Steroidal Alkaloid Glycosides Research Articles

Steroidal alkaloid glycosides from tomato (Lycopersicon esculentum).

Three new steroidal alkaloid glycosides, lycoperosides F-H (1-3), were isolated from tomato fruits (Lycopersicon sculentum) along with lycoperosides A-D, esculeoside A, and rutin. The structures of these glycosides were characterized as the 3-O-beta-lycotetraosides of 23(R)-23-acetoxy-27-hydroxy-27-O-beta-d-glucopyranosyltomatidine (1), (23S,24R)-23-acetoxy-24-O-beta-d-glucopyranosylsoladulcidine-24-ol (2), and 22-isopimpifolidine (3), by means of their spectroscopic data. Also obtained was the new natural product lycoperodine-1 (4).

Cytotoxic Major Saponin from Tomato Fruits.

AbstractFor Abstract see ChemInform Abstract in Full Text.

Cytotoxic major saponin from tomato fruits.

A major novel steroidal alkaloid glycoside, possessing cytotoxic activity has been isolated from the fruits of Lycopersicon esculentum.

<b>A novel glycosidic steroidal alkaloid from <i>Solanum aculeastrum</i></b>

The root bark of Solanum aculeastrum Dunal yielded a new steroidal alkaloid glycoside characterised as (25R)-3b-{O-a-L-rhamnopyranosyl-(1®2)-[O-b-D-glucopyranosyl-(1®4)-O-a-L-rhamnopyranosyl-(1®4)]-b-D-glucopyranosyl}-22a-N-spirosol-5-ene. The structure was established by spectroscopic analysis and comparison with published data of similar compounds reported in literature. KEY WORDS: Solanum aculeastrum Dunal, (25R)-3b-{O-a-L-Rhamnopyranosyl-(1®2)-[O-b-Dglucopyranosyl-(1®4)-O-a-L-rhamnopyranosyl-(1®4)]-b-D-glucopyranosyl}-22a-N-spirosol-5-ene Bull. Chem. Soc. Ethiop. 2003, 17(1), 61-66.

Anticancer activity evaluation of the Solanum glycoalkaloid solamargine : Triggering apoptosis in human hepatoma cells

Solamargine, an herbal and molluscicidal medicine derived from Solanum incanum, is a steroidal alkaloid glycoside. To characterize the anticancer mechanism of solamargine on human hepatoma cells (Hep3B), changes of cell morphology, DNA content, and gene expression of cells after solamargine treatment were studied. The appearance in solamargine-treated cells of chromatin condensation, DNA fragmentation, and a sub-G 1 peak in a DNA histogram suggests that solamargine induces cell death by apoptosis. The maximum number of dead Hep3B cells was detected within 2 hr of incubation with constant concentrations of solamargine, and no further cell death was observed after an extended incubation with solamargine, indicating that the action of solamargine was irreversible. To determine the susceptibility of cell phases to solamargine-mediated apoptosis, Hep3B cells were synchronized at defined cell cycles by cyclosporin A, colchicine, and genistein, followed by solamargine treatment. The ic 50 values of solamargine for control, G 0/G 1-, M-, and G 2/M-synchronized Hep3B cells were 5.0, > 10, 3.7, and 3.1 μg/mL, implying that cells in the G 2/M phases are relatively susceptible to solamargine-mediated apoptosis. In addition, a parallel up-regulation of tumor necrosis factor receptor (TNFR)-I and -II on Hep3B cells was detected after solamargine treatment, and the solamargine-mediated cytotoxicity could be neutralized with either TNFR-I or -II specific antibody. Therefore, these results reveal that the actions of TNFR-I and -II on Hep3B cells may be independent, and both are involved in the mechanism of solamargine-mediated apoptosis.

Steroidal alkaloid glycosides from Solanum orbignianum

Aerial parts of Solanum orbignianum afforded a new steroidal alkaloid glycoside, leptinidine 3- O-β- d-glucopyranoside, together with the known alkaloids leptinidine, leptinine I and leptinine II. Their structures were established by spectroscopic methods.

