Structure Determination of 3-O-Caffeoyl-epi-γ-quinide, an Orphan Bitter Lactone in Roasted Coffee

被引：44

作者：

Frank, Oliver ^{[1
]}

Blumberg, Simone ^{[1
]}

Kruempel, Gudrun ^{[2
]}

Hofmann, Thomas ^{[1
]}

机构：

[1] Tech Univ Munich, Lehrstuhl Lebensmittelchem & Mol Sensor, D-85350 Freising Weihenstephan, Germany

[2] Univ Munster, Inst Lebensmittelchem, D-48149 Munster, Germany

来源：

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | 2008年 / 56卷 / 20期

关键词：

Coffee; bitter taste; chlorogenic acid; 5-O-caffeoylquinic acid; lactones; caffeoyl quinides;

D O I：

10.1021/jf802210a

中图分类号：

S [农业科学];

学科分类号：

09 ;

摘要：

Recent investigations on the bitterness of coffee as well as 5-O-caffeoyl quinic acid roasting mixtures indicated the existence of another, yet unknown, bitter lactone besides the previously identified bitter compounds 5-O-caffeoyl-muco-gamma-quinide, 3-O-caffeoyl-gamma-quinide, 4-O-caffeoyl-muco-gamma-quinide, 5-O-caffeoyl-epi-delta-quinide, and 4-O-caffeoyl-gamma-quinide. In the present study, this orphan bitter lactone was isolated from the reaction products generated by dry heating of 5-O-caffeoylquinic acid model, and its structure was determined as the previously unreported 3-O-caffeoyl-epi-gamma-quinide by means of liquid chromatography-mass spectrometry (LC-MS) and one-/two-dimensional NMR experiments. The occurrence of this bitter lactone, exhibiting a low bitter recognition threshold of 58 mu mol/L, in coffee beverages could be confirmed by LC-MS/MS (negative electrospray ionization) operating in the multiple reaction monitoring mode.

引用

页码：9581 / 9585

页数：5

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