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PubMed1999

Steroidal saponins from Asparagus africanus.

The structures of two new monodesmosidic spirostanosides and a new bisdesmosidic furostanol glycoside isolated from the roots of Asparagus africanus Lam. (Liliaceae) have been elucidated as (25R)-3 beta-hydroxy-5 beta-spirostan-12-one 3-O-{beta-D-glucopyranosyl-(1-->2)-[alpha-1-arabinopyranosyl-(1--> 6)]-beta- D-glucopyranoside} (1), (25R)-5 beta-spirostan-3 beta-ol 3-O-{beta-D-glucopyranosyl-(1-->2)-[alpha-L-arabinopyranosyl-(1--> 6)]-beta- D-glucopyranoside} (2) and 26-O-beta-D-glucopyranosyl]-22 alpha-methoxy-(25R)-furostan-3 beta,26-diol 3-O-{beta-D-glucopyranosyl-(1-->2)-[beta-D-glucopyranoside} (3), respectively, by the combined use of one and two dimensional NMR experiments. The complete 13C and 1H assignments of the peracetyl spirostanosides and the furostanol oligoside were derived. The interconversions between the methoxyl and hydroxyl group at C-22 of the furostanol glycoside was investigated and the genuine furostanol oligoside of A. africanus appears to be the hydroxyl type based on the comparative study of the methanol, pyridine and dioxane extracts.

Carbohydrate Conformation↗
PubMed1978

A quantitative gas-liquid chromatographic method for the estimation of hecogenin and tigogenin in the leaves, juice and sapogenin concentrates of Agave sisalana.

A gas-liquid chromatographic method has been devised for the routine estimation of the hecogenin [3beta-hydroxy-(25R)-5beta-spirostan-12-one] and tigogenin [ (25R)-5beta-spirostan-3beta-ol] contents of Agave sisalana leaf and juice samples and of the crude sapogenin concentrates known as "coffee grounds". Because of partial degradation of the sapogenins in the GLC system it was found necessary to acetylate the compounds prior to their estimation. In East African samples the tigogenin proportion of the total sapogenin content is usually about 10%. At this level, the 95% inverse tolerance limits on predicted tigogenin weights are approximately +/- 7%.

Chromatography, Gas↗
PubMed2002

Five new steroidal saponins from Solanum chrysotrichum leaves and their antimycotic activity.

Using bioactivity-directed isolation procedures, five new spirostan saponins and two sterol glycosides have been isolated from Solanum chrysotrichum leaves. The structure of these compounds was established based upon spectroscopic measurements, especially 1D and 2D NMR data of their peracetate derivatives. These compounds showed antimycotic activity. The most active compound is 6alpha-O-beta-d-xylopyranosyl-(1-->3)-beta-d-quinovopyranosyl-(25R)-5alpha-spirostan-3beta,23alpha-ol (2) (MIC =12.5, 12.5, 100, and 200 microg/mL against Trichophyton mentagrophytes, T. rubrum, Aspergillis niger, and Candida albicans, respectively).

Acetylation↗
PubMed2004

Antimycotic spirostanol saponins from Solanum hispidum leaves and their structure-activity relationships.

A new spirostanol saponin, together with three known saponins, were isolated from the leaves of Solanum hispidum. The structure of the new saponin was elucidated as 6alpha-O-beta-D-quinovopyranosyl-(25S)-5alpha-spirostan-3beta-ol (1) on the basis of spectroscopic analysis (1H NMR, 13C NMR, 1H-1H COSY, HMQC, HMBC, and HRFABMS). All of the isolated compounds showed antimycotic activity. The most active compound was 6alpha-O-[beta-D-xylopyranosyl-(1-->3)-beta-D-quinovopyranosyl]-(25S)-5alpha-spirostan-3beta-ol (2) (MIC = 25 microg/mL against both Trichophyton mentagrophytes and T. rubrum). The structure-activity relationships of the isolated compounds and those isolated from S. chrysotrichum are discussed.

Antifungal Agents↗
PubMed2005

Cytotoxic steroidal saponins from the rhizomes of Asparagus oligoclonos.

