Chen Zhifei, Liu Qiang, Zhao Zhiwei, Bai Bing, Sun Zhitao, Cai Lili, Fu Yufeng, Ma Yuping, Wang Qingfu, Xi Gaolei
Technology Center, China Tobacco Henan Industrial Co., Ltd. Zhengzhou Henan 450016 China
School of Food & Biological Engineering, Zhengzhou University of Light Industry Zhengzhou Henan 450002 China.
RSC Adv. 2021 Oct 25;11(55):34456-34461. doi: 10.1039/d1ra06317k.
It is well known that 2,3-dihydro-3,5-dihydroxy-6-methyl-4-pyran-4-one (DDMP) is usually formed in the Maillard reaction and it contributes to the antioxidant properties of Maillard reaction intermediates. A series of hydroxyl group protected DDMP derivatives were synthesized to further understand the source of antioxidant activity. Antioxidant abilities of the DDMP derivatives were evaluated by scavenging the 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS˙), 2,2'-diphenyl-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, respectively. It was found that the introduction of protecting groups to the free hydroxyl groups of DDMP decreases their reducing abilities. In particular, the hydroxyl group at the olefin position exhibited a remarkable impact on the antioxidant activity of DDMP, indicating that the unstable enol structure in the DDMP moiety is the key factor for its antioxidant activity.
众所周知，2,3 - 二氢 - 3,5 - 二羟基 - 6 - 甲基 - 4 - 吡喃 - 4 - 酮（DDMP）通常在美拉德反应中形成，并且它有助于美拉德反应中间体的抗氧化性能。合成了一系列羟基保护的DDMP衍生物，以进一步了解抗氧化活性的来源。分别通过清除2,2'-偶氮双（3 - 乙基苯并噻唑啉 - 6 - 磺酸盐）阳离子自由基（ABTS˙）、2,2'-二苯基 - 1 - 苦基肼自由基（DPPH）和加尔维诺克斯自由基来评估DDMP衍生物的抗氧化能力。发现将保护基团引入DDMP的游离羟基会降低它们的还原能力。特别是，烯烃位置的羟基对DDMP的抗氧化活性表现出显著影响，这表明DDMP部分中不稳定的烯醇结构是其抗氧化活性的关键因素。
