Соламаргин

Description

Solamargine is a steroidal glycoalkaloid from the nightshade family, a triglycoside of solasodine. The sugar part is β-chacotriose: a glucose residue and two rhamnose residues. It is the composition of the sugar chain that distinguishes solamargine from solasonine, which has the same aglycone and a different trisaccharide (galactose, glucose, rhamnose). Sources: Solanum sodomaeum (S. linnaeanum), black nightshade, Solanum melongena eggplant peel.

Identification

• CAS No.: 20311-51-7
• Chemical formula: C45H73NO15
• English name: Solamargine
• UNII: 8KG991E7BN
• NSC number: 407810
• Synonyms: α-solamargin, solamargin, δ-solanigrin
• Class: alkaloids, steroidal glycoalkaloids of the spirosolane series

Basic Attributes

• Molecular Weight: 868.064
• Exact weight: 868.06
• PSA Specifications: 239
• XLogP3: 1.1
• Density: 1.4 ± 0.1 g/cm³
• Melting point: 301 °C
• Refractive index: 1.619

What do these numbers mean for work?

PSA 239 with XLogP3 1.1 - the molecule is polar due to three sugar residues and works in methanol, ethanol, DMSO, pyridine and water-alcohol mixtures. The high melting point of 301 °C is typical for glycosides with a developed network of hydrogen bonds. The density is given with a spread - the calculated value.

Described biological activity

• Solamargine is part of BEC, a standard mixture of solasodin glycosides extracted from the fruit of Solanum sodomaeum; in addition to it, the mixture includes solasonin, as well as solasodin di- and monoglycosides
• A 10% BEC cream (Curaderm) has been studied in benign and malignant skin lesions; BEC is used in low concentrations for solar keratoses
• Selectivity is associated with rhamnose-binding protein: it is expressed on tumor cells and is practically absent on normal cells, and the rhamnose sugar chain acts as a ligand for it. Aglycone without sugars does not exhibit such activity
• Solamargine has been shown to be cytotoxic against a number of human tumor cell lines, including hepatocellular carcinoma - when isolating glycoalkaloids from the peel of eggplant fruits

Scope of application

• analytical standard for the determination of glycoalkaloids in nightshade raw materials, vegetables and processed products by HPLC-MS methods
• control of the content of natural toxicants in food raw materials
• studies of cytotoxicity and mechanisms of selective action of glycoalkaloids
• raw material for the production of solasodine by acid hydrolysis

Storage and handling

The container is tightly closed, the room is dark and dry. Glycosidic bonds are cleaved by acids and are a sample preparation factor when heated. Solanaceous glycoalkaloids are toxic when ingested: work with gloves, without dust, taking into account weighing.