Cycloartane-type glycosides from Astragalus schottianus

Three new cycloartane-type triterpene glycosides were isolated from the roots of Astragalus schottianus Boiss. Their structures were established as 20(R),25-epoxy-3-O-β-d-xylopyranosyl-24-O-β-d-glucopyranosyl-3β,6α,16β,24α-tetrahydroxycycloartane (1), 20(R),25-epoxy-3-O-[β-d-glucopyranosyl(1 → 2)]-β-d-xylopyranosyl-24-O-β-d-glucopyranosyl-3β,6α,16β,24α-tetrahydroxycycloartane (2), 3-O-β-d-xylopyranosyl-3β,6α,16β,20(S),24(S),25-hexahydroxycycloartane (3) by the extensive use of 1D and 2D-NMR techniques and mass spectrometry.     

Saponins from Astragalus hareftae (NAB.) SIRJ.

Four cycloartane- (hareftosides A–D) and oleanane-type triterpenoids (hareftoside E) were isolated from Astragalus hareftae along with fifteen known compounds. Structures of the compounds were established as 3,6-di-O-β-d-xylopyranosyl-3β,6α,16β,24(S),25-pentahydroxycycloartane (1), 3,6,24-tri-O-β-d-xylopyranosyl-3β,6α,16β,24(S),25-pentahydroxycycloartane (2), 3-O-β-d-xylopyranosyl-3β,6α,16β,25-tetrahydroxy-20(R),25(S)-epoxycycloartane (3), 16-O-β-d-glucopyranosyl-3β,6α,16β,25-tetrahydroxy-20(R),24(S)-epoxycycloartane (4), 3-O-[β-d-xylopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucuronopyranosyl]-soyasapogenol B (5) by the extensive use of 1D- and 2D-NMR experiments along with ESI-MS and HR-MS analyses.     

Triterpene glycosides from Astragalus icmadophilus

Six cycloartane-type triterpene glycosides were isolated from Astragalus icmadophilus along with two known cycloartane-type glycosides, five known oleanane-type triterpene glycosides and one known flavonol glycoside. The structures of the six compounds were established as 3-O-[α-L-arabinopyranosyl-(1 → 2)-O-3-acetoxy-α-L-arabinopyranosyl]-6-O-β-D-glucopyranosyl-3β,6α,16β,24(S),25-pentahydroxycycloartane, 3-O-[α-L-rhamnopyranosyl-(1 → 2)-O-α-L-arabinopyranosyl-(1 → 2)-O-β-D-xylopyranosyl]-6-O-β-D-glucopyranosyl-3β,6α,16β,24(S),25-pentahydroxy cycloartane, 3-O-[α-L-arabinopyranosyl-(1 → 2)-O-3,4-diacetoxy-α-L-arabinopyranosyl]-6-O-β-D-glucopyranosyl-3β,6α,16β,24(S),25-pentahydroxycycloartane, 3-O-[α-L-arabinopyranosyl-(1 → 2)-O-3-acetoxy-α-L-arabinopyranosyl]-6-O-β-D-glucopyranosyl-3β,6α,16β,25-tetrahydroxy-20(R),24(S)-epoxycycloartane, 3-O-[α-L-arabinopyranosyl-(1 → 2)-O-β-D-xylopyranosyl]-6-O-β-D-glucopyranosyl-3β,6α,16β,24α-tetrahydroxy-20(R),25-epoxycycloartane, 3-O-[α-L-rhamnopyranosyl-(1 → 2)-O-α-L-arabinopyranosyl-(1 → 2)-O-β-D-xylopyranosyl]-6-O-β-D-glucopyranosyl-3β,6α,16β,24α-tetrahydroxy-20(R),25-epoxycycloartane by the extensive use of 1D- and 2D-NMR experiments along with ESIMS and HRMS analysis.The first four compounds are cyclocanthogenin and cycloastragenol glycosides, whereas the last two are based on cyclocephalogenin as aglycone, more unusual in the plant kingdom, so far reported only from Astragalus spp.     

