ABSTRACT
The present study has found that dried potato samples yielded significantly higher levels of steroidal alkaloids such as α-solanine and α-chaconine than the corresponding fresh samples, as determined by the UPLC-MS/MS technique. Among the drying techniques used, air drying had the highest effect on steroidal alkaloid contents, followed by freeze drying and vacuum oven drying. There was no significant difference between the freeze dried and vacuum oven dried samples in their α-chaconine contents. However, freeze dried potato shoots and berries had significantly higher α-solanine contents (825 µg/g dry weight (DW) in shoots and 2453 µg/g DW in berries) than the vacuum oven dried ones (325 µg/g dry weight (DW) in shoots and 2080 µg/g DW in berries). The kinetics of steroidal alkaloid contents of potato shoots during air drying were monitored over a period of 21 days. Both α-solanine and α-chaconine content increased to their maximum values, 875 µg/g DW and 3385 µg/g DW, respectively, after 7 days of drying. The steroidal alkaloid contents of the shoots decreased significantly at day 9, and then remained unchanged until day 21. In line with the potato shoots, air dried potato tuber peels also had higher steroidal alkaloid content than the freeze dried and vacuum oven dried samples. However, a significant decrease of steroidal alkaloid content was observed in air dried potato berries, possibly due to degradation during slicing of the whole berries prior to air drying. Remarkable variation in steroidal alkaloid contents among different tissue types of potato plants was observed with the potato flowers having the highest content.
Subject(s)
Alkaloids/isolation & purification , Phytosterols/isolation & purification , Solanine/analogs & derivatives , Alkaloids/chemistry , Chromatography, High Pressure Liquid , Freeze Drying , Fruit/chemistry , Phytosterols/chemistry , Plant Shoots/chemistry , Solanine/chemistry , Solanine/isolation & purification , Solanum tuberosum/chemistry , Tandem Mass SpectrometryABSTRACT
AIMS: To study the antifungal effects of the potato secondary metabolites α-solanine, α-chaconine, solanidine and caffeic acid, alone or combined. METHODS AND RESULTS: Resistance to glycoalkaloids varied among the fungal species tested, as derived from minimum inhibitory concentrations assays. Synergistic antifungal activity between glycoalkaloids and phenolic compounds was found. Changes in the fluidity of fungal membranes caused by potato secondary plant metabolites were determined by calculation of the generalized polarization values. The results partially explained the synergistic effect between caffeic acid and α-chaconine and supported findings on membrane disruption mechanisms from previous studies on artificial membranes. LC/MS analysis was used to determine variability and relative amounts of sterols in the different fungal species. Results suggested that the sterol pattern of fungi is related to their resistance to potato glycoalkaloids and to their taxonomy. CONCLUSION: Fungal resistance to α-chaconine and possibly other glycoalkaloids is species dependent. α-Chaconine and caffeic acid show synergistic antifungal activity. The taxonomic classification and the sterol pattern play a role in fungal resistance to glycoalkaloids. SIGNIFICANCE AND IMPACT OF THE STUDY: Results improve the understanding of the antifungal mode of action of potato secondary metabolites, which is essential for their potential utilization as antifungal agents in nonfood systems.
Subject(s)
Antifungal Agents/pharmacology , Diosgenin/pharmacology , Fungi/drug effects , Solanine/analogs & derivatives , Antifungal Agents/isolation & purification , Antifungal Agents/metabolism , Caffeic Acids/isolation & purification , Caffeic Acids/metabolism , Caffeic Acids/pharmacology , Diosgenin/isolation & purification , Diosgenin/metabolism , Microbial Sensitivity Tests , Phenols/metabolism , Solanine/isolation & purification , Solanine/metabolism , Solanine/pharmacology , Solanum tuberosum/metabolismABSTRACT
The aim of this investigation was the preparative isolation of solanidine (aglycone of the two main potato glycoalkaloids: α-chaconine and α-solanine) from fresh Solanum tuberosum (cv. Pompadour) material by implementing a new preparation scheme using centrifugal partition chromatography (CPC). A setup for obtaining solanidine by hydrolysis of the glycoalkaloids found in the skin and sprouts of S. tuberosum was first developed. Then its isolation was carried out by the development of CPC conditions: the solvent system used for separation was ethyl acetate/butanol/water in the ratio 42.5:7.5:50 v/v/v, 0.6 g of crude extract were separated with a 8 mL/min flow rate of mobile phase while rotating at 2500 rpm. A run yielded 98 mg of solanidine (86.7% recovery from the crude extract) in a one-step separation. The purity of the isolated solanidine was over 98%. Thus, CPC has proven to be the method of choice to get solanidine of very high purity from S. tuberosum biomass in large quantities.
