Bidesmosidic Triterpenoid Saponins from Wild and Cultivated Gypsophila Paniculata L. (Caryophyllaceae)

Abstract

Glucuronide oleanane-type triterpenoid carboxylic acid 3, 28-bidesmosides (GOTCAB) of wild and in vivo cultivated Gypsophila paniculata L. roots were assayed by ultra high-performance liquid chromatography coupled with hybrid quadrupole-Orbitrap high resolution mass spectrometry (UHPLCHRMS). More than 20 gypsogenin- and quillaic acid-based GOTCAB saponins were tentatively annotated including isobaric isomers. They are substituted at C-3 with a common 3-O-β-d-galactopyranosyl-(1→2)-[pentosyl-(1→3)]-βd-glucuronopyranoside. C-28 ester-bonded chain is mono- and diacetylated tetra- and pentasaccharide or possesses a methoxycinnamoyl residue. Nine core GOTACBs have not been previously reported in native G. paniculata. The structure of the major saponin of the wild G. paniculata roots was established by 1D and 2D NMR experiments as 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosyl quillaic acid 28-O − α-larabinopyranosyl-(1→4)-α-l-arabinopyranosyl-(1→3)-β-d-xylopyranosyl- (1→4)-α-l-rhamnopyranosyl-(1→2)-β-d-fucopyranosyl ester. For the first time the saponin was isolated from the G. paniculata roots.