The Ohio State University, Department of Food Science and Technology, 2015 Fyffe Rd., Columbus, OH 43210-1007, USA.
The Ohio State University, Department of Food Science and Technology, 2015 Fyffe Rd., Columbus, OH 43210-1007, USA.
Food Chem. 2023 Nov 30;427:136705. doi: 10.1016/j.foodchem.2023.136705. Epub 2023 Jun 24.
Pyranoanthocyanins are anthocyanin-derived pigments with vivid colors and enhanced stability, making them promising food colorants. We evaluated two 4-vinylphenols, decarboxylated p-coumaric (pCA) and ferulic acid (FA), as cofactors for pyranoanthocyanin formation. Cyanidin-3-glycosides from saponified black carrot were incubated with 4-vinylphenol or 4-vinylguaiacol in different anthocyanin-to-cofactor molar ratios (1:1-1:30) to form pyranoanthocyanins. Formation efficiency (45 °C, ≤96 h) was compared to their respective precursors at a 1:30 ratio. Composition changes were monitored using uHPLC-PDA-ESI-MS/MS. Pyranoanthocyanin yields with 4-vinylphenol (13.8-33.4%) were ∼12× higher than with pCA and yields with 4-vinylguaiacol (8.1-31.0%) were ∼6.5× higher than with FA. Molar ratios of 1:5 and 1:10 yielded significantly more pyranoanthocyanins. Pyranoanthocyanin formation with 4-vinylphenols followed first-order kinetics, whereas formation with hydroxycinnamic acids followed zero-order kinetics. Detection of intermediate compounds was consistent with a nucleophilic addition and aromatization formation mechanism. Overall, pyranoanthocyanin formation with 4-vinylphenols was more efficient than with hydroxycinnamic acids.
吡喃花青素是一种来源于花青素的色素，具有鲜艳的颜色和增强的稳定性，是很有前途的食品着色剂。我们评估了两种 4-乙烯基苯酚，去羧基对香豆酸（pCA）和阿魏酸（FA），作为吡喃花青素形成的辅因子。从水解的黑胡萝卜中得到的矢车菊素-3-糖苷，与 4-乙烯基苯酚或 4-乙烯基愈创木酚在不同的花青素-辅因子摩尔比（1:1-1:30）下孵育，形成吡喃花青素。在 1:30 的比例下，与各自的前体相比，比较了形成效率（45°C，≤96 h）。使用 uHPLC-PDA-ESI-MS/MS 监测组成变化。与 pCA 相比，4-乙烯基苯酚（13.8-33.4%）形成吡喃花青素的效率约高 12 倍，与 FA 相比，4-乙烯基愈创木酚（8.1-31.0%）形成吡喃花青素的效率约高 6.5 倍。摩尔比为 1:5 和 1:10 产生的吡喃花青素明显更多。4-乙烯基苯酚形成吡喃花青素遵循一级动力学，而羟基肉桂酸形成吡喃花青素遵循零级动力学。中间化合物的检测结果与亲核加成和芳构化形成机制一致。总的来说，4-乙烯基苯酚形成吡喃花青素的效率高于羟基肉桂酸。
