A steroidal alkaloid with diverse biological activities
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Tomatidine (hydrochloride)

Item No. 16938

Technical Information
Formal Name
(3β,5α,22β,25S)-spirosolan-3-ol, monohydrochloride
CAS Number
6192-62-7
Molecular Formula
C27H45NO2 • HCl
Formula Weight
Purity
≥90%
A crystalline solid
Methanol: 10 mg/ml
SMILES
C[C@@H](CC1)CN[C@@]21O[C@@]3([H])C[C@@]4([H])[C@]5([H])CC[C@@]6([H])C[C@@H](O)CC[C@]6(C)[C@@]5([H])CC[C@]4(C)[C@@]3([H])[C@@H]2C.Cl
InChi Code
InChI=1S/C27H45NO2.ClH/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;1H/t16-,17-,18-,19-,20+,21-,22-,23-,24-,25-,26-,27-;/m0./s1
InChi Key
SXXHVPYRDFJKPG-VXJLCZPPSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Tomatidine is a steroidal alkaloid that has been found in the skins and leaves of tomatoes.1 It suppresses NF-κB signaling in LPS-stimulated macrophages, blocking induced expression of inducible nitric oxide synthase (iNOS) and COX-2. Tomatidine inhibits acid sphingomyelinase activity by 84.2% when used at a concentration of 10 mM.2 It also has antibacterial properties, preferentially blocking the replication of S. aureus variants that are pathogenic in cystic fibrosis over normal strains (MICs = 0.12 and >16 µg/ml, respectively).3 It prevents skeletal muscle atrophy associated with fasting or spinal cord injury in mice.4 Tomatidine has also been used as a negative control for cyclopamine (Item No. 11321) in studies involving signaling mediated by the hedgehog pathway.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Chiu, F.L., and Lin, J.K. Tomatidine inhibits iNOS and COX-2 through suppression of NF-κB and JNK pathways in LPS-stimulated mouse macrophages. FEBS Lett. 582(16), 2407-2412 (2008).

    2. Kornhuber, J., Muehlbacher, M., Trapp, S., et alIdentification of novel functional inhibitors of acid sphingomyelinase. PLoS One 6(8), e23852 (2011).

    3. Mitchell, G., Gattuso, M., Grondin, G., et alTomatidine inhibits replication of Staphylococcus aureus small-colony variants in cystic fibrosis airway epithelial cells. Antimicrob. Agents Chemother. 55(5), 1937-1945 (2011).

    4. Dyle, M.C., Ebert, S.M., Cook, D.P., et alSystems-based discovery of tomatidine as a natural small molecule inhibitor of skeletal muscle atrophy. The Journal of Biological Chemisty 289(21), 14913-14924 (2014).

    5. Zhao, C., Chen, A., Jamieson, C.H., et alHedgehog signalling is essential for maintenance of cancer stem cells in myeloid leukaemia. Nature 458(7239), 776-779 (2009).