phytosterols and beta-solamarine

A cream formulation containing high concentrations (10%) of a standard mixture of solasodine glycosides (BEC) has been shown to be effective in the treatment of malignant and benign human skin tumours. We now report that a preparation (Curaderm) which contains very low concentrations of BEC (0.005%) is effective in the treatment of keratoses, basal cell carcinomas (BCCs) and squamous cell carcinomas (SCCs) of the skin of humans. In an open study, clinical and histological observations indicated that all lesions (56 keratoses, 39 BCCs and 29 SCCs) treated with Curaderm had regressed. A placebo formulation had no effect on a smaller number of treated lesions. Curaderm had no adverse effect on the liver, kidneys or haematopoietic system.

Topics: Administration, Topical; Carcinoma, Basal Cell; Carcinoma, Squamous Cell; Glycosides; Humans; Keratosis; Pharmaceutical Vehicles; Phytosterols; Precancerous Conditions; Skin Neoplasms; Solanaceous Alkaloids

To investigate the steroidal glycoside constituents of Solanum cumingii.. The compounds were isolated by silica gel, Sephadex LH-20, RP-C18 column and Pre-HPLC chromatography. Their structures were identified by ESI-MS and NMR.. Six known compounds including torvoside K (1), torvoside J (2), torvoside L (3), khasianine (4), aculeatiside A (5) and solamargine (6) were isolated from Solanum cumingii.. All compounds are isolated from Solanum cumingii for the first time.

Topics: Chromatography, High Pressure Liquid; Glycosides; Magnetic Resonance Spectroscopy; Phytosterols; Solanaceous Alkaloids; Solanum; Spirostans

A new high-performance thin-layer chromatographic (HPTLC) method has been developed for the simultaneous quantitation of three bioactive steroidal glycoalkaloid (SGA) markers, solasonine (SN), solamargine (SM) and khasianine (KN) in the plant Solanum xanthocarpum. Extraction efficiency of targeted SGAs from plant matrix using methanol and acidified methanol were studied using percolation, ultrasonication and microwave techniques. The separation was achieved on silica gel 60F(254) TLC plates using chloroform-methanol-water as mobile phase. The quantitation of SGAs was carried out using the densitometric reflection/absorption mode at 520 nm after post chromatographic derivatization using Dragendorff's reagent. The method was validated for peak purity, precision, accuracy, robustness, limit of detection (LOD) and quantitation (LOQ). Method specificity was confirmed using retention factor (R(f)), Vis spectral correlation and electrospray ionization mass spectra (ESI-MS) of marker compounds in the sample track.

Topics: Chromatography, Thin Layer; Densitometry; Mass Spectrometry; Phytosterols; Plant Components, Aerial; Plant Extracts; Reproducibility of Results; Sensitivity and Specificity; Solanaceous Alkaloids; Solanum; Steroids

A new method for simultaneous determination of solasonine (1), solamargine (2) and khasianine (3) in Solanum Nigrum by reversed-phase HPLC was developed.. The samples were separated at 30 degrees C on Agilent Zorbax SB C18 (4.6 mm x 150 mm, 5 microm) column with acetonitrile-water-phosphoric as mobile phase. Flow rate was 1.0 mL x min(-1) and the detection wavelength was 205 nm.. There was good linearity between the peak area and concentration at the ranges of 0.860-10.320 microg (r = 0.999 7), 0.726-8.710 microg (r = 0.999 7), 0.856-10.270 microg (r = 0.999 7) for 1, 2 and 3 respectively. The average recoveries of 1, 2 and 3 were 101.04%, 99.65%, 100.17%.. The method is rapid, simple and accurate, and it can be used for the evaluation of Solanum Nigrum L.

