Steroid saponins II. Glycosides of Tribulus terrestris

Summary 1. It has been established that the epigeal part ofTribulus terrestris L. contains five steroid saponins. Diosgenin was identified as the aglycone of all these compounds.2. The carbohydrate compositions of the saponins have been determined.For Communication I, see Izv. Akad. Nauk MSSR Ser. Khim. i Biol. Nauk,1971, No. 4, 76.Institute of Chemistry, Academy of Sciences of the Moldavian SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 475–477, July–August, 1972.     

Steroid saponins XV. Preliminary characterization of the steroid glycosides from Polygonatum latifolium

Chemistry of Natural Compounds -     

Two new furostanol saponins from Tribulus terrestris L.

<正>Two new furostanol glycoside,26-O-β-D-glucopyranosyl-(25S)-5α-furost-3β,22α,26-triol-3-O-β-D-rhamnopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→4)]-β-D-galactopyranoside(1) and 26-O-β-D-glucopyranosyl-(25S)-5α-furost-20(22)-en-2α,3β,26-triol-3-O-β-D-glucopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside(2) were isolated fromthe fruits of Tribulus terrestris L.The structures of two new furostanol saponins were elucidated by spectroscopic methods.     

Steroid saponins X. Glycosides of Allium narcissiflorum the structure of glycosides A and B

Summary FromAllium narcissiflorum Wells have been isolated for the first time trillin and a glycoside B, which proved to be 3-O-[-O-D-glucopyranosyl-(1 3)-O--D-glucopyranosyl-(1 6)-O--D-glucopyranosyl-(1 ]-26-O-[-D-glucopyranosyl-(1 ]-25R-furost-5-ene-3,22 , 26-triol.Institute of Chemistry, Academy of Sciences of the Moldavian SSR, Kishinev. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 55–58, January–February, 1976.     

Steroid glycosides. XIX. A chemical study of funkiosides E and G from the leaves ofFunkia ovata

Summary 1. Gitogenin, diosgenin, kogagenin, ruscogenin, and tokorogenin have been isolated for the first time fromFunkia ovata Spr.2. Structures of two new steroid glycosides — funkiosides E and G — have been determined.Institute of Chemistry, Academy of Sciences of the Moldavian SSR, Kishinev. Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 69–72, January–February, 1977.     

A new steroidal saponin from Tribulus terrestris Linn

A new steroidal saponin containing six monosaccharides was obtained from the total plant of Tribulus terrestris and elucidated based on chemical spectroscopic analysis, especially on 2D-NMR technology as 26-0-beta-D-glucopyranosyl-22-methoxy-furostane-3-O-[beta-D-xylopyranosyl(l --> 3)-[beta-D-xylopyranosyl(l --> 2)-beta-D-glucopyranosyl(1 --> 4)]]-[alpha-L-rhamnopyranosy(l --> 2)]-beta-D-galactopyranoside.     

A new feruloyl amide derivative from the fruits of Tribulus terrestris

A new feruloyl amide derivative, named tribulusamide C, was isolated from the fruits of Tribulus terrestris. Its structure was determined on the basis of spectroscopic analysis including IR, 1-D-, 2-D-NMR and HR-ESI-MS. The structure of tribulusamide C was characterised by a unit of pyrrolidine-2,5-dione, which distinguished it from other lignanamides previously isolated from the fruits of T. terrestris.     

Steroid saponins and sapogenins of Allium IV. Karatavigenin — A new sapogenin from Allium karataviense

Summary For all the bisbenzyltetrahydroisoquinoline alkaloids considered except thalisopine, positive CEs are found in the case of the SS configuration and negative CEs in the case of the RS configuration.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 705–708, November–December, 1970.     

Pregnane glycosides and steroid saponins from Smilax bockii Warb. and their NGF-potentiating activity

The chemical constituents of the roots of Smilax bockii Warb. were investigated and two pregnane glycosides and three steroid saponins were isolated. Their structures were established as 3beta-hydroxypregna-5,16-dien-20-one-3-O-alpha-L-rhamnopyranosyl(1 --> 4)-alpha-L-rhamnopyranosyl(1 --> 4)-[alpha-L-rhamnopyranosyl(1 --> 2)]-beta-D-glucopyranoside (1), 3beta-hydroxypregna-5,16-dien-20-one-3-O-alpha-L-rhamnopyranosyl(1 --> 2)-[alpha-L-rhamnopyranosyl(1 --> 4)]-beta-D-glucopyranoside (2), dioscin (3), methyl protodioscin (4), 26-O-beta-D-glucopyranosyl-22alpha-methoxyl-(25R)-furost-5-en-3beta, 26-diol 3-O-alpha-L-rhamnopyranosyl(1 --> 4)-alpha-L-rhamnopyranosyl(1 --> 4)-[alpha-L-rhamnopyranosyl(1 --> 2)]-beta-D-glucopyranoside (5) on the basis of spectral analysis and chemical methods. Compound 1 is a new natural product and compounds 2, 5 were first isolated from the genus Smilax. Compound 5 showed enhancing activity of nerve growth factor (NGF)-induced neurite outgrowth in PC 12D cells.     

Exploring the in vitro anti-inflammatory activity of gross saponins of Tribulus terrestris L. fruit by using liquid chromatography-mass spectrometry-based cell metabolomics approach

Our previous studies confirmed the efficacy of gross saponins of Tribulus terrestris L. fruit in treating cerebral ischemia. This study aimed to investigate the related mechanisms in vitro. The lipopolysaccharide-induced BV2 cells model was constructed and treated with gross saponins at different concentrations to explore its anti-inflammatory activity. The cell metabolite changes were tracked by liquid chromatography-mass spectrometry (LC-MS)-based metabolomics, and the metabolic biomarkers and related metabolic pathways were analyzed. Molecular biochemistry analysis was further used to verify the relevant inflammatory pathways. The results showed that the saponins reduced nitric oxide release and the secretion of tumor necrosis factor-alpha, interleukin-1β, and interleukin-6 from lipopolysaccharide-induced BV2 cells. Metabolic perturbations occurred in lipopolysaccharide-treated BV2 cells, which could be reversed by drug treatment via mainly regulating glycerophospholipid metabolism, tryptophan metabolism, purine metabolism pathways, etc. The western blot analysis demonstrated that saponin could suppress the activation of the inflammatory-related signaling pathway. The present study explored the in vitro anti-inflammatory mechanism of gross saponins of Tribulus terrestris L. fruit using an LC-MS-based cell metabolomics approach, which confirms the great potential of LC-MS for drug efficacy evaluation and can be applied in other herbal medicine-related analyses.