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PubMed1982

Molluscicidal steroid glycoalkaloids possessing stereoisomeric spirosolane structures.

Both the steroidal glycoalkaloid mixture obtained from Solanum mammosum fruits (solasonine 1 and solamargine 2) and the stereoisomeric glycosidic alkaloid tomatine 3 are toxic at 10 and 25 ppm to Lymnaea cubensis and Biomphalaria glabratus, respectively. Their aglycones solasodine 4 and tomatidine 5 obtained by hydrolysis of the glycosides showed no toxicity to either mollusk under the test conditions used. Preliminary structure-activity correlations indicate that the molluscicidal properties depend on the type of aglycones and on the glycoside bond. A common molecular structure in molluscicidal spirosolane and spirostane glycosides is recognized.

Alkaloids↗

PubMed2006

Saponins from Allium minutiflorum with antifungal activity.

Three saponins, named minutoside A (1), minutoside B (2), minutoside C (3), and two known sapogenins, alliogenin and neoagigenin, were isolated from the bulbs of Allium minutiflorum Regel. Elucidation of their structure was carried out by comprehensive spectroscopic analyses, including 2D NMR spectroscopy and mass spectrometry. The structures of the new compounds were identified as (25R)-furost-2alpha,3beta,6beta,22alpha,26-pentaol 3-O-[beta-D-xylopyranosyl-(1-->3)-O-beta-D-glucopyranosyl-(1-->4)-O-beta-D-galactopyranosyl] 26-O-beta-D-glucopyranoside (1), (25S)-spirostan-2alpha,3beta,6beta-triol 3-O-beta-D-xylopyranosyl-(1-->3)-O-beta-D-glucopyranosyl-(1-->4)-O-beta-D-galactopyranoside (2), and (25R)-furost-2alpha,3beta,5alpha,6beta,22alpha,26-esaol 3-O-[beta-D-xylopyranosyl-(1-->3)-O-beta-D-glucopyranosyl-(1-->4)-O-beta-D-galactopyranosyl] 26-O-beta-D-glucopyranoside (3). The isolated compounds were evaluated for their antimicrobial activity. All the novel saponins showed a significant antifungal activity depending on their concentration and with the following rank: minutoside B>minutoside C>>minutoside A. No appreciable antibacterial activity was recorded. The possible role of these saponins in plant-microbe interactions is discussed.

Allium↗

PubMed2001

Application of MS and NMR to the structure elucidation of complex sugar moieties of natural products: exemplified by the steroidal saponin from Yucca filamentosa L.

An approach, using well characterized procedures, is presented that should be of general applicability for the structural elucidation of complex sugar moieties of natural products. The methods used are exemplified by the structure elucidation of a new gitogenin-based steroidal saponin that has a strong leishmanicidal activity similar to preparations used in clinical practice and has been isolated by bioactivity-guided fractionation of the ethanolic extract of Yucca filamentosa L. leaves. The saponin has been characterized as 3-O-((beta-D-glucopyranosyl-(1-->3)- beta-D-glucopyranosy-(1-->2))(alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3))-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranosyl)-25R,5alpha-spirostan-2alpha,3beta-diol.

Biological Products↗

PubMed2000

Cytotoxic saponins from bulbs of Allium porrum L.

An extensive phytochemical analysis of the saponin content has been undertaken on leek, Allium porrum L., sown and collected at different seasons. As a result of this investigation, eight saponins (1-8) have been isolated, four of them (5-8) being novel compounds. Compounds 5 and 6, possessing the same tetrasaccharide moiety of compounds 1 and 3, display very unusual spirostane aglycones, 12-ketoporrigenin and 2,12-diketoporrigenin (named porrigenin C), respectively, recently isolated for the first time as free sapogenin in the same plant. Compounds 7 and 8 are rare cholestane bidesmosides possessing a di- and trisaccharide residues linked to a polyhydroxycholesterol aglycone, respectively. The structures of the isolated compounds have been determined by nondegradative spectroscopic analysis, mainly based on NMR. All the eight saponins isolated from leek were tested for their cytotoxic activity against two different cell lines in vitro, and compounds 1, 2, and 6 resulted particularly active.

Allium↗

PubMed1998

Stereospecific Synthesis of 1,6-Dioxadecalins and 2,2'-Linked Ditetrahydrofurans by Rearrangement of Steroidal Spiroacetals.

