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Nucleoside 2′,3′-Cyclic Monophosphates in Aphanizomenon flos-aquae Detected through Nuclear Magnetic Resonance and Mass Spectrometry

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    Nucleoside 2′,3′-Cyclic Monophosphates in Aphanizomenon flos-aquae Detected through Nuclear Magnetic Resonance and Mass Spectrometry
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    • Alfonso Zambon
      Alfonso Zambon
      Dipartimento di Scienze Chimiche e Geologiche, Università di Modena e Reggio Emilia, Via G. Campi 103, 41125 Modena, Italy
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    • Valeria Righi
      Valeria Righi
      Dipartimento di Scienze per la Qualità della Vita, Università di Bologna, Campus Rimini, Corso D’Augusto 237, 49921 Rimini, Italy
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      Orcidhttp://orcid.org/0000-0003-2394-8462
    • Francesca Parenti
      Francesca Parenti
      Dipartimento di Scienze Chimiche e Geologiche, Università di Modena e Reggio Emilia, Via G. Campi 103, 41125 Modena, Italy
      More by Francesca Parenti
    • Emanuela Libertini
      Emanuela Libertini
      Dipartimento di Scienze Chimiche e Geologiche, Università di Modena e Reggio Emilia, Via G. Campi 103, 41125 Modena, Italy
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    • Maria Cecilia Rossi
      Maria Cecilia Rossi
      Centro Interdipartimentale Grandi Strumenti, Università di Modena e Reggio Emilia, via G. Campi 213/A, 41125 Modena, Italy
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    • Adele Mucci*
      Adele Mucci
      Dipartimento di Scienze Chimiche e Geologiche, Università di Modena e Reggio Emilia, Via G. Campi 103, 41125 Modena, Italy
      *E-mail: [email protected]
      More by Adele Mucci
      Orcidhttp://orcid.org/0000-0003-3303-8761
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    Journal of Agricultural and Food Chemistry

    Cite this: J. Agric. Food Chem. 2019, 67, 46, 12780–12785
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    https://doi.org/10.1021/acs.jafc.9b05991
    Published October 24, 2019
    Copyright © 2019 American Chemical Society
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    Abstract

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    Aphanizomenon flos-aquae (AFA) cyanobacteria from Klamath Lake (Oregon) are considered a “superfood” due to their broad nutritional profile that has proved to have health-enhancing properties. The AFA metabolome is quite complex. Here, we present a study that, combining multinuclear 1H, 31P, and 13C Nuclear Magnetic Resonance (NMR) spectroscopy and high-resolution mass spectrometry, led to the detection of uncommon phosphorylated metabolites in AFA. We focused our attention on 31P NMR signals at 20 ppm, a chemical shift that usually points to the presence of phosphonates. The molecules contributing to 20 ppm 31P NMR signals revealed, instead, to be nucleoside 2′,3′-cyclic monophosphates. These metabolites were fully characterized by multinuclear 1H, 31P, and 13C NMR spectroscopy and high-resolution mass spectrometry.

    Copyright © 2019 American Chemical Society

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.jafc.9b05991.

    • Partial H,C-HSQC, H,C-HMBC, COSY, TOCSY, and ROESY spectra and CID MS/MS spectra (PDF)

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    This article is cited by 3 publications.

    1. Nick J. Marotta, Emily E. Weinert. Insights into the metabolism, signaling, and physiological effects of 2’,3’-cyclic nucleotide monophosphates in bacteria. Critical Reviews in Biochemistry and Molecular Biology 2023, 58 (2-6) , 118-131. https://doi.org/10.1080/10409238.2023.2290473
    2. Kanakarajan Vijayakumari Rakhesh, Sunkarankutty Nair Ashalatha, Karthikeyan Mahima, Venkidasamy Baskar, Muthu Thiruvengadam. Untargeted Metabolomic Approach to Determine the Regulatory Pathways on Salicylic Acid-Mediated Stress Response in Aphanamixis polystachya Seedlings. Molecules 2022, 27 (9) , 2966. https://doi.org/10.3390/molecules27092966
    3. Abdul-Hamid Emwas, Kacper Szczepski, Benjamin Gabriel Poulson, Ryan McKay, Leonardo Tenori, Edoardo Saccenti, Joanna Lachowicz, Mariusz Jaremko. Nuclear magnetic resonance in metabolomics. 2022, 149-218. https://doi.org/10.1016/B978-0-323-85062-9.00005-2
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    Journal of Agricultural and Food Chemistry

    Cite this: J. Agric. Food Chem. 2019, 67, 46, 12780–12785
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.jafc.9b05991
    Published October 24, 2019
    Copyright © 2019 American Chemical Society
    Request reuse permissions

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