Subject(s)
Chromatography/methods , Plant Extracts/isolation & purification , Solanine/isolation & purification , Solanum tuberosum/chemistry , Chromatography/instrumentationABSTRACT
The main glycoalkaloids of a commercial potato cultivar, α-chaconine and α-solanine, were extracted from sprouts of Solanum tuberosum cv. Pompadour by a mixture of MeOH/H(2)O/CH(3)COOH (400/100/50, v/v/v). In these conditions, 2.8±0.62g of crude extract were obtained from 50g of fresh sprouts and the total glycoalkaloid content was determined by analytical HPLC at 216.5mg/100g. α-Chaconine and α-solanine were separated in a preparative scale using centrifugal partition chromatography (CPC). In a solvent system composed of a mixture of ethyl acetate/butanol/water (15/35/50, v/v/v), α-chaconine (54mg) and α-solanine (15mg) were successfully isolated from the crude extract in one step of purification. The purity of isolated compounds was determined to be higher than 92% by HPLC analysis.
Subject(s)
Centrifugation/methods , Chromatography, High Pressure Liquid/methods , Solanine/analogs & derivatives , Organic Chemicals/chemistry , Plant Extracts/chemistry , Solanine/analysis , Solanine/chemistry , Solanine/isolation & purification , Solanum tuberosum/chemistry , Water/chemistryABSTRACT
Alkaloids are well known for their antimicrobial activity. Though all natural alkaloids come from plants, not all plants produce alkaloids. Plants of the Solanaceae family are known for their high alkaloid content. Alkaloids are found in all plant parts like roots, stems, leaves, flowers, fruits and seeds. In the present study, those plant parts of Solanum dulcamara were selected which have been reported to produce a high content of a specific alkaloid: solanine (from unripe fruits), solasodine (from flowers) and beta-solamarine (from roots). These alkaloids were extracted from various parts of S. dulcamara by well-established methods and were screened for their antibacterial activity. Human pathogenic bacteria, viz., Enterobacter aerogenes, Escherichia coli, Staphylococcus aureus, were selected for the study. All three alkaloids inhibited the growth of E. coli and S. aureus. However, no significant activity was observed against E. aerogenes. Minimum inhibitory concentration and minimum bactericidal concentration were also evaluated.
Subject(s)
Alkaloids/pharmacology , Solanum/chemistry , Alkaloids/isolation & purification , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Enterobacter aerogenes/drug effects , Escherichia coli/drug effects , Flowers/chemistry , Fruit/chemistry , Microbial Sensitivity Tests , Plant Leaves/chemistry , Plant Roots/chemistry , Plant Stems/chemistry , Seeds/chemistry , Solanaceous Alkaloids/isolation & purification , Solanaceous Alkaloids/pharmacology , Solanine/isolation & purification , Solanine/pharmacology , Staphylococcus aureus/drug effectsABSTRACT
The interaction of main potato glycoalkaloids alpha-solanine and alpha-chaconine in inhibition of horse serum butyryl cholinesterases immobilized on the pH-sensitive field-effect transistors has been investigated. The method of isobol diagram of Loewe and Muishnek has been used for interpretation of results. It has been shown the alpha-chaconine inhibits the immobilized bytyryl cholinesterases more strongly than alpha-solanine, and their mixture has the addition effect.