Steroidal alkaloid glycosides from Solanum suaveolens

Four known and three new alkaloids have been isolated. The structures of the latter have been assigned. In addition to khasianine, solamargine, xylosylsolamargine and solasonine, three steroidal alkaloid glycosides, solasuaveoline, dihydrosolasuaveoline and isosolasuaveoline, have been isolated from aerial parts of Solanum suaveolens . The structures have been assigned by NMR investigations as (25 R )-3β-{ O -β- d -glucopyranosyl-(1 → 2)- O -β- d -glucopyranosyl-(1 → 4)-[ O -α- l -rhamnopyranosyl-(1 → 2)]-β- d -galactopyranosyloxy}-22α N -spirosol-5-ene, (25 R )-3β-{ O -β- d -glucopyranosyl-(1 → 2)- O -β- d -glucopyranosyl-(1 → 4)-[ O -α- l -rhamnopyranosyl-(1 → 2)]-β- d -galactopyranosyloxy}-5α,22α N -spirosolane and (25 R )-3β-{ O -β- d -glucopyranosyl-(1 → 6)- O -β- d -glucopyranosyl-(1 → 3)-[ O -α- l -rhamnopyranosyl-(1 → 2)]-β- d -galactopyranosyloxy}-22α N -spirosol-5-ene, respectively.

Steroidal alkaloid glycosides from Solanum suaveolens

In addition to khasianine, solamargine, xylosylsolamargine and solasonine, three steroidal alkaloid glycosides, solasuaveoline, dihydrosolasuaveoline and isosolasuaveoline, have been isolated from aerial parts of Solanum suaveolens. The structures have been assigned by NMR investigations as (25 R)-3β-{ O-β- d-glucopyranosyl-(1 → 2)- O-β- d-glucopyranosyl-(1 → 4)-[ O-α- l-rhamnopyranosyl-(1 → 2)]-β- d-galactopyranosyloxy}-22α N-spirosol-5-ene, (25 R)-3β-{ O-β- d-glucopyranosyl-(1 → 2)- O-β- d-glucopyranosyl-(1 → 4)-[ O-α- l-rhamnopyranosyl-(1 → 2)]-β- d-galactopyranosyloxy}-5α,22α N-spirosolane and (25 R)-3β-{ O-β- d-glucopyranosyl-(1 → 6)- O-β- d-glucopyranosyl-(1 → 3)-[ O-α- l-rhamnopyranosyl-(1 → 2)]-β- d-galactopyranosyloxy}-22α N-spirosol-5-ene, respectively.

A simple determination of steroidal alkaloid glycosides by thin-layer chromatography immunostaining using monoclonal antibody against solamargine

A method of determination for solasodine glycosides by using thin-layer chromatography (TLC) immunostaining was investigated. Solasodine glycosides separated by silica gel TLC were transferred to a polyvinylidene difluoride membrane. The membrane was treated with sodium periodate solution followed by bovine serum albumin (BSA), resulting in a solasodine glycoside-BSA conjugate. Conjugation was confirmed by matrix-assisted laser desorption/ionization mass spectrometry. Individual spots were stained by monoclonal antibody against solamargine. Immunostaining of solasodine glycosides was more sensitive compared to other stainings. The newly established immunostaining method can be extended to analysis of the distribution of solasodine glycoside in the plant body. © 1997 Federation of European Biochemical Societies.

Steroidal alkaloid glycosides from Solanum uporo

In addition to solamargine, anguivine and isoanguivine, two new steroidal alkaloid glycosides, (23 S)-23-hydroxyanguivine and (23 S)-23-hydroxyisoanguivine, have been isolated from roots of Solanum uporo, the structures of which have been assigned by comparison with literature data as (23S,25R)-3β-{O-α- l-rhamnopyranosyl -(1 → 2)-O-[β- d-xylopyranosyl -(1 → 3)]-β- d-glucopyranosyloxy }-22α spirosol-5-en-23-ol and (23S,25R)-3β-{O-α- l-rhamnopyranosyl -(1 a ̊ 2)-O-[β- d-xylopyranosyl -(1 → 3)]-β- d-galactopyranosyloxy } 22αN- spirosol-5-en-23-ol .

