Identification of a new tetrahydropyrimidine compound derived from glycation mimic reaction of spermidine and methylglyoxal in wheat germ crackers

IF 1.5 4区 化学 Q3 CHEMISTRY, ORGANIC Tetrahedron Letters Pub Date : 2025-02-28 Epub Date: 2025-01-27 DOI:10.1016/j.tetlet.2025.155491
Koki Sugiura , Yuta Morishita , Yuto Shimoda , Takashi Fujimoto , Tomoyuki Fujita , Ayumi Tsutsui
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Abstract

Polyamines are important biological compounds. Mammals, including humans, biosynthesize polyamines in vivo or ingest them as food constituents. Spermidine is a reactive nucleophilic polyamine that reacts readily with aldehydes and carbonyls. In this study, a new tetrahydropyrimidine compound (MG-HSpd) is reported from the reaction of spermidine with methylglyoxal, a carbonyl stress substance produced by autoxidation of glucose. MG-HSpd was confirmed as a constituent of wheat germ crackers after the reaction of spermidine and methylglyoxal during the baking process.

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小麦胚芽裂解物中亚精胺与甲基乙二醛糖基化模拟反应合成的新型四氢嘧啶化合物的鉴定
多胺是重要的生物化合物。哺乳动物,包括人类,在体内生物合成多胺或将其作为食物成分摄入。亚精胺是一种反应性的亲核多胺,容易与醛和羰基反应。本文报道了一种新的四氢嘧啶化合物(MG-HSpd),该化合物由亚精胺与葡萄糖自氧化产生的羰基应激物质甲基乙二醛反应而得。在发酵过程中,经亚精胺与甲基乙二醛反应,确定MG-HSpd为小麦胚芽裂解物的组成成分。
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来源期刊
Tetrahedron Letters
Tetrahedron Letters 化学-有机化学
CiteScore
3.50
自引率
5.60%
发文量
521
审稿时长
28 days
期刊介绍: Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.
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