Tomatine

CAS# 17406-45-0

Tomatine

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Quality Control of Tomatine

Number of papers citing our products

Chemical structure

Tomatine

3D structure

Chemical Properties of Tomatine

Cas No. 17406-45-0 SDF Download SDF
PubChem ID 28523 Appearance White-beige powder
Formula C50H83NO21 M.Wt 1034.2
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Lycopersicin
Solubility DMSO : 250 mg/mL (241.74 mM; Need ultrasonic)
SMILES CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CCC(C6)OC7C(C(C(C(O7)CO)OC8C(C(C(C(O8)CO)O)OC9C(C(C(CO9)O)O)O)OC2C(C(C(C(O2)CO)O)O)O)O)O)C)C)C)NC1
Standard InChIKey REJLGAUYTKNVJM-SGXCCWNXSA-N
Standard InChI InChI=1S/C50H83NO21/c1-20-7-12-50(51-15-20)21(2)32-28(72-50)14-26-24-6-5-22-13-23(8-10-48(22,3)25(24)9-11-49(26,32)4)65-45-40(63)37(60)41(31(18-54)68-45)69-47-43(71-46-39(62)36(59)34(57)29(16-52)66-46)42(35(58)30(17-53)67-47)70-44-38(61)33(56)27(55)19-64-44/h20-47,51-63H,5-19H2,1-4H3/t20-,21-,22-,23-,24+,25-,26-,27+,28-,29+,30+,31+,32-,33-,34+,35+,36-,37+,38+,39+,40+,41-,42-,43+,44-,45+,46-,47-,48-,49-,50-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Tomatine

1 Solanum sp.

Biological Activity of Tomatine

DescriptionTomatine is a natural glycoalkaloid with anti-inflammatory, fungicidal, antimicrobial, and insecticidal properties. alpha-Tomatine activates phosphotyrosine kinase and monomeric G-protein signaling pathways leading to Ca(2+) elevation and ROS burst in F. oxysporum cells.
TargetsNF-kB | PI3K | Akt | ERK | MMP(e.g.TIMP) | AP-1 | ROS | Calcium Channel
In vivo

Alpha-tomatine induces apoptosis and inhibits nuclear factor-kappa B activation on human prostatic adenocarcinoma PC-3 cells.[Pubmed: 19755056]

Acta Chir. Orthop. Traumatol. Cech.,2009,76(4):314-8.

One of the methods used for treatment of Kienböck's disease is based on transposition of the pisiform bone into free space created by removal of the lunate bone. It is performed in patients with stage IIIB to IV, as assessed by Lichtmann's score. However, this operative procedure has so far lacked an unequivocal assessment of its therapeutic value. The aim of our work was to assess the therapeutic effect of the Kuhlmann method in the treatment of advanced stages of Kienböck's disease.
METHODS AND RESULTS:
From January 1996, eighteen patients (18 wrists) diagnosed with Kienböck's disease were operated on, using the Kuhlmann method, and the group of these patients was included in this follow-up study. The average follow-up time was 7.6 +/- 2.3 years. The results were evaluated on the basis of subjective (VAS) and functional criteria (ROM, grip force, DASH questionnaire and combined Cooney score questionnaires) and radiological assessment (arthritis evaluation, C.H.I., Natrass index, RSA). All patients experienced pain relief. The average pain assessment by VAS (10-point scale) before and after the procedure was 8.76 +/- 0.9 and 2.94 +/- 1.59, respectively. The range of motion was reduced on the operated extremity (70% compared to non-operated) as well as the grip test (57%). The average DASH score at the time of study was 20.9 +/- 12.2 and the average Cooney score was 67.6 +/- 17.4. Before the operation, eleven wrists showed signs of osteoarthritis. At the follow-up evaluation, arthritis was present in fifteen patients.We found a significant difference in average radiological parameters characterizing a carpal collapse deformity (C.H.I., Natrass index, RSA) - all parameters showed deteriorating tendencies. In nine patients, necrotic changes of the lunate occurred. In the patients whose pisiforme was not affected, a moderate retardation of carpal collapse occurred. However, the discrepancy between relevant indicators (C.H.I, Natrass index, RSA) was not statistically significant when comparing both groups. Therefore, we cannot conclude as to whether or not a vital transposed pisiforme bone impedes the development of carpal collapse. The only proved difference between these two groups was in pain evaluation, measured by VAS, after the procedure
CONCLUSIONS:
Although there was a good subjective assessment of the operation results, we are of the opinion that this method should not be used as a routine surgical procedure for advanced Kienböck disease. In view of a large number of failed cases we believe that this method should be considered very carefully.

Protocol of Tomatine

Kinase Assay

alpha-Tomatine, the major saponin in tomato, induces programmed cell death mediated by reactive oxygen species in the fungal pathogen Fusarium oxysporum.[Pubmed: 17585910 ]

FEBS lett., 2007, 581(17):3217-22.

The tomato saponin alpha-Tomatine has been proposed to kill sensitive cells by binding to cell membranes followed by leakage of cell components. However, details of the modes of action of the compound on fungal cells are poorly understood.
METHODS AND RESULTS:
In the present study, mechanisms involved in alpha-Tomatine-induced cell death of fungi were examined using a filamentous pathogenic fungus Fusarium oxysporum. alpha-Tomatine-induced cell death of F. oxysporum (TICDF) occurred only under aerobic conditions and was blocked by the mitochondrial F(0)F(1)-ATPase inhibitor oligomycin, the caspase inhibitor D-VAD-fmk, and protein synthesis inhibitor cycloheximide. Fungal cells exposed to alpha-Tomatine showed TUNEL-positive nuclei, depolarization of transmembrane potential of mitochondria, and reactive oxygen species (ROS) accumulation.
CONCLUSIONS:
These results suggest that TICDF occurs through a programmed cell death process in which mitochondria play a pivotal role. Pharmacological studies using inhibitors suggest that alpha-Tomatine activates phosphotyrosine kinase and monomeric G-protein signaling pathways leading to Ca(2+) elevation and ROS burst in F. oxysporum cells.

