State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-products, Key Laboratory of Post-Harvest Handling of Fruits, Ministry of Agriculture and Rural Affairs, Key Laboratory of Fruits and Vegetables Postharvest and Processing Technology Research of Zhejiang Province, Food Science Institute, Zhejiang Academy of Agricultural Sciences, Hangzhou 310021, China.
School of Food and Biological Engineering, Shaanxi University of Science and Technology, Xi'an 710021, China.
Food Chem. 2023 Jun 15;411:135409. doi: 10.1016/j.foodchem.2023.135409. Epub 2023 Jan 5.
Co-pigmentation effect of phenolic acids on cyanidin-3-O-glucoside (C3G) and the mechanisms were investigated. Sinapic acid (SIA), ferulic acid (FA), p-coumaric acid (p-CA) and syringic acid (SYA) significantly enhanced C3G stability (P < 0.05), whereas vanillic acid (VA) and gallic acid (GA) showed no influence (P > 0.05). Among these phenolic acids, SIA and FA had higher binding coefficient with C3G (48.83 and 43.38), reduced degradation rate constant by 40.0 ∼ 50.0 %, prolonged half-life by 74.6 ∼ 94.7 % at 323 K, and significantly inhibited C3G hydration reaction (pK = 2.87 and 2.80, P < 0.05). Molecular docking revealed that C3G and co-pigments were connected by hydrogen bond and π-π stacking interaction. Hydroxycinnamic acids of SIA, FA and p-CA bound with ring B and ring C of C3G, while hydroxybenzoic acids of SYA, VA and GA hardly interacted with ring C. Generally, the protection effect of hydroxycinnamic acids on C3G was better than that of hydroxybenzoic acids, exhibiting stronger hyperchromic effect.
研究了酚酸对矢车菊素-3-O-葡萄糖苷(C3G)的共色效应及其机制。阿魏酸(FA)、咖啡酸(p-CA)、丁香酸(SYA)和芥子酸(SIA)显著提高了 C3G 的稳定性(P<0.05),而香草酸(VA)和没食子酸(GA)则没有影响(P>0.05)。在这些酚酸中,SIA 和 FA 与 C3G 的结合系数较高(分别为 48.83 和 43.38),在 323 K 时,降低降解速率常数 40.0∼50.0%,延长半衰期 74.6∼94.7%,并显著抑制 C3G 的水合反应(pK=2.87 和 2.80,P<0.05)。分子对接表明,C3G 和共色剂通过氢键和π-π堆积相互作用连接。SIA、FA 和 p-CA 的羟基肉桂酸与 C3G 的环 B 和环 C 结合,而 SYA、VA 和 GA 的羟基苯甲酸几乎不与环 C 相互作用。总的来说,羟基肉桂酸对 C3G 的保护作用优于羟基苯甲酸,表现出更强的增色效应。