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.
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 micronucleated mouse peripheral reticulocytes.
Li
X
X
School of Pharmacy, Tokyo University of Pharmacy and Life Science, Hachioji, Japan.
Hiramoto
K
K
Yoshida
M
M
Kato
T
T
Kikugawa
K
K
D000818:Animals; D002850:Chromatography, Gel; D002851:Chromatography, High Pressure Liquid; D004249:DNA Damage / Q000187:drug effects*; D004578:Electron Spin Resonance Spectroscopy; D004587:Electrophoresis, Agar Gel; D005503:Food Additives / Q000737:chemistry* / Q000633:toxicity*; D005663:Furans / Q000737:chemistry* / Q000633:toxicity*; D007501:Iron / Q000737:chemistry; D008297:Male; D051379:Mice; D008813:Mice, Inbred ICR; D015162:Micronucleus Tests; D009152:Mutagenicity Tests; D019163:Reducing Agents / Q000737:chemistry; D013025:Glycine max / Q000737:chemistry*; D017365:Spices / Q000032:analysis*
D005503:Food Additives; D005663:Furans; D019163:Reducing Agents; C058427:furaneol; D007501:Iron; C112945:4-hydroxy-2-ethyl-5-methyl-3(2H)-furanone