Rapid Screening and Identification of Daidzein Metabolites in Rats Based on UHPLC-LTQ-Orbitrap Mass Spectrometry Coupled with Data-Mining Technologies

Abstract

Daidzein, the main bioactive soy isoflavone in Nature, has been found to possess many biological functions. It has been investigated in particular as a phytoestrogen owing to the similarity of its structure with that of the human hormone estrogen. Due to the lack of comprehensive studies on daidzein metabolism, further research is still required to clarify its in vivo metabolic fate and intermediate processes. In this study, an efficient strategy was established using UHPLC-LTQ-Orbitrap mass spectrometry to profile the metabolism of daidzein in rats. Meanwhile, multiple data-mining methods including high-resolution extracted ion chromatogram (HREIC), multiple mass defect filtering (MMDF), neutral loss fragment (NLF), and diagnostic product ion (DPI) were utilized to investigate daidzein metabolites from the HR-ESI-MS1 to ESI-MSn stage in both positive and negative ion modes. Consequently, 59 metabolites, including prototype compounds, were positively or tentatively elucidated based on reference standards, accurate mass measurements, mass fragmentation behaviors, chromatographic retention times, and corresponding calculated ClogP values. As a result, dehydration, hydrogenation, methylation, dimethylation, glucuronidation, glucosylation, sulfonation, ring-cleavage, and their composite reactions were ascertained to interpret its in vivo biotransformation. Overall, our results not only revealed the potential pharmacodynamics forms of daidzein, but also aid in establishing a practical strategy for rapid screening and identifying metabolites of natural compounds.

Screening the Marker Components in Psoralea corylifolia L. with the Aids of Spectrum-Effect Relationship and Component Knock-Out by UPLC-MS2

“…The HPLC four stage rod-electrostatic field orbit trap higher solution mass spectrometry analysis results of knocked-out components were shown in Figure 4 . Protonated ions, adducted ions, and fragment ions of each peak were then elucidated in accordance with reference HPLC chromatogram of standard solutions and related data in the literatures [ 35 , 36 , 37 , 38 , 39 , 40 , 41 ]. The formula of compound P2 with [M + H] + ions at m / z 254, C 15 H 10 O 4 , produced ion fragments of 136/118, and were tentatively characterized as daidzein ( Figure 5 a).…”

Chemical Constituent Profiling of Paecilomyces cicadae Liquid Fermentation for Astragli Radix

“…It is well documented that compounds with similar backbone structure exhibit comparable fragmentation patterns, resulting in certain diagnostic product ions (DPIs) and regular neutral loss fragments (NLFs). Consequently, the combination of DPIs and NLFs was helpful to rapidly performing the structural elucidation [20,21].…”

Rapid Screening of Forskolin-Type Diterpenoids of Blumea aromatica DC Using Ultra-High-Performance Liquid Chromatography Tandem Quadrupole Time-Of-Flight Mass Spectrometry Based on the Mass Defect Filtering Approach

“…The mass defect profile of the compounds that share a similar carbon skeleton structure or substructure usually change within a limited range. Therefore, when analyzing a crude extract, a majority of interfering components can be excluded automatically from the complex samples by a defined MDF value which facilitate the identification of target structural analogues in TCM [8,9,10].…”