Two new furostanol saponins fromTribulus terrestrisL.

Abstract

Two new furostanol saponins, tribufurosides B (1) and C (2), were isolated from the fruits of Tribulus terrestris L. With the help of chemical and spectral analyses (IR, MS, 1D NMR and 2D NMR), the structures of two new furostanol saponins were established as 26-O-beta-d-glucopyranosyl-(25S)-5alpha-furost-20(22)-en-2alpha,3beta,26-triol-3-O-beta-d-galactopyranosyl(1 --> 2)-beta-d-glucopyranosyl(1 --> 2)-beta-d-galactopyranoside (1) and (25S)-5alpha-furost-20(22)-en-12-one-3beta, 26-diol-26-O-beta-d-glucopyranoside (2).

Two new furostanol saponins fromTribulus terrestris

“…The NMR signals of 2 were assigned in detail with the aid of 1 H-1 H COSY, HMQC, and HMBC spectra, as shown in Table 1. In a comparison of the 13 C NMR signals for aglycone of 2 with those of the known saponin of tribufuroside C [9], all signals due to the aglycone of 2 were almost superimposable with those of tribufuroside C, indicating that the aglycone of 2 was the same as that of tribufuroside C. The 25S configuration of 2 was confirmed by comparison of 26-methylene signals of 2 with those of trigoneosides Ia and Xa [11,14] in the 1 H NMR spectrum. The chemical shifts of the 26-methylene at d 4.06 (1H, m, H-26) and 3.47 (1H, dd, J ¼ 7.5, 8.5 Hz, H-26) of 2 were very similar to those of trigoneosides Ia and Xa [14,15].…”

“…Some chemical constituents of this plant have been reported [4 -8]. In the preceding paper, we had reported the isolation and structural elucidation of three steroidal glycosides obtained from the fruits of this plant [9,10].…”

Exploring glycolate oxidase (GOX) as an antiurolithic drug target: Molecular modeling and in vitro inhibitor study

“…Epidemiological studies are also convincing and shown positive correlations. The major constituents of Tt are steroidal saponins [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28] and flavonoids [29,30]. Although the crude extracts of Tt was found to be effective in kidney stone management, a detailed study of its contents for therapeutic intervention of kidney stone is not sufficiently explored yet.…”

A New Furostanol Glycoside from Tribulus terrestris

“…The 13 C-NMR specrum of 1 showed signals of four angular methyl groups ( δ 12.0, 11.8, 14.3, and 17.2), and four anomeric carbons (δ 100.1, 102.5, 105.3, and 107.3). The assignments of the aglycone moiety were determined by DEPT, HMQC, HMBC, and comparison with the aglycone moiety of tribufuroside C [ 15 ]. The 1 H- and 13 C-NMR signals of the aglycone moiety of 1 were superimposable on those of tribufuroside C, indicating the aglycone of 1 was same as that of tribufuroside C, which is 5 α -furost-20(22)-en-12-one-3 β , 26-triol.…”

“…Recently, more than fifty steroidal saponins have been isolated from this plant [ 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 ]. In a preceding paper, we had reported the isolation and structural elucidation of three steroidal glycosides obtained from the fruits of this plant [ 14 , 15 ]. As a continuation to this study, we now describe the isolation and structural elucidation of a new furostanol glycoside obtained from the crude saponins of the fruits of T. terrestris .…”