Essential structure of co-pigment for blue sepal-color development of hydrangea
Essential structure of co-pigment for blue sepal-color development of hydrangea
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DOI：
10.1016/j.tetlet.2005.07.146
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发表时间：
2005-09-26
影响因子：
1.8
通讯作者：
Yoshida, K
中科院分区：
文献类型：
--
作者：
Kondo, T;Yuki, TK;Yoshida, K
八仙花之所以呈蓝色，可能是由于在pH值为4.0左右的水溶液中形成了一种超分子金属络合物色素，该色素由飞雀素-3-葡萄糖苷(1)、共色素(5-O-咖啡酰奎宁酸(2)和/或5-O-对香豆酰奎宁酸(3))和Al3+组成。为了阐明绣球花的蓝色萼片颜色的形成机制，我们尝试在pH值为4.0的Al3+存在下，将1与设计的合成共色素混合，在体外重现蓝色。我们首先成功地澄清了形成稳定蓝色溶液的共颜料中的基本功能结构。在这里，我们提出了蓝色颜料的结构，它是由B环、1-羟基、1-羧酸的邻位二羟基上的铝络合物与酯中2和/或3的5位上的羰基残基配位形成的。5位上的芳香族酰基残基与1的核之间的疏水相互作用也可能有助于稳定该络合物。(C)2005爱思唯尔有限公司。保留所有权利。
Blue sepal-color of Hydrangea macrophylla might be due to a supramolecular metal-complex pigment consisting of delphinidin 3-glucoside (1), co-pigments (5-O-caffeoylquinic acid (2), and/or 5-O-p-coumaroylquinic acid (3)) and Al3+ in an aqueous solution around pH 4.0. To clarify the mechanism of blue sepal-color development of hydrangea, we tried to reproduce the blue color in vitro by mixing 1 with designed synthetic co-pigments in the presence of Al3+ at pH 4.0. We at first succeeded in clarifying the essential functional structure in the co-pigment that could form the stable blue solution. Here, we present the structure of the blue pigment caused by an Al-complex coordinating of I at ortho-dihydroxyl groups of the B-ring, 1-hydroxy, 1-carboxylic acid, and the carbonyl residue in the ester at 5-position of 2 and/or 3. The hydrophobic interaction between the aromatic acyl residue at 5-position and the nucleus of 1 may also contribute to stabilize the complex. (c) 2005 Elsevier Ltd. All rights reserved.