title: Structural elucidation of in vivo metabolites of isobavachalcone in rat by LC-ESI-MS(n) and LC-NMR.
abstract: Isobavachalcone (IBC) is a prenylated chalcone and belongs to the class of flavonoids, which is an active component isolated from Psoralea corylifolia L. IBC showed a range of significant pharmacological activities, including antibacterial, anticancer, anti-reverse transcriptase and antioxidant actions. In this research, the mass spectral fragmentation pattern of IBC was investigated to predict the in vivo metabolites, and five phase I metabolites and ten phase II metabolites of IBC in rat bile were elucidated and identified after oral administration using novel LC-ESI-MS(n) and LC-NMR method. The molecular structures of these metabolites were proposed on the basis of the characteristics of their precursor ions, product ions, MS/MS fragment behaviors and chromatographic retention time. The phase I metabolites were mainly biotransformed via the hydroxylation, reduction, cyclization and oxidative cleavage reactions. The phase II metabolites were mainly identified as the glucuronide conjugates and sulfated conjugates. All these findings were reported for the first time and would contribute to a further understanding of the in vivo intermediate processes and metabolic mechanism of isobavachalcone and its analogs.
authors.affiliation: Department of Pharmacology, School of Basic Medical Sciences, Capital Medical University, Beijing 100069, China; Department of Pharmacy, Xuanwu Hospital, Capital Medical University, Beijing 100053, China.
authors.forename: Su
authors.initials: S
authors.lastname: Su
authors.affiliation: State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China.
authors.forename: Yanan
authors.initials: Y
authors.lastname: Wang
authors.affiliation: Department of Pharmacology, School of Basic Medical Sciences, Capital Medical University, Beijing 100069, China.
authors.forename: Lu
authors.initials: L
authors.lastname: Bai
authors.affiliation: Department of Pharmacology, School of Basic Medical Sciences, Capital Medical University, Beijing 100069, China.
authors.forename: Binbin
authors.initials: B
authors.lastname: Xia
authors.affiliation: Department of Pharmacology, School of Basic Medical Sciences, Capital Medical University, Beijing 100069, China; Beijing Laboratory for Biomedical Detection Technology and Instrument, Beijing 100069, China.
authors.forename: Xiaorong
authors.initials: X
authors.lastname: Li
authors.affiliation: Department of Pharmacology, School of Basic Medical Sciences, Capital Medical University, Beijing 100069, China.
authors.forename: Yu
authors.initials: Y
authors.lastname: Tang
authors.affiliation: Department of Pharmacology, School of Basic Medical Sciences, Capital Medical University, Beijing 100069, China; Beijing Laboratory for Biomedical Detection Technology and Instrument, Beijing 100069, China.
authors.forename: Pingxiang
authors.initials: P
authors.lastname: Xu
authors.affiliation: Department of Pharmacology, School of Basic Medical Sciences, Capital Medical University, Beijing 100069, China; Beijing Laboratory for Biomedical Detection Technology and Instrument, Beijing 100069, China. Electronic address: xuem@ccmu.edu.cn.
authors.forename: Ming
authors.initials: M
authors.lastname: Xue
mesh_terms: D000818:Animals; D001711:Biotransformation; D047188:Chalcones / Q000493:pharmacokinetics*; D002853:Chromatography, Liquid / Q000379:methods; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008297:Male; D013058:Mass Spectrometry / Q000379:methods; D051381:Rats; D017207:Rats, Sprague-Dawley
chemical_list: D047188:Chalcones; C468754:isobavachalcone
keywords: Isobavachalcone; LC–ESI-MS(n); Metabolites; NMR; Structural elucidation