LC-MSn analysis of the cis isomers of chlorogenic acids

被引：223

作者：

Clifford, Michael N. ^{[1
]}

Kirkpatrick, Jo

Kuhnert, Nikolai

Roozendaal, Hajo

Salgado, Paula Rodrigues

机构：

[1] Univ Surrey, Sch Biomed & Mol Sci, Ctr Nutr & Food Safety, Surrey GU2 7XH, England

[2] Jacobs Univ Bremen, Sch Sci & Engn, D-28759 Bremen, Germany

[3] Univ Sao Paulo, Escola Superior Agr Luiz Queiroz, Dept Producao Vegetal, Sao Paulo, Brazil

来源：

FOOD CHEMISTRY | 2008年 / 106卷 / 01期

关键词：

caffeoylquinic acids; chlorogenic acids; coffee; p-coumaroylquinic acids; cynarin; dicaffeoylquinic acids; feruloylquinic acids; LC-MSn; leaves; UV-irradiation;

D O I：

10.1016/j.foodchem.2007.05.081

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The behaviour of cis isomers of selected mono- and di-acyl chlorogenic acids produced by UV-irradiation has been investigated by LC-MSn. cis Isomers fragment identically to the more common trans isomers. cis-5-Acyl chlorogenic acids are more hydrophobic and elute later than their mono- or di-trans counterparts whereas the reverse is true for cis-3-acyl and cis-4-acyl chlorogenic acids. The cis isomers of 1,3-dicaffeoylquinic acid, the only I-acyl chlorogenic acid investigated, are also more hydrophobic than the di-trans isomer. Coffee leaves had a proportionately greater content of cis isomers relative to trans isomers compared with coffee beans suggesting that UV-irradiation in vivo may also cause geometric isomerisation. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：379 / 385

页数：7

共 21 条

[1]

[Anonymous], 1976, Biochem J, V153, P23

[2] Profiling the chlorogenic acids of aster by HPLC-MSn [J].

Clifford, Michael N. ;

Zheng, Wang ;

Kuhnert, Nikolai .

PHYTOCHEMICAL ANALYSIS, 2006, 17 (06) :384-393

[3] CHARACTERIZATION OF CAFFEOYLFERULOYLQUINIC ACIDS BY SIMULTANEOUS ISOMERIZATION AND TRANS-ESTERIFICATION WITH TETRAMETHYLAMMONIUM HYDROXIDE [J].

CLIFFORD, MN ;

KELLARD, B ;

BIRCH, GG .

FOOD CHEMISTRY, 1989, 34 (02) :81-88

[4] CHARACTERIZATION OF CHLOROGENIC ACIDS BY SIMULTANEOUS ISOMERIZATION AND TRANS-ESTERIFICATION WITH TETRAMETHYLAMMONIUM HYDROXIDE [J].

CLIFFORD, MN ;

KELLARD, B ;

BIRCH, GG .

FOOD CHEMISTRY, 1989, 33 (02) :115-123

[5] Characterization by LC-MSn of four new classes of chlorogenic acids in green coffee beans:: Dimethoxycinnamoylquinic acids, diferuloylquinic acids, caffeoyl-dimethoxycinnamoylquinic acids, and feruloyl-dimethoxycinnamoylquinic acids [J].

Clifford, MN ;

Knight, S ;

Surucu, B ;

Kuhnert, N .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2006, 54 (06) :1957-1969

[6] The chlorogenic acids of Hemerocallis [J].

Clifford, MN ;

Wu, WG ;

Kuhnert, N .

FOOD CHEMISTRY, 2006, 95 (04) :574-578

[7] Discriminating between the six isomers of dicaffeoylquinic acid by LC-MSn [J].

Clifford, MN ;

Knight, S ;

Kuhnert, N .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2005, 53 (10) :3821-3832

[8] Hierarchical scheme for LC-MSn identification of chlorogenic acids [J].

Clifford, MN ;

Johnston, KL ;

Knight, S ;

Kuhnert, N .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2003, 51 (10) :2900-2911

[9]

Clifford MN, 2002, METHODS IN POLYPHENOL ANALYSIS, P314

[10]

Clifford MN, 2000, J SCI FOOD AGR, V80, P1033, DOI [10.1002/(SICI)1097-0010(20000515)80:7&lt

← 1 2 3 →