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Identification of bio‐active metabolites of gentiopicroside by UPLC/Q‐TOF MS and NMR
Author(s) -
Zeng Wenliang,
Han Han,
Tao Yanyan,
Yang Li,
Wang Zhengtao,
Chen Kaixian
Publication year - 2013
Publication title -
biomedical chromatography
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.4
H-Index - 65
eISSN - 1099-0801
pISSN - 0269-3879
DOI - 10.1002/bmc.2917
Subject(s) - chemistry , aglycone , chromatography , quadrupole time of flight , biotransformation , high performance liquid chromatography , glycoside , mass spectrometry , metabolomics , fragmentation (computing) , tandem mass spectrometry , stereochemistry , biochemistry , enzyme , computer science , operating system
ABSTRACT Gentiopicroside (GPS), the main bioactive component in Gentiana scabra Bge., has attracted our attention owing to its high bioactivity, especially the treatment of hepatobiliary disorders. The aglycone form of GPS, a typical secoiridoid glycoside, is considered to be more readily absorbed than its parent drug. This study aimed to identify and characterize the metabolites after GPS incubated with β ‐glucosidase in buffer solution at 37°C. Samples of biotransformed solution were collected and analyzed by ultraperformance liquid chromatography (UPLC)/quadrupole–time‐of‐flight mass spectrometry (Q‐TOF MS). A total of four metabolites were detected: two were isolated and elucidated by preparative‐HPLC and NMR techniques, and one of those four is reported for the first time. The mass spectral fragmentation pattern and accurate masses of metabolites were established on the basis of UPLC/Q‐TOF MS analysis. Structure elucidation of metabolites was achieved by comparing their fragmentation pattern with that of the parent drug. A fairly possible metabolic pathway of GPS by β ‐glucosidase was proposed. The hepatoprotective activities of metabolites M1 and M2 were investigated and the results showed that their hepatoprotective activities were higher than that of parent drug. Our results provided a meaningful basis for discovering lead compounds from biotransformation related to G . scabra Bge. in traditional Chinese medicine. Copyright © 2013 John Wiley & Sons, Ltd.