Oleanolic acid saponins from root bark of Aralia elata

Abstract

Three new oleanolic acid glycosides, tarasaponins I-III, were isolated as their methyl esters from the root bark of Aralia elata together with four known glycosides, the methyl esters of chikusetsusaponins IVa, IV, 28-desglucosyl-chikusetsusaponin IV and pseudoginsenoside RT1. Tarasaponins I-III were characterized as oleanolic acid 3-O-[beta-D-glucopyranosyl(1-->3)][alpha-L-arabinofuranosyl(1-->4)[- beta-D-glucuronopyranoside, oleanolic acid 3-O-[beta-D-xylopyranosyl(1-->2)][beta-D-galactopyranosyl(1-->3)]-beta- D-glucuronopyranoside and beta-D-glucopyranosyl oleanolate 3-O-beta-D-galactopyranosyl(1-->3)-beta-D-glucuronopyranoside, respectively.

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).…”

Saponins and Other Constituents from the Leaves of Aralia elata

“…Many saponins have been isolated from this plant, [2][3][4][5][6][7][8][9][10][11][12][13][14][15][16] and were reported to show anti-diabetic activity, 17) cytoprotective effect on CCl 4 -induced hepatic injury, 7) ethanol absorption inhibitory effect, 6,14) and hypoglycemic activity. [10][11][12] Recently, we reported the isolation and identification of various triterpenoid saponins including two new saponins, durupcosides A and B, 2,3) and a cerebroside, aralia cerebroside 18) from the root bark of this plant.…”

Oleanolic Triterpene Saponins from the Roots of Panax bipinnatifidus

“…The H 2 O layer was subjected to Diaion HP-20 column chromatography, followed by various silica gel and C-18 reversed-phase columns to afford three new saponins, bifinosides A-C (1-3), and seven known compounds including narcissiflorine methyl ester (4), 6) chikusetsusaponin IVa (5), 5) pseudoginsenoside RP 1 methyl ester (6), 5) stipuleanoside R 1 (7), 7) pseudoginsenoside RT 1 methyl ester (8), 5) momordin IIe (9), 8) and stipuleanoside R 2 methyl ester (10), 5) respectively (Fig. 1 heteronuclear multiple bond correlation (HMBC) spectrum, suggested the presence of glucuronate methyl ester (GluAMe) moiety.…”