Tomatidine CAS NO.77-59-8

Min.Order: 10 Milligram
Payment Terms: T/T
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Product Details

Keywords

Tomatidine
77-59-8
standard supplier in China

Quick Details

ProName: Tomatidine
CasNo: 77-59-8
Molecular Formula: C27H45NO2
Appearance: detailed see specifications
Application: analysis,activity test,Botanical Refer...
DeliveryTime: 1-3?working?days?after?confirming?the?...
PackAge: According to the clients requirement.
Port: China main port
ProductionCapacity: 1 Metric Ton/Day
Purity: ≥98%
Storage: Store at 2~8°C
Transportation: by air or by ocean shipping
LimitNum: 10 Milligram
Plant of Origin: Chinese herbal medicine
Testing Method: NMR/MS/HPLC
Product Ecification: 1mg-1kg
Heavy Metal: <10ppm
Voluntary Standards: company standard
Storage: Store in dry, dark and ventilated plac...
PackAge: Brown vial HDPE plastic bottle

Superiority

Hubei CuiRan Biotechnology Co., Ltd is a leading company in the research, development, manufacture and marketing of High Quality Phytochemicals and Extracts(especially Active Ingredients from Traditional Chinese Medicine，Traditional Chinese Medicine), Natural Active Pharmaceutical Ingredients worldwide. From small quantities for R&D or reference standard, to large quantities for customizing or manufacturing, Biopurify emphasizes on consistent and reliable services for his customers.
With excellent quality products and good service, we have clients from more than dozens countries and regions, and we pride ourselves in providing our customers with a total satisfaction experiences.
We are doing our best to be your reliable partner for high quality Phytochemicals and Reference Standards from china.

Our main services:
A. Supply active ingredients and reference standards ofTraditional Chinese Medicine, from mgs to kgs scale.
B. Custom extraction and purification, target Herb Active Ingredients
C. Custom synthesis and semi-synthesis for Natural Active Ingredients
D. CR, CM and PD services from lab scale, pilot scale to commercial scale(GMP is also available)
E.Traditional Chinese Medicine compounds library

1.Provide traditional Chinese medicine reference materials and natural active ingredients;
2.More than 2200 compounds are available for selection, continuously building high-quality natural product libraries for drug research and development;
3.Provide various screening libraries and more inhibitor products;
4.Provide separation and structural determination of natural products;
5.Laboratory scale pilot to commercial scale collaborative research and process development services.More than 180 experiences in phytochemistry (still increasing)
Each product has passed very strict testing (NMR/MS/HPLC)
Agents from many countries

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.

Details

Chemical Properties of Tomatidine

Cas No.	77-59-8
PubChem ID	65576	Appearance	Powder
Formula	C₂₇H₄₅NO₂	M.Wt	415.65
Type of Compound	Alkaloids	Storage	Desiccate at -20°C
Solubility	DMSO : 2.86 mg/mL (6.88 mM; Need ultrasonic) H2O : < 0.1 mg/mL (insoluble)
SMILES	CC1CCC2(C(C3C(O2)CC4C3(CCC5C4CCC6C5(CCC(C6)O)C)C)C)NC1
Standard InChIKey	XYNPYHXGMWJBLV-VXPJTDKGSA-N
Standard InChI	InChI=1S/C27H45NO2/c1-16-7-12-27(28-15-16)17(2)24-23(30-27)14-22-20-6-5-18-13-19(29)8-10-25(18,3)21(20)9-11-26(22,24)4/h16-24,28-29H,5-15H2,1-4H3/t16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26-,27-/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 Tomatidine

The fruits of Lycopersicon esculentum Mill.