Two new steroidal saponins, aspaoligonins A (2) and B (3), were isolated from the methanolic extract of the rhizomes of Asparagus oligoclonos together with a known spirostanol saponin, asparanin A (1). Aspaoligonins A and B were characterized as (25S*)-5beta-spirostan-3beta,17alpha-diol 3-O-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranoside and (25S*)-5beta-spirostan-3beta,17alpha-diol 3-O-alpha-L-rhamnopyanosyl (1-->4)-[beta-D-xylopyranosyl-(1-->2)]-beta-D-glucopyranoside, respectively, by spectrometric analyses including HRFABMS and 2D NMR. Compounds 1-3 were cytotoxic against five human tumor cell lines with IC50 values of 2.05-2.84 microg/mL.

Antineoplastic Agents, Phytogenic↗
PubMed1993

A screen for inhibitors of DNA recombination: identification of two new spirostanol glycosides from Chamaedorea linearis.

Two new glycosides have been isolated from the MeOH extract of the stem wood and stem bark of an Ecuadorian plant Chamaedorea linearis, and their structures have been determined by spectroscopic means and X-ray analysis of the aglycone to be 1-O-[beta-L-fucopyranosyl-(4'-sulfate)]-25R,5 alpha-spirostane-1 beta, 3 beta-diol [1]) and 1-O-[beta-L-fucopyranosyl-(4'-sulfate)]-25R,5 alpha-spirostane-1 alpha, 3 beta-diol [2]. These compounds were identified in a screen for inhibitors of recombinational DNA repair. Cytotoxic activity was also demonstrated.

Animals↗
PubMed1999

Two new spirostanol saponins from Allium tuberosum.

Two new spirostanol saponins, tuberosides D and E, have been isolated from the seeds of Allium tuberosum. On the basis of spectral data and chemical reactions, their structures were established as (25S)-5alpha-spirostane-2alpha,3beta-diol 3-O-alpha-L-rhamnopyranosyl-(1-->2)-O-[alpha-L-rhamnopyranosyl-(1-->4 )]-O-beta-D-glucopyranoside and (25S)-5alpha-spirostan-2alpha, 3beta-diol 3-O-beta-D-glucopyranosyl-(1-->2)-O-[alpha-L-rhamnopyranosyl-(1-->4)] -O-beta-D-glucopyranoside, respectively.

Allium↗
PubMed1991

Structures of two new steroidal glycosides, soladulcosides A and B from Solanum dulcamara.

The structures of two new steroidal glycosides named soladulcosides A and B, isolated from the aerial parts of Solanum dulcamara including new sapogenols, were elucidated as (22R, 25R)-3 beta, 15 alpha, 23 alpha-trihydroxy-5 alpha-spirostan-26-one 3-O-alpha-L-rhamnopyranosyl-(1----2)-beta-D-glucopyranoside and (22R, 25R)-3 beta,23 alpha-dihydroxy-5 alpha-spirostan-26-one 3-O-alpha-L-rhamnopyranosyl-(1----2)-[alpha-L-rhamnopyranosyl-(1----4)]- beta-D-glucopyranoside, respectively.

Glycosides↗
PubMed2000

Steroidal oligoglycosides from Solanum nigrum.

Two new steroidal saponins, named nigrumnins I and II, together with two known saponins were obtained from the whole plant of Solanum nigrum L. On the basis of spectroscopic analysis (1H-NMR, 13C-NMR, 1H-1H COSY, TOCSY, HMQC, HMBC and FAB-MS), nigrumnin I was established as (25R)-5alpha-spirostan-3beta-ol 3-O-betaD-xylopyranosyl-(1-->3)-[alpha-L-arabinopyranosyl-(1 -->2)]-beta-D- glucopyranosyl-(1-->4)-[alpha-L-rhamnopyranosyl(1-->2)]-beta-D- galactopyranoside (1), and nigrumnin II was elucidated as (25R)-3beta,17alpha-dihydroxy-5alpha-spirostan-1 2-one 3-O-beta-D-xylopyranosyl-(1-->3)-[alpha-L-arabinopyranosyl-(1--> 2)]-beta-D-glucopyranosyl-(1-->4)-[alpha-L-rhamnopyra- nosyl-(1-->2)l-beta-D-galactopyranoside (2).

