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A new furostanol saponin, (25R)-26-O-(α-d-glucopyranosyl)-(1→2)-α-l-rhamnopyranosyl-furost-5-ene-3β, 22α, 26-triol-3-O-α-d-glucopyranoside (1), together with four known compounds 2–5 were isolated from the ethanolic extract of the stems of Dendrobium chrysanthum Lindl. The structures of these new compounds were identified by extensive spectroscopic analysis including 1D and 2D NMR and HR-ESI-MS, as well as chemical methods. Compounds 1–3 were isolated from D. chrysanthum for the first time. Furthermore, the inhibitory effects of the compounds on tumor cells were evaluated, and compounds 1–2 exhibited significant cytotoxic activities potentially against SPC-A1, MCF-7 and HeLa human cancer cell lines. Compounds 3–5 showed inhibitory activity against the SPC-A1 and MCF-7.

Four new furostanol saponins, named padelaosides C-F (1-4), together with four known spirostanol saponins 5-8 were isolated from the rhizomes of Paris delavayi Franchet. Their structures were elucidated on the basis of extensive spectroscopic analysis and chemical evidences. The discovery of the new compounds 1-4 extended the diversity and complexity of this furostanol saponin family. The cytotoxicity of all the saponins was evaluated for their cytotoxicity against human glioblastoma U87MG and human hepatocellular carcinoma Hep-G2 cell lines. The known spirostanol saponins 7 and 8 exhibited notable cytotoxicity against the two tumor cell lines with IC50 values of 1.13 and 3.42μM, respectively, while the new furostanol saponins 3 and 4 showed moderate cytotoxicity with IC50 values of 15.28 to 16.98μM.

Eleven novel furostanol saponins, named ophiofurospisides C–E, G–N (1–3, 5–12), one new spirostanol saponin, named ophiopogonin R (13), were isolated from the fresh tubers of Ophiopogon japonicus. Their structures were determined on the basis of spectroscopic techniques (1D and 2D NMR) and HRESIMS. The isolated furostanol saponins possessed two sugar chains located at C-3 and C-26, respectively. Six furostanol saponins (1, 5–9) with disaccharide moiety linked at position C-26 of the aglycone were rare in the plant kingdom.

An extensive phytochem. anal. of the polar exts. from bulbs of Welsh onion Allium fistulosum L. led to the isolation of nine saponins, four of them, named fistulosaponins G (1a/1b), H (2), I (3a/3b), and J (4), have never been reported previously. Fistulosaponins G and I were isolated as a couple of isomers in equil. On the basis of 2D NMR and mass spectrometry data, the structure of the novel compds. were elucidated as (25R)-26-[(β-D-glucopyranosyl)oxy]-3β,22β-dihydroxyfurost-5-en-1β-yl O-α-L-rhamnopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranoside (1a) with its 22α epimer (1b), (25R)-26-[(β-D-glucopyranosyl)oxy]-3β-hydroxyfurost-5,20-dien-1β-yl O-α-L-rhamnopyranosyl-(1 → 4)-O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranoside (2), (25R)-26-[(β-D-glucopyranosyl)oxy]-3β,22β-dihydroxyfurost-5-en-1β-yl O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranoside (3a) with its 22α epimer (3b), and (25R)-26-[(β-D-glucopyranosyl)oxy]-3β-hydroxyfurost-5,20-dien-1β-yl O-α-L-rhamnopyranosyl-(1 → 4)-β-D-glucopyranoside (4). This is the first report of furostanol saponins in A. fistulosum bulbs. In addn., data on the antibacterial tests of the isolated saponins against Escherichia coli and Enterococcus faecalis are reported. [on SciFinder(R)]

Four new steroid saponins 1–4 were isolated from the rhizomes of Anemarrhena asphodeloides (Asparagaceae), as well as four known saponins: anemarsaponin B (5) timosaponin D (6), timosaponin E1 (7) anemarsaponin B II (8). Their structures were established through UV and NMR as well as MS data. All the compounds were evaluated for cytotoxicity against HepG2 and SGC7901 human cancer lines. Compounds 3 and 7 displayed medium antiproliferative activities on HepG2 and SGC7901 cells, with IC50 values of 43.90 and 57.90 μM, respectively.