Biological Activity of Tomatidine

Description	Tomatidine shows antibiotic, and anti-inflammatory activities, it significantly suppresses the activity of ACAT and leads to reduction of atherogenesis. Tomatidine inhibits the invasion of A549 cells by reducing the expression of MMPs, also inhibits ERK and Akt signaling pathways and NF-κB activity, suggests a new therapeutic potential for Tomatidine in anti-metastatic therapy.
Targets	mTOR \| Antifection \| MMP(e.g.TIMP) \| Akt \| ERK \| NF-kB \| PI3K \| LDL
In vitro	Unraveling the structure-activity relationship of tomatidine, a steroid alkaloid with unique antibiotic properties against persistent forms of Staphylococcus aureus.[Pubmed: 24877760] Eur J Med Chem. 2014 Jun 10;80:605-20. Staphylococcus aureus (S. aureus) is responsible for difficult-to-treat and relapsing infections and constitutes one of the most problematic pathogens due to its multiple resistances to clinically available antibiotics. Additionally, the ability of S. aureus to develop small-colony variants is associated with a reduced susceptibility to aminoglycoside antibiotics and in vivo persistence. METHODS AND RESULTS: We have recently demonstrated that Tomatidine, a steroid alkaloid isolated from tomato plants, possesses anti-virulence activity against normal strains of S. aureus as well as the ability to potentiate the effect of aminoglycoside antibiotics. In addition, Tomatidine has shown antibiotic activity against small-colony variants of S. aureus. CONCLUSIONS: We herein report the first study of the structure-activity relationship of Tomatidine against S. aureus. Tomatidine inhibits invasion of human lung adenocarcinoma cell A549 by reducing matrix metalloproteinases expression.[Pubmed: 23566884] Chem Biol Interact. 2013 May 25;203(3):580-7. Tomatidine is an aglycone of glycoalkaloid tomatine in tomato. Tomatidine is found to possess anti-inflammatory properties and may serve as a chemosensitizer in multidrug-resistant tumor cells. However, the effect of Tomatidine on cancer cell metastasis remains unclear. METHODS AND RESULTS: This study examines the effect of Tomatidine on the migration and invasion of human lung adenocarcinoma A549 cell in vitro. The data demonstrates that Tomatidine does not effectively inhibit the viability of A549 cells. When treated with non-toxic doses of Tomatidine, cell invasion is markedly suppressed by Boyden chamber invasion assay, while cell migration is not affected. Tomatidine reduces the mRNA level of matrix metalloproteinase-2 (MMP-2), MMP-9 and increases the expression of reversion-inducing cysteine-rich protein with kazal motifs (RECK), as well as tissue inhibitor of metalloproteinase-1 (TIMP-1). The immunoblotting assays indicate that Tomatidine is very effective in suppressing the phosphorylation of Akt and extracellular signal regulating kinase (ERK). In addition, Tomatidine significantly decreases the nuclear level of nuclear factor kappa B (NF-κB), which suggests that Tomatidine inhibits NF-κB activity. Furthermore, the treatment of inhibitors specific for PI3K/Akt (LY294002), ERK (U0126), or NF-κB (pyrrolidine dithiocarbamate) to A549 cells reduced cell invasion and MMP-2/9 expression. CONCLUSIONS: The results suggest that Tomatidine inhibits the invasion of A549 cells by reducing the expression of MMPs. It also inhibits ERK and Akt signaling pathways and NF-κB activity. These findings demonstrate a new therapeutic potential for Tomatidine in anti-metastatic therapy. Tomatidine inhibits replication of Staphylococcus aureus small-colony variants in cystic fibrosis airway epithelial cells.[Pubmed: 21357296] Antimicrob Agents Chemother. 2011 May;55(5):1937-45. Small-colony variants (SCVs) often are associated with chronic Staphylococcus aureus infections, such as those encountered by cystic fibrosis (CF) patients. METHODS AND RESULTS: We report here that Tomatidine, the aglycon form of the plant secondary metabolite tomatine, has a potent growth inhibitory activity against SCVs (MIC of 0.12 μg/ml), whereas the growth of normal S. aureus strains was not significantly altered by Tomatidine (MIC, >16 μg/ml). The specific action of Tomatidine was bacteriostatic for SCVs and was clearly associated with their dysfunctional electron transport system, as the presence of the electron transport inhibitor 4-hydroxy-2-heptylquinoline-N-oxide (HQNO) caused normal S. aureus strains to become susceptible to Tomatidine. Inversely, the complementation of SCVs' respiratory deficiency conferred resistance to Tomatidine. Tomatidine provoked a general reduction of macromolecular biosynthesis but more specifically affected the incorporation of radiolabeled leucine in proteins of HQNO-treated S. aureus at a concentration corresponding to the MIC against SCVs. Furthermore, Tomatidine inhibited the intracellular replication of a clinical SCV in polarized CF-like epithelial cells. CONCLUSIONS: Our results suggest that Tomatidine eventually will find some use in combination therapy with other traditional antibiotics to eliminate persistent forms of S. aureus.
In vivo	Tomatidine, a tomato sapogenol, ameliorates hyperlipidemia and atherosclerosis in apoE-deficient mice by inhibiting acyl-CoA:cholesterol acyl-transferase (ACAT).[Pubmed: 22224814] J Agric Food Chem. 2012 Mar 14;60(10):2472-9. It was previously revealed that esculeoside A, a new glycoalkaloid, and esculeogenin A, a new aglycon of esculeoside A, contained in ripe tomato ameliorate atherosclerosis in apoE-deficent mice. METHODS AND RESULTS: This study examined whether Tomatidine, the aglycone of tomatine, which is a major tomato glycoalkaloid, also shows similar inhibitory effects on cholesterol ester (CE) accumulation in human monocyte-derived macrophages (HMDM) and atherogenesis in apoE-deficient mice. Tomatidine significantly inhibited the CE accumulation induced by acetylated LDL in HMDM in a dose-dependent manner. Tomatidine also inhibited CE formation in Chinese hamster ovary cells overexpressing acyl-CoA:cholesterol acyl-transferase (ACAT)-1 or ACAT-2, suggesting that Tomatidine suppresses both ACAT-1 and ACAT-2 activities. Furthermore, the oral administration of Tomatidine to apoE-deficient mice significantly reduced levels of serum cholesterol, LDL-cholesterol, and areas of atherosclerotic lesions. CONCLUSIONS: The study provides the first evidence that Tomatidine significantly suppresses the activity of ACAT and leads to reduction of atherogenesis.

