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

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 met...

Full description

Saved in:
Bibliographic Details
Published in:Analytical and bioanalytical chemistry 2022-09, Vol.414 (22), p.6695-6705
Main Authors: Spano, Mattia, Andreani, Stéphane, Naubron, Jean-Valère, Mannina, Luisa, Pricl, Sabrina, Muselli, Alain, Tintaru, Aura
Format: Article
Language:English
Subjects:
Analysis
Analytical Chemistry
Biochemistry
Characterization and Evaluation of Materials
Chemistry
Chemistry and Materials Science
Composition
Diastereoisomers
Diastereomers
Endemic plants
Essences and essential oils
Essential oils
Food Science
Ionic mobility
Laboratory Medicine
Lamiales
Mass spectrometry
Mass spectroscopy
Materia medica, Vegetable
Monitoring/Environmental Analysis
NMR
Nuclear magnetic resonance
Oils & fats
Plant extracts
Reliability analysis
Research Paper
Senecio
Structure
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. Graphical abstract
ISSN:1618-2642
1618-2650
DOI:10.1007/s00216-022-04232-y