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Application of ultra‐performance liquid chromatography coupled with quadrupole time‐of‐flight mass spectrometry in identification of three isoflavone glycosides and their corresponding metabolites
Author(s) -
Xu Xiafen,
Li Xinhui,
Liang Xianrui
Publication year - 2018
Publication title -
rapid communications in mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.528
H-Index - 136
eISSN - 1097-0231
pISSN - 0951-4198
DOI - 10.1002/rcm.8038
Subject(s) - chemistry , glycoside , chromatography , mass spectrometry , isoflavones , quadrupole time of flight , metabolic pathway , tandem mass spectrometry , metabolomics , fragmentation (computing) , liquid chromatography–mass spectrometry , metabolite , biochemistry , metabolism , stereochemistry , computer science , operating system
Rationale Metabolites of isoflavones have attracted much attention in recent years due to their potential bioactivities. However, the complex constituents of the metabolic system and the low level of metabolites make them difficult to analyze. A mass spectrometry (MS) method was applied in our identification of metabolites and study of their fragmentation pathways due to the advantages of rapidity, sensitivity, and low level of sample consumption. Methods Three isoflavone glycosides and their metabolites were identified using ultra‐performance liquid chromatography coupled with quadrupole time‐of‐flight tandem mass spectrometry (UPLC/QTOF‐MS). These metabolites were obtained by anaerobically incubating three isoflavone glycosides with human intestinal flora. The characteristic fragments of isoflavone glycosides and their metabolites were used for the identification work. Results Two metabolites from ononin, three metabolites from irilone‐4′‐ O ‐β‐D‐glucoside, and five metabolites from sissotrin were identified respectively by the retention time (RT), accurate mass, and mass spectral fragmentation patterns. The losses of the glucosyl group, CO from the [M+H] + ion were observed for all the three isoflavone glycosides. The characteristic retro‐Diels‐Alder (RDA) fragmentation patterns were used to differentiate the compounds. The metabolic pathways of the three isoflavone glycosides were proposed according to the identified chemical structures of the metabolites. Conclusions A selective, sensitive and rapid method was established for detecting and identifying three isoflavone glycosides and their metabolites using UPLC/QTOF‐MS. The established method can be used for further rapid structural identification studies of metabolites and natural products. Furthermore, the proposed metabolic pathways will be helpful for understanding the in vivo metabolic process of isoflavone.