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
| Molecular Formula | C27H45NO2 |
| Molecular Weight | 415.6517 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 11 / 12 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|
| Determination of glycoalkaloids and relative aglycones by nonaqueous capillary electrophoresis coupled with electrospray ionization-ion trap mass spectrometry. | 2002 Sep |
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| Effect of feeding solanidine, solasodine and tomatidine to non-pregnant and pregnant mice. | 2003 Jan |
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| Dehydrotomatine and alpha-tomatine content in tomato fruits and vegetative plant tissues. | 2004 Apr 7 |
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| Tomatidine and lycotetraose, hydrolysis products of alpha-tomatine by Fusarium oxysporum tomatinase, suppress induced defense responses in tomato cells. | 2004 Jul 30 |
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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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| Activation of the hedgehog pathway in advanced prostate cancer. | 2004 Oct 13 |
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| A novel glucosyltransferase involved in steroid saponin biosynthesis in Solanum aculeatissimum. | 2005 Jan |
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| Influence of incorporated wild Solanum genomes on potato properties in terms of starch nanostructure and glycoalkaloid content. | 2005 Jun 29 |
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| Glycoalkaloid aglycone accumulations associated with infection by Clavibacter michiganensis ssp. sepedonicus in potato species Solanum acaule and Solanum tuberosum and their interspecific somatic hybrids. | 2005 Mar |
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| Identification of a tomatinase in the tomato-pathogenic actinomycete Clavibacter michiganensis subsp. michiganensis NCPPB382. | 2005 Oct |
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| Wnt and Hedgehog are critical mediators of cigarette smoke-induced lung cancer. | 2006 Dec 20 |
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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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| Efficient conversion of tomatidine into neuritogenic pregnane derivative. | 2007 Jul |
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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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| Musashi1 modulates cell proliferation genes in the medulloblastoma cell line Daoy. | 2008 Sep 30 |
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| Hedgehog signaling regulates the survival of gastric cancer cells by regulating the expression of Bcl-2. | 2009 Jul 6 |
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| Evidence for allosteric interactions of antagonist binding to the smoothened receptor. | 2009 Jun |
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| Distortion of trichome morphology by the hairless mutation of tomato affects leaf surface chemistry. | 2010 Feb |
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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.
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
ENY5VJU5UB
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| Record Status |
Validated (UNII)
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| Record Version |
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