Stereochemistry and glycosidic linkages of C3-glycosylations affected the reactivity of cyanidin derivatives
Stereochemistry and glycosidic linkages of C3-glycosylations affected the reactivity of cyanidin derivatives
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DOI：
10.1016/j.foodchem.2018.11.076
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发表时间：
2019-04-25
期刊：
影响因子：
8.8
通讯作者：
Giusti, M. Monica
中科院分区：
文献类型：
--
作者：
Farr, Jacob E.;Sigurdson, Gregory T.;Giusti, M. Monica
糖基化对花青素稳定性的影响很大程度上与糖的类型、位置和大小有关，糖基立体化学尚未得到充分的研究。用高效液相色谱法分离出7种花青素-3-苷，在pH 1-9中稀释，在pH 3时与亚硫酸氢盐或抗坏血酸混合，保存8周（25℃，暗处）。测定光谱变化、半衰期和漂白率。与花青素-3-葡萄糖苷相比，花青素-3-半乳糖苷的反应性更强（对水化和漂白敏感）。1 - bbbb2双糖表现出更大的λ (vis-max)(6)双糖。1 - bbb6双糖的λ (vis-max) （2 nm）与单糖相似，但对水化和漂白的抗性略有提高。三糖基基花青素稳定性最好，其光谱和漂白特性介于1 -> - 2和1 -> - 6双糖之间。与单糖相比，1 - >2双糖通常具有较低的半衰期；而1 - >6双糖则表现出较高的稳定性。这些发现强调了糖基组装对花青素反应性和稳定性的作用。
The impact of glycosylation on anthocyanin stability has largely been associated with sugar type, site, and size, with glycosyl stereochemistry being under-explored. Seven cyanidin-3-glycosides were isolated by HPLC, diluted in pH 1-9, mixed with bisulfite or ascorbic acid at pH 3, and stored for 8 weeks ( 25 degrees C, dark). Spectral changes, half-lives, and bleaching rates were determined. Cyanidin-3-galactoside was more reactive ( susceptible to hydration and bleaching) than cyanidin-3-glucoside. The 1 -> 2 disaccharides exhibited greater lambda(vis-max) ( 6 disaccharides. The 1 -> 6 disaccharides had similar lambda(vis-max) (similar to 2 nm) to the monosaccharides but slightly improved resistance to hydration and bleaching. The tri-gly-cosylated anthocyanin had the greatest stability and its spectral and bleaching characteristics was intermediate to 1 -> 2 and 1 -> 6 disaccharides. The 1 -> 2 disaccharides generally exhibited lower half-lives compared to monosaccharides; whereas, 1 -> 6 disaccharides exhibited higher stability. These findings highlight the role of glycosyl assembly on anthocyanin reactivity and stability.