Two novel oleanolic acid saponins having a sialyl Lewis X mimetic structure 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].…”

The Cytotoxic Saponin from Heat-Processed Achyranthes fauriei Roots

“…8,9) Therefore, it is considered that A. fauriei roots undergo the reaction in the similar way by heatprocessing. Therefore, it can be inferred that chikusetsusaponin IVa was generated additionally from several triterpenoid saponins of A. fauriei roots such as achyranthosides A, B, C, and D 13) which might undergo hydrolysis by heatprocessing and it enhanced the cytotoxic activity of A. fauriei roots. Further study on changes of other components of A. fauriei roots by heat-processing is in progress.…”

RETRACTED ARTICLE: SHINBARO, a new herbal medicine with multifunctional mechanism for joint disease: First therapeutic application for the treatment of osteoarthritis

“…Although active ingredients of this mixture have not been completely identified, recent studies have reported analgesic and/or anti-inflammatory effect of Ledebouriellae Radix (Kim et al, 2002), antioxidant activity and/or anti-inflammatory effect of Achyranthis Radix (Ida et al, 1998), and antioxidant activity and/or analgesic effect of Eucommiae Cortex (Hong et al, 1988). Chinese Traditional Medicine Pharmacopeia described antiinflammatory effect of Acanthopanacis Cortex, analgesic effect of Cibotii Rhizoma, and antiedemic effect of Glycine Semen (Fig.…”