Carbohydrate Sequence↗
PubMed2001

Two steroidal saponins from Camassia cusickii induce L1210 cell death through the apoptotic mechanism.

Two steroidal saponins, tigogenin hexasaccharide-1 (TGHS-1, (25R)-5alpha-spirostan-3beta-yl 4-O-[2-0-[3-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl]-3-0-[4-0- (alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl]-beta-D-glucopyranosyl]-3-D- galactopyranoside) and tigogenin hexasaccharide-2 (TGHS-2, (25R)-5alpha-spirostan-3beta-yl 4-O-[2-0-[3-0-(beta-D-glucopyranosyl)-beta-D-glucopyranosyl]-3-0-[4-0- (alpha-L-rhamnopyranosyl)-beta-D-glucopyranosyl]-beta-D-glucopyranosyl]beta-D-galactopyranoside), were isolated from the fresh bulbs of Camassia cusickii. In murine leukemic L1210 cells, both compounds showed cytotoxicity with an EC50 value of 0.06 microM. The morphological observation revealed that TGHS-1 and TGHS-2 induced shrinkage in cell soma and chromatin condensation, suggesting apoptotic cell death. The cell death was confirmed to be apoptosis by Annexin V binding to phosphatidylserine in the cell membrane and excluding propidium iodide. A typical apoptotic DNA ladder and the cleavage of caspase-3 were observed after treatment with TGHS-1 and TGHS-2. In the presence of both the compounds, cells with sub-G1 DNA content were detected by flow cytometric analysis, indicating that TGHS-1 and TGHS-2 (each EC50 value of 0.1 microM) are the most powerful apoptotic saponins known. These results suggest that TGHS-1 and TGHS-2 induce apoptotic cell death through caspase-3 activation.

Animals↗
PubMed1995

A plant steroid, diosgenin, a new megakaryocytic differentiation inducer of HEL cells.

We investigated the effect of plant steroids 5 alpha-spirosten-3 beta-ol (diosgenin), 5 alpha-spirostan-3 beta-ol (tigogenin) and 5 alpha-spirostan-3 beta-ol-12-one (hecogenin) on the human erythroleukemia cell line (HEL TIB 180) and found that diosgenin addition to HEL cell cultures induces morphological and biochemical changes characteristic for megakaryocyte cells. Diosgenin-treated cells exhibit, at the ultrastructural level, increases in size in cytoplasmic and nuclear complexity. At the biochemical level, we demonstrated that diosgenin-treated HEL cells increased glycoprotein Ib (GpIb) expression as previously described in the megakaryocytic differentiation of HEL cells induced by nanomolar dose phorbol myristate acetate treatment.

Cell Differentiation↗
PubMed1996

A chemical study on the steroidal glycosides from Atropa belladonna L. seeds.

Eight steroidal glycosides of the spirostane type tentatively named atroposides A, B, C, D, E, F, G, and H (according to their increase in polarity) have been isolated from the methanolic extract of Atropa belladonna L. seeds by Sephadex gel filtration and column chromatography on silica gel impregnated with AgNO3. The structure of atroposides A, C, E, G has been elucidated as 3-O-alpha-D-galactopyranoside; 3-O-beta-D-glucopyranosyl(1-->4)-beta-D-galactopyranoside; 3-O-beta-D-glucopyranosyl (1-->2) -beta-D-glucopyranosyl(1-->4)-beta-D-galactopyranoside; and 3-O-alpha-L-rhamnopyranosyl (1-->4)-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside, each of (25R)-5 alpha-spirostane-3 beta-ol, respectively. The structure of atroposides B, D, F, and H has been elucidated as 3-O-beta-D-galactopyranoside; 3-O-beta-D-glucopyranosyl (1-->4)beta-D-galactopyranoside; 3-O-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside; 3-O-alpha-L-rhamnopyranosyl (1-->4)-B-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->4)-beta-D-galactopyranoside, each of (25R)-spirost-5-en-3-b-0l, respectively.

