Tomatidine

Names

[ CAS No. ]:
77-59-8

[ Name ]:
Tomatidine

[Synonym ]:
(3b,5a,22b,25S)-Spirosolan-3-ol
(3β,5α,22β,25S)-spirosolan-3-ol
Spirosolan-3-ol, (3β,5α,22β,25S)- (9CI)
5alpha-Tomatidan-3beta-ol
(22S,25S)-5α-spirosolan-3β-ol
(2S,4aS,4bS,5'S,6aS,6bR,7S,8S,9aS,10aS,10bR,12aS)-4a,5',6a,7-Tetramethyloctadecahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-8,2'-piperidin]-2-ol
(2S,4aS,4bS,5'S,6aS,6bR,7S,8S,9aS,10aS,10bR,12aS)-4a,5',6a,7-Tétraméthyloctadécahydrospiro[naphto[2',1':4,5]indéno[2,1-b]furane-8,2'-pipéridin]-2-ol
5a,20bF,22aF,25bF,27-azaspirostan-3b-ol
(3β,5α,25S)-Spirosolan-3-ol
Tomatidine
Spirosolan-3-ol, (3β,5α,25S)-
Tomatidin

Biological Activity

[Description]:

Tomatidine acts as an anti-inflammatory agent by blocking NF-κB and JNK signaling.

[Related Catalog]:

Signaling Pathways >> MAPK/ERK Pathway >> JNK

Signaling Pathways >> NF-κB >> NF-κB

Natural Products >> Alkaloid

Research Areas >> Inflammation/Immunology

[Target]

p65

JNK

[In Vitro]

Tomatidine decreases inducible NO synthase and COX-2 expression through suppression of I-κBα phosphorylation, NF-κB nuclear translocation and JNK activation, which in turn inhibits c-jun phosphorylation and Oct-2 expression. Tomatidine, solasodine and diosgenin (40 μM) show 66%, 22% and 41% inhibition of nitrite production, respectively. The iNOS protein is barely detectable in unstimulated cells but markedly increases after LPS treatment, and Tomatidine causes dose-dependent inhibition of LPS-induced iNOS expression. p65 is the major component of NF-κB in LPS-stimulated macrophages, the effect of Tomatidine on p65 DNA-binding activity is determined. In the presence of Tomatidine at 10-40 μM, the binding activity of NF-κB is suppressed in a dose-dependent manner. Tomatidine inhibits the phosphorylation of I-κB, blocks the I-κB production, and furthermore suppresses p65 NF-κB translocation to the nucleus and modulated binding activity[1].

[Cell Assay]

RAW 264.7 cells, derived from murine macrophages, are cultured in DMEM supplemented with 10% endotoxin-free, heat-inactivated fetal calf serum, Penicillin (100 units/mL), and Streptomycin (100 μg/mL) in a 5% CO2 atmosphere at 37°C in a humidified incubator. For all assay, cell is plated at 2×105 cells/cm2 in culture dishes or plates. Treatment with vehicle (0.1% DMSO or 0.1% ethanol), test compounds and/or LPS is carried out under serum-free conditions[1].

[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.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
527.2±25.0 °C at 760 mmHg

[ Melting Point ]:
210.5℃

[ Molecular Formula ]:
C₂₇H₄₅NO₂

[ Molecular Weight ]:
415.652

[ Flash Point ]:
272.7±23.2 °C

[ Exact Mass ]:
415.345032

[ PSA ]:
41.49000

[ LogP ]:
6.15

[ Vapour Pressure ]:
0.0±3.1 mmHg at 25°C

[ Index of Refraction ]:
1.560

[ Storage condition ]:
-20°C

Safety Information

[ Risk Phrases ]:
23/25

[ Safety Phrases ]:
1-45

[ RIDADR ]:
UN 1544

Related Compounds

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