Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C27H45NO2.ClH |
| Molecular Weight | 452.113 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 12 / 12 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.[H][C@]12C[C@@]3([H])[C@]4([H])CC[C@@]5([H])C[C@@H](O)CC[C@]5(C)[C@@]4([H])CC[C@]3(C)[C@@]1([H])[C@H](C)[C@]6(CC[C@H](C)CN6)O2
InChI
InChIKey=SXXHVPYRDFJKPG-VXJLCZPPSA-N
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
Tomatidine is a steroidal alkaloid derived from green tomato. Tomatitidine has been identified as a potential therapeutic agent or lead compound for the treatment of skeletal muscle atrophy. It has been shown to increase skeletal muscle mTORC1 signaling, reduce skeletal muscle atrophy, enhance recovery from skeletal muscle atrophy, stimulate skeletal muscle hypertrophy, and increase strength and exercise capacity. In addition, tomatidine has been identified as a potential therapeutic agent or lead compound for reducing the activity of Activating Transcription Factor 4 (ATF4).
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Hedgehog signalling within airway epithelial progenitors and in small-cell lung cancer. | 2003 Mar 20 |
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| Dehydrotomatine and alpha-tomatine content in tomato fruits and vegetative plant tissues. | 2004 Apr 7 |
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| Glycoalkaloids and metabolites inhibit the growth of human colon (HT29) and liver (HepG2) cancer cells. | 2004 May 19 |
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| A novel glucosyltransferase involved in steroid saponin biosynthesis in Solanum aculeatissimum. | 2005 Jan |
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| Hedgehog signaling pathway is inactive in colorectal cancer cell lines. | 2007 Dec 15 |
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| Diosgenin, a naturally occurring steroid, suppresses fatty acid synthase expression in HER2-overexpressing breast cancer cells through modulating Akt, mTOR and JNK phosphorylation. | 2007 Dec 22 |
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| Simultaneously cycled NMR spectroscopy. | 2008 Apr 9 |
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| Autonomous Hedgehog signalling is undetectable in PC-3 prostate cancer cells. | 2008 Aug 15 |
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| Tomatidine inhibits iNOS and COX-2 through suppression of NF-kappaB and JNK pathways in LPS-stimulated mouse macrophages. | 2008 Jul 9 |
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| Heterologous expression of Fusarium oxysporum tomatinase in Saccharomyces cerevisiae increases its resistance to saponins and improves ethanol production during the fermentation of Agave tequilana Weber var. azul and Agave salmiana must. | 2008 Mar |
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| Hedgehog signalling is essential for maintenance of cancer stem cells in myeloid leukaemia. | 2009 Apr 9 |
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| Plant antimicrobial agents and their effects on plant and human pathogens. | 2009 Jul 31 |
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| Tomatine-containing green tomato extracts inhibit growth of human breast, colon, liver, and stomach cancer cells. | 2009 Jul 8 |
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| Evidence for allosteric interactions of antagonist binding to the smoothened receptor. | 2009 Jun |
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| Resistance of wild Solanum accessions to aphids and other potato pests in Quebec field conditions. | 2010 |
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| Chemoprotective Effect of Sobatum against Lithium-Induced Oxidative Damage in Rats. | 2010 Jan |
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| Smoothened as a new therapeutic target for human osteosarcoma. | 2010 Jan 12 |
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| Gli2 expression and human bladder transitional carcinoma cell invasiveness. | 2010 Jul |
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| Tomatidine inhibits invasion of human lung adenocarcinoma cell A549 by reducing matrix metalloproteinases expression. | 2013 May 25 |
Sample Use Guides
To test this hypothesis, we incubated C2C12 myotubes with 1 μm tomatidine for 1 h. We found that tomatidine increased phosphorylation of a key mTORC1 substrate, S6 kinase (S6K) (Fig. 3A). In addition, tomatidine increased protein synthesis (Fig. 3B) and IGF1 and PGC-1α1 mRNAs (Fig. 3C). To determine if mTORC1 signaling is required for tomatidine-mediated cell growth, we tested the effect of an mTORC1 inhibitor, rapamycin. As expected, rapamycin abolished the effect of tomatidine on S6K phosphorylation (Fig. 3D). Moreover, rapamycin inhibited tomatidine-mediated protein accretion and myotube growth (Fig. 3, E and F). Collectively, these data indicate that tomatidine stimulates muscle cell growth by activating mTORC1 signaling.
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735985
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60196284
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DTXSID9045978
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6192-62-7
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m10973
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ENY5VJU5UB
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SUBSTANCE RECORD