Tomatine Dilution Calculator

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Tomatine Molarity Calculator

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Preparing Stock Solutions of Tomatine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 0.9669 mL 4.8347 mL 9.6693 mL 19.3386 mL 24.1733 mL
5 mM 0.1934 mL 0.9669 mL 1.9339 mL 3.8677 mL 4.8347 mL
10 mM 0.0967 mL 0.4835 mL 0.9669 mL 1.9339 mL 2.4173 mL
50 mM 0.0193 mL 0.0967 mL 0.1934 mL 0.3868 mL 0.4835 mL
100 mM 0.0097 mL 0.0483 mL 0.0967 mL 0.1934 mL 0.2417 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Tomatine

alpha-Tomatine, the major saponin in tomato, induces programmed cell death mediated by reactive oxygen species in the fungal pathogen Fusarium oxysporum.[Pubmed:17585910]

FEBS Lett. 2007 Jul 10;581(17):3217-22.

The tomato saponin alpha-Tomatine has been proposed to kill sensitive cells by binding to cell membranes followed by leakage of cell components. However, details of the modes of action of the compound on fungal cells are poorly understood. In the present study, mechanisms involved in alpha-Tomatine-induced cell death of fungi were examined using a filamentous pathogenic fungus Fusarium oxysporum. alpha-Tomatine-induced cell death of F. oxysporum (TICDF) occurred only under aerobic conditions and was blocked by the mitochondrial F(0)F(1)-ATPase inhibitor oligomycin, the caspase inhibitor D-VAD-fmk, and protein synthesis inhibitor cycloheximide. Fungal cells exposed to alpha-Tomatine showed TUNEL-positive nuclei, depolarization of transmembrane potential of mitochondria, and reactive oxygen species (ROS) accumulation. These results suggest that TICDF occurs through a programmed cell death process in which mitochondria play a pivotal role. Pharmacological studies using inhibitors suggest that alpha-Tomatine activates phosphotyrosine kinase and monomeric G-protein signaling pathways leading to Ca(2+) elevation and ROS burst in F. oxysporum cells.

[Os Pisiforme transposition in the treatment of Kienbock's disease - long term results].[Pubmed:19755056]

Acta Chir Orthop Traumatol Cech. 2009 Aug;76(4):314-8.

PURPOSE OF THE STUDY: One of the methods used for treatment of Kienbock's disease is based on transposition of the pisiform bone into free space created by removal of the lunate bone. It is performed in patients with stage IIIB to IV, as assessed by Lichtmann's score. However, this operative procedure has so far lacked an unequivocal assessment of its therapeutic value. The aim of our work was to assess the therapeutic effect of the Kuhlmann method in the treatment of advanced stages of Kienbock's disease. MATERIAL: From January 1996, eighteen patients (18 wrists) diagnosed with Kienbock's disease were operated on, using the Kuhlmann method, and the group of these patients was included in this follow-up study. The average follow-up time was 7.6 +/- 2.3 years. METHODS: The results were evaluated on the basis of subjective (VAS) and functional criteria (ROM, grip force, DASH questionnaire and combined Cooney score questionnaires) and radiological assessment (arthritis evaluation, C.H.I., Natrass index, RSA). RESULTS: All patients experienced pain relief. The average pain assessment by VAS (10-point scale) before and after the procedure was 8.76 +/- 0.9 and 2.94 +/- 1.59, respectively. The range of motion was reduced on the operated extremity (70% compared to non-operated) as well as the grip test (57%). The average DASH score at the time of study was 20.9 +/- 12.2 and the average Cooney score was 67.6 +/- 17.4. Before the operation, eleven wrists showed signs of osteoarthritis. At the follow-up evaluation, arthritis was present in fifteen patients.We found a significant difference in average radiological parameters characterizing a carpal collapse deformity (C.H.I., Natrass index, RSA) - all parameters showed deteriorating tendencies. DISCUSSION: In nine patients, necrotic changes of the lunate occurred. In the patients whose pisiforme was not affected, a moderate retardation of carpal collapse occurred. However, the discrepancy between relevant indicators (C.H.I, Natrass index, RSA) was not statistically significant when comparing both groups. Therefore, we cannot conclude as to whether or not a vital transposed pisiforme bone impedes the development of carpal collapse. The only proved difference between these two groups was in pain evaluation, measured by VAS, after the procedure CONCLUSION: Although there was a good subjective assessment of the operation results, we are of the opinion that this method should not be used as a routine surgical procedure for advanced Kienbock disease. In view of a large number of failed cases we believe that this method should be considered very carefully.

Description

Tomatine is a glycoalkaloid, found in the tomato plant (Lycopersicon esculentum Mill.). Tomatine elicits neurotoxicity in RIP1 kinase and caspase-independent manner. Tomatine promotes the upregulation of nuclear apoptosis inducing factor (AIF) in neuroblastoma cells. Tomatine also inhibits 20S proteasome activity.

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