Enzymatic acylation of cyanidin-3-O-glucoside with aromatic and aliphatic acid methyl ester : Structure–stability relationships of acylated derivatives

: Li, Zhiying; Teng, Wei; Xie, Xu; Bao, Yiwen; Xu, Aihua; Sun, Yongxin; Yang, Baoru; Tian, Jinlong; Li, Bin

Publisher: Elsevier

: 2024

: Food Research International

: 114824

: 192

: 0963-9969

: 1873-7145

DOI: https://doi.org/10.1016/j.foodres.2024.114824

: https://doi.org/10.1016/j.foodres.2024.114824

Anthocyanins are water-soluble pigments, but they tend to be unstable in aqueous solutions. Modification of their molecular structure offers a viable approach to alter their intrinsic properties and enhance stability. Aromatic and aliphatic acid methyl esters were used as acyl donors in the enzymatic acylation of cyanidin-3-O-glucoside (C3G), and their analysis was conducted using ultraperformance liquid chromatography–mass spectrometry (UPLC-MS). The highest conversion rate achieved was 96.41 % for cyanidin-3-O-(6″-feruloyl) glucoside. Comparative evaluations of stability revealed that aromatic acyl group–conjugated C3G exhibited superior stability enhancement compared with aliphatic acyl group derivatives. The stability of aliphatic C3G decreased with increasing carbon chain length. The molecular geometries of different anthocyanins were optimized, and energy level calculations using density functional theory (DFT) identified their sites with antioxidant activities. Computational calculations aligned with the in vitro antioxidant assay results. This study provided theoretical support for stabilizing anthocyanins and broadened the application of acylated anthocyanins as food colorants and nutrient supplements.

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This work was supported by The National Key Research and Development Plan of China ( 2022YFD2100803 ), the National Natural Science Foundation of China ( U21A20273 ) and Zhejiang Leading Geese Project ( 2023C02046 ).