Subject(s)
Biosensing Techniques/methods , Butyrylcholinesterase/chemistry , Cholinesterase Inhibitors/analysis , Enzymes, Immobilized/chemistry , Solanine/analogs & derivatives , Solanine/analysis , Solanum tuberosum/chemistry , Animals , Biosensing Techniques/instrumentation , Cholinesterase Inhibitors/isolation & purification , Cholinesterase Inhibitors/pharmacology , Drug Synergism , Horses , Hydrogen-Ion Concentration , Solanine/isolation & purification , Solanine/pharmacology , Transistors, ElectronicABSTRACT
A sample purification technique was developed for the detection of potato glycoalkaloids (GAs) in blood serum by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS). GAs were extracted from spiked serum (5 mL) using a C(18) solid-phase extraction cartridge. The GAs were then selectively captured on antibody-coated agarose beads. The agarose beads were washed with water and the GAs eluted with 25 microL of methanol. MALDI-TOF MS was used to detect the GAs in the methanol eluent. Immunoaffinity sample purification of the GAs effectively reduced the signal suppression observed during the analysis of unpurified samples. alpha-Chaconine and alpha-solanine were detected in serum spiked with 1 ng/mL of each GA.
Subject(s)
Solanine/blood , Animals , Antibodies , Chromatography, Affinity/methods , Female , Rabbits , Sensitivity and Specificity , Solanine/analogs & derivatives , Solanine/isolation & purification , Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization/methodsABSTRACT
Potato glycoalkaloids were extracted from potato sprout and then analyzed to determine their purity by using TLC and HPLC methods and compare with pure alpha-Solanine and alpha-Chaconine of Sigma. The result indicated that the purity of potato glycoalkaloids is 78. 31%, which contains 73.64% alpha-Solanine and 4.67% alpha-Chaconine. The LD50 of mice was 44.721 +/- 5.860 4 mg/kg. In order to determine the toxicity and teratogenicity of potato glycoalkaloids, the effect of potato glycoalkaloids on Kunming pregnant mice were studied. The results showed that: (1) potato glycoalkaloids have teratogenic effects on embryos of mice. It could induce neural tube defects (NTDs), and may be an important teratogen of NTDs. (2) potato glycoalkaloids have embryo toxicity. It could cause the death of embryos and result in absorbed and dead fetuses. (3) potato glycoalkaloids could evidently affect the development of embryos and lead to intrauterine growth retardation (IUGR). An interesting phenomena which just like the clinical manifestation of miscarriage in human being was noticed. If potato glycoalkaloids were given to the pregnant mice on the 5th or 6th day of gestation intraabdominally, vaginal bleeding and abortion would occur, and this has not been reported yet. The animal model of NTDs in this experiments supported our hypothesis that sprouted potato could be a teratogen of NTDs.
Subject(s)
Abnormalities, Drug-Induced/etiology , Neural Tube Defects/chemically induced , Solanine/analogs & derivatives , Solanine/toxicity , Solanum tuberosum/chemistry , Animals , Female , Fetal Death/chemically induced , Fetal Growth Retardation/chemically induced , Lethal Dose 50 , Mice , Pregnancy , Solanine/isolation & purificationABSTRACT
The development of a high-performance liquid chromatography (HPLC) method for the separation and quantification of potato glycoalkaloids and their aglycone solanidine in blood serum is reported. High selectivity was obtained by using solid-phase extraction followed by off-line dual-column HPLC. Injections were made via a sample enrichment column to achieve maximum sensitivity in the assay. The potato alkaloids in the HPLC effluents were detected by ultraviolet absorption at 200 nm. The detection limits were estimated to be 0.3 ng/ml of serum for each of the alkaloids. The method was used to study the pharmacokinetics of potato glycoalkaloids in humans. alpha-Solanine and alpha-chaconine were detected in all blood serum samples collected from seven volunteers 1-25 h after a meal of potatoes. Solanidine was detected in some samples, but there were no traces of the mono- or diglycosides. The average apparent biological half-lives for alpha-solanine and alpha-chaconine were 11 and 19 h, respectively.
