Catalogue number C108001
Chemical nameSolasonine
CAS Number19121-58-5
SynonymsSolasonin; Tomatine solaradixine; alpha-Solasonine; beta-D-Galactopyranoside, (3beta,22alpha,25R)-spirosol-5-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-(beta-D-glucopyranosyl-(1-3))- (9CI); (3beta,22alpha,25S)-spirosol-5-en-3-yl 6-deoxyhexopyranosyl-(1->2)-[hexopyranosyl-(1->3)]hexopyranoside
Molecular WeightC45H73NO16
Physical DescriptionPowder
SolventChloroform, Dichloromethane,DMSO
StorageStored at 2-8°C, Protected from air and light, refrigerate or freeze

Solasonine is a poisonous chemical compound. It is a glycoside of solasodine. Solasonine was one component of the unsuccessful experimental cancer drug candidate Coramsine.

Two genetically diverse strains of Trypanosoma cruzi were tested in vitro for susceptibility to the solanum-derived triglycoside alkaloids solasonine and solamargine. Cytolytic assays were performed on epimastigotes (EMs) and bloodstream form trypomastigotes (BSFs) lifecycle stages by using serial dilutions of each alkaloid. Each alkaloid effectively lysed both lifecycle stages, although solasonine routinely required higher concentrations to induce similar results. EMs demonstrated greater resistance to cytolysis than BSFs at equal concentrations of either alkaloid. No significant resistance could be correlated to parasite strain. The reported synergistic cytolytic effects observed upon compounding solasonine and solamargine together were also tested. We failed to identify any cytolytic synergism in cultures of EMs or BSFs. The role of rhamnose-binding proteins (RBPs) in mediating cytolysis was investigated through competitive inhibition experiments. The addition of exogenous L: -rhamnose to the media failed to reduce parasite attrition independent of the parasite lifecycle stage. Based on these results, we suggest the mechanisms involved in cytolysis of T. cruzi by solasonine and solamargine are largely independent of rhamnose receptor-specific interactions.

Experiments with solasonine at pH 6 and 8 suggest that the unprotonated form of the glycoalkaloids appears to be involved in the membrane effects. The nature of the carbohydrate side-chains of the steroidal glycosides governs relative potencies. The possible significance of the findings to food safety and plant physiology and possible application of the membrane assays to bacterial toxins are discussed.

References1. Phytochemistry, 1988, 27(2), 603-605.
2. Phytochemistry, 1980, 19(9), 2017-2020.
3. J. Chem. Ecol., 2006, 32(11), 2405-2416.
4. Food and Chemical Toxicology, 1998, 36(5), 383-389.
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