Triterpenoid saponins from Astragalus wiedemannianus Fischer

Three cycloartane-type triterpene glycosides were isolated from Astragalus wiedemannianus together with eight known secondary metabolites namely cycloastragenol, cycloascauloside B, astragaloside IV, astragaloside VIII, brachyoside B, astragaloside II, astrachrysoside A, and astrasieversianin X. The structures were established mainly by a combination of 1D and 2D-NMR techniques as 3-O-[α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl]-25-O-β-D-glucopyranosyl-20(R),24(S)-epoxy-3β,6α,16β,25-tetrahydroxycycloartane, 3-O-[α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyl]-6-O-β-D-glucopyranosyl-24-O-α-(4’-O-acetoxy)-L-arabinopyranosyl-16-O-acetoxy-3β,6α,16β,24(S),25-pentahydroxycycloartane, 3-O-[α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyl]-6-O-β-D-glucopyranosyl-24-O-α-L-arabinopyranosyl-16-O-acetoxy-3β,6α,16β,24(S),25-pentahydroxycycloartane. To the best of our knowledge, the presence of an arabinose moiety on the acyclic side chain of cycloartanes is reported for the first time.     

Cycloartane glycosides from Astragalus gombo

Six new cycloartane-type triterpene glycosides named 3-O-[β-d-glucopyranosyl(1 → 2)-β-d-xylopyranosyl]-3β,16β,23(R),24(R),25-pentahydroxycycloartane (1), 3-O-[β-d-glucopyranosyl(1 → 2)-β-d-xylopyranosyl]-3β,16β,23(R),24(R)-tetrahydroxy-25-dehydrocycloartane (2), 3-O-[β-d-xylopyranosyl]-6α-acetoxy-23α-methoxy-16β,23(R)-epoxy-24,25,26,27-tetranorcycloartane (3), 3-O-[β-d-xylopyranosyl]-6α-acetoxy-23α-butoxy-16β,23(R)-epoxy-24,25,26,27-tetranorcycloartane (4), 3-O-[β-d-glucopyranosyl(1 → 2)]-β-d-xylopyranosyl]-6α-acetoxy-23α-methoxy-16β,23(R)-epoxy-24,25,26,27-tetranorcycloartane (5), 3-O-[β-d-glucopyranosyl(1 → 2)]-β-d-xylopyranosyl]-23α-methoxy-16β,23(R)-epoxy-4,25,26,27-tetranorcycloartane (6), in addition to three known secondary metabolites consisting of another cycloartane triterpene glycoside and two flavonol glycosides, were isolated from the aerial parts of Astragalus gombo Coss. & Dur. (Fabaceae). The structures of the isolated compounds were established by spectroscopic methods, including 1D and 2D-NMR, mass spectrometry and comparison with literature data.     

Triterpene glycosides from red ginseng marc and their anti-inflammatory activities

Three new triterpene glycosides ursan-3β,19α,22β-triol-3-O-β-d-glucopyranosyl (2′→1″)-β-d-glucopyranoside (1), ursan-3α,11β-diol-3-O-α-d-glucopyranosyl-(6′→1″)-α-d-glucopyranosyl-(6″→1‴)-α-d-glucopyranosyl-(6‴→1‴′)-α-d-glucopyranoside (2) and lanost-5,24-dien-3β-ol-3-O-β-d-glucopyranosyl-(6′→1″)-β-d-glucopyranosyl-(6″→1‴)-β-d-glucopyranoside (3), together with one known compound were isolated and identified from the marc of red ginseng. Their structures were elucidated by spectroscopic data analysis. Compounds (1–3) were investigated for anti-inflammatory effects using the RAW 264.7 macrophage cell line. In the cell proliferation assay, lipopolysaccharide stimulation decreased cell proliferation of RAW 264.7 macrophage cells, but the suppression of cell proliferation was significantly protected by treatment with compounds 2 and 3. Compounds 2 and 3 had a suppressive effect on the production of nitric oxide (NO), and they inhibited mRNA expression of proinflammatory mediators such as inducible nitric oxide synthase, and cyclooxygenase-2, and proinflammatory cytokines such as two interleukins and tumor necrosis factor-α. These findings suggest that compounds 2 and 3 have potential anti-inflammatory activities.     

