SYNTHESIS OF 3-METHOXY-FLAVYLIUM AND 3-(BETA-D-GLUCOPYRANOSYLOXY)FLAVYLIUM IONS - INFLUENCE OF THE FLAVYLIUM SUBSTITUTION PATTERN ON THE REACTIVITY OF ANTHOCYANINS IN AQUEOUS-SOLUTION

被引：56

作者：

DANGLES, O

ELHAJJI, H

机构：

[1] Laboratoire de Chimie des Polyphénols, Université Louis Pasteur, Faculté de Chimie, Strasbourg, F-67008, 1, rue Blaise Pascal

来源：

HELVETICA CHIMICA ACTA | 1994年 / 77卷 / 06期

关键词：

D O I：

10.1002/hlca.19940770616

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The synthesis of 3-glycosyloxylated flavylium ions (anthocyanins), in particular of callistephin (4), a natural anthocyanin, is described. The structural transformations in aqueous solution and molecular complexation with chlorogenic acid (7) and caffeine (8) of the synthesized pigments 3 and 4 are investigated and compared to those of the corresponding 3-methoxyflavylium ions 1 and 2 and to those of oenin (5) and malvin (6), two very common natural anthocyanins. The results are discussed in terms of the role played by the glycosyloxy residues in the chemical properties of anthocyanins. Anthocyanin molecular complexation (copigmentation) is quantitatively investigated by UV/VIS spectroscopy and H-1-NMR. In particular, the UV/VIS spectroscopic data are interpreted using a general theoretical treatment, which, e.g., allows to demonstrate the formation of molecular complexes between the colourless forms of an anthocyanin and 8.

引用

页码：1595 / 1610

页数：16

共 37 条

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