The reduction of steroidal spiroacetal methanesulfonate derivatives, containing the 1,6-dioxaspiro[4.5]decan-10-yl ring system, with DIBALH promotes a new rearrangement to give steroidal 1,6-dioxadecalin (octahydropyrano[3,2-b]pyran) or 2,2'-linked ditetrahydrofuran (octahydro[2,2']bifuranyl) derivatives. To study the scope and selectivity of the reaction, several steroidal spiroacetals such as (23R,25R)-3beta-methoxy-5alpha-spirostan-23-yl methanesulfonate (2) and its 23S-isomer (5) and (22R,23R,25R)-3beta-acetoxy-16beta,23:23,26-diepoxycholest-5-en-22-yl methanesulfonate (15) and its 22S-isomer (19) have been synthesized. Compound 2 was rearranged with absolute regio- and stereoselectivity to give (22S,23S,25R)-3beta-methoxy-16beta,23:22,26-diepoxy-5alpha-cholestane (3) which possesses a cis-fused 1,6-dioxadecalin ring system. The reaction of compound 5 gave exclusively (22S,23R,25R)-3beta-methoxy-23,26-epoxy-5alpha-furostane (6) in which the spiroacetal was converted into a ditetrahydrofuran subunit. The two other isomeric spiroacetals 15 and 19 were also mainly transformed into (22S,23S,25R)-3beta-acetoxy-16beta,23:22,26-diepoxycholest-5-ene (16) and (22R,23R,25R)-3beta-acetoxy-23,26-epoxyfurost-5-ene (20), respectively. A mechanism is proposed to explain the regio- and sterospecificity observed in the rearrangement.

Journal Article↗

PubMed2000

New steroidal glycosides from the fruits of Tribulus terrestris.

Three new steroidal saponins (1-3) were isolated from the fruits of Tribulus terrestris. Their structures were assigned by spectroscopic methods (IR, HRESIMS, 1D- and 2D-NMR) as 26-O-beta-D-glucopyranosyl-(25S)-5beta-furost-20(22)-en-3bet a, 26-diol-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl- (1-->4)]-beta-D-glucopyranoside (1), 26-O-beta-D-glucopyranosyl-(25S)-5beta-furost-20(22)-en-3bet a, 26-diol-3-O-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1 -->4)]-beta-D-galactopyranoside (2), and 25(S)-5beta-spirostan-3beta-ol-3-O-alpha-L-rhamnopyranosyl-( 1-->2)-[b eta-D-glucopyranosyl-(1-->4)]-beta-D-galactopyranoside (3). Compound 3 showed cytotoxicity against a human malignant melanoma cell line (SK-MEL).

Animals↗

PubMed2004

Nor-lignans and steroidal saponins from Asparagus gobicus.

From the roots of Asparagus gobicus, four new nor-lignans, 3'-methoxynyasin, iso-agatharesinol, gobicusins A, B and one new steroidal saponin, 3-O-[beta-D-xylopyranosyl(1-4)-beta-D-glucopyranosyl(1-2)-beta-D-glucopyranosyl]-(25S)-5beta-spirostan-3beta-ol (11) were isolated, together with twelve known compounds. The structures of the new compounds were established by spectroscopic methods including 2D-NMR techniques (1H-1H COSY, HMBC, HMQC) and chemical transformations. Nyasol (5) and 11 exhibited remarkable in vitro cytotoxic activity against cultured HO-8910 (human ovarian carcinoma) and Bel-7402 (human hepatoma) cells with IC50 vales of 30.6 and 29.4 microM, 5.2 and 5.2 microM, respectively.

Antineoplastic Agents, Phytogenic↗

PubMed1999

Steroidal saponins from Anemarrhena asphodeloides and their effects on superoxide generation.

A new steroidal saponin, timosaponin F, along with six known compounds was isolated from the rhizomes of Anemarrhena asphodeloides Bge. On the basis of chemical and spectroscopic evidence, the structure of timosaponin F was elucidated as (5beta, 25 S):-spirostan-3beta,15alpha,23alpha-triol-3-O-beta- glucopyranosyl-(1--->2)-beta-galactopyranoside. The six known compounds were anemarrhenasaponin I, anemarrhenasaponin Ia, timosaponin BI, timosaponin BII, timosaponin B, timosaponin AIII; their effects on superoxide generation are also reported.

Drugs, Chinese Herbal↗

PubMed2002

Tuberoside M, a new cytotoxic spirostanol saponin from the seeds of Allium tuberosum.

