School of Biological Sciences, The University of Hong Kong, Pokfulam Road, Hong Kong, People's Republic of China.
Chem Res Toxicol. 2009 Aug;22(8):1483-9. doi: 10.1021/tx9001644.
Chemical model reactions were carried out to investigate the effect of a citrus flavonoid, naringenin, on the formation of acrylamide under mild heating conditions. Results showed that naringenin significantly and dose dependently inhibited the formation of acrylamide (20-50% relative to the control), although not in a linear manner. Moreover, the presence of naringenin in acrylamide-producing models effectively reduced the extent of browning. Careful comparison of the HPLC chromatograms of samples from the chemical model reactions revealed that naringenin likely reacted with Maillard intermediates, giving rise to new derivatives. Subsequent LC-MS analyses suggested that the proposed derivatives have a predicted molecular mass of 341 Da. Eventually, two derivatives were purified and characterized with LC-MS/MS and NMR spectroscopy as 8-C-(E-propenamide)naringenin and 6-C-(E-propenamide)naringenin, respectively. In other words, naringenin, a rather weak antioxidant, strongly inhibited acrylamide formation probably by directly reacting with acrylamide precursors, thus diverting them from the pathways that lead to acrylamide formation.
进行了化学模型反应，以研究一种柑橘类黄酮柚皮素在温和加热条件下对丙烯酰胺形成的影响。结果表明，柚皮素能显著且剂量依赖性地抑制丙烯酰胺的形成（相对于对照物，抑制率为 20-50%），尽管不是线性方式。此外，在丙烯酰胺产生模型中存在柚皮素可有效降低褐变程度。仔细比较化学模型反应样品的 HPLC 色谱图表明，柚皮素可能与美拉德中间体反应，产生新的衍生物。随后的 LC-MS 分析表明，所提出的衍生物的预测分子量为 341 Da。最终，两种衍生物通过 LC-MS/MS 和 NMR 光谱法进行了纯化和表征，分别为 8-C-（E-丙烯酰胺）柚皮素和 6-C-（E-丙烯酰胺）柚皮素。换句话说，柚皮素作为一种相当弱的抗氧化剂，通过直接与丙烯酰胺前体反应，强烈抑制丙烯酰胺的形成，从而使它们偏离导致丙烯酰胺形成的途径。
