Identification of 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) and 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone (HEMF) with DNA breaking activity in soy sauce

Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association
X LiK Kikugawa

Abstract

Components with DNA breaking activity in soy sauce were investigated. It was found that there were water soluble high molecular weight DNA breaking components in soy sauce. Two DNA breaking components in the ethyl acetate extract of soy sauce were identified as fragrant components, 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) and 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone (HEMF), in addition to the previously characterized DNA breaking fragrant component 4-hydroxy-5-methyl-3(2H)-furanone (HMF) (Hiramoto et al., 1996b). Characterization of DNA breaking activity of HEMF was performed, and the mechanisms for the breaking were considered. HEMF cleaved the single strands of supercoiled pBR 322 DNA at pH 7.4 dose dependently and time dependently. DNA breaking was inhibited by superoxide dismutase, catalase, hydroxyl radical scavengers, spin trapping agents and metal chelators, and enhanced by Fe(III) ion. Electron spin resonance-spin trapping technique revealed the generation of hydroxyl radical. Hence, active oxygen species derived from interaction of HEMF with metal ions and oxygen participated in the cleavage. HEMF exhibited mutagenicity to Salmonella typhimurium TA100 without metabolic activation and induced micronucle...Continue Reading

References

Apr 1, 1977·Mutation Research·T YahagiT Sugimura
Jan 1, 1987·Free Radical Biology & Medicine·G R Buettner
Oct 1, 1995·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·K HiramotoK Kikugawa

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Citations

Dec 4, 2001·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·D MarkoT Hofmann
Jun 15, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Wilfried Schwab
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
Apr 3, 2009·Journal of Agricultural and Food Chemistry·Nicole Christina StadlerWilfried Schwab
Apr 16, 2003·Chemical Research in Toxicology·Doris MarkoThomas Hofmann
Sep 4, 2020·Journal of Agricultural and Food Chemistry·Carmen Diez-SimonRobert D Hall

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