Semipapposides A-M, triterpenoid bidesmosides saponins from the roots of Scabiosa semipapposa

Abstract

Phytochemical investigations of the roots of Scabiosa semipapposa Salzem ex D.C. have led to the isolation of 12 undescribed triterpenoid saponins named semipapposides A-L, one undescribed saponin semipapposide M obtained as an inseparable mixture, together with three known oleanolic acid glycosides. Their structures were elucidated by analysis of 1D and 2D-NMR (¹H-¹H COSY, TOCSY, HSQC-TOCSY, HSQC, ROESY or NOESY, and HMBC) spectroscopic data and mass spectrometry (HR-ESI-MS), and by comparison with those of related metabolites. All saponins possess a partial sequence rhamnopyranosyl-(1 → 2)-xylopyranosyl or rhamnopyranosyl-(1 → 2)-arabinopyranosyl- at C-3 of the aglycon and a gentiobiose unit at C-28. These results represent a contribution to the knowledge of the saponins of Scabiosa species and their chemotaxonomy.

Keywords: Caprifoliaceae; Scabiosa semipapposa Salzem ex D.C.; Semipapposides A-M; Triterpenoid saponins.