A new cytotoxic steroidal saponin from the rhizomes and roots ofSmilax scobinicaulis

Abstract

A phytochemical investigation of the EtOH extract from the rhizomes and roots of Smilax scobinicaulis resulted in the isolation of a new isospirostanol-type steroidal saponin, namely (25 R)-5α-spirostan-3β,6β-diol 3-O-β-D-glucopyranosyl-(1 → 4)-[α-L-arabinopyranosyl-(1 → 6)]-β-D-glucopyranoside (1), along with four known steroidal saponins (2-5). The structures of these compounds were determined by 1D- and 2D-NMR spectroscopic analysis, FABMS and HR-ESI-MS as well as chemical degradation. The isolated saponins were evaluated for their in vitro cytotoxicity against A549, LAC and Hela human cancer cell lines, which demonstrated that only compound 1 possessed significant cytotoxic activity with IC₅₀ values of 3.70, 5.70 and 3.64 µM, respectively.

Steroidal Saponins from the Genus Smilax and Their Biological Activities

“…The occurrences of parisyunnanoside in the genus Smilax indicated the close chemtaxonomic relationship between the genus Smilax and Paris . Three isonarthogenin glycosides 24 , 25 , and 28 were isolated from S. scobinicaulis , together with two tigogenin glycosides 38 – 39 [21]. Sieboldogenin ( 33 ), with an additional hydroxyl substitution on C-27 in comparison with laxogenin, was identified from the ethyl acetate fraction of S. china [22].…”

“…Compounds 24 , 25 , 28 , 38 , and 39 , were evaluated for the cytotoxicities against three human cancer cell lines (A549, LAC and Hela). Only compound 38 possessed significant cytotoxicities with IC 50 values of 3.70, 5.70 and 3.64 μM, respectively [21]. Another cytotoxic compound is isospirostane glycoside 32 , which displayed potent cytotoxicities against the Hela and SMMC-7221 cancer cell lines with IC 50 values of 9.73 ± 1.64 and 21.54 ± 1.64 μM, respectively [28].…”

Four New Furostanol Saponins from the Rhizomes and Roots of Smilax scobinicaulis and Their Cytotoxicity

“…The rhizomes and roots of this plant, known as “Jin Gang Teng” and “Wei Ling Xian” in North China, have long been used in folk medicine for the treatment of rheumatic arthritis, lumbago, gout, tumor and inflammatory diseases [1]. Previous phytochemical investigations of this plant led to the isolation of steroidal saponins [4], flavonoids [5] and phenylpropanoids [6]. Bioactivity investigations showed that some of the isolated steroidal saponins had antimicrobial and cytotoxic activity [4,7].…”

“…Previous phytochemical investigations of this plant led to the isolation of steroidal saponins [4], flavonoids [5] and phenylpropanoids [6]. Bioactivity investigations showed that some of the isolated steroidal saponins had antimicrobial and cytotoxic activity [4,7].…”

Steroidal Saponins and Cell Death in Cancer

“…Researchers have isolated compounds that have been used individually or in combination to induce cell death in different cancer type cells. The steroidal saponins(25 R)-5α-spirostan-3β,6β-diol 3-O-β-D-glucopyranosyl-(1-4)-[β-L-arabinopyranosyl-(1-6)]-β-D-glucopyranoside was cytotoxic for A549, HeLa, and LAC human cancer cell lines[49]. The steroidal saponin tupichinin A, together with seven known compounds isolated from rhizomes of Tupistra chinensis Baker, showed potent cytotoxicity against the cancer cell lines HL-60, SMMC-7721, A-549, MCF-7, and SW480[50], while the mixed saponins balanitin-6 and -7 showed anti-tumor activity in both in vivo and in vitro systems[51].…”