Atropa belladonna↗
PubMed1992

Steroidal glycosides from the bulbs of Lilium dauricum.

The bulbs of Lilium dauricum yielded 11 compounds, including six new steroidal glycosides. The structures have been determined by spectral analysis and hydrolysis to be (25R,26R)-26-methoxyspirost-5-en-3 beta-ol 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[alpha-L-arabinopyranosyl-( 1----3)]- beta-D-glucopyranoside, (25R,26R)-26-methoxyspirost-5-en-3 beta-ol 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[beta-D-glucopyranosyl-(1----4)]- beta-D-glucopyranoside, (25R)-spirost-5-en-3 beta-ol (diosgenin) 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[alpha-L-arabinopyranosyl- (1----3)]-beta-D-glucopyranoside, (25R)-3 beta,17 alpha-dihydroxy-5 alpha-spirostan-6-one 3-O-alpha-L-rhamnopyranosyl-(1----2)-beta-D-glucopyranoside, (25R)-3 beta, 17 alpha-dihydroxy-5 alpha-spirostan-6-one 3-O-alpha-L-rhamnopyranosyl-(1----2)-O-[alpha-L- arabinopyranosyl-(1----3)]-beta-D-glucopyranoside and (20R,22R)-3 beta,20,22-trihydroxy-5 alpha-cholestan-6-one (tenuifoliol) 3-O-alpha-L-rhamnopyranosyl-(1----2)-beta-D-glucopyranoside. The absolute configurations of C-20 and C-22 of tenuifoliol were further confirmed by detailed analysis of the NOE difference spectrum of the corresponding isopropylidene derivative. Several known compounds were also isolated and identified.

Carbohydrate Sequence↗
PubMed1992

Steroidal saponins from Smilax lebrunii.

Two new steroidal saponins, (25 R)-spirostan-3 beta-ol-6-one-3-O-[alpha-L-arabinopyranosyl (1----6)]-beta-D-glucopyranoside and (25 R)-spirostan-3 beta-ol-6-one-3-O-[beta-D-glucopyranosyl(1---4)] [alpha-L-arabinopyranosyl(1----6)]-beta-glucopyranoside, were isolated from the rhizomes of Smilax lebrunii. Their structures have been established by chemical and spectral methods.

Carbohydrate Sequence↗
PubMed1993

Steroidal glycosides from Allium albopilosum and A. ostrowskianum.

Chemical studies of the bulbs of Allium albopilosum and A. ostrowskianum have led to the isolation of two new steroidal saponins and four new cholestane glycosides together with several known compounds. The structures of the new compounds were established by the spectroscopic data, hydrolysis and chemical correlations as (25 R and S)-5 alpha-spirostane-2 alpha,3 beta,6 beta-triol 3-O-(O-beta-D-glucopyranosyl-(1-->2)-O-[3-O-acetyl-beta-D-xylopyranosyl- (1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside), (25R)-2-O-[(S)-3-hydroxy-3-methylglutaroyl]-5 alpha-spirostane-2 alpha, 3 beta, 6 beta-triol 3-O-(O-beta-D-glucopyranosyl-(1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O- beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside), (22S)-cholest-5-ene-1 beta,3 beta,16 beta,22-tetraol 1-O-alpha-L-rhamnopyranoside 16-O-(O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-glucopyranoside), 1 beta,3 beta,16 beta-trihydroxycholest-5-en-22-one 1-O-alpha-L-rhamnopyranoside 16-O-(O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-glucopyranoside), 1 beta,3 beta,16 beta-trihydroxy-5 alpha-cholestan-22-one 1-O-alpha-L-rhamnopyranoside 16-O-(O-alpha-L-rhamnopyranosyl-(1-->3)-beta-D-glucopyranoside) and (22S)-cholest-5-ene-1 beta,3 beta,16 beta,22-tetraol 16-O-(O-beta-D-glucopyranosyl-(1-->3)-beta-D-glucopyranoside).

