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Mass spectrometrically detected directly coupled high performance liquid chromatography/nuclear magnetic resonance spectroscopy/mass spectrometry for the identification of xenobiotic metabolites in maize plants

2000; Wiley; Volume: 14; Issue: 8 Linguagem: Inglês

10.1002/(sici)1097-0231(20000430)14

1097-0231

Nigel J. Bailey, Paul D. Stanley, Stephen T. Hadfield, John C. Lindon, Jeremy K. Nicholson,

Electrochemical sensors and biosensors

Rapid Communications in Mass SpectrometryVolume 14, Issue 8 p. 679-684 Research Article Mass spectrometrically detected directly coupled high performance liquid chromatography/nuclear magnetic resonance spectroscopy/mass spectrometry for the identification of xenobiotic metabolites in maize plants Nigel J. C. Bailey, Corresponding Author Nigel J. C. Bailey [email protected] Biological Chemistry, Sir Alexander Fleming Building, Imperial College of Science, Technology and Medicine, Exhibition Road, South Kensington, London SW7 2AZ, UKBiological Chemistry, Sir Alexander Fleming Building, Imperial College of Science, Technology and Medicine, Exhibition Road, South Kensington, London SW7 2AZ, UKSearch for more papers by this authorPaul D. Stanley, Paul D. Stanley Zeneca Agrochemicals, Jealotts Hill Research Station, Bracknell, Berkshire RG12 6EY, UKSearch for more papers by this authorStephen T. Hadfield, Stephen T. Hadfield Zeneca Agrochemicals, Jealotts Hill Research Station, Bracknell, Berkshire RG12 6EY, UKSearch for more papers by this authorJohn C. Lindon, John C. Lindon Biological Chemistry, Sir Alexander Fleming Building, Imperial College of Science, Technology and Medicine, Exhibition Road, South Kensington, London SW7 2AZ, UKSearch for more papers by this authorJeremy K. Nicholson, Jeremy K. Nicholson Biological Chemistry, Sir Alexander Fleming Building, Imperial College of Science, Technology and Medicine, Exhibition Road, South Kensington, London SW7 2AZ, UKSearch for more papers by this author Nigel J. C. Bailey, Corresponding Author Nigel J. C. Bailey [email protected] Biological Chemistry, Sir Alexander Fleming Building, Imperial College of Science, Technology and Medicine, Exhibition Road, South Kensington, London SW7 2AZ, UKBiological Chemistry, Sir Alexander Fleming Building, Imperial College of Science, Technology and Medicine, Exhibition Road, South Kensington, London SW7 2AZ, UKSearch for more papers by this authorPaul D. Stanley, Paul D. Stanley Zeneca Agrochemicals, Jealotts Hill Research Station, Bracknell, Berkshire RG12 6EY, UKSearch for more papers by this authorStephen T. Hadfield, Stephen T. Hadfield Zeneca Agrochemicals, Jealotts Hill Research Station, Bracknell, Berkshire RG12 6EY, UKSearch for more papers by this authorJohn C. Lindon, John C. Lindon Biological Chemistry, Sir Alexander Fleming Building, Imperial College of Science, Technology and Medicine, Exhibition Road, South Kensington, London SW7 2AZ, UKSearch for more papers by this authorJeremy K. Nicholson, Jeremy K. Nicholson Biological Chemistry, Sir Alexander Fleming Building, Imperial College of Science, Technology and Medicine, Exhibition Road, South Kensington, London SW7 2AZ, UKSearch for more papers by this author First published: 15 May 2000 https://doi.org/10.1002/(SICI)1097-0231(20000430)14:8 3.0.CO;2-VCitations: 36Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat Abstract Reconstructed ion chromatograms have been used to identify relevant high performance liquid chromatography (HPLC) peaks in a directly coupled high performance liquid chromatography/nuclear magnetic resonance spectroscopy/mass spectrometry (HPLC/NMR/MS) experiment. This has been applied to a study of the metabolism of a model compound, 5-nitropyridone (2-hydroxy-5-nitropyridine), in maize plants grown hydroponically. By monitoring the on-flow reconstructed ion chromatogram corresponding to the 5-nitropyridone fragment at m/z 143, and additional molecular ions corresponding to metabolites identified as products from similar compounds,1 relevant peaks were identified rapidly for subsequent stopped-flow 1H NMR spectroscopic analysis. The combination of coupled HPLC/NMR/MS enabled the direct identification of three metabolites, namely the N-glucoside, N-malonylglucoside, and O-malonylglucoside. This work demonstrates the power of HPLC/NMR/MS for the structural elucidation of xenobiotic metabolites in complex biological matrices (such as plant material) with minimal sample preparation. In particular, using mass spectrometry for the initial identification of relevant HPLC peaks allows the analysis of complex samples without the necessity for other spectroscopic markers, such as 19F NMR signal for fluorinated compounds or UV spectroscopy for molecules with strong UV chromophores Copyright © 2000 John Wiley & Sons, Ltd. REFERENCES 1Bailey NJC, Cooper P, Hadfield ST, Lenz EM, Lindon JC, Nicholson JK, Stanley PD, Wilson ID, Wright B, Taylor SD. J. Agric. Food Chem. 2000; 48: 42. 2Albert K. J. Chromatogr. A 1995; 703: 123. 3Lindon JC. Prog. NMR. Spectrosc. 1996; 29: 1. 4Lindon JC, Nicholson JK, Sidelmann UG, Wilson ID. Drug Met. Rev. 1997; 29: 705. 5Lindon JC, Farrant RD, Sanderson PN, Doyle PM, Gough SL, Spraul M, Hofmann H, Nicholson JK. Mag. Res. 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