Cytotoxic Triterpenoid Saponins from the Rhizomes ofAnemone taipaiensis

Abstract

Two new oleanane-type triterpenoid saponins, 1 and 2, and a new natural product, 3, together with five known saponins, 4- 8, were isolated from the rhizomes of ANEMONE TAIPAIENSIS. Their structures were elucidated by extensive spectroscopic analysis and chemical evidences. Six saponins, 1, 2, 4- 7, which possessed a free carboxylic group at C-28, exhibited significant cytotoxicity against human leukemia HL-60 cells and human hepatocellular carcinoma Hep-G2 cells with IC (50) values in the range of 1.31-10.12 µM.

Triterpenoid Saponins from the Roots of Clematis argentilucida and Their Cytotoxic Activity

“…Saponins 14 and 16 possessed the same oligosaccharide chain, but 14 with hederagenin (C-23 hydroxylated) as the aglycone exhibited weaker cytotoxicity than 16 with oleanolic acid as the aglycone. This was in agreement with those reporting that the hydroxyl group at C-23 of the aglycone had a negative effect on the cytotoxicity of oleanane-type saponins [17][18][19]. Saponins 4 and 17 possessed the same oleanolic acid aglycone, and 8 and 14 possessed the same hederagenin aglycone, but exhibited different cytotoxicities.…”

“…They were obtained from C. argentilucida for the first time. The other known saponins 9-18 were identified as huzhangoside D (9) (17), and saponin CP 7 (18), respectively, by comparison of their HPLC retention times with those of the authentic samples isolated previously [3][4][5].…”

“…Chemical studies led to the isolation of four new saponins, 1-4, four known saponins, 5-8, first isolated from the plant (l " Fig. 1), along with ten saponins, [9][10][11][12][13][14][15][16][17][18], which have been obtained and reported in our preceding papers (Fig. 1S, Supporting Information) [3][4][5].…”

New cytotoxic triterpenoid saponins from the whole plant of Clematis lasiandra Maxim

“…The structure-activity relationships (SAR) about the antitumor activity of saponins involved the type, position, and number of sugar moieties attached by a glycosidic bond at different positions [23]. Compounds 2 and 6 structurally related to the active saponins 1, 3-5 and 7 without the free carboxylic acid group at position C-28, indicated it played an important role in the expression of cytotoxicities for triterpenoid saponins [24,25]. Compared to the oligosaccharide chain at C-3 for the active saponins, compounds 4 and 7 possessed common 3-O-β-D-Rib(1 → 3)-α-L-Rha(1 → 2)-α-L-Ara chain displayed relatively stronger cytotoxicities than 1, 3 and 5.…”

Two New Triterpenoid Saponins from the Root of <i>Platycodon grandiflorum</i>

“…It should be noted that the significant cytotoxic activities of compounds 1 and 2 against HepG-2 and A549 may be due to their free carboxylic group at C-28. 12) Early studies on the cytotoxicity of similar compounds against several human cancer cell lines have reached the same results. 13,14) Experimental General Experimental Procedures Optical rotations were determined on a Perkin-Elmer 341 digital polarimeter.…”