Yoshida K, Toyama Y, Kameda K, Kondo T
School of Life Studies, Sugiyama Jogakuen University, Nagoya, Japan.
Phytochemistry. 2000 May;54(1):85-92. doi: 10.1016/s0031-9422(00)00049-2.
To clarify the function of each caffeoyl residue in the diacylated anthocyanin gentiodelphin, a pigment from the blue flower of Gentiana makinoi, two mono-deacyl derivatives were compared for both color development and stability. In neutral solution, 3,5-di-O-beta-D-glucopyranosyl-3'-O-(6-O-caffeoyl-beta-D- glucopyranosyl)delphinidin was both bluer and more stable than 3,3'-di-O-beta-D-glucopyranosyl-5-O-(6-O-caffeoyl-beta-D- glucopyranosyl)delphinidin. Conformational analysis of each derivative under acidic conditions revealed only the 3'-O-caffeoylglucopyranosyl derivative to demonstrate intramolecular stacking. Additionally, the acyl residue in the B-ring contributed more to blue color development than that in the A-ring.
为阐明二酰化花青素龙胆花翠雀素（一种来自马钱子龙胆蓝色花朵的色素）中每个咖啡酰残基的功能，对两种单脱酰衍生物的显色和稳定性进行了比较。在中性溶液中，3,5-二-O-β-D-吡喃葡萄糖基-3'-O-(6-O-咖啡酰-β-D-吡喃葡萄糖基)飞燕草素比3,3'-二-O-β-D-吡喃葡萄糖基-5-O-(6-O-咖啡酰-β-D-吡喃葡萄糖基)飞燕草素更蓝且更稳定。在酸性条件下对每种衍生物进行构象分析发现，只有3'-O-咖啡酰吡喃葡萄糖基衍生物表现出分子内堆积。此外，B环中的酰基残基对蓝色显色的贡献比A环中的更大。
