Tomatidine hydrochloride

Tomatidine hydrochloride acts as an anti-inflammatory agent by blocking NF-κB and JNK signaling. Tomatidine hydrochloride activates autophagy either in mammal cells or C elegans.

Product information

CAS Number: 6192-62-7

Molecular Weight: 452.11

Formula: C27H46ClNO2

Chemical Name: (1R, 2S, 4S, 5'S, 6S, 7S, 8R, 9S, 12S, 13S, 16S, 18S)-5', 7, 9, 13-tetramethyl-5-oxaspiro[pentacyclo[10.8.0.0, .0, .0, ]icosane-6, 2'-piperidin]-16-ol hydrochloride

Smiles: Cl.C[C@@H]1CN[C@@]2(CC1)O[C@H]1C[C@H]3[C@@H]4CC[C@H]5C[C@@H](O)CC[C@]5(C)[C@H]4CC[C@]3(C)[C@H]1[C@@H]2C

InChiKey: SXXHVPYRDFJKPG-VXJLCZPPSA-N

InChi: 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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: Ethanol : 3.45 mg/mL (7.63 mM; Need ultrasonic) DMSO : < 1 mg/mL (ultrasonic;adjust pH to 9 with NaOH) (insoluble or slightly soluble)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

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.

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.
2. Anil Ahsan, et al. Tomatidine Protects Against Ischemic Neuronal Injury by Improving Lysosomal Function. Eur J Pharmacol. 2020 Jun 21;173280.

Products are for research use only. Not for human use.