Identification | Back Directory | [Name]
TOMATIDINE | [CAS]
77-59-8 | [Synonyms]
Tomatidin omatidine NSC 226903 TOMATADINE TOMATIDINE TOMATIDINE(RG) Spirosolan-3-ol Tomatidine, >98% 5alpha-Tomatidan-3beta-ol Spirosolan-3-ol,(3β,5α,22β,25S)- 22S,25S,5ALPHA-TOMATANIN-3BETA-OL Spirosolan-3-ol, (3beta,5alpha,22beta,25S)- SPIROSOLAN-3-OL-(3BETA,5ALPHA,22BETA,25ALPHA) SPIRPSOLAN-3-OL-(3BETA,5ALPHA,22BETA,25ALPHA) SPIRPSOLAN-3-OL-(3beta,5alpha,22beta,25delta) Tomatidine, 98%, from Lycopersicon esculentum Mill. | [EINECS(EC#)]
201-040-3 | [Molecular Formula]
C27H45NO2 | [MDL Number]
MFCD00075644 | [MOL File]
77-59-8.mol | [Molecular Weight]
415.65 |
Chemical Properties | Back Directory | [Melting point ]
210.5℃ | [alpha ]
D25 +8° (chloroform) | [Boiling point ]
534.2°C (rough estimate) | [density ]
1.0048 (rough estimate) | [refractive index ]
1.6840 (estimate) | [storage temp. ]
Store at -20°C | [solubility ]
DMSO : 2.86 mg/mL (6.88 mM);Water : < 0.1 mg/mL (insoluble) | [form ]
Solid | [pka]
15.14±0.70(Predicted) | [color ]
White to off-white | [LogP]
6.150 (est) |
Questions And Answer | Back Directory | [Definition]
Tomatidine is the aglycone derivative of tomatine. Tomatidine belongs to the chemical family known as Spirosolanes and Derivatives. These are steroidal alkaloids whose structure contains a spirosolane skeleton. Tomatine (the glycosylated form of tomatidine) is a mildly toxic glycoalkaloid or glycospirosolane found in the stems and leaves of tomato plants as well as in the fruit of unripened (green) tomatoes (up to 500 mg/kg).
| [Pharmaceutical Properties]
Red, ripe tomatoes have somewhat reduced amounts of tomatine and tomatidine. Both tomatine and tomatidine possess antimicrobial, antifungal and antiviral properties. Tomatidine has been shown to exhibit anti-virulence activity against normal strains of Staphylococcus aureus as well as the ability to potentiate the effect of aminoglycoside antibiotics. Recent studies have shown that tomatidine stimulates mTORC1 signaling and anabolism, leading to accumulation of protein and mitochondria, and ultimately, cell growth. Furthermore, in mice, tomatidine 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. Tomatidine has also been shown to significantly inhibit cholesterol ester accumulation induced by acetylated LDL in human monocyte-derived macrophages in a dose-dependent manner. Tomatidine also inhibits cholesterol ester 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. The oral administration of tomatidine to apoE-deficient mice significantly reduces levels of serum cholesterol, LDL-cholesterol, and the size of atherosclerotic lesions.
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Hazard Information | Back Directory | [Chemical Properties]
Crystals. Decomposes at 275–280C. | [Uses]
Tomatidine acts as an anti-inflammatory agent by blocking NF-κB and JNK signaling[1]. Tomatidine activates autophagy either in mammal cells or C elegans[2]. | [IC 50]
p65; JNK | [storage]
Store at -20°C | [Purification Methods]
Tomatidine forms plates from EtOAc. It is also purified by dissolving 80mg in *C6H6 and applying to an Al2O3 column (3.0g) and eluting with *C6H6, evaporating and recrystallising the residue three times from EtOAc. The hydrochloride has m 265-270o from EtOH and [] D 25 -5o (MeOH). [IR: Uhle J Am Chem Soc 83 1460 1961, Kessar et al. Tetrahedron 27 2869 1971, Schreiber & Adams Experientia 17 13 1961, Beilstein 27 III/IV 1950.] | [References]
[1] Chiu FL, et al. Tomatidine inhibits iNOS and COX-2 through suppression of NF-kappaB and JNK pathways in LPS-stimulated mouse macrophages. FEBS Lett. 2008 Jul 9;582(16):2407-12. DOI:10.1016/j.febslet.2008.05.049 [2] Anil Ahsan, et al. Tomatidine Protects Against Ischemic Neuronal Injury by Improving Lysosomal Function. Eur J Pharmacol. 2020 Jun 21;173280. DOI:10.1016/j.ejphar.2020.173280 |
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