Cytotoxic steroidal saponins from Trillium kamtschaticum

Bioactive Steroids and Saponins of the Genus Trillium

“…Thus far, several steroidal saponins have been isolated and purified from the plants belonging to this genus and, at present, novel metabolites/phytochemicals from Trillium ssp. are investigating using the latest technologies [ 30 , 31 , 32 , 33 , 34 ]. The secondary metabolites/phytochemicals of species belonging to the genus Trillium are reported in Table 2 .…”

New Steroidal Saponins Isolated from the Rhizomes of Paris mairei

“…The pseudomolecular ion peak was detected in the HR-ESI-MS spectrum at m/z 995.4824 [M + Na] + (calculated for C 48 H 76 O 20 Na, 995.4828), corresponding to the molecular formula C 48 H 76 O 20 . Four methyl groups were tested in the 1 H-NMR spectrum at δ H 0.82 (3H, s, H-18), 1.12 (3H, s, H- 19), δ H 0.80 (3H, d, J = 6.35 Hz, H-27), and 0.96 (3H, d, J = 6.90 Hz, H-21). Meanwhile, one olefinic methine proton signal was observed at δ H 5.56 (1H, br s, H-6).…”

“…The sequence of a tetrasaccharide chain was confirmed by the HMBC spectrum, which acted as the correlations from Rha H-1 (δ H 5.31) to Ara C-3 (δ C 80.45), Api H-1 (δ H 5.19) to Xyl C-4 (δ C 70.54), Xyl H-1 (δ H 4.41) to Ara C-4 (δ C 85.29), and the crosspeak between Ara H-1 (δ H 4.34) and C-1 (δ C 84.79) demonstrated the location of a sugar linkage. The anomeric proton coupling constants of D-xylopyranose (J = 7.1 Hz > 7.0 Hz) and L-arabopyranose (J = 7.35 Hz > 7.0 Hz) suggested that the configurations had a β-orientation and an α-orientation, respectively [18,19]. The β configuration of D-apiose was determined by the chemical shifts of δ C 112.17 (C-1), δ C 78.23(C-2), δ C 80.49(C-3), δ C 75.18 (C-4), and δ C 65.56 (C-5) [20]; the α anomeric configuration of L-rhamnopyranosyl was confirmed by the chemical shifts of Rha C-5 at δ C 69.84 [21].…”

Untiring Researches for Alternative Resources of Rhizoma Paridis

“…All these information strongly inspired us to investigated the hemostatic constituents of the whole plats of T. kamtschaticum , resulting in the isolation of 18 new steroidal saponins (Fig. 3 ; Table 3 ), named trillikamtosides A–R ( 74 – 91 ) [ 51 , 52 ]. Interestingly, some of them were determined to have rare aglycone moieties.…”

“…A number of saponins were proved to have cytotoxicity against various human tumor cells. Two Trillium saponis with a double bond between C-13 and 14 isolated from T. kamtschaticum , trillikamtosides P ( 89 ) and R ( 91 ), showed cytotoxic effect against HCT116 (colorectal carcinoma) cells with the MIC values of 4.92 and 5.84 μM, respectively [ 52 ]. Ypsilandroside G ( 43 ) obtained from Y. thibetica displayed cytotoxic effect against K562 (leukemia) cells with an MIC value of 4.7 μM, and paris saponin VII ( 141 ) identified from the same species was cytotoxic towards SPC-A-1 (lung carcinoma) and BGC-823 (gastric carcinoma) with the IC 50 values of 2.6 and 4.0 μM, respectively [ 38 ].…”