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LibGen: Generating High Quality Spectral Libraries of Natural Products for EAD-, UVPD-, and HCD-High Resolution Mass Spectrometers
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    LibGen: Generating High Quality Spectral Libraries of Natural Products for EAD-, UVPD-, and HCD-High Resolution Mass Spectrometers
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    • Fanzhou Kong
      Fanzhou Kong
      Chemistry Department, One Shields Avenue, University of California−Davis, Davis, California 95616, United States
      West Coast Metabolomics Center, University of California−Davis, Davis, California 95616, United States
      More by Fanzhou Kong
    • Uri Keshet
      Uri Keshet
      West Coast Metabolomics Center, University of California−Davis, Davis, California 95616, United States
      More by Uri Keshet
    • Tong Shen
      Tong Shen
      West Coast Metabolomics Center, University of California−Davis, Davis, California 95616, United States
      More by Tong Shen
    • Elys Rodriguez
      Elys Rodriguez
      Chemistry Department, One Shields Avenue, University of California−Davis, Davis, California 95616, United States
      West Coast Metabolomics Center, University of California−Davis, Davis, California 95616, United States
    • Oliver Fiehn*
      Oliver Fiehn
      West Coast Metabolomics Center, University of California−Davis, Davis, California 95616, United States
      *Phone: +1-530-754-8258. Fax: +1-530754-9658. E-mail: [email protected]
      More by Oliver Fiehn
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    Analytical Chemistry

    Cite this: Anal. Chem. 2023, 95, 46, 16810–16818
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    https://doi.org/10.1021/acs.analchem.3c02263
    Published November 8, 2023
    Copyright © 2023 American Chemical Society

    Abstract

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    Compound annotation using spectral-matching algorithms is vital for (MS/MS)-based metabolomics research, but is hindered by the lack of high-quality reference MS/MS library spectra. Finding and removing errors from libraries, including noise ions, is mostly done manually. This process is both error-prone and time-consuming. To address these challenges, we have developed an automated library curation pipeline, LibGen, to universally build novel spectral libraries. This pipeline corrects mass errors, denoises spectra by subformula assignments, and performs quality control of the reference spectra by calculating explained intensity and spectral entropy. We employed LibGen to generate three high-quality libraries with chemical standards of 2241 natural products. To this end, we used an IQ-X orbital ion trap mass spectrometer to generate 1947 classic high-energy collision dissociation spectra (HCD) as well as 1093 ultraviolet-photodissociation (UVPD) mass spectra. The third library was generated by an electron-activated collision dissociation (EAD) 7600 ZenoTOF mass spectrometer yielding 3244 MS/MS spectra. The natural compounds covered 140 chemical classes from prenol lipids to benzypyrans with >97% of the compounds showing <0.2 Tanimoto-similarity, demonstrating a very high structural variance. Mass spectra showed much higher information content for both UVPD- and EAD-mass spectra compared to classic HCD spectra when using spectral entropy calculations. We validated the denoising algorithm by acquiring MS/MS spectra at high concentration and at 13-fold diluted chemical standards. At low concentrations, a higher proportion of spectra showed apparent fragment ions that could not be explained by subformula losses of the parent molecule. When more than 10% of the total intensity of MS/MS fragments was regarded as noise ions, spectra were considered as low quality and were not included in the libraries. As the overall process is fully automated, LibGen can be utilized by all researchers who create or curate mass spectral libraries. The libraries we created here are publicly available at MassBank.us.

    Copyright © 2023 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.analchem.3c02263.

    • Additional methods and materials including program implantations, representative good quality spectra, library coverage, and statistics (PDF)

    • Complete annotation results (XLSX)

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    Cited By

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    This article is cited by 5 publications.

    1. Michael W. Christopher, Aiden C. Ericson, Alexander C. Klug, Rhoel R. Dinglasan, Boone M. Prentice, Timothy J. Garrett. Divergent Metabolic Fates of Aromatic Amino Acid-Derived Isomers: Insights from Ex Vivo Metabolomics and HDX-HRMS/MS-Based Resolution of Tautomers. Analytical Chemistry 2024, 96 (42) , 16917-16925. https://doi.org/10.1021/acs.analchem.4c03862
    2. Axel Dablanc, Solweig Hennechart, Amélie Perez, Guillaume Cabanac, Yann Guitton, Nils Paulhe, Bernard Lyan, Emilien L. Jamin, Franck Giacomoni, Guillaume Marti. FragHub: A Mass Spectral Library Data Integration Workflow. Analytical Chemistry 2024, 96 (30) , 12489-12496. https://doi.org/10.1021/acs.analchem.4c02219
    3. Yunjia Lai, Jeremy P. Koelmel, Douglas I. Walker, Elliott J. Price, Stefano Papazian, Katherine E. Manz, Delia Castilla-Fernández, John A. Bowden, Vladimir Nikiforov, Arthur David, Vincent Bessonneau, Bashar Amer, Suresh Seethapathy, Xin Hu, Elizabeth Z. Lin, Akrem Jbebli, Brooklynn R. McNeil, Dinesh Barupal, Marina Cerasa, Hongyu Xie, Vrinda Kalia, Renu Nandakumar, Randolph Singh, Zhenyu Tian, Peng Gao, Yujia Zhao, Jean Froment, Pawel Rostkowski, Saurabh Dubey, Kateřina Coufalíková, Hana Seličová, Helge Hecht, Sheng Liu, Hanisha H. Udhani, Sophie Restituito, Kam-Meng Tchou-Wong, Kun Lu, Jonathan W. Martin, Benedikt Warth, Krystal J. Godri Pollitt, Jana Klánová, Oliver Fiehn, Thomas O. Metz, Kurt D. Pennell, Dean P. Jones, Gary W. Miller. High-Resolution Mass Spectrometry for Human Exposomics: Expanding Chemical Space Coverage. Environmental Science & Technology 2024, 58 (29) , 12784-12822. https://doi.org/10.1021/acs.est.4c01156
    4. Wenyi Yu, Xunhao Zheng, Xiaonong Li, Jinfeng Zhu, Hongjiang Liu, Qing Xu, Aijin Shen, Yanfang Liu, Xinmiao Liang. An algorithm-driven intelligent mining and identification strategy for natural product mass spectrometry. Journal of Chromatography A 2024, 1734 , 465288. https://doi.org/10.1016/j.chroma.2024.465288
    5. Tomas Cajka. Liquid chromatography–mass spectrometry–based metabolomics approaches for foodomics research. Current Opinion in Food Science 2024, 58 , 101201. https://doi.org/10.1016/j.cofs.2024.101201

    Analytical Chemistry

    Cite this: Anal. Chem. 2023, 95, 46, 16810–16818
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.analchem.3c02263
    Published November 8, 2023
    Copyright © 2023 American Chemical Society

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