Chemistry:Tomatidine
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| IUPAC name
(1R,2S,4S,5′S,6S,7S,8R,9S,12S,13S,16S,18S)-5′,7,9,13-tetramethylspiro[5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icosane-6,2′-piperidine]-16-ol
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Other names
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| Identifiers | |
3D model (JSmol)
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| 91747 | |
| ChEBI | |
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PubChem CID
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| Properties | |
| C27H45NO2 | |
| Molar mass | 415.662 g·mol−1 |
| Hazards | |
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| GHS Signal word | Danger |
| H301, H302, H331 | |
| P261, P264, P270, P271, P301+310, P301+312, P304+340, P311, P321, P330, P403+233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Tomatidine is an anabolic chemical compound that prevents muscle wasting.[1] It is naturally found in leaves of tomatoes and green tomatoes.[1] Chemically, it is the aglycone of tomatine. It has been shown to have multiple health benefits.[2] Tomatidine is an inhibitor of skeletal muscle atrophy, and a potential therapeutic agent for aging-associated sarcopenia, reducing weakness and atrophy in aged skeletal muscle by interaction with the ATF4 (a critical mediator of age-related muscle weakness and atrophy).[3][4]
Dietary supplementation with ~0.04% tomatidine for 10 weeks reduces plasma cholesterol and atherosclerosis in ApoE-deficient mice without evidence of toxicity.[5]
Research
It is investigated as compound to increase longevity and it increased lifespan and healthspan of C. elegans.[6] It is also investigated in osteoporosis.[7][8]
See also
References
- ↑ 1.0 1.1 "Green is good: Natural compound from green tomatoes increases muscle, protects against muscle wasting". https://www.sciencedaily.com/releases/2014/04/140409134638.htm.
- ↑ Friedman, Mendel (2013). "Anticarcinogenic, Cardioprotective, and Other Health Benefits of Tomato Compounds Lycopene, α-Tomatine, and Tomatidine in Pure Form and in Fresh and Processed Tomatoes". Journal of Agricultural and Food Chemistry 61 (40): 9534–50. doi:10.1021/jf402654e. PMID 24079774.
- ↑ Dyle, M. C.; Ebert, S. M.; Cook, D. P.; Kunkel, S. D.; Fox, D. K.; Bongers, K. S.; Bullard, S. A.; Dierdorff, J. M. et al. (2014). "Systems-based Discovery of Tomatidine as a Natural Small Molecule Inhibitor of Skeletal Muscle Atrophy". Journal of Biological Chemistry 289 (21): 14913–14924. doi:10.1074/jbc.M114.556241. PMID 24719321.
- ↑ Ebert, S. M.; Dyle, M. C.; Bullard, S. A.; Dierdorff, J. M.; Murry, D. J.; Fox, D. K.; Bongers, K. S.; Lira, V. A. et al. (2015). "Identification and Small Molecule Inhibition of an Activating Transcription Factor 4 (ATF4)-dependent Pathway to Age-related Skeletal Muscle Weakness and Atrophy". Journal of Biological Chemistry 290 (42): 25497–25511. doi:10.1074/jbc.M115.681445. PMID 26338703.
- ↑ Fujiwara, Y; Kiyota, N; Tsurushima, K; Yoshitomi, M; Horlad, H; Ikeda, T; Nohara, T; Takeya, M et al. (2012). "Tomatidine, a tomato sapogenol, ameliorates hyperlipidemia and atherosclerosis in apoE-deficient mice by inhibiting acyl-CoA:cholesterol acyl-transferase (ACAT)". Journal of Agricultural and Food Chemistry 60 (10): 2472–9. doi:10.1021/jf204197r. PMID 22224814.
- ↑ "Tomatidine enhances lifespan and healthspan in C. elegans through mitophagy induction via the SKN-1/Nrf2 pathway". Scientific Reports 7: 46208. April 2017. doi:10.1038/srep46208. PMID 28397803. Bibcode: 2017NatSR...746208F.
- ↑ "Tomatidine suppresses osteoclastogenesis and mitigates estrogen deficiency-induced bone mass loss by modulating TRAF6-mediated signaling". FASEB Journal 33 (2): 2574–2586. February 2019. doi:10.1096/fj.201800920R. PMID 30285579.
- ↑ "Tomatidine Alleviates Osteoporosis by Downregulation of p53". Medical Science Monitor 26: e923996. April 2020. doi:10.12659/MSM.923996. PMID 32300098.
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