Synthesis and Quantitative Analysis of Plasma-Targeted Metabolites of Catechin and Epicatechin

被引：23

作者：

Blount, Jack W. ^{[1
]}

Redan, Benjamin W. ^{[2
]}

Ferruzzi, Mario G. ^{[2
,3
]}

Reuhs, Bradley L. ^{[2
]}

Cooper, Bruce R. ^{[6
]}

Harwood, John S. ^{[7
,8
]}

Shulaev, Vladimir ^{[1
]}

Pasinetti, Giulio ^{[4
,5
]}

Dixon, Richard A. ^{[1
]}

机构：

[1] Univ N Texas, Dept Biol Sci, Denton, TX 76203 USA

[2] Purdue Univ, Dept Nutr Sci, W Lafayette, IN 47907 USA

[3] Purdue Univ, Dept Food Sci, W Lafayette, IN 47907 USA

[4] Mt Sinai Sch Med, Dept Psychiat, New York, NY 10029 USA

[5] James J Peters Vet Affairs Med Ctr, Bronx, NY USA

[6] Purdue Univ, Bindley Biosci Ctr Metabolite Profiling Facil, W Lafayette, IN 47907 USA

[7] Purdue Univ, Purdue Interdept NMR Facil, W Lafayette, IN 47907 USA

[8] Purdue Univ, Dept Chem, W Lafayette, IN 47907 USA

来源：

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | 2015年 / 63卷 / 08期

基金：

美国国家科学基金会; 美国国家卫生研究院;

关键词：

catechin; glucuronosylation; O-methylation; phase II metabolites; semisynthesis; structure determination; two-site validation; (-)-EPICATECHIN METABOLITES; MATRIX; BIOAVAILABILITY; PROCYANIDINS; FLAVAN-3-OLS; POLYPHENOLS; INGESTION; EXCRETION; BRAIN;

D O I：

10.1021/jf505922b

中图分类号：

S [农业科学];

学科分类号：

09 ;

摘要：

Grape seed polyphenolic extract (GSPE) rich in the flavan-3-ols (+)-catechin and (-)-epicatechin beneficially modulates Alzheimer's Disease phenotypes in animal models. The parent molecules in the extract are converted to a series of methylated and glucuronidated derivatives. To fully characterize these metabolites and establish a robust quantitative assay of their levels in biological fluids, we have implemented a partial synthetic approach utilizing chemical methylation followed by enzymatic glucuronidation. Liquid chromatography/time-of-flight mass spectrometry (LC-TOF-MS) and nuclear magnetic resonance (NMR) spectroscopy were used to assign unequivocal structures to the compounds. An analytical method using solid-phase extraction and LC-MS/MS in selective reaction monitoring mode (SRM) was validated for their quantitation in plasma. These studies provide a basis for improvements in future work on the bioavailability, metabolism, and mechanism of action of metabolites derived from dietary flavan-3-ols in a range of interventions.

引用

页码：2233 / 2240

页数：8

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