Topics: Alkaloids; Chromatography, High Pressure Liquid; Phytosterols; Solanaceous Alkaloids; Solanum nigrum

Solasodine glycosides were analyzed for the selection of higher-producing natural resources in the fruits of Solanum spp. by western blotting and ELISA using anti-solamargine monoclonal antibody (MAb). Western blotting of Solanum khasianum showed a correlation with the analysis by ELISA. The results indicated that the fruits of S. khasianum contained the highest level of solasodine glycosides, compared to other species having 53.43 +/- 3.90 microg/mg dry wt. The high level of solasodine glycosides in S. khasianum suggests that it may be suitable for commercial production.

Topics: Antibodies, Monoclonal; Blotting, Western; Calibration; Carbohydrate Sequence; Cross Reactions; Enzyme-Linked Immunosorbent Assay; Fruit; Glycosides; Humans; Molecular Sequence Data; Phytosterols; Solanaceae; Solanaceous Alkaloids

Solamargine, solasodine and khasianine steroidal alkaloids are utilized to determine the role of carbohydrate moiety in the mechanism of apoptosis. The C3 side chain of solamargine, khasianine and solasodine contains 4'Rha-Glc-Rha2', 4'Rha-Glc and H, respectively. Solamargine possessed potent cytotoxicity to human hepatoma cells, while the cytotoxicity of khasianine was greatly diminished. Nevertheless, only solamargine could induced "sub-G1" of apoptotic feature in flowcytometry. Thus, the 2'Rha moiety of solamargine may play a crucial role in triggering cell death by apoptosis. In addition, the molecular modeling of solamargine indicated that the 2'Rha moiety was adjacent to the rigid steroid structure, and drastically changed the dihedral angle of the glycosidic bond. The regulations of TNFR I and II expression by different carbohydrate moieties were also distinct. It implied that the carbohydrate moieties of steroidal alkaloids might alter the binding specificity to steroid receptors and consequently regulate the gene expression in different manners.

Topics: Antigens, CD; Apoptosis; Carcinoma, Hepatocellular; Dose-Response Relationship, Drug; Gene Expression Regulation, Neoplastic; Humans; Liver Neoplasms; Molecular Conformation; Phytosterols; Receptors, Tumor Necrosis Factor; Receptors, Tumor Necrosis Factor, Type I; Receptors, Tumor Necrosis Factor, Type II; Rhamnose; Solanaceous Alkaloids; Structure-Activity Relationship; Tumor Cells, Cultured

As part of an effort to improve the safety of plant foods, a need exists to define the relative toxicities of structurally different glycoalkaloids and metabolites which may be present in Solanum plant species such as potatoes, tomatoes and eggplants. The objectives of this study were to determine the relative toxicities and the modes of action of the eggplant (Solanum melongena) glycoalkaloids solamargine and solasonine in Xenopus laevis frog embryos, using membrane potential and embryo growth and teratogenicity assays. In the cell membrane assays, adverse effects on embryos were evaluated by measuring membrane potentials using an electrochromic dye, di-4-ANEPPS, as a fluorescence probe for the integrity of the membranes. In the embryo growth and teratogenesis assays, the survival of the embryos and organ malformations was used as an index of embryo toxicity. The relative potencies of glycoalkaloids are similar for frog embryo effects (survival and teratogenicities) and for membrane effects (membrane potential). Experiments with solasonine at pH 6 and 8 suggest that the unprotonated form of the glycoalkaloids appears to be involved in the membrane effects. The nature of the carbohydrate side-chains of the steroidal glycosides governs relative potencies. The possible significance of the findings to food safety and plant physiology and possible application of the membrane assays to bacterial toxins are discussed.

Topics: Animals; Antifungal Agents; Cell Membrane; Dose-Response Relationship, Drug; Embryo, Nonmammalian; Lethal Dose 50; Phytosterols; Plant Extracts; Plant Growth Regulators; Solanaceae; Solanaceous Alkaloids; Survival Rate; Xenopus laevis

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.