Tuberoside M (1), isolated from the seeds of Allium tuberosum, shows a significant inhibitory effect on the growth of the human promyelocytic leukemia cell line (HL-60) with IC50 value of 6.8 microg/ml. On the basis of spectral data and chemical reaction, its structure was established as (25S)-5beta-spirostane-1beta,3beta-diol 3-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranoside.

Allium↗

PubMed2002

Asparosides A and B, two new steroidal saponins from Asparagus meioclados.

Asparosides A (1) and B (2), two new saponins, were isolated from the roots of Asparagus meioclados. On the basis of chemical and spectroscopic evidence, their structures were elucidated as 23-O-alpha-arabinopyranosyl-(5beta,25s)-spirostan-3beta,23alpha-diol-3-O-[beta-D-xylopyranosyl(1-->4)]-beta-D-glucopyranoside and 26-O-beta-glucopyranosyl-5beta-furost-20(22)-ene-3beta,26-diol-3-O-[beta-D-xylopyranosyl(1-->4)]-beta-D-glucopyranoside, respectively.

Asparagus Plant↗

PubMed2004

Furostanol oligoglycosides from Asparagus cochinchinensis.

Three new furostanol oligoglycosides, named aspacochioside A (1), B (2) and C (3), together with the known compound 3-O-[(alpha-L-rhamnopyranosyl-(1 --> 4))(beta-D-glucopyranosyl)]-26-O[beta-D-glucopyranosyl]-(25S)-5beta-spirostane-3beta-ol were isolated from the roots of Asparagus cochinchinensis. Their structures were elucidated by spectroscopic techniques (IR, HR-ESIMS, ESIMS/MS, ID and 2D NMR) and chemical methods as 3-O-[(alpha-L-rhamnopyranosyl-(1 --> 4))(beta-D-glucopyranosyl)]-26-O-[beta-D-glucopyranosyl]-(25S)-5beta-furostane-3beta,22alpha,26-triol (1), 3-O-[(alpha-L-rhamnopyranosyl-(1 --> 4))(beta-D-glucopyranosyl)]-26-O-[beta-D-glucopyranosyl]-22alpha-methoxy-(25S)-5beta-furostane-3beta,26-diol (2), and 3-O-[(alpha-L-rhamnopyranosyl-(1 --> 4))(beta-D-glucopyranosyl)]-26-O-[beta-D-glucopyranosyl]-(25S)-5beta-furost-20(22)-en-3beta,26-diol (3).

Asparagus Plant↗

PubMed2004

A new steroidal saponin from Agave attenuata.

A new steroidal saponin was isolated from the leaves of Agave attenuata. Its structure was established as (3beta,beta,25S)-spirostan-3-yl O-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 2)-O-[beta-D-glucopyranosyl-(1 --> 3)]-beta-D-glucopyranosyl-(1 --> 4)-beta-D-galactopyranoside. The structural identification was performed using detailed analyses of 1H- and 13C-NMR spectra including 2D NMR spectroscopic techniques (COSY, HETCOR, and COLOC) and chemical conversions. The hemolytic activity of the steroidal saponin was evaluated using an in vitro assay.

Agave↗

PubMed2004

Cytotoxicity of the phytosterol diosgenin and its derivatives in rat cultured hepatocytes and V79 fibroblasts.

In this work, the cytotoxic effects of some spirostane derivatives were examined in cultured hepatocytes and V79 fibroblasts using different viability assays. The derivatives were obtained by modifying the A and B rings of diosgenin. Diosgenin and its derivatives were more toxic in V79 fibroblasts (IC50 40-300 microM) than in hepatocytes (IC50 280-1000 microM). Inhibition of cytochrome P450IIIA in cultured hepatocytes by incubation with 1 mM cimetidine did not alter the toxicity of these compounds in these cells. These observations suggest that other pathways of detoxification may be involved in hepatocytes. In conclusion, the compounds studied merit investigation for their potential pharmacological and industrial applicability.

Animals↗

PubMed1999

Steroidal saponins from the bulbs of Allium karataviense.

Chemical examination of the bulbs of Allium karataviense led to the isolation of five new spirostanol saponins (7-11) and a new furostanol saponin (12), together with a known steroidal sapogenin (1) and five known saponins (2-6). The structures of the new saponins were determined by detailed analysis of their spectral data, including two-dimensional NMR spectroscopy. The steroidal saponins produced by A. karataviense, except for 5 and 6, were found to be based upon (25R)-5 alpha-spirostane-2 alpha,3 beta,5,6 beta-tetrol (alliogenin) and contain a beta-D-glucopyranosyl moiety with the formation of an O-glycoside linkage to C-2 of the polyhydroxylated steroidal skeleton as the common structural feature. The isolated compounds were evaluated for cytostatic activity against human promyelocytic leukemia HL-60 cells.

