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Ononis arvensis L. can be found overall in Europe and is used to treat infections of the urinary tract and skin diseases in ethnopharmacology. Flavonoids, hydroxycinnamic acids, oxycoumarin, scopoletin and scopolin, phytosterols, lectins, and some selected isoflavonoids were identified in O. arvensis till date; however, there is a lack of the detailed investigation of the isoflavonoid profile of the plant. With the application of high‐resolution tandem mass spectrometry, the fragmentation patterns of isoflavonoid derivatives found in O. arvensis roots and aerial parts were investigated and discussed. Isoflavonoid glucosides, glucoside malonates, aglycones, and beta amino acid derivatives were characterized, among which homoproline isoflavonoid glucoside esters were described for the first time. Besides the known isoflavonoid aglycones described earlier in other Ononis species, two 2′‐methoxy isoflavonoid derivatives were detected. The presence of licoagroside B was verified, and its structure was also corroborated by NMR experiments. Altogether, the high‐resolution fragmentation pattern of 47 isoflavonoids and glycosides is presented, and their relative quantity in the roots and the aerial parts can be evaluated. Based on this information, the chemotaxonomic relation of Ononis species and the biosynthesis of their compounds could be comprehended to a greater depth.

Introduction: The root of the Ononis species has been used internally and externally in ethnomedicine for centuries and contains biologically valuable isoflavonoid compounds. Therefore, it is important to obtain quantitative information about the isoflavonoid profile of these plants.Objectives: In this article we aimed to develop an optimised sample preparation protocol alongside a validated method for the quantitative measurement of isoflavones, isoflavanones and pterocarpans in the form of glucosides and aglycones, in order to compare the specialised metabolites of Ononis spinosa L. and O. arvensis L.Material and methods: Quantitative determination was carried out by the means of ultra-performance liquid chromatography coupled with ultraviolet diode-array detection (UPLC-UV-DAD).Results: An optimised sample preparation method was developed to transform malonyl glucosides to their glucosidic forms. Chromatographic methods were created for the baseline separation of isoflavones, isoflavanones and pterocarpans alongside with their glucosides. Altogether 12 compounds were evaluated quantitatively in samples of O. spinosa and O. arvensis. Conclusion:As a result, no characteristic change could be observed between the two species regarding their isoflavonoid pattern.