Topics: Antibodies, Monoclonal; Carbohydrate Sequence; Chromatography, Thin Layer; Glycosides; Humans; Immunoblotting; Molecular Sequence Data; Molecular Structure; Phytosterols; Serum Albumin; Serum Albumin, Bovine; Solanaceous Alkaloids

Solamargine possessed a potent cytotoxicity to human hepatocyte (Hep3B) and normal skin fibroblast. The inhibition curves of solamargine to the both cells were essentially overlapped, suggesting a parallel effect for the cell death. To define mechanism of cytotoxicity of solamargine, the changes of morphology and DNA content in cells were studied. A sub-G1 cell stage was drastically increased after 3-h incubation with solamargine. The results evidence that solamargine arises cell death by apoptosis. In addition, the gene expression of TNFR I were up-regulated within 30 min of solamargine treatment. Since TNF Receptor I has been involved in apoptosis, the overexpression of TNF receptor I may be related with the mechanism of cytotoxicity of solamargine. This communication is the first report that a component of Chinese herbs triggers gene expression of human TNFR I which may lead to cell apoptosis.

Topics: Antigens, CD; Apoptosis; Carcinoma, Hepatocellular; Cells, Cultured; Drugs, Chinese Herbal; Fibroblasts; Gene Expression; Humans; Phytosterols; Plants, Medicinal; Receptors, Tumor Necrosis Factor; Receptors, Tumor Necrosis Factor, Type I; Skin; Solanaceous Alkaloids

Inhibition of mycelium development in Phoma medicaginis and Rhizoctonia solani by solamargine and solasonine generally increased with increasing pH. P. medicaginis was the more susceptible species and solamargine the more potent compound. Solasonine was inactive against R. solani over the tested pH range (5-8). Dose-response curves confirmed these differential effects. Solamargine caused 50% growth inhibition in P. medicaginis at 60 microM (at pH 7) whereas no other treatment achieved this effect at 100 microM. Combinations of 50 microM of each glycoalkaloid produced synergistic effects against both fungi, especially R. solani which was essentially unaffected by either compound, by significantly inhibited by a 1:1 mixture of the two. The magnitude of the synergism was not affected by a pH change between 6 and 7. Spore germination in Alternaria brassicicola was markedly inhibited by 100 microM solamargine but unaffected by 100 microM solasonine or either compound at 50 microM. In P. medicaginis, neither glycoalkaloid was inhibitory up to 150 microM. In combination, the two compounds caused synergistic effects in both species, but to a much greater extent in A. brassicicola.

Topics: Alternaria; Antifungal Agents; Drug Interactions; Hydrogen-Ion Concentration; Mitosporic Fungi; Molecular Structure; Phytosterols; Rhizoctonia; Solanaceous Alkaloids

A strain of Aspergillus ochraceus, a microorganism classically used for bioconversions of the steroid nucleus, was tested on solasodine glucosides. It induced specific modifications to the oside chain of the solamargine molecule, without modifying the genin nucleus. These modifications depended on the composition of the culture medium and the aeration, and led under certain conditions to a single isomer of the secondary glucoside beta 2-solamargine or Khasianine: o-alpha-L-rhamnopyranosyl-(1-->4 glu)-O-(3)-beta-D-glucopyranosyl solasodine.

Topics: Aspergillus ochraceus; Fermentation; Phytosterols; Solanaceous Alkaloids

Using a bioassay for inhibition of plant growth and a combination of two countercurrent chromatographies: rotation locular countercurrent chromatography and droplet countercurrent chromatography, two biologically active glycosidal alkaloids, solasonine and solamargine were isolated from fresh ripe fruit of Solanum incanum. The combination of these chromatographic techniques has established an efficient isolation of polar phytochemicals of steroidal glycoalkaloids.

Topics: Carbohydrate Sequence; Molecular Sequence Data; Molecular Structure; Phytosterols; Plant Growth Regulators; Plants; Solanaceous Alkaloids