Allium↗

PubMed2003

Steroidal saponins from rhizomes of Tupistra wattii Hook. f.

Chemical examination of the fresh rhizomes of Tupistra wattii HOOK. f. led to the isolation of three new steroidal saponins, wattoside G (1), H (2), and I (3), together with one known steroidal saponin, (25S)-1beta,3beta,4beta-trihydroxyspirotan-5beta-yl-O-beta-D-glucopyranoside (4). The structures of 1-3 were established to be (25R)-1beta,2beta,3beta,5beta-tetrahydroxyspirostan-4beta-yl-O-beta-D-xylopyranoside (1), (24S,25S)-24-[(beta-D-glucopyranosyl)oxy]-1beta,2beta,3beta,4beta,5beta,7beta-hexahydroxyspirostan-6-one (2), and (24S,25S)-1beta,3beta-dihydroxy-5beta-spirostan-24-yl-O-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside (3) on the basis of detailed analyses of physical, chemical, and spectral data. The isolated compounds were evaluated for cytotoxic activity against the cancer cell line K562 in vitro.

Humans↗

PubMedDate not supplied

A new steroidal saponin from AGAVE brittoniana and its biphasic effect on the Na+-ATPase activity.

A new steroidal saponin, 3-{(O-6-deoxy-a-L-mannopyranosyl-(1 --> 4)-O-beta-D-glucopyranosyl-(1 --> 3)-O-[O-beta-D-glucopyranosyl-(1 --> 3)-beta-D-glucopyranosyl-(1 --> 2)]-O-beta-D-glucopyranosyl-(1 --> 4)-beta-D-galactopyranosyl)oxy}-6-hydroxy-(3beta,5alpha,6alpha,25R)-spirostan-12-one, was isolated from Agave brittoniana Trel. The structure was determined by extensive NMR spectroscopy studies and chemical conversions. Its effects on the Na+-ATPase and (Na+ + K+)-ATPase activities of the proximal tubule from pig kidney were evaluated. It was observed that this steroidal saponin exerts a biphasic effect on the Na+-ATPase activity. It is concluded that the effect of the aqueous extract as a diuretic is due, at least in part, to the action of saponin on the ouabain-insensitive Na+-ATPase.

Agave↗

PubMed2002

New steroidal saponins from Agave lophantha Schiede and their pharmacological evaluation.

The structures of one new monodesmosidic spirostanoside and one new bisdesmosidic furanostanol glycoside isolated from leaves of Agave lophantha Schiede have been determined by means of spectroscopic and chemical methods as (25R)-5 beta-spirostan-3 beta-ol-3-O-(beta-D-apiofuranosyl(1-->4)beta-D -glucopyranosyl(1-->3)[beta-D-glucopyranosyl(1-->2)]beta-D -galactopyranoside) and 26-O-beta-D-glucopyranosyl(25R)-5 beta-furost-20(22)-ene-3 beta, 26-diol-3-O-(beta-D-xylopyranosyl(1-->3)-[beta-D-glucopyranosyl(1--2)] beta-D-galactopyranoside), respectively. The 1H and 13C NMR resonances of the two compounds were assigned by NMR (1H, 13C, HOHAHA, 1H-1H COSY, HMQC, HMBC, NOE difference) studies. The pharmacological activities of the saponin containing fraction are discussed.

Agave↗

PubMed2005

Methodology for multi-site ligand-protein docking identification developed for the optimization of spirostenol inhibition of beta-amyloid-induced neurotoxicity.

Spirostenol steroids have been found to inhibit beta-amyloid-induced neurotoxicity. We have evaluated in parallel experimental and molecular-modeling studies the relative effectiveness of 17 (22R)-hydroxycholesterol derivatives in binding to the target peptide. Our results support the previous evidence that beta-amyloid offers multiple docking sites for these steroids. Molecular modeling allowed for the correlation of spirostenol candidate structural differences with a choice of proposed active sites. A multi-site identification technique based on a Site-Identifier Matrix (SIM) was developed that clearly showed the uniqueness of our lead (maximum neurotoxicity inhibition) candidate SP233, with a nearly equal docking affinity for two sites.

Amyloid beta-Peptides↗