An ultra-performance liquid chromatography coupled with a hybrid quadrupole time-of-flight tandem mass spectrometry method was established to rapidly identify and guide the isolation of target saponins from fenugreek seeds. Based on the online screening performance, totally forty-six furostanol saponins were detected and elucidated. Among them, twenty compounds were predicted to be new. To rapidly obtain new furostanol saponins from these seeds, a further phytochemical study was carried out under the guidance of the ultra-performance liquid chromatography coupled with a hybrid quadrupole time-of-flight tandem mass spectrometry. Finally, six new furostanol saponins, named as trigoneosides XIV (1), XV (2), XVI (3), XVIIa (4), XVIIb (5), and XIV (6), together with one known furostanol saponin, parvifloside (7), were rapidly obtained, and their definitive structures were determined by NMR and chemical evidence.

Nine spirostanol saponins (1-9) and seven mixtures of 25 R and 25 S spirostanol saponin isomers (10-16) were obtained from the seeds of Trigonella foenum-graecum after enzymatic hydrolysis of the furostanol saponin fraction by β-glucosidase. Their structures were determined by NMR and MS spectroscopy. Among them, 1- 4, 6, 8, and 9 were new compounds and five, 11B, 12A, 13B, 14A, and 14B, were new structures observed from seven mixtures. In addition, the inhibitory effects of all saponins on rat platelet aggregation were evaluated.

A new furostanol saponin, sisalasaponin C (1), and a new spirostanol saponin, sisalasaponin D (2), were isolated from the fresh leaves of Agave sisalana, along with three other known steroidal saponins and two stilbenes. Their structures were identified as (3β,5α,6α,22α,25R)-3,26-bis[(β-D-glucopyrano- syl)oxy]-22-hydroxyfurostan-6-yl β-D-glucopyranoside (1), (3β,5α,25R)-12-oxospirostan-3-yl 6-deoxy-α-L-mannopyranosyl-(14)-β-D-glucopyranosyl-(13)-[β-D-xylopyranosyl-(13)-β-D-glucopyranosyl-(12)]-β-D-glucopyranosyl-(14)-β-D-galactopyranoside (2), (3β,5α,6α,22α,25R)-22-methoxyfurostane-3,6,26-triyl tris-β-D-glucopyranoside, cantalasaponin-1, polianthoside D, (E)- and (Z)-2,3,4′,5-tetrahydroxystilbene 2-O-β-D-glucopyranosides. The last three known compounds were isolated from the fresh leaves of Agavaceae for the first time. The structures of the new compounds were elucidated by detailed spectroscopic analysis, including 1D- and 2D-NMR experiments, and chemical techniques.

Two new furostanol saponins were isolated from the fruits of Tribulus terrestris L. Their structures were established as 26-O-beta-D-glucopyranosyl-(25S)-5alpha-furost-20(22)-en-3beta,26-diol-3-O-alpha-L-rhamnopyranosyl-(1 --> 2)-[beta-D-glucopyranosyl-(1 --> 4)]-beta-D-galactopyranoside (1) and 26-O-beta-D-glucopyranosyl-(25S)-5alpha-furost-20(22)-en-12-one-3beta,26-diol-3-O-beta-D-galactopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 4)-beta-D-galactopyranoside (2) on the basis of spectroscopic data as well as chemical evidence.

AIM To study the furostanol saponins from the fruits of Tribulus terrestris . METHODS The constituents from T. terrestris were separated and purified by silica gel chromatography, reversed-phase silica gel chromatography and RP-HPLC. Their structures were elucidated on the basis of chemical evidence, spectral data and chemical reactions. RESULTS Two furostanol saponin were identified as 3- O -{β- D -xylopyranosyl(1→3)-[β- D -xylopyranosyl(1→2)]-β- D -glucopyranosyl (1→4)-[α- L -rhamnopyranosyl (1→2)]-β- D -galactopyranosy}-26- O -β- D -glucopyranosyl-5α-furost-12-one-22-methoxyl-3β,26-diol(named terrestroside A) and 3- O -{β- D -xylopyranosyl(1→3)-[β- D -xylopyranosyl(1→2)]-β- D -glucopyranosyl(1→4)-[α- L -rhamnopyranosyl(1→2)]-β- D -galactopyranosy}-26- O -β- D -glucopyranosyl-5a-furost-22-methoxyl-3β,26-diol. CONCLUSION Terrestroside A is a new furostanol saponin.