Protocol of Tomatidine

Kinase Assay

Systems-based discovery of tomatidine as a natural small molecule inhibitor of skeletal muscle atrophy.[Pubmed: 24719321]

J Biol Chem. 2014 May 23;289(21):14913-24.

Skeletal muscle atrophy is a common and debilitating condition that lacks an effective therapy.
METHODS AND RESULTS:
To address this problem, we used a systems-based discovery strategy to search for a small molecule whose mRNA expression signature negatively correlates to mRNA expression signatures of human skeletal muscle atrophy. This strategy identified a natural small molecule from tomato plants, Tomatidine. Using cultured skeletal myotubes from both humans and mice, we found that Tomatidine stimulated mTORC1 signaling and anabolism, leading to accumulation of protein and mitochondria, and ultimately, cell growth. Furthermore, in mice, Tomatidine increased skeletal muscle mTORC1 signaling, reduced skeletal muscle atrophy, enhanced recovery from skeletal muscle atrophy, stimulated skeletal muscle hypertrophy, and increased strength and exercise capacity.
CONCLUSIONS:
Collectively, these results identify Tomatidine as a novel small molecule inhibitor of muscle atrophy. Tomatidine may have utility as a therapeutic agent or lead compound for skeletal muscle atrophy.

Preparing Stock Solutions of Tomatidine

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	2.4059 mL	12.0294 mL	24.0587 mL	48.1174 mL	60.1468 mL
5 mM	0.4812 mL	2.4059 mL	4.8117 mL	9.6235 mL	12.0294 mL
10 mM	0.2406 mL	1.2029 mL	2.4059 mL	4.8117 mL	6.0147 mL
50 mM	0.0481 mL	0.2406 mL	0.4812 mL	0.9623 mL	1.2029 mL
100 mM	0.0241 mL	0.1203 mL	0.2406 mL	0.4812 mL	0.6015 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.

References on Tomatidine

Tomatidine inhibits replication of Staphylococcus aureus small-colony variants in cystic fibrosis airway epithelial cells.[Pubmed:21357296]

Antimicrob Agents Chemother. 2011 May;55(5):1937-45.

Small-colony variants (SCVs) often are associated with chronic Staphylococcus aureus infections, such as those encountered by cystic fibrosis (CF) patients. We report here that Tomatidine, the aglycon form of the plant secondary metabolite tomatine, has a potent growth inhibitory activity against SCVs (MIC of 0.12 mug/ml), whereas the growth of normal S. aureus strains was not significantly altered by Tomatidine (MIC, >16 mug/ml). The specific action of Tomatidine was bacteriostatic for SCVs and was clearly associated with their dysfunctional electron transport system, as the presence of the electron transport inhibitor 4-hydroxy-2-heptylquinoline-N-oxide (HQNO) caused normal S. aureus strains to become susceptible to Tomatidine. Inversely, the complementation of SCVs' respiratory deficiency conferred resistance to Tomatidine. Tomatidine provoked a general reduction of macromolecular biosynthesis but more specifically affected the incorporation of radiolabeled leucine in proteins of HQNO-treated S. aureus at a concentration corresponding to the MIC against SCVs. Furthermore, Tomatidine inhibited the intracellular replication of a clinical SCV in polarized CF-like epithelial cells. Our results suggest that Tomatidine eventually will find some use in combination therapy with other traditional antibiotics to eliminate persistent forms of S. aureus.

