花青素A：一种由锦葵色素3 - O - 葡萄糖苷降解产生的苯并吡喃盐衍生物。

Anthocyanone A: a quinone methide derivative resulting from malvidin 3-O-glucoside degradation.

作者信息

Lopes Paulo, Richard Tristan, Saucier Cédric, Teissedre Pierre-Louis, Monti Jean-Pierre, Glories Yves

机构信息

Faculté d'Oenologie de Bordeaux, Université Victor Segalen Bordeaux 2, UMR 1219 INRA, 351 Cours de la Libération, 33405 Talence Cedex, France.

出版信息

J Agric Food Chem. 2007 Apr 4;55(7):2698-704. doi: 10.1021/jf062875o. Epub 2007 Mar 6.

DOI:10.1021/jf062875o

PMID:17338545

Abstract

A new compound resulting from the oxidative degradation of maldivin 3-O-glucoside under acid conditions was detected in a wine model solution stored under 90 and 25 degrees C. It was isolated by semipreparative HPLC, and its structure was elucidated by UV-vis spectra, mass spectrometry (LC/MS), and NMR spectroscopy (1-D and 2-D). The compound was identified as 8-beta-d-glucopyranosyl-2,4-dihydroxy-6-oxo-cyclohexa-2,4-dienyl acetic acid (anthocyanone A), which results from nucleophilic attack of hydrogen peroxide to maldivin 3-O-glucoside through a Baeyer-Villiger oxidation followed by other oxidations steps.

摘要

在90℃和25℃储存的葡萄酒模型溶液中，检测到了马尔维丁3-O-葡萄糖苷在酸性条件下氧化降解产生的一种新化合物。通过半制备高效液相色谱法对其进行分离，并利用紫外可见光谱、质谱（液相色谱/质谱联用）和核磁共振光谱（一维和二维）对其结构进行了阐明。该化合物被鉴定为8-β-D-吡喃葡萄糖基-2,4-二羟基-6-氧代-环己-2,4-二烯基乙酸（花青素酮A），它是由过氧化氢通过拜耳-维利格氧化，随后经过其他氧化步骤对马尔维丁3-O-葡萄糖苷进行亲核攻击而产生的。