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    Tomatidine
    Tomatidine
    Information
    CAS No. 77-59-8 Price $368 / 10mg
    Catalog No.CFN90632Purity>=98%
    Molecular Weight415.65Type of CompoundAlkaloids
    FormulaC27H45NO2Physical DescriptionPowder
    Download Manual    COA    MSDSSimilar structuralComparison (Web)
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    Biological Activity
    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:
    Eur J Med Chem. 2014 Jun 10;80:605-20.
    Unraveling the structure-activity relationship of tomatidine, a steroid alkaloid with unique antibiotic properties against persistent forms of Staphylococcus aureus.[Pubmed: 24877760]
    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.
    Chem Biol Interact. 2013 May 25;203(3):580-7.
    Tomatidine inhibits invasion of human lung adenocarcinoma cell A549 by reducing matrix metalloproteinases expression.[Pubmed: 23566884]
    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.
    Antimicrob Agents Chemother. 2011 May;55(5):1937-45.
    Tomatidine inhibits replication of Staphylococcus aureus small-colony variants in cystic fibrosis airway epithelial cells.[Pubmed: 21357296]
    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:
    J Agric Food Chem. 2012 Mar 14;60(10):2472-9.
    Tomatidine, a tomato sapogenol, ameliorates hyperlipidemia and atherosclerosis in apoE-deficient mice by inhibiting acyl-CoA:cholesterol acyl-transferase (ACAT).[Pubmed: 22224814]
    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.
    Tomatidine Description
    Source: The fruits of Lycopersicon esculentum Mill.
    Solvent: Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
    Storage: Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C).

    Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour.

    Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com

    After receiving: The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
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    Calculate Dilution Ratios(Only for Reference)
    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 need to make the dilution ratios of the samples. The dilution data of the sheet for your reference. Normally, it's can get a better solubility within lower of Concentrations.
    Protocol
    Kinase Assay:
    J Biol Chem. 2014 May 23;289(21):14913-24.
    Systems-based discovery of tomatidine as a natural small molecule inhibitor of skeletal muscle atrophy.[Pubmed: 24719321]
    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.