Oxidation of flavonols with Cu(II), Fe(II) and Fe(III) in aqueous media

被引:60
作者
Jungbluth, G [1 ]
Rühling, I [1 ]
Ternes, W [1 ]
机构
[1] Tierarztliche Hsch Hannover, Zentrum Lebensmittelwissensch, ZA Chem Analyt & Endokrinol, D-30173 Hannover, Germany
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 2000年 / 09期
关键词
D O I
10.1039/b002323j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reactions of flavonols, 3-methoxyflavones, and flavones with Cu2+, Fe3+, and Fe2+ in acidic aqueous solutions with three different organic modifiers are investigated. Complexation may be followed by an oxidation of flavonols, yielding additional peaks in HPLC chromatograms of the reaction mixtures. The products are synthesized with high yields and isolated in mg amounts. They are characterized as 2-(hydroxybenzoyl)-2-hydroxybenzofuran-3(2H)-ones, using two-dimensional NMR techniques and PBI-NCI and -EI-MS. The electrochemical behaviour of the compounds is further investigated with cyclic voltammetry.
引用
收藏
页码:1946 / 1952
页数:7
相关论文
共 33 条
[11]   ELECTROCHEMISTRY OF CATECHOL-CONTAINING FLAVONOIDS [J].
HENDRICKSON, HP ;
KAUFMAN, AD ;
LUNTE, CE .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 1994, 12 (03) :325-334
[12]  
HIROSE Y, 1994, 36 S CHEM NATURAL PR, V36, P649
[13]  
Hollman P C, 1998, Arch Toxicol Suppl, V20, P237
[14]   2,5,7,3',4'-PENTAHYDROXYFLAVAN-3,4-DIONE AS AN INTERMEDIATE PRODUCT IN THE ENZYME-CATALYZED OXIDATION OF QUERCETIN [J].
IGARASHI, K ;
KOMATSU, C ;
SHIMADA, T .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1991, 55 (03) :855-857
[15]   Oxidation of the flavonol quercetin by polyphenol oxidase [J].
Jiménez, M ;
García-Carmona, F .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1999, 47 (01) :56-60
[16]   Two-electron electrochemical oxidation of quercetin and kaempferol changes only the flavonoid C-ring [J].
Jorgensen, LV ;
Cornett, C ;
Justesen, U ;
Skibsted, LH ;
Dragsted, LO .
FREE RADICAL RESEARCH, 1998, 29 (04) :339-350
[17]   HPLC separation of flavonols, flavones and oxidized flavonols with UV-, DAD-, electrochemical and ESI-ion trap MS detection [J].
Jungbluth, G ;
Ternes, W .
FRESENIUS JOURNAL OF ANALYTICAL CHEMISTRY, 2000, 367 (07) :661-666
[18]   Quercetinase model studies.: The oxygenation of flavonol catalyzed by a cationic 2,2′-bipyridine copper(II) flavonolate complex [J].
Lippai, I ;
Speier, G .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 1998, 130 (1-2) :139-148
[19]  
Marmolle F, 1997, ANALUSIS, V25, pM53
[20]  
McAnlis Gareth T., 1997, Biochemical Society Transactions, V25, p142S