Food Science and Human Nutrition Department, Institute of Food and Agricultural Sciences, University of Florida , Gainesville, Florida 32611, United States.
School of Environmental and Biological Engineering, Nanjing University of Science and Technology , Nanjing, Jiangsu, China 210094.
J Agric Food Chem. 2015 Nov 4;63(43):9488-95. doi: 10.1021/acs.jafc.5b03949. Epub 2015 Oct 20.
The objective of this study was to investigate the ability of resveratrol and hesperetin to scavenge acrolein at pH 7.4 and 37 °C. About 6.4 or 5.2% of acrolein remained after reaction with resveratrol or hesperetin for 12 h at equimolar concentrations. An acrolein-resveratrol adduct and two acrolein-hesperetin adducts were isolated. Their structures were elucidated using mass and NMR spectroscopy. Acrolein reacted with resveratrol at the C-2 and C-3 positions through nucleophilic addition and formed an additional heterocyclic ring. Two similar monoacrolein-conjugated adducts were identified for hesperetin. Spectroscopic data suggested each acrolein-hesperetin adduct was a mixture of four stereoisomers due to the existence of two chiral carbon atoms. Yield of adducts was low at pH 5.4 but increased at pH 7.4 and 8.4. Higher pH also promoted the formation of diacrolein adducts. Results suggest that resveratrol and hesperetin exert health benefits in part through neutralizing toxic acrolein in vivo.
本研究旨在探讨白藜芦醇和橙皮苷在 pH 7.4 和 37°C 条件下清除丙烯醛的能力。在等摩尔浓度下，反应 12 小时后，丙烯醛与白藜芦醇或橙皮苷反应后仍残留约 6.4%或 5.2%。分离得到丙烯醛-白藜芦醇加合物和两种丙烯醛-橙皮苷加合物。采用质谱和 NMR 光谱法阐明了它们的结构。丙烯醛通过亲核加成与白藜芦醇在 C-2 和 C-3 位置反应，形成额外的杂环。鉴定出橙皮苷有两种类似的单丙烯醛缀合加合物。由于存在两个手性碳原子，光谱数据表明每个丙烯醛-橙皮苷加合物都是四种立体异构体的混合物。在 pH 5.4 时加合物的产率较低，但在 pH 7.4 和 8.4 时增加。较高的 pH 值也促进了二丙烯醛加合物的形成。结果表明，白藜芦醇和橙皮苷通过在体内中和有毒的丙烯醛发挥一定的健康益处。
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