Cycloartane-type glycosides from Astragalus amblolepis

Five cycloartane-type triterpene glycosides were isolated from the methanol extract of the roots of Astragalus amblolepis Fischer along with one known saponin, 3-O-β-D-xylopyranosyl-16-O-β-D-glucopyranosyl-3β,6α,16β,24(S),25-pentahydroxy-cycloartane. Structures of the compounds were established as 3-O-β-D-xylopyranosyl-25-O-β-D-glucopyranosyl-3β,6α,16β,24(S),25-pentahydroxy-cycloartane, 3-O-[β-D-glucuronopyranosyl-(1 → 2)-β-D-xylopyranosyl]-25-O-β-D-glucopyranosyl-3β,6α,16β,24(S),25-pentahydroxy-cycloartane, 3-O-β-D-xylopyranosyl-24,25-di-O-β-D-glucopyranosyl-3β,6α,16β,24(S),25-pentahydroxy-cycloartane, 6-O-α-L-rhamnopyranosyl-16,24-di-O-β-D-glucopyranosyl-3β,6α,16β,24(S),25-pentahydroxy-cycloartane, 6-O-α-L-rhamnopyranosyl-16,25-di-O-β-D-glucopyranosyl-3β,6α,16β,24(S),25-pentahydroxy-cycloartane by using 1D and 2D-NMR techniques and mass spectrometry. To the best of our knowledge, the glucuronic acid moiety in cycloartanes is reported for the first time.     

Cycloartane glycosides from Astragalus campylosema Boiss. ssp. campylosema

Four cycloartane glycosides, 3-O-[α-l-arabinopyranosyl-(1 → 2)-β-d-xylopyranosyl]-3β,6α,16β,23α,25-pentahydroxy-20(R),24(S)-epoxycycloartane (1), 3-O-[α-l-arabinopyranosyl-(1 → 2)-β-d-xylopyranosyl]-16-O-hydroxyacetoxy-23-O-acetoxy-3β,6α,25-trihydroxy-20(R),24(S)-epoxycycloartane (2), 3-O-[α-l-arabinopyranosyl-(1 → 2)-β-d-xylopyranosyl]-3β,6α,23α,25-tetrahydroxy-20(R),24(R)-16β,24;20,24-diepoxycycloartane (3), 3-O-[α-l-arabinopyranosyl-(1 → 2)-β-d-xylopyranosyl]-25-O-β-d-glucopyranosyl-3β,6α,16β,25-tetrahydroxy-20(R),24(S)-epoxycycloartane (4), along with three known cycloartane glycosides were isolated from the MeOH extract of the roots of Astragalus campylosema ssp. campylosema. Their structures were established by the extensive use of 1D- and 2D-NMR experiments along with ESIMS and HRMS analysis. The occurrence of the hydroxyl function at position 23 (1-2) and of the ketalic function at C-24 (3) are very unusual findings in the cycloartane class.     

New triterpene saponins from Phryna ortegioides

Four new and three known oleanane-type saponins have been isolated from the methanolic extract of Phryna ortegioides, a monotypic and endemic taxon of Caryophyllaceae.The structures of the new compounds were determined as gypsogenic acid 28-O-β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→6)-O-β-d-glucopyranosyl ester (1), 3-O-α-l-arabinofuranosyl-gypsogenic acid 28-O-β-d-glucopyranosyl-(1→3)-O-[β-d-glucopyranosyl-(1→6)]-O-β-d-glucopyranosyl ester (2), 3-O-α-l-arabinofuranosyl-gypsogenic acid 28-O-β-d-glucopyranosyl-(1→3)-O-[β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→6)-O-]-β-d-glucopyranosyl ester (3), 3-O-α-l-arabinofuranosyl-16α-hydroxyolean-12-en-23,28-dioic acid-28-O-β-d-glucopyranosyl-(1→3)-O-[β-d-glucopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→6)]-O-β-d-glucopyranosyl ester (4). Their structures were established by a combination of one- and two-dimensional NMR techniques, and mass spectrometry. Noteworthy, none of isolated compounds possesses as aglycone moiety gypsogenin, considered a marker of Caryophyllaceae family.The cytotoxic activity of the isolated compounds was evaluated against three cancer cell lines including A549 (human lung adenocarcinoma), A375 (human melanoma) and DeFew (human B lymphoma) cells. Only compound 6 showed a weak activity against A375 and DeFew cell lines with IC₅₀ values of 77 and 52 μM, respectively. None of the other tested compounds, in a range of concentrations between 12.5 and 100 μM, caused a significant reduction of the cell number.     

