Rapid identification of triterpenoid saponins in the roots of Codonopsis lanceolata by liquid chromatography–mass spectrometry

Abstract

Liquid chromatography coupled with sequential mass spectrometry (LC-MS(n)) has been used to identify 3,28-bidesmosidic triterpenoid saponins, lancemaside A (1), foetidissimoside A (2), aster saponin Hb (3), lancemaside E (4), lancemaside B (5), lancemaside F (6), lancemaside G (7), lancemaside C (8), and lancemaside D (9) in the roots of Codonopsis lanceolata. Structural information about both the aglycone and the sugar moiety at the C-3 position of saponins was obtained in the negative-ion mode. On the other hand, positive-ion spectra mainly provide structural information about the sugar chains of saponins, especially the oligosaccharide moiety at the C-28 position. During subsequent fragmentation of the product ions derived from the oligosaccharide moiety at the C-28 position, fragments produced by sequential loss of a monosaccharide unit were observed. Furthermore, the structural features of two unknown saponins in the roots of C. lanceolata were assigned on the basis of the fragmentation patterns of the known saponins. These studies demonstrate that LC-MS(n) analysis has great potential for the identification and characterization of triterpenoid saponins in plant extracts.

Murine metabolism and absorption of lancemaside A, an active compound in the roots of Codonopsis lanceolata

“…The mass spectrum of peak 3 (5.8 min) showed the ions to be at m/z 471, corresponding to the aglycone (echinocystic acid) moiety of 1. In MS n spectra (Table 2), the m/z 471 ions from peaks 1-5 produced the same product ions, at m/z 425, 409, and 407, with similar intensities, and this fragmentation pattern was similar to that reported previously for echinocystic acid moiety [19]. The data suggest the presence of an echinocystic acid moiety in the structure of these compounds.…”

Simultaneous determination of seven saponins in the roots of Codonopsis lanceolata by liquid chromatography–mass spectrometry

“…The data demonstrated baseline separation of all peaks for the seven saponins (1-7) and the internal standard in a complex plant matrix within 5 min. These peaks were identified as saponins 1-7 on the basis of their retention times and mass fragmentation patterns compared with those of authentic compounds [13].…”

Recent developments in qualitative and quantitative analysis of phytochemical constituents and their metabolites using liquid chromatography–mass spectrometry

“…Triterpenoid saponins are complex molecules consisting of aglycone coupled to sugar chain units, exhibiting various pharmacological activities including anti-inflammatory, molluscicidal, analgesic and cytotoxic activities. Ichikawa et al applied LC-MS n (n = 6) to elucidate two unknown saponins in the roots of Codonopsis lanceolata (Campanulaceae) [119]. C. lanceolata is native to East Asia and its root extracts have been found to inhibit the reduction of blood testosterone levels induced by stress in mice.…”