A fragmentation study of isoflavones in negative electrospray ionization by MSn ion trap mass spectrometry and triple quadrupole mass spectrometry
- PMID: 17294515
- DOI: 10.1002/rcm.2897
A fragmentation study of isoflavones in negative electrospray ionization by MSn ion trap mass spectrometry and triple quadrupole mass spectrometry
Abstract
This study has elucidated the fragmentation pathway for deprotonated isoflavones in electrospray ionization using MS(n) ion trap mass spectrometry and triple quadrupole mass spectrometry. Genistein-d(4) and daidzein-d(3) were used as references for the clarification of fragment structures. To confirm the relationship between precursor and product ions, some fragments were traced from MS(2) to MS(5). The previous literature for the structurally related flavones and flavanones located the loss of ketene (C(2)H(2)O) to ring C, whereas the present fragmentation study for isoflavones has shown that the loss of ketene occurs at ring A. In the further fragmentation of the [M-H-CH(3)](-*) radical anion of methoxylated isoflavones, loss of a hydrogen atom was commonly found. [M-H-CH(3)-CO-B-ring](-) is a characteristic fragment ion of glycitein and can be used to differentiate glycitein from its isomers. Neutral losses of CO and CO(2) were prominent in the fragmentation of deprotonated anions in ion trap mass spectrometry, whereas recyclization cleavage accounted for a very small proportion. In comparison with triple quadrupole mass spectrometry, ion trap MS(n) mass spectrometry has the advantage of better elucidation of the relationship between precursor and product ions.
Similar articles
-
Characterisation of nicotine and related compounds using electrospray ionisation with ion trap mass spectrometry and with quadrupole time-of-flight mass spectrometry and their detection by liquid chromatography/electrospray ionisation mass spectrometry.Rapid Commun Mass Spectrom. 2007;21(4):557-66. doi: 10.1002/rcm.2871. Rapid Commun Mass Spectrom. 2007. PMID: 17245795
-
Re-examination of the anion derivatives of isoflavones by radical fragmentation in negative electrospray ionization tandem mass spectrometry: experimental and computational studies.Rapid Commun Mass Spectrom. 2011 Jul 30;25(14):2020-6. doi: 10.1002/rcm.5075. Rapid Commun Mass Spectrom. 2011. PMID: 21698684
-
New features on the fragmentation patterns of homoisoflavonoids in Ophiopogon japonicus by high-performance liquid chromatography/diode-array detection/electrospray ionization with multi-stage tandem mass spectrometry.Rapid Commun Mass Spectrom. 2010 Aug 15;24(15):2193-206. doi: 10.1002/rcm.4608. Rapid Commun Mass Spectrom. 2010. PMID: 20583326
-
Strategy for structural elucidation of drugs and drug metabolites using (MS)n fragmentation in an electrospray ion trap.J Mass Spectrom. 2003 Aug;38(8):793-808. doi: 10.1002/jms.511. J Mass Spectrom. 2003. PMID: 12938100 Review.
-
Triple quadrupole linear ion trap mass spectrometer for the analysis of small molecules and macromolecules.J Mass Spectrom. 2004 Aug;39(8):845-55. doi: 10.1002/jms.659. J Mass Spectrom. 2004. PMID: 15329837 Review.
Cited by
-
A Comprehensive Screening and Identification of Genistin Metabolites in Rats Based on Multiple Metabolite Templates Combined with UHPLC-HRMS Analysis.Molecules. 2018 Jul 26;23(8):1862. doi: 10.3390/molecules23081862. Molecules. 2018. PMID: 30049985 Free PMC article.
-
Flavonoid Profile of the Genista tridentata L., a Species Used Traditionally to Treat Inflammatory Processes.Molecules. 2020 Feb 13;25(4):812. doi: 10.3390/molecules25040812. Molecules. 2020. PMID: 32069907 Free PMC article.
-
Identification Markers Responsible for Differentially Processed Polygonatum cyrtonema Hua by Ultra-Performance Liquid Chromatography with Quadruple-Time-of-Flight Mass Spectrometry.Molecules. 2024 Mar 30;29(7):1559. doi: 10.3390/molecules29071559. Molecules. 2024. PMID: 38611838 Free PMC article.
-
Rapid Screening and Identification of Daidzein Metabolites in Rats Based on UHPLC-LTQ-Orbitrap Mass Spectrometry Coupled with Data-Mining Technologies.Molecules. 2018 Jan 12;23(1):151. doi: 10.3390/molecules23010151. Molecules. 2018. PMID: 29329272 Free PMC article.
-
Structure-based identification and pathway elucidation of flavonoids in Camptotheca acuminate.Synth Syst Biotechnol. 2022 Apr 18;7(2):824-836. doi: 10.1016/j.synbio.2022.03.007. eCollection 2022 Jun. Synth Syst Biotechnol. 2022. PMID: 35510090 Free PMC article.
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Research Materials
Miscellaneous