Allium↗
PubMed1995

Steroidal saponins from the tubers of Dichelostemma multiflorum and their inhibitory activity on cyclic-AMP phosphodiesterase.

Phytochemical examination of the tubers of Dichelostemma multiflorum led to the isolation of three new steroidal saponins together with two known saponins. The structures of the new compounds were determined by spectral data and a few chemical transformations to be (25R)-5 alpha-spirostane- 1 beta,3 beta-diol (brisbagenin) 1-O-[O-alpha-L-rhamnopyranosyl-(1-->3)-4-O- acetyl-alpha-L-arabinopyranoside], brisgabenin 1-O-[O-alpha-L-rhamnopyranosyl-(1-->2)-O- [alpha-L-rhamnopyranosyl-(1-->3)]-4-O-acetyl-alpha-L-arabinopyranosid e] and (22S,25S)-5 alpha-spirostan-3 beta-o1 3-O-[O-beta-D-galactopyranosyl- (1-->2)-O-[beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4) -beta-D-galactopyranoside]. The known compounds were identified as desglucolanatigonin II and gitonin, with certain amounts of the corresponding C-25S isomers. Inhibitory activity of the isolated saponins and their derivatives on cAMP phosphodiesterase was evaluated to identify new compounds with medicinal potential.

3',5'-Cyclic-AMP Phosphodiesterases↗
PubMed1995

Steroidal saponins from Allium chinense and their inhibitory activities on cyclic AMP phosphodiesterase and Na+/K+ ATPase.

The saponin fraction prepared from the methanolic extract of Allium chinense bulbs exhibited inhibitory activities on cyclic AMP phosphodiesterase (cAMP PDE) (43.5%) and Na+/K+ ATPase (59.3%) at a sample concentration of 100 micrograms ml-1, respectively. Attempted purification of the active fraction through column chromatography on silica gel and ODS silica gel resulted in the isolation of six steroidal saponins, one of which appeared to be a new compound and one to be the first isolation from a natural source. (25R,S)-5 alpha-Spirostan-3 beta-ol tetrasaccharide showed inhibitory activities on both cAMP PDE and Na+/K+ ATPase, while (25R)-3 beta-hydroxy-5 alpha-spirostan-6-one di- and tri-saccharides inhibited only cAMP PDE.

3',5'-Cyclic-AMP Phosphodiesterases↗
PubMed1996

Steroidal saponins from the underground parts of Chlorophytum comosum and their inhibitory activity on tumour promoter-induced phospholipids metabolism of HeLa cells.

Three new spirostanol pentaglycosides embracing beta-D-apiofuranose were isolated from the fresh underground parts of Chlorophytum comosum together with four known saponins. The structures of new compounds were determined by spectroscopic data, including two-dimensional NMR, and partial acid-catalysed hydrolysis to be (25R)-5 alpha-spirostane-2 alpha,3 beta-diol 3-O-[O-beta-D-glucopyranosyl- (1-->2)-O-[O-beta-D-apiofuranosyl-(1-->4)-beta-D-glucopyranosyl-(1 -->3)]-O- beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranoside], (25R)-3 beta-hydroxy-5 alpha-spirostan-12-one (hecogenin) 3-O-[O-beta-D-glucopyranosyl-(1-->2)-O-[O-beta-D-apiofuranosyl-(1- ->4)- beta-D-xylopyranosyl-(1-->3)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D- galactopyranoside] and hecogenin 3-O-[O-beta-D-glucopyranosyl-(1-->2)-O-[O-beta-D- apiofuranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->3)]-O-beta-D-gluc opyranosyl- (1-->4)-beta-D-galactopyranoside], respectively. The isolated saponins were examined for inhibitory activity using 12-O-tetradecanoylphorbor-13-acetate-stimulated 32P-incorporation into phospholipids of HeLa cells as the primary screening test to identify new antitumour-promoter compounds.

Anticarcinogenic Agents↗