Kikugawa K, Hiramoto K, Kato T, Yanagawa H
School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo, Japan.
Mutat Res. 2000 Feb 16;465(1-2):183-90. doi: 10.1016/s1383-5718(99)00227-2.
One of the possible pathways of the formation of mutagens in heated foods is through the pyrazine cation radical generated in the early stage of the Maillard reaction. The aim of the present study was to elucidate how food reductones contribute to the pyrazine cation radical generation in the reaction of glucose (Glc) and glycine (Gly), and to the formation of the mutagens in the reaction of Glc, Gly and creatinine. Electron spin resonance (ESR) studies showed that fragrant reductones, 2,5-dimethyl-4-hydroxy-3(2H)-furanone (DMHF) and 4-hydroxy-2(or 5)-ethyl-5(or 2)-methyl-3(2H)-furanone (HEMF), generated in the Maillard reactions, enhanced the generation of the pyrazine cation radical in the reaction of Glc and Gly, and the reaction of DMHF or HEMF with Gly generated a larger amount of the pyrazine cation radical than the reaction of Glc and Gly, indicating that the furanones were intermediates of the pyrazine cation radical. By contrast, food antioxidants, ascorbic acid and erythorbic acid, effectively scavenged the pyrazine cation radical generated in the reaction of Glc and Gly. DMHF and HEMF were not effective to modulate the mutagen formation in the reaction of Glc, Gly and creatinine, and the mutagenicity produced in the reaction of DMHF or HEMF, Gly and creatinine was lower than that produced in the reaction of Glc, Gly and creatinine. On the other hand, ascorbic acid and erythorbic acid were effective to decrease the mutagen formation in the reaction of Glc, Gly and creatinine.
加热食品中诱变剂形成的可能途径之一是通过美拉德反应早期产生的吡嗪阳离子自由基。本研究的目的是阐明食品还原酮如何在葡萄糖（Glc）和甘氨酸（Gly）反应中促进吡嗪阳离子自由基的产生，以及在Glc、Gly和肌酐反应中促进诱变剂的形成。电子自旋共振（ESR）研究表明，美拉德反应中产生的香味还原酮，2,5-二甲基-4-羟基-3（2H）-呋喃酮（DMHF）和4-羟基-2（或5）-乙基-5（或2）-甲基-3（2H）-呋喃酮（HEMF），增强了Glc和Gly反应中吡嗪阳离子自由基的产生，并且DMHF或HEMF与Gly的反应比Glc和Gly的反应产生了更多的吡嗪阳离子自由基，这表明呋喃酮是吡嗪阳离子自由基的中间体。相比之下，食品抗氧化剂抗坏血酸和异抗坏血酸有效地清除了Glc和Gly反应中产生的吡嗪阳离子自由基。DMHF和HEMF对调节Glc、Gly和肌酐反应中的诱变剂形成无效，并且DMHF或HEMF、Gly和肌酐反应中产生的诱变性低于Glc、Gly和肌酐反应中产生的诱变性。另一方面，抗坏血酸和异抗坏血酸有效地减少了Glc、Gly和肌酐反应中的诱变剂形成。
