C, O – flavonoid glycosides and oleanane-type bidesmosides from Gypsophila perfoliata L. “tekirae” (Caryophyllaceae): Chemophenetic implications

In-depth characterization of specialized metabolites in the endemic Gypsophila perfoliata L. “tekirae” (G. tekirae Stef.) by liquid chromatography – quadrupol-Orbitrap mass spectrometry allowed dereplication/annotation of 22 flavonoids including 11 2″-O-pentosyl/deoxyhexosyl/hexosyl-C-hexosyl-flavones in the aerial parts and 23 gypsogenin- and quillaic acid-bidesmosides in the roots. Saponins were mainly mono-and diacetyl, and methoxycinnamoyl derivatives of 16 core structures forming isobaric isomers. Three acetylated derivatives of 2″-O-deoxyhexosyl-6-C-hexosyl-flavones are annotated for the first time in the genus Gypsophila together with five quillaic acid-based saponins. Aerial parts extract revealed prominent antioxidant and tyrosinase inhibitory activity, while roots demonstrated higher capacity against acetylcholinesterase, butyrylcholinesterase and α-glucosidase. The chemophenetic significance of acetylated 2″-O-glycosyl-6-C-hexosyl-flavones and GOTCAB saponins with methoxycinnamoyl-substituted α-chains was discussed.