Metabolic studies of four soy isoflavones in rats by HPLC–HR-MS

In this paper, the metabolites of four soy isoflavones, daidzein, daidzin, genistein, and genistin, on perfused rat intestine–liver model were investigated by high-performance liquid chromatography coupled with high-resolution mass spectrometer/tandem mass spectrometer. Totally 16 metabolites were d...

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Bibliographic Details
Published in:Journal of asian natural products research 2014-05, Vol.16 (5), p.497-510
Main Authors: Li, Ying-Fei, Ren, Qiang, Jin, Ying, Wu, Cai-Sheng, Wang, Cai-Hong, Jia, Zhi-Xin, Zhang, Jin-Lan
Format: Article
Language:English
Subjects:
Animals
biochemical pathways
Chromatography
Chromatography, High Pressure Liquid
daidzein
daidzin
Disease Models, Animal
genistein
Genistein - pharmacology
genistin
high performance liquid chromatography
HPLC-HR-MS/MS
Humans
Isoflavones - pharmacology
Male
metabolic studies
Metabolites
methylation
Molecular Structure
nuclear magnetic resonance spectroscopy
Rats
soy isoflavones
Soy products
soybeans
spectrometers
sulfates
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Summary:In this paper, the metabolites of four soy isoflavones, daidzein, daidzin, genistein, and genistin, on perfused rat intestine–liver model were investigated by high-performance liquid chromatography coupled with high-resolution mass spectrometer/tandem mass spectrometer. Totally 16 metabolites were detected and identified based on accurate mass, fragmentation patterns, and multiple-stage mass data (MS ⁿ). The metabolic site of dadzein-7-methyl ether (D-7-M) was further confirmed by nuclear magnetic resonance. Methylation, glucuronide conjugation, and sulfate conjugation were the primary metabolic processes. Among them, six metabolites, daidzin-4′,7-diglucoside, genistein-4′-glucoside, D-7-M, dadzein-4′,7-dimethyl ether, genistein-4′-methyl ether, and genistein-7-methyl ether were detected in rats for the first time and not reported in humans. The metabolic pathways of daidzein, daidzin genistein, and genistin in rats were postulated. The biological effects of these metabolites are worthy of further investigation.
ISSN:1477-2213
1028-6020
1477-2213
DOI:10.1080/10286020.2014.902939