Synthesis of quercetin glycosides and their melanogenesis stimulatory activity in B16 melanoma cells

4′-O-β-d-Glucopyranosyl-quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyra-noside (3) was isolated from Helminthostachys zeylanica root extract as a melanogenesis acceleration compound and was synthesized using rutin as the starting material. Related compounds were also synthesized to understand the structure–activity relationships in melanin biosynthesis.Melanogenesis activities of the glycosides were determined by measuring intracellular melanin content in B16 melanoma cells. Among the synthesized quercetin glycosides, quercetin-3-O-β-d-glucopyranoside (1), quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside (2), and 3 showed more potent intracellular melanogenesis acceleration activities than theophyline used as positive control in a dose-dependent manner with no cytotoxic effect.     

Chalcone glycosides from aerial parts of Brassica rapa L. ‘hidabeni’, turnip

A phytochemical investigation of the aerial parts of Brassica rapa L. ‘hidabeni’, turnip resulted in the isolation of three new chalcone glycosides, 4′-O-β-d-glucopyranosyl-4-hydroxy-3′-methoxychalcone (1), 4′-O-β-d-glucopyranosyl-3′,4-dimethoxychalcone (2) and 4,4′-di-O-β-d-glucopyranosyl-3′-methoxychalcone (3) along with three known glycosides. The structures of the three newly isolated chalcone glycosides were elucidated on the basis of 1D and 2D NMR and mass spectroscopy.     

6-Methoxyflavonols from the aerial parts of Tetragonia tetragonoides (Pall.) Kuntze and their anti-inflammatory activity

Dried aerial parts of Tetragonia tetragonoides were extracted with 70% EtOH, and the evaporated residue was successively separated into EtOAc, n-BuOH, and H₂O fractions. As a result of repeated SiO₂, ODS, and Sephadex LH-20 column chromatography, four new 6-methoxyflavonol glycosides (2–4, 8) along with four known ones (1, 5–7) were isolated. Several spectroscopic data led to determination of chemical structures for four new 6-methoxyflavonol glycosides (2–4, 8) and four known ones, 6-methoxykaempferol 3-O-β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl-7-O-(6‴′-(E)-caffeoyl)-β-d-glucopyranoside (1), 6-methoxyquercetin (5), 6-methoxykaempferol (6), and 6-methoxykaempferol 7-O-β-d-glucopyranoside (7). Methoxyflavonol glycosides 2–8 also have never been reported from T. tetragonoides in this study. 6-Methoxyflavonols 5 and 6 showed high radical scavenging potential in DPPH and ABTS test. Also, all compounds showed significant anti-inflammatory activities such as reduction of NO and PGE₂ formation and suppression of TNF-α, IL-6, IL-1β, iNOS, and COX-2 expression in LPS-stimulated RAW 264.7 macrophages. In general, the aglycones exhibited higher activity than the glycosides. In addition, quantitative analysis of 6-methoxyflavonols in the T. tetragonoides aerial parts extract was conducted through HPLC.     

Nebulosides A–B,novel triterpene saponins from under-ground parts of Gypsophila arrostii Guss. var. nebulosa

A bioassay-guided phytochemical analysis of the triterpene saponins from under ground parts of Gypsophila arrostii var. nebulosa allowed the isolation of two triterpene saponins; nebuloside A, B based on gypsogenin and quillaic acid aglycone. Two new oleanane type triterpenoid saponins (nebuloside A, B) and three known saponins (1–3) were isolated from the root bark of Gypsophila arrostii var. nebulosa. The structures of the two new compounds were elucidated as 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]-β-d-glucuronopyranosyl quillaic acid 28-O-β-d-glucopyranosyl-(1→3)-[β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)]-α-l-rhamnopyranosyl-(1→2)-β-d-fucopyranosyl ester (nebuloside A) and 3-O-β-d-xylopyranosyl-(1→3)-[β-d-galactopyranosyl(1→3)-β-d-galactopyranosyl-(1→2)]-β-d-glucuronopyranosyl gypsogenin 28-O-β-d-glucopyranosyl-(1→3)-[β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)]-α-l-rhamnopyranosyl-(1→2)-β-d-fucopyranosyl ester (nebuloside B), on the basis of extensive spectral analysis and chemical evidence. Nebuloside A and B showed toxicity enhancing properties on saporin a type-I RIP without causing toxicity by themselves at 15 μg/mL.     

