Imahori Daisuke, Matsumoto Takahiro, Kojima Naoto, Hasei Tomohiro, Sumii Megumi, Sumida Taishi, Yamashita Masayuki, Watanabe Tetsushi
Kyoto Pharmaceutical University.
Chem Pharm Bull (Tokyo). 2018;66(4):363-367. doi: 10.1248/cpb.c17-00809.
Two novel and two known compounds, 4-quinolylaldoxime and indole-3-aldehyde, were isolated from a reaction mixture consisting of D-glucose and L-tryptophan at physiological temperature and pH. The chemical structures of the two novel compounds were elucidated by spectroscopic analysis such as X-ray crystallography. One of the novel compound and the indole-3-aldehyde showed mutagenicity toward Salmonella typhimurium YG1024 with S9 mix. Furthermore, 4-quinolylaldoxime was detected from streptozotocin-induced diabetic rat plasma by LC-MS/MS analysis; however, the isolated compounds were not detected in rat diet extracts. To our knowledge, this is the first report in which 4-quinolylaldoxime was detected in rat plasma. These results suggest that amino-carbonyl reaction products may be formed in diabetic condition and induce genetic damage.
在生理温度和pH条件下，从由D - 葡萄糖和L - 色氨酸组成的反应混合物中分离出两种新型化合物和两种已知化合物，即4 - 喹啉醛肟和吲哚 - 3 - 甲醛。通过诸如X射线晶体学等光谱分析阐明了这两种新型化合物的化学结构。其中一种新型化合物和吲哚 - 3 - 甲醛对带有S9混合物的鼠伤寒沙门氏菌YG1024表现出致突变性。此外，通过LC - MS/MS分析在链脲佐菌素诱导的糖尿病大鼠血浆中检测到了4 - 喹啉醛肟；然而，在大鼠饮食提取物中未检测到分离出的化合物。据我们所知，这是首次在大鼠血浆中检测到4 - 喹啉醛肟的报告。这些结果表明，氨基 - 羰基反应产物可能在糖尿病状态下形成并诱导基因损伤。
