Identification of Glycosylated and Prenylated (Iso)flavonoids Using cIMS-MS.

Flavonoids; Glycosylation; Prenylation; Isomerism; Flavonoids/analysis; Flavonoids/chemistry; Ion Mobility Spectrometry/methods; Mass Spectrometry/methods

Abstract :

[en] Separation and identification of (iso)flavonoids, including their isomers, is of great interest due to their differential bioactivity. Yet, identification of substituted (iso)flavonoids and differentiation of their isomers in complex plant extracts by LC-MSn is complicated due to the large diversity of these compounds, along with the subtle differences in their structures that result in highly similar retention times and fragmentation patterns. In this study, a cyclic ion mobility-MS (cIMS-MS) method was developed to strengthen the identification of prenylated and glycosylated (iso)flavonoids using collisional cross section (cIMSCCSN2) values. Among the ions investigated, the lithium adducts were most stable and offered high-resolution separation. We created a library containing the cIMSCCSN2 values of lithium adducts of 51 (iso)flavonoids. For 47 of the 50 isomer pairs, the cIMSCCSN2 values of the two isomers within the pair were statistically significantly different, confirming that the cIMSCCSN2 values in the library can be used in combination with retention times, m/z values, and fragmentation patterns to achieve identification of these compounds. Furthermore, pre-cIMS trap fragmentation of (iso)flavonoid glycosides can be used to determine cIMSCCSN2 values of the corresponding aglycones for their identification. In addition, a modeling approach was explored, revealing the potential of integrating molecular dynamics simulations for CCS prediction and identification of unknowns. The combined LC-MSn and cIMS-MS approach was able to strengthen identification of several prenylated and glycosylated (iso)flavonoids in a proof of concept analysis of a licorice root extract, thereby demonstrating the power of this approach for the identification of substituted (iso)flavonoids in complex extracts.

Disciplines :

Chemistry

Author, co-author :

de Bruin, Carlo Roberto ; Laboratory of Food Chemistry, Department of Agrotechnology and Food Sciences, Wageningen University, 6708 WG Wageningen, The Netherlands

DUEZ, Quentin ; Université de Mons - UMONS > Faculté des Sciences > Service de Synthèse et spectrométrie de masse organiques

Hennebelle, Marie; Laboratory of Food Chemistry, Department of Agrotechnology and Food Sciences, Wageningen University, 6708 WG Wageningen, The Netherlands

Vincken, Jean-Paul ; Laboratory of Food Chemistry, Department of Agrotechnology and Food Sciences, Wageningen University, 6708 WG Wageningen, The Netherlands

de Bruijn, Wouter J C ; Laboratory of Food Chemistry, Department of Agrotechnology and Food Sciences, Wageningen University, 6708 WG Wageningen, The Netherlands

Language :

English

Title :

Identification of Glycosylated and Prenylated (Iso)flavonoids Using cIMS-MS.

Publication date :

12 May 2026

Journal title :

Analytical Chemistry

ISSN :

0003-2700

eISSN :

1520-6882

Publisher :

American Chemical Society (ACS), United States

Volume :

Issue :

Pages :

13269 - 13282

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

https://pubs.acs.org/doi/pdf/10.1021/acs.analchem.5c06302

Research unit :

S836 - Synthèse et spectrométrie de masse organiques

Research institute :

Biosciences
Matériaux

Funders :

F.R.S.-FNRS - Fonds de la Recherche Scientifique

Funding text :

Mandat de Chargé de Recherches

Available on ORBi UMONS :

since 14 May 2026

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