Quinovic acid glycosides from Guettarda angelica

Two new triterpene glycosides isolated from the root bark Guettarda angelica were proven to be quinovic acid-3β-O-[β-d-glucopyranosyl-(1 → 3)-α-l-rhamnopyranoside] and quinovic acid-3β-O-β-d-glucopyranosyl-(28 → 1)-β-d-glucopyranosyl ester. In addition quinovic acid and two known glycoside derivatives (quinovic acid-3β-O-β-d-glucopyranoside and quinovic acid-3β-O-α-l-rhamnopyranoside) were isolated. The structures were elucidated by spectroscopic analysis of the peracetyl methyl ester derivatives.     

Cycloartane glycosides from Astragalus aureus

Eight cycloartane-type triterpene glycosides (1-8) were isolated from Astragalus aureus Willd along with ten known cycloartane-type glycosides (9-18). Their structures were established by the extensive use of 1D and 2D-NMR experiments along with ESIMS and HRMS analyses. Compounds 1-5 are cyclocanthogenin glycosides, whereas compounds 6-8 are based on cyclocephalogenin as aglycon, more unusual in the plant kingdom, so far reported only from Astragalus spp. Moreover, for the first time monoglycosides of cyclocanthogenin (5) and cyclocephalogenin (7, 8) are reported. All of the compounds tested for their cytotoxic activities against a number of cancer cell lines. Among the compounds, only 8 exhibited activity versus human breast cancer (MCF7) at 45 μM concentration.     

Phenylethanoid glycosides from the leaves of Magnolia hodgsonii

Three new phenylethanoid glycosides, 2-(3-hydroxy-4-methoxyphenyl)ethyl 1-O-β-d-allopyranoside (hodgsonialloside A, 1), 2-(3-hydroxy-4-methoxyphenyl)ethyl 1-O-β-d-glucopyranosyl-(1 → 4)-β-d-allopyranoside (hodgsonialloside B, 2) and 2-(3-methoxy-4-hydroxyphenyl)ethyl 1-O-β-d-allopyranoside (hodgsonialloside C, 3) were isolated from the leaves of Magnolia hodgsonii in addition to six known compounds, tyrosol 4-O-β-d-xylopyranosyl-(1 → 6)-β-d-glucopyranoside (4), kaempferol 3-O-neohesperidoside (5), kaempferol 3-O-rutinoside (6), kaempferol 3-O-α-l-rhamnopyranosyl-(1 → 2)-[α-l-rhamnopyranosyl-(1 → 6)]-β-d-glucopyranoside (7), (+)-syringaresinol O-β-d-glucopyranoside (8), and oblongionoside C (9). The structure elucidation of these compounds was based on analyses of physical and spectroscopic data including 1D and 2D NMR experiments.     

Three new 18,19-seco-ursane glycosides from Elsholtzia bodinieri

Chromatographic separation of an extract of the aerial part of Elsholtzia bodinieri resulted in the isolation of three new 18,19-seco-ursane glycosides, bodiniosides E-G (1–3). Their structures were elucidated as 2α,12β,23-trihydroxy-3-(β-d-glucopyranosyl)-19-oxo-18,19-seco-urs-13(18)-en-28-O-β-d-glucopyranosyl ester (1), 3-β-d-glucopyranosyl-19-β-d-glucopyranosyl-12β,21-dihydroxy-18,19-seco-urs-13(18)-en-28-oic acid (2), and 2α,12β,21-trihydroxy-3-β-d-glucopyranosyl-19-β-d-glucopyranosyl-18,19-seco-urs-13(18)-en-28-oic acid (3), respectively, by extensive NMR techniques, including 1D- and 2D-NMR experiments, as well as comparing with spectral data with those of the known analogues.     

Steroidal saponins from Tribulus terrestris

Five new steroidal saponins were isolated from the fruits of Tribulus terrestris. Their structures were fully established by spectroscopic and chemical analysis as (23S,25S)-5α-spirostane-24-one-3β,23-diol-3-O-{α-l-rhamnopyranosyl-(1 → 2)-O-[β-d-glucopyranosyl-(1 → 4)]-β-d-galactopyranoside} (1), (24S,25S)-5α-spirostane-3β,24-diol-3-O-{α-l-rhamnopyranosyl-(1 → 2)-O-[β-d-glucopyranosyl-(1 → 4)]-β-d-galactopyranoside} (2), 26-O-β-d-glucopyranosyl-(25R)-5α-furostan-2α,3β,22α,26-tetraol-3-O-{β-d-glucopyranosyl-(1 → 2)-O-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside} (3), 26-O-β-d-glucopyranosyl-(25R)-5α-furostan-20(22)-en-2α,3β,26-triol-3-O-{β-d-glucopyranosyl-(1 → 2)-O-β-d-glucopyranosyl-(1 → 4)-β-d-galactopyranoside} (4), and 26-O-β-d-glucopyranosyl-(25S)-5α-furostan-12-one-22-methoxy-3β,26-diol-3-O-{α-l-rhamnopyranosyl-(1 → 2)-O-[β-d-glucopyranosyl-(1 → 4)]-β-d-galactopyranoside} (5). The isolated compounds were evaluated for cytostatic activity against HL-60 cells.     

Bioactive saponins from Microsechium helleri and Sicyos bulbosus

Eleven oleanane-type saponins (1-11) have been isolated from Microsechium helleri and Sicyos bulbosus roots and were evaluated for their antifeedant, nematicidal and phytotoxic activities. Saponins {3-O-β-d-glucopyranosyl (1 → 3)-β-d-glucopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12-en-28-oic acid 28-O-α-l-rhamnopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 4)-[β-d-xylopyranosyl-(1 → 3)]-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranoside} (1), and {3-O-β-d-glucopyranosyl-2β,3β,16α,23-tetrahydroxyolean-12-en-28-oic acid 28-O-α-l-rhamnopyranosyl-(1 → 3)-β-d-xylopyranosyl-(1 → 4)-[β-d-xylopyranosyl-(1 → 3)]-α-l-rhamnopyranosyl-(1 → 2)-α-l-arabinopyranoside} (2) were also isolated from M. helleri roots together with the two known compounds 3 and 4. Seven known structurally related saponins (5-11) were isolated from S. bulbosus roots. The structures of these compounds were established as bayogenin and polygalacic glycosides using one- and two-dimensional NMR spectroscopy and mass spectrometry. Compounds 7, 10, bayogenin (12) and polygalacic acid (13) showed significant (p < 0.05) postingestive effects on Spodoptera littoralis larvae, compounds 5-11 and 12 showed variable nematicidal effects on Meloydogyne javanica and all tested saponins had variable phytotoxic effects on several plant species (Lycopersicum esculentum, Lolium perenne and Lactuca sativa). These are promising results in the search for natural pesticides from the Cucurbitaceae family.     

Saponins in aerial parts of Helleborus viridis L.

In the search of natural compounds inhibiting methane production in ruminants three novel steroidal saponins have been isolated from the aerial parts of Helleborus viridis L. Their structures have been established based on spectral analyses as: (25R)-26-O-β-d-glucopyranosyl-5β-furostan-3β,22α,26-triol 3-O-β-d-glucopyranosyl-(1 → 6)-O-β-d-glucopyranoside, (25R)-26-O-β-d-glucopyranosyl-5α-furostan-3β,22α,26-triol 3-O-β-d-glucopyranosyl-(1 → 6)-O-β-d-glucopyranoside and (25R)-26-O-β-d-glucopyranosyl-furost-5-ene-1β,3β,22α,26-tetraol 1-O-{α-l-rhamnopyranosyl-(1 → 2)-O-[β-d-glucopyranosyl-(1 → 3)]-6-O-acetoxy-β-d-glucopyranoside}.