Ilexpublesnins C–M, Eleven New Triterpene Saponins from the Roots of Ilex pubescens

Abstract

Eleven new triterpene saponins, ilexpublesnins C?M (1?11), along with ten known analogues were isolated from the roots of Ilex pubescens. Their structures were elucidated on the basis of extensive spectroscopic analysis, including 1D and 2D?NMR experiments. Compounds 1, 2, 10, and 11 contain a 24-aldehyde, which is rare for triterpene saponins from Ilex. These compounds were evaluated in vitro for their cytotoxic effects on human cancer cell lines HepG2, HLE, BEL7402, BEL7403, BEL7405, MCF-7, and HeLa. Among them, only compounds 6 and 19 showed cytotoxicity against the MCF-7 cell line [inhibition (%): 33.14 and 34.03, respectively].

The Apoptotic Effect of D Rhamnose β-Hederin, a Novel Oleanane-Type Triterpenoid Saponin on Breast Cancer Cells

“…Ginsenosides are one of the most widely recognized triterpenoid saponins and have attracted great attention worldwidely on the anti-breast cancer activity with diverse underlying mechanisms [18]–[21]. However, studies on other kinds of triterpenoid saponins such as oleanane-type triterpenoids are scarce till now, most of which focus on biological activity [22], [23], while the mechanisms have not been widely reported yet. DRβ-H was one of oleanane-type triterpenoid derivatives and belonged to pentacyclic triterpenoid saponins.…”

Ursane‐ and oleane‐type triterpene glycosides from Ilex godajam

“…[5] a C of 3β-[(α-L-arabinopyranosyl)oxy]-19α-hydroxyolean-12-en-28-oic acid 28-β-D-glucopyranosyl ester in pyridine-d5, [6] b recorded in CD3OD, c  of ilexoside XXXI in pyridine-d5, [7] d recorded in pyridine-d5, e C of silphioside B in pyridine-d5. [8] 13 C-NMR data for the two sugars as shown in table 1. Comparison of these data with the reported values suggested these two sugars are α-L-arabinopyranose and β-D-glucopyranose.…”

“…[6] Compound 6 was also isolated as a white powder. Its 1 H-and 13 C-NMR data were similar to those of 5, except for presence of a glucuronic acid moiety [C 106.30 (C-1), 74.88 (C-2), 77.77 (C-3), 73.27 (C-4), 75.80 (C-5), and 175.69 (C-6)/H 4.80 (1H, d, J = 7.5 Hz, H-1)] [13] in 6 replaced for the arabinose unit in 5. The anomeric proton H-1 (H 4.80) exhibited an HMBC cross-peak with C-3 (C 89.08) confirming attached position of the glucuronic acid at this carbon.…”

“…3β-[(α-L-arabinopyranosyl)oxy]-19α-hydroxyolean-12-en-28-oic acid 28-β-D-glucopyranosyl ester(5): White powder; [α]D +15 (c 0.05, MeOH); 1 H-NMR (500 MHz, CD3OD) and13 C-NMR (125 MHz, CD3OD) see table 2; ESI-MS m/z 767 [M+H] + (C41H66O13, M = 766). Ilexoside XXXI (6): White powder; [α]D 2 (c 0.05, MeOH); 1 H-NMR (500 MHz, pyridine-d5) and 13 C-NMR (125 MHz, pyridine-d5) see table 2; ESI-MS m/z 811 [M+H] + (C42H66O15, M = 810).…”

Triterpenoids

“…338 Ilexpublesnin F is a taraxastane saponin with a known genin from Ilex pubescens. 227 The 3-acetate of 12,20(30)-taraxastadiene-3β,11α,21α-triol has been isolated from Echinops galalensis. 339 …”