Two furostanol saponins were obtained from the n-butanol fraction of methanol extract from Tupistra chinensis rhizomes, a folk medicine of Shennongjia Forest District of Hubei Province. Their structures were determinedas (25S)-26-O-(beta-D-glucopyranosyl)-furost-1 beta, 3 beta, 22 alpha, 26-tetrol-3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(l -> 2)-beta-D-glucopyranoside (1) and (25R)26-O-(beta-D-glucopyranosyl)-furost-1 beta, 3 beta 22a, 26-tetrol 3-O-beta-D-glucopyranosyl-(l -> 4)-beta-D-glucopyranosyl-(l -> 2)-beta-D-glucopyranoside (2), on basis of chemical and spectroscopic evidences. 1 and 2 displayed marked inhibitory action towards COX-2 production in macrophages of the rat abdomen induced by LPS at 20 mu g/mL. (c) 2007 Kun Zou. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

A new bisdesmosidic furostanol saponin was isolated from leaves of Agave brittoniana Trel. Its structure was established as 3-[O-6-deoxy-α-L-mannopyranosyl-(1→4)-O-β -D-glucopyranosyl-( 1→3)-O]-[O-β -D-glucopyranosyl-(1→3)-β -D-glucopyranosyl-(1→2)-O-β -D-glucopyranosyl- (1→4)-β -D-galactopyranosyl)oxy]-(3β ,5α,6α,22α,2R)-26-(β -D-glucopyranosyloxy)-6,22-dihydroxy- furost-12-one. Its structural identification was performed using detailed analyses of 1H and 13C NMR spectra including 2D NMR spectroscopic techniques (DEPT, COSY, HETCOR and COLOC) and chemical conversions. The steroidal saponin showed no haemolytic effects in the in vitro assays and demonstrated antiinflammatory activity using in vivo models.

A pair of diastereoisomeric furostanol saponins was obtained from the n-butanol fraction of methanol extract from Tupistra chinensis rhizomes, a folk medicine of Shennongjia Forest District of Hubei Province. Their structures were determined, on the basis of chemical and spectroscopic evidences. (c) 2006 Kun Zou. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

A new bidesmosidic furostanol saponin was isolated from leaves of Furcraea gigantea Vent. Its structure was established as 3-[(O-6-deoxy-α-L-mannopyranosyl-(1→4)-O-β -D-glucopyranosyl-( 1→3)-O-[O-β -D-glucopyranosyl-(1→3)-β -D-glucopyranosyl-(1→2)-O-β -D-glucopyranosyl- (1→4)-β -D-galactopyranosyl)oxy]-(3β ,5α,15α,22α,25R)-26-(β -D-glucopyranosyloxy)-15,22-dihydroxy- furost-12-one. Its structural identification was performed using detailed analyses of 1H and 13C NMR spectra including 2D NMR spectroscopic techniques (DEPT, COSY, HETCOR and COLOC) and chemical conversions. The steroidal saponin showed no haemolytic effects in the in vitro assays and demonstrated inhibition of the capillary permeability activity.

A new bisdesmosidic furostanol saponin, along with a known spirostanol saponin, furcreastatin, were isolated from Furcraea gigantea Vent. (Agavaceae). The structure of the new saponin was elucidated as 3-[(O-6-deoxy-α-L-mannopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1a 3)-O-[O-β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl-(1→2)-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranosyl)oxy]-(3β, 5α, 25R)-26-(β-D-glucopyranosyloxy)-22-hydroxyfurost-12-one. The structural identification was performed using a combination of spectroscopic techniques and chemical conversions. Furcreastatin showed a powerful haemolytic effect in the in vitro assay, but the new bisdesmosidic furostanol saponin demonstrated only a significant inhibition of the capillary permeability activity.

Plants belonging to the genera Allium and Aster are widely distributed in nature and have been used as food and/or medicine. Their wide use was mainly due to the medicinal properties attributed to these plants since ancient times, recently supported by epidemiological and laboratory studies. Saponin compounds, responsible for many pharmacological activities, are quite abundant in these plants. Thus, a deep knowledge about the saponin composition of these vegetables appears to be essential and could promote the discovery of new potential leads. As part of our continuing research aimed at the identification of bioactive metabolites, we have addressed our attention to several Allium and Aster species. The study resulted in the isolation of over fifty saponins of furostane, spirostane, cholestane, and oleane-type structures. Some of the isolated compounds exhibited promising antiproliferative, antifungal, and antispasmodic activities. Their structure, distribution and bioactivity will be reported here together with a brief overview of the literature on Allium and Aster saponins.

