract

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. It was found that the breaking activity was due to multiple components with different molecular weight and polarity. One of the components with the breaking activity was purified successively by extraction with ethyl acetate, thin-layer chromatography and high performance liquid chromatography, and identified as 4-hydroxy-5-methyl-3(2H)-furanone (HMF), one of the fragrant components in soy sauce. Formation of this component was found due to Maillard reaction of pentoses/amino acids. HMF was readily degraded into the compound with an endiol-ketol structure and reducing activity. Using 5,5-dimethyl-1-pyrroline N-oxide (DMPO) in an electron spin resonance-spin trapping technique, generation of hydroxyl radical in an aqueous solution of HMF was confirmed. While DNA breaking by soy sauce was little inhibited by the scavengers of active oxygen radicals, the breaking by HMF was effectively inhibited by superoxide dismutase, catalase, hydroxyl radical scavengers, spin-trapping agents, thiol compounds and metal chelating agents. Hence, DNA breaking a...Continue Reading

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Citations

Aug 1, 1997·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·R RoscherW Schwab
Jul 3, 1998·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·X LiK Kikugawa
Apr 6, 2002·Current Opinion in Microbiology·Klaus WinzerPaul Williams
May 3, 2005·Nature Reviews. Microbiology·Agnès VendevilleKim R Hardie
Jun 14, 2005·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Robert L SmithUNKNOWN Expert Panel of the Flavor and Extract Manufacturers Association
Oct 4, 2016·Journal of Agricultural and Food Chemistry·Clemens KanzlerLothar W Kroh
Jul 23, 2005·Annals of the New York Academy of Sciences·Katarína SebekováVeronika Somoza
May 2, 2021·Genes and Environment : the Official Journal of the Japanese Environmental Mutagen Society·Toshio KasamatsuMasamitsu Honma
Apr 3, 2009·Journal of Agricultural and Food Chemistry·Nicole Christina StadlerWilfried Schwab
Feb 24, 2007·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·K MurakamiM Yoshino
May 31, 2018·Journal of Chemical Information and Modeling·Timothy E H AllenPaul J Russell

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