Солазонин

Description

Solasonine is a steroidal glycoalkaloid from the nightshade family. Structurally, it is a triglycoside of solasodin: a β-solatriose sugar chain, composed of galactose, glucose and rhamnose, is attached to the aglycone. Found in plants of the Solanum genus - Solanum sodomaeum (aka S. linnaeanum, devil's apple), eggplant Solanum melongena, black nightshade. Together with solamargine, it is included in the standard mixture of BEC glycoalkaloids studied in dermatology.

Identification

• CAS No: 19121-58-5
• Chemical formula: C45H73NO16
• English name: Solasonine
• EU number: 242-826-6
• Synonyms: α-solasonin, solazonin, SNB 82149
• Class: alkaloids, steroidal glycoalkaloids of the spirosolane series

Basic Attributes

• Molecular weight: 884.06
• Exact weight: 884.06
• PSA Specifications: 258.71000
• XLogP3: 0.11590
• Density: 1.42
• Melting point: 284–285 °C (with decomposition)
• Refractive index: 1.628
• Specific rotation: D23 −88° (c = 1.01 in pyridine); D22 −74.5° (c = 0.51 in methanol)

What do these numbers mean for work?

PSA 258.71 and XLogP3 0.12 are a consequence of three sugar residues: the molecule is polar, soluble in methanol, ethanol, pyridine, DMSO and water-alcohol mixtures. Melting at 284–285 °C comes with decomposition, so the value serves more as a sign of identity than as a thermal characteristic. Two specific rotation values ​​are given for different solvents and concentrations - when checking the authenticity, the measurement conditions are accurately reproduced, otherwise the results are not comparable.

Described biological activity

• Solasonine is a component of BEC, a standard mixture of solasodin glycosides (trigliosides solasonine and solamargine plus di- and monoglycosides) extracted from the fruit of Solanum sodomaeum
• A mixture of BEC at a concentration of 10% is included in Curaderm topical cream, used for skin neoplasms; BEC is also included in small quantities in formulations for treating solar keratoses
• The proposed mechanism of selectivity: binding of the glycosidic part to rhamnose-binding protein, present on tumor cells and practically absent on normal ones; The aglycone solasodine itself does not have such activity - it is caused precisely by sugar residues, including rhamnose
• Solasonine and solamargine have been shown to be cytotoxic against a number of human tumor cell lines

Scope of application

• analytical standard for the determination of glycoalkaloids in nightshade raw materials, vegetables and their processed products using HPLC-MS methods
• control of the safety of food raw materials: nightshade glycoalkaloids are standardized as natural toxicants
• studies of cytotoxicity and mechanisms of selective action of glycoalkaloids
• raw material for the production of solasodine by acid hydrolysis of the sugar part

Storage and handling

Store in a tightly closed container, in the dark and dry. Glycosidic bonds are hydrolyzed in an acidic environment and upon heating, which is taken into account during sample preparation. Treat as toxic: Solanaceous glycoalkaloids are toxic if ingested; work with gloves, avoid dust, keep records of samples.