Lycoperosides A-C, three stereoisomeric 23-acetoxyspirosolan-3β-ol β-lycotetraosides from Lycopersicon esculentum

Three new steroidal alkaloid glycosides, lycoperosides A-C, were isolated from leaves and fruits of tomato, Lycopersicon esculentum, and structurally elucidated as the 3- O- β-lycotetraosides of (23 R)-23-acetoxy-tomatidine, (23 S)-23-acetoxysoladulcidine and (23 S,25 S)-23-acetoxy-5 α,22 αN-spirosolan-3 β-ol. In addition to these glycosides, leaves and fruits were found to contain the known major alkaloid tomatine (tomatidine 3- O- β-lycotetraoside) and leaves a small amount of γ-tomatine (tomatidine 3-O-[β- d-glucopyranosyl -(1 → 4)-β- d-galactopyranoside ] , lycoperoside D).

Antifilarial Effect of Solamargine Isolated from Solatium khasianum

AbstractAn active principle isolated from the ripe berries of Solarium khasianum is a steroidal alkaloid glycoside, solamargine, which killed in vitro 100% adults and microfilariae (mf) of Setaria cervi at a 4 mg/ml concentration in 60 and 88 min, respectively. The drug, when administered orally at 100 mg/ kg to rats, in which S. cervi adults were implanted intraperitoneally, reduced the blood mf count by more than 30% after the first phase of treatment for 10 days. The mf count showed an increase of 72% after the second phase of treatment. Following the third and the fourth phases of treatments, the mf density was reduced by more than 90%. One hundred percent reduction of mf count was obtained 15 days after the fourth and final phase of treatment which was of 5 days duration. At the evaluated dose (100 mg/kg × 4 phases), solamargine killed 100% of adult worms without incident toxicity.

The Cytotoxic Principles of Solanum incanum

In continuation of work on Solanum incanum a new steroidal alkaloid glycoside has been isolated from the fresh berries, which is named incanumine, and characterized as O(3)-[beta-D-xylopyranosyl-(1----3glu)-[beta-D-xylopyranosyl-(1--- -4rha)- alpha-L-rhamnopyranosyl-(1----4)]-beta-D-glucopyranosyl)-solasodine++ +. Solamargine, solasodine, ursolic acid, and ursolic acid derivatives (3-O-palmitoyl ursolic acid, 3-O-crotonyl ursolic acid, 3-O-propionyl ursolic acid) exhibited significant cytotoxic effects against human PLC/PRF/5 cells in vitro. Esterification of ursolic acid with aliphatic acids clearly enhanced the cytotoxic effects against human PLC/PRF/5 cells in vitro.

Structures of three new steroidal alkaloid glycosides, solaverines I, II and III from Solanum toxicarium and S. verbascifolium.

The structures of three new steroidal alkaloid glycosides named solaverines I, II and III were isolated from the aerial parts of Solanum toxicarium and S. verbascifolium and their structures, including the new sapogenols solaverols A and B, were elucidated

Steroidal alkaloid glycosides from Lilium cordatum

Two new steroidal alkaloid glycosides named cordatine A and B were isolated from the petals of Lilium cordatum. Their structures were elucidated by spectral data as (25R)- and (25S)-22,26-epimino-5α-cholest-22(N)-en-3β,6β-diol O(3)-β-D-glucopyranoside.

Studies on the constituents of Solanum plants. V. The constituents of S. lyratum Thunb. II.

Two new steroidal alkaloid glycosides, tentatively named SL-c (1) and SL-d (2), were obtained from the stems of Solanum lyratum THUNB. The chemical structures of 1 and 2 were characterized respectively as β-lycotrioside and β-lycotetraoside, both having a mixture of (25ζ)-solanidan-3β, 23β-diol and (25ζ)-Δ5-solaniden-3β, 23β-diol as the aglycone moiety. These compounds markedly inhibited the growth of a human cervical cancer cell line, JTC-26.

Havanine—a steroidal alkaloid glycoside from Solanum havanense

A new steroidal alkaloid glycoside named havanine has been isolated from the leaves of Solanum havanense and its structure elucidated by spectral data as (25 S)- O(3)-β- D-glucopyranosyl-16α-acetoxy-22,26-epiminocholesta-5,22( N)-dien-3β-ol.

Constituents of local plants. 8. The steroidal constituents of Solanum torvum S w.

The unripe fruits of Solatium torvum S w. were found to contain one steroidal alkaloid glycoside, solasonine (I), which was characterised through hydrolysis to solasodine. The neutral glycoside fraction afforded, after hydrolysis, one steroid sapogenin identified as chlorogenin (II).