Tomatidine inhibits invasion of human lung adenocarcinoma cell A549 by reducing matrix metalloproteinases expression.[Pubmed:23566884]

Chem Biol Interact. 2013 May 25;203(3):580-7.

Tomatidine is an aglycone of glycoalkaloid tomatine in tomato. Tomatidine is found to possess anti-inflammatory properties and may serve as a chemosensitizer in multidrug-resistant tumor cells. However, the effect of Tomatidine on cancer cell metastasis remains unclear. This study examines the effect of Tomatidine on the migration and invasion of human lung adenocarcinoma A549 cell in vitro. The data demonstrates that Tomatidine does not effectively inhibit the viability of A549 cells. When treated with non-toxic doses of Tomatidine, cell invasion is markedly suppressed by Boyden chamber invasion assay, while cell migration is not affected. Tomatidine reduces the mRNA level of matrix metalloproteinase-2 (MMP-2), MMP-9 and increases the expression of reversion-inducing cysteine-rich protein with kazal motifs (RECK), as well as tissue inhibitor of metalloproteinase-1 (TIMP-1). The immunoblotting assays indicate that Tomatidine is very effective in suppressing the phosphorylation of Akt and extracellular signal regulating kinase (ERK). In addition, Tomatidine significantly decreases the nuclear level of nuclear factor kappa B (NF-kappaB), which suggests that Tomatidine inhibits NF-kappaB activity. Furthermore, the treatment of inhibitors specific for PI3K/Akt (LY294002), ERK (U0126), or NF-kappaB (pyrrolidine dithiocarbamate) to A549 cells reduced cell invasion and MMP-2/9 expression. The results suggest that Tomatidine inhibits the invasion of A549 cells by reducing the expression of MMPs. It also inhibits ERK and Akt signaling pathways and NF-kappaB activity. These findings demonstrate a new therapeutic potential for Tomatidine in anti-metastatic therapy.

Systems-based discovery of tomatidine as a natural small molecule inhibitor of skeletal muscle atrophy.[Pubmed:24719321]

J Biol Chem. 2014 May 23;289(21):14913-24.

Skeletal muscle atrophy is a common and debilitating condition that lacks an effective therapy. To address this problem, we used a systems-based discovery strategy to search for a small molecule whose mRNA expression signature negatively correlates to mRNA expression signatures of human skeletal muscle atrophy. This strategy identified a natural small molecule from tomato plants, Tomatidine. Using cultured skeletal myotubes from both humans and mice, we found that Tomatidine stimulated mTORC1 signaling and anabolism, leading to accumulation of protein and mitochondria, and ultimately, cell growth. Furthermore, in mice, Tomatidine increased skeletal muscle mTORC1 signaling, reduced skeletal muscle atrophy, enhanced recovery from skeletal muscle atrophy, stimulated skeletal muscle hypertrophy, and increased strength and exercise capacity. Collectively, these results identify Tomatidine as a novel small molecule inhibitor of muscle atrophy. Tomatidine may have utility as a therapeutic agent or lead compound for skeletal muscle atrophy.

Unraveling the structure-activity relationship of tomatidine, a steroid alkaloid with unique antibiotic properties against persistent forms of Staphylococcus aureus.[Pubmed:24877760]

Eur J Med Chem. 2014 Jun 10;80:605-20.

Staphylococcus aureus (S. aureus) is responsible for difficult-to-treat and relapsing infections and constitutes one of the most problematic pathogens due to its multiple resistances to clinically available antibiotics. Additionally, the ability of S. aureus to develop small-colony variants is associated with a reduced susceptibility to aminoglycoside antibiotics and in vivo persistence. We have recently demonstrated that Tomatidine, a steroid alkaloid isolated from tomato plants, possesses anti-virulence activity against normal strains of S. aureus as well as the ability to potentiate the effect of aminoglycoside antibiotics. In addition, Tomatidine has shown antibiotic activity against small-colony variants of S. aureus. We herein report the first study of the structure-activity relationship of Tomatidine against S. aureus.

Description

Tomatidine acts as an anti-inflammatory agent by blocking NF-κB and JNK signaling.

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