Паразитозид

Description

Verminoside (listed in the original card as “Parasitoside”) is an iridoid glycoside, whose structure is a 6-caffeate catalpol, that is, caffeoylcatalpol. The molecule combines an iridoid scaffold with an epoxy ring, a β-D-glucopyranose residue, and caffeic acid linked by an ester linkage. Hence the high polarity of the connection: PSA more than 208, XLogP3 −1.81.

Basic Attributes

• CAS No: 50932-19-9 (also 70681-78-6)
• Chemical formula: C24H28O13
• Molecular weight: 524.5
• Exact weight: 524.47
• PSA Specifications: 208.13000
• XLogP3: −1.81
• Density: 1.6 ± 0.1 g/cm³
• Boiling point: 739.1 ± 60.0 °C at 760 mmHg. Art.
• Flash point: 253.2 ± 26.4 °C
• Refractive index: 1.671

Synonyms

• Verminoside, (−)-Verminoside
• Coffeeoilcatalpol
• Catalpol 6-coffee

Natural spring

The main source is Kigelia africana, Bignoniaceae, a tropical plant of traditional medicine. The main iridoids of its root and stem bark are catalpol derivatives esterified at the C6 position with phenylpropanoic acid derivatives: specioside, verminoside, minecoside, norviburtinal. Verminoside is described as the main component of the polar fruit extract of K. africana, where it is accompanied by polyphenols, in particular verbascoside; Catalpol, specioside, verminoside and caffeic acid were identified in ethanol extracts of shoots. Iridoid glucosides of this series have also been studied in species of the genus Veronica.

Activity studied

• anti-inflammatory effect: in in vitro experiments, verminoside suppressed the expression of iNOS