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Smart IM-MS and NMR study of natural diastereomers: the study case of the essential oil from Senecio transiens

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Abstract

Unambiguous identification of the components of a natural mixture remains a challenging and meticulous issue. Usually, different analytical techniques and laborious separation protocols are employed; nevertheless, in some cases, delicate and equivocal problems are hardly addressed by traditional methods. In this context, an original methodology for the analysis of natural samples consisting of recent mass spectrometry methods based on ion mobility (MS-IM) is proposed. As an example, a polar fraction obtained by the essential oil prepared from Senecio transiens, an endemic plant harvested on the Corsica Island, was selected for this study to show how IM-MS-based methods easily provide very useful insights suggesting the presence of two diastereomers. To unambiguously confirm this hypothesis and verify reliability of the IM-MS results, the purified compounds were further analysed by means of nuclear magnetic resonance (NMR) methodologies, allowing the structural elucidation and the identification of two new natural compounds, diastereomers of 4-acetoxy-5,9-dimethyl-3-(2-methylpropenyl)-2-oxabicyclo[4.4.0] dec-9-ene, reported here for the first time.

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Acknowledgements

AT acknowledge Spectropole (FSCM FR1739) for privileged access to the instrumental park. This article is based upon work from COST Action CA 17140 — “Cancer Nanomedicine from Bench to the Bedside” supported by COST (European Cooperation in Science and Technology). This work was supported by the computing facilities of the CRCMM, “Centre Régional de Compétences en Modélisation Moléculaire de Marseille.”

Funding

This research received funding from Aix-Marseille University annual funding research support; it was not supported by any specific grant from funding agencies in the public, commercial, or not-for-profit sectors.

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Authors and Affiliations

  1. Department of Chemistry and Technology of Drugs, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185, Rome, Italy

    Mattia Spano & Luisa Mannina

  2. Aix Marseille Univ, CNRS, UMR 7325 Centre Interdisciplinaire de Nanoscience de Marseille (CINaM), 13288, Marseille, France

    Mattia Spano & Aura Tintaru

  3. Université de Corse, CNRS, UMR 6134 Sciences Pour L’Environnement (SPE), Laboratoire Chimie Des Produits Naturels, BP 52, 20250, Corte, France

    Stéphane Andreani & Alain Muselli

  4. Aix Marseille Univ, CNRS, Centrale Marseille, Spectropole, FR1739, Marseille, France

    Jean-Valère Naubron

  5. Molecular Biology and Nanotechnology (MolBNL@UniTS) Laboratory, DEA, University of Trieste, Piazzale Europa 1, 34127, Trieste, Italy

    Sabrina Pricl

  6. Department of General Biophysics, Faculty of Biology and Environmental Protection, University of Lodz, Lodz, Poland

    Sabrina Pricl

Authors
  1. Mattia Spano
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  2. Stéphane Andreani
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  3. Jean-Valère Naubron
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  4. Luisa Mannina
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  7. Aura Tintaru
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All the authors read and approved the final version of the manuscript.

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Correspondence to Aura Tintaru.

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Spano, M., Andreani, S., Naubron, JV. et al. Smart IM-MS and NMR study of natural diastereomers: the study case of the essential oil from Senecio transiens. Anal Bioanal Chem 414, 6695–6705 (2022). https://doi.org/10.1007/s00216-022-04232-y

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  • DOI: https://doi.org/10.1007/s00216-022-04232-y

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