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Impact of location, type, and number of glycosidic substitutions on the color expression of o-dihydroxylated anthocyanidins
Food Chemistry ( IF 8.5 ) Pub Date : 2018-06-19 , DOI: 10.1016/j.foodchem.2018.06.079
Gregory T. Sigurdson , Rebecca J. Robbins , Thomas M. Collins , M. Mónica Giusti

Anthocyanins express many hues depending on environmental factors and structural aspects, of which aglycone structure and acylation have been considered most impactful. Effects of different glycosylations on anthocyanins’ colors are less known. Twelve cyanidin and 3-deoxy-cyanidin (luteolinidin) derivatives were isolated from red cabbage and black carrot hydrolysates and from black sorghum, diluted in pH 1–9, and analyzed by spectrophotometry and colorimetry. Location, number, and structure of glycosylations affected λmax and spectral shape of o-dihydroxylated anthocyanins, playing important roles on color expression. Generally, glycosylation of cyanidin decreased its λmax (≤27 nm), greatest decreases by 3-monoglycosylation. All cyanidin-glycosides appeared red in pH 1–3 and paled in pH 4–6. However, cyanidin-3-glycosides did not decolor completely like 3,5-glycosides. In alkaline pH, glycosylation patterns affected color more greatly: Cy-3-glycosides expressed maroon-purple hues (300–20°), 5-glycosides were green (100–115°), and only 3,5-glycosides expressed blue (240–250°). Luteolinidin derivatives shifted from yellow to red–purple hues with increasing pH.



中文翻译:

糖苷取代的位置,类型和数目对二羟基化花青素颜色表达的影响

花青素根据环境因素和结构方面表现出许多色调,其中糖苷配基结构和酰化作用被认为最有影响。不同糖基化对花青素颜色的影响尚不清楚。从红甘蓝和黑胡萝卜水解产物以及黑高粱中分离出十二种花青素和3-脱氧花青素(木犀草素)衍生物,将其稀释至pH 1–9,然后通过分光光度法和比色法进行分析。糖基化的位置,数量和结构影响二羟基化花色苷的λmax和光谱形状,在颜色表达中起重要作用。通常,花色素的糖基化作用会降低其λmax(≤27nm),最大减少是通过3-单糖基化。所有的花青素-糖苷在pH 1-3时呈红色,在pH 4-6时呈浅色。但是,花青素-3-糖苷没有像3,5-糖苷那样完全脱色。在碱性pH下,糖基化模式对颜色的影响更大:Cy-3-糖苷表示栗色-紫色色调(300–20°),5-糖苷表示绿色(100–115°),只有3,5-糖苷表示蓝色( 240–250°)。随着pH值的增加,木犀草素衍生物从黄色变为红色-紫色。

更新日期:2018-06-19
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