Phytochemical analysis of Ononis arvensis L. by liquid chromatography coupled with mass spectrometry

Abstract

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.

Aqueous Root Extract from Ononis spinosa Exerts Anti-adhesive Activity against Uropathogenic Escherichia coli

“…Assignments were based on the comparison of pseudo-molecular ions and major fragmentsʼ exact m/z values with published data of Ononis constituents. Dereplication indicated that OSE was mainly characterized by the presence of different isomers of licoagroside B, condensation products from hydroxy-methylglutaric acid with glucose, and a hydroxymethyl-4-pyrone [19]. Additionally, different isoflavones such as calycosin, formononetin, and pseudobabtigenin and their respective glycosides were detected as well as different isoflavanones, including onogenin and sativanone in addition to pterocarparns, saponin-like triterpene glycosides, and tartaric acid derivatives.…”

“…For pinpointing functional aspects towards the underlying molecular mechanism of the observed anti-adhesive effect, the influence of OSE on type-1 fimbriae of UPEC UTI89 was investigated. This adhesion is mediated by the tip adhesin FimH and can be monitored by an agglutination assay against Saccharomyces cerevisiae, as the type-1 fimbriae are mannose-sensitive structures, [19], peak 27 [30], peak 33 [31], peak 35 [32], peak 40 [31]. Other peaks were characterized on the basis of the de novo interpretation of MS and MS² spectra which strongly interact with mannosylated polysaccharides from the yeast cell wall [21].…”

Qualitative and Quantitative Phytochemical Analysis of Ononis Hairy Root Cultures

“…Beside isoflavonoid derivatives, special phenolic lactones (norneolignans) were detected in the forms of glucosides (9 and 11) and aglycones (15 and 23). These derivatives of puerol A and clitorienolactone B were known in Ononis species before (Ghribi et al, 2015;Addotey et al, 2018;Gampe et al, 2018b). Surprisingly, a compound (peak 26) with a different fragmentation profile and a rather unusual UV spectrum with two absorption maxima was also observed eluting with the aglycones (Figure 4).…”

“…The structural motif, which could be drawn up regarding the information gained from the NMR experiments, showed a close similarity with the structure of puerol A (Ghribi et al, 2015), so that the presence of a δ-lactone was presumed, which could be confirmed by the HMBC correlations of H-2 with both C-3 and C-4. In the case of puerol derivatives or clitorienolactones (Addotey et al, 2018;Gampe et al, 2018b), one of the phenolic rings (ring A) is linked to the lactone ring through a methylene group. However, in our case, a CH 2 unit could not be observed, and the other phenolic ring (ring B) showed a linkage through a quaternary carbon atom based on HMBC experiments.…”

“…For example, Ononis species are well-known herbal remedies in the Mediterranean region. As a member of the Fabaceae (Leguminosae) family, they are rich in isoflavonoids, and beside isoflavones, they produce less-prevalent isoflavanones and pterocarpans (Gampe et al, 2016(Gampe et al, , 2018b. Despite the medicinal benefits (Addotey et al, 2018;Deipenbrock et al, 2020;Spiegler et al, 2020;Stojkovic et al, 2020;Stojković et al, 2020), the plant is not cultivated.…”