Achyranthosides A and B, novel cytotoxic saponins from Achyranthes fauriei root

Two new glucuronide saponins, Achyranthosides G and H, from Achyranthes fauriei root

“…The column was washed with H 2 O and then eluted with MeOH to give MeOH eluent (42.1 g). The MeOH eluent was treated repeatedly with excess diazomethane etherate in MeOH, and the reaction mixture was separated by repeated column chromatography (CC) on SiO 2 and ODS to afford the following 16 compounds: 1a (188 mg), 2a (25 mg), achyranthoside A methyl ester (191 mg), achyranthoside B methyl ester (93 mg) [8], achyranthoside C methyl ester (3a, 425 mg), achyranthoside D methyl ester (4a, 339 mg) [9], achyranthoside E methyl ester (576 mg), achyranthoside F methyl ester (39 mg) [10], chikusetsusaponin IVa methyl ester (689 mg), chikusetsusaponin V methyl ester (147 mg), 28-deglucosyl chikusetsusaponin V methyl ester (472 mg), pseudoginsenoside RT 1 methyl ester (105 mg) [7], oleanolic acid 3-O-b-D-glucuronopyranoside 28,6'-dimethyl ester (332 mg) [14], oleanolic acid 28-O-b-Dglucopyranoside (97 mg) [15], b-ecdysterone (5.69 g) and polypodine B (480 mg) [16] (Fig. 1).…”

“…In continuation of our phytochemical investigation on A. fauriei root, two new analogous saponins named achyranthosides G (1) and H (2) were isolated as methyl esters from the crude saponin fraction after methylation with diazomethane etherate, together with 12 known oleanolic acid glycosides (methyl esters of achyranthosides A -F chikusetsusaponins IVa, V, 28-deglucosyl chikusetsusaponin V, pseudoginsenoside RT 1 , and oleanolic acid 3-O-b-D-glucuronopyranoside) as well as oleanolic acid 28-O-b-D-glucopyranoside and two phytoecdysones, b-ecdysterone and polypodine B. The present paper describes the isolation of all the compounds from A. fauriei root and the structure determination of the new glycosides, 1 and 2, because the other achyranthosides were only reported as short communications [8][9][10].…”

“…We reported previously the isolation and characterization of six novel triterpene glycosides, achyranthosides A -F, together with four known saponins, chikusetsusaponins IVa, V, 28-deglucosyl chikusetsusaponin V and pseudoginsenoside RT 1 from dried A. fauriei root [7][8][9][10]. Later, Mitaine-Offer et al reported analogous saponins, named bidentatosides I and II [11,12], and then Li et al also reported 14 analogous saponins as methyl and butyl esters [13].…”

Achyranthoside H methyl ester, a novel oleanolic acid saponin derivative from Achyranthes fauriei roots, induces apoptosis in human breast cancer MCF-7 and MDA-MB-453 cells via a caspase activation pathway

“…Achyranthosides are oleanolic acid saponins isolated from the roots of Achyranthes fauriei, which is a medicinal plant utilized in East Asia from ancient times. Our group has so far isolated six methyl esters of achyranthosides (A-F) from the crude saponin fraction of dried Achyranthes roots after methylation with diazomethane etherate [2,3]. In addition, we reported that one of the achyranthosides, achyranthoside A methyl ester (AA-Me), is cytotoxic to human colon carcinoma and murine melanoma cells [2].…”

“…Our group has so far isolated six methyl esters of achyranthosides (A-F) from the crude saponin fraction of dried Achyranthes roots after methylation with diazomethane etherate [2,3]. In addition, we reported that one of the achyranthosides, achyranthoside A methyl ester (AA-Me), is cytotoxic to human colon carcinoma and murine melanoma cells [2]. During the course of our continuous phytochemical investigation of Achyranthes roots, we additionally isolated two new saponins, named achyranthoside G and H, as their methyl esters [3], and found that the latter compound, achyranthoside H methyl ester (AH-Me), has significant cytotoxicity against human breast cancer MCF-7 and MDA-MB-453 cells.…”