Tomatine

Tomatine is a glycoalkaloid, found in the tomato plant (Lycopersicon esculentum Mill.). Tomatine elicits neurotoxicity in RIP1 kinase and caspase-independent manner. Tomatine promotes the upregulation of nuclear apoptosis inducing factor (AIF) in neuroblastoma cells. Tomatine also inhibits 20S proteasome activity.

Product information

CAS Number: 17406-45-0

Molecular Weight: 1034.19

Formula: C50H83NO21

Synonym:

α-Tomatine

Lycopersicin

Tomatin

Chemical Name: (2S, 3R, 4S, 5S, 6R)-2-[(2S, 3R, 4S, 5R, 6R)-2-[(2R, 3R, 4R, 5R, 6R)-4, 5-dihydroxy-2-(hydroxymethyl)-6-[(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-yl]oxyoxan-3-yl]oxy-5-hydroxy-6-(hydroxymethyl)-4-[(2S, 3R, 4S, 5R)-3, 4, 5-trihydroxyoxan-2-yl]oxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3, 4, 5-triol

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

InChiKey: REJLGAUYTKNVJM-SGXCCWNXSA-N

InChi: InChI=1S/C50H83NO21/c1-20-7-12-50(51-15-20)21(2)32-28(72-50)14-26-24-6-5-22-13-23(8-10-48(22,3)25(24)9-11-49(26,32)4)65-45-40(63)37(60)41(31(18-54)68-45)69-47-43(71-46-39(62)36(59)34(57)29(16-52)66-46)42(35(58)30(17-53)67-47)70-44-38(61)33(56)27(55)19-64-44/h20-47,51-63H,5-19H2,1-4H3/t20-,21-,22-,23-,24+,25-,26-,27+,28-,29+,30+,31+,32-,33-,34+,35+,36-,37+,38+,39+,40+,41-,42-,43+,44-,45+,46-,47-,48-,49-,50-/m0/s1

Technical Data

Appearance: Solid Power

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

Solubility: DMSO : 250 mg/mL (241.74 mM; Need ultrasonic)

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:

Tomatine inhibits gastric carcinoma cell line (AGS), neuroblastoma cell line (SH-SY5Y) and non-small cell lung cancer cell line (A549) with IC50s of 2 µM, 1.6 µM and 1.1 µM, respectively.

References:

1. da Silva DC, et al. Neurotoxicity of the steroidal alkaloids tomatine and tomatidine is RIP1 kinase- and caspase-independent and involves the eIF2α branch of the endoplasmic reticulum. J Steroid Biochem Mol Biol. 2017 Jul;171:178-186.

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