The phytochemical investigation of the aerial parts of Tribulus terrestris of Bulgarian origin has resulted in the isolation of the novel furostanol saponin 1, named tribol, together with the known spirostanol saponins 2 and 3 and sitosterol glucoside. The structure of tribol was determined as (25R)-furost-5(6)-ene-3beta,16,26-triol-3-O-alpha-rhamnopyranosyl-(1--2)-[alpha-rhamnopyranosyl-(1--4)]-beta-glucopyranoside (1) by spectral analysis, including extensive 1D and 2D-NMR experiments.

Two new furostanol saponins ophiopogonins J (1) and K (2) were isolated from the fibrous roots of Ophiopogon japonicus. The structures of 1 and 2 were established as (25R)-26-O-[(β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-14-hydroxy-furost-5,20(22)-diene 3-O-[α-l-rhamnopyranosyl-(1 → 2)]-β-d-glucopyranoside (1), and (25R)-26-O-[(β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl)]-furost-5,20(22)-diene 3-O-α-l-rhamnopyranosyl-(1 → 2)[(β-d-xylopyranosyl-(1 → 4)-β-d-glucopyranoside)] (2) on the basis of spectroscopic means including HRESIMS, 1D, and 2D NMR experiments.

Akın, Sebahat (Balikesir Author), A furostanol saponin mixture and a known phytoecdysteroid were isolated from the roots of Helleborus orientalis Lam. Their structures were established as 26-[(beta-D-glucopyranosyl)oxy]-22 alpha-hidroxyfurosta-5,25(27)-dien-1 beta,3 beta,11 alpha-triol (1a), 26-[(beta-D-glucopyranosyl)oxy]-22 alpha-methoxyfurosta-5,25(27)-dien-1 beta,3 beta,11 alpha-triol (1b), and 20-hydroxy-beta-ecdyson-3-O-beta-D-glycoside (2). Acid hydrolysis of 1a,b gave (1 beta,3 beta,11 alpha,22 alpha)-22,26-dimethoxyfurosta-5,25(27)-dien-1,3,11-triol (aglycone 1) and of 2 gave 20-hydroxy-beta-ecdyson (aglycone 2). Their structures were elucidated by spectral analysis.

A new furostanol saponin, named hypoglaucin F, was isolated from the rhizomes of Dioscorea collettii var. hypoglauca, along with seven known compounds. On the basis of detailed chemical and spectroscopic evidence, the structure of hypoglaucin F was determined as (25S)-26-O-β- d -glucopyranosyl 22-hydroxy-5-en-furostane-3β, 26, 27-triol 3-O-α- l -rhamnopyranosyl-(1 → 2)-[α- l -rhamnopyranosyl-(1 → 4)]-β- d -glucopyranoside .

Phytochemical investigation of the fresh tubers of Ophiopogon japonicus led to the isolation of two new furostanol saponins (1 and 2) together with two known steroidal saponins (3 and 4). Comprehensive spectroscopic analysis allowed the chemical structures of two new compounds to be elucidated as (25R)-26-O-[β-d-glucopyranosyl-(1 → 2)-β-d-glucopyranosyl]-5-ene-furost-1β,3β,22α,26-tetraol-3-O-α-l-rhamnopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-glucopyranoside (1, ophiopogonin P) and (25R)-26-O-[β-d-glucopyranosyl-(1 → 6)-β-d-glucopyranosyl]-5-ene-furost-1β,3β,22α,26-tetraol-3-O-α-l-rhamnopyranosyl-(1 → 2)-[β-d-xylopyranosyl-(1 → 4)]-β-d-glucopyranoside (2, ophiopogonin Q). Furostanol saponins with the disaccharide chain linked at C-26 hydroxy group of the aglycone have been rarely reported from natural sources.

Two new furostanol saponins 1–2 and three new sulphated glycosides 3a,b and 4 were isolated from the underground parts of Ruscus aculeatus L., along with four known furostanol and one spirostanol saponins 5–9 and three free sterols. All of the structures have been elucidated on the basis of spectroscopic data 1D and 2D NMR experiments, MS spectra and GC analyses.

Dichotomin, a furostanol saponin derived from diosgenin, has been isolated from Panicum dichotomiflorum and its structure determined by mass spectrometry, one- and two-dimensional NMR techniques, and acidic and enzymatic hydrolyses to known compounds. The 1 H and 13 C NMR resonances for dichotomin (1a) were assigned by analogy with those for its 26-deglucosoylated spirostanol derivative (2), which were unambiguously assigned in a series of one- and two-dimensional NMR experiments. Revisions to the published 13 C NMR assignments of 2 are presented

A new furostanol saponin, (25S)-26-O-β-D-glucopyranosyl-5β-furost-20(22)-en-3β, 15β,26-triol-3-O-[α-L-rhamnopyranosyl-(1-4)]-β-D: -glucopyranoside, namely, aspacochioside D (1) were isolated from Asparagus cochinchinensis (Lour.) Merr, along with three known saponins, aspacochioside C (2), (25S)-5β-spirostan-3β-yl-O-[O-α-L-rhamnopyranosyl-(1-4)]-β-D-glucopyranoside (3), and pseudoprotoneodioscin (4). The structure of 1 was elucidated on the basis of chemical reactions and spectral analysis (IR, GC, ESI-MS, (1)H-NMR, (13)C-NMR, DEPT, HMBC, HMQC and NOESY). The antiproliferative effects of 1-4 were evaluated in a cytotoxicity assay against the human tumor cell line, A549. Compound 2 (Aspacochioside C) exhibited moderate cytotoxicity against A-549, with an IC(50) value of 3.87 μg/mL.

Two furostanol saponins helleboroside A (1) and helleboroside B (2) were isolated from the methanol extract of Helleborus bocconei Ten. subsp. intermedius (Guss.) Greuter and Burdet, along with the furospirostanol saponin 4 and two ecdysones: ecdysterone (5) and polypodyne B (6). Compound 2 was enzymatically hydrolysed to give product 3. The biological activity of all compounds was tested against rat C6 glioma cells showing a significant cytotoxicity for compounds 3, 4 and 6. Copyright © 2009 John Wiley & Sons, Ltd.

A new furostanol saponin was isolated from the mesocarp of Balanites aegyptiaca fruits and identified as 26-O-beta-D-glucopyranosyl-(25R)-furost-5-ene-3,22,26-triol 3-O-[[alpha-L-rhamnopyranosyl-(1--2)]-[beta-D-xylopyranosyl-(1--2)]-be ta- D-xylopyranosyl-(1--2)]-beta-D-xylopyranoside (balanitesin).

Four steroidal saponins were isolated from the leaves of Furcraea selloa var. marginata. These included one furostanol saponin, furcreafurostatin (1), and three known spirostanol saponins, furcreastatin (3), yuccaloeside C (4) and cantalasaponin-1 (5). The 22-O-methyl ether (2) of furcreafurostatin (1) was also characterized. The structures were determined by using a combination of spectroscopic techniques.

An effective synthetic route towards four types of bisdesmosidic furostanol saponin was developed and 36 derivatives were designed and synthesized for antitumor investigation. The chemical intertra...

A new furostanol steroidal saponin, shatavaroside C (1), and a new diphenylpentendiol, shatavarol (2), together with five known compounds, shatavarin IV (3), racemoside A (4), β-sitosterol (5) stigmasterol (6) and ursolic acid (7), have been isolated from the roots of Asparagus racemosus. This is the first report on the isolation of racemoside A (4) from roots of the plant. Structures of isolated compounds were determined on the basis of detailed analysis of their 1D, 2D NMR and mass spectral data.

The saponin fraction prepared from the methanolic extract of the underground parts of Agapanthus inapertus was found to exhibit inhibitory activity on cAMP phosphodiesterase (55.2%) at a concentration of 100 micrograms/ml. From this fraction, four new steroidal saponins, designated as agapanthussaponin A (1), B (2), C (3) and D (4), were isolated as the active principles, along with an inactive new furostanol saponin (5). The structures of 1-5 were determined by spectroscopic data and hydrolysis. The IC50 of 1-4 on cAMP phosphodiesterase were 0.7, 1.2, 1.1 and 2.0 (x 10(-5) M), respectively, which are more potent than that of papaverine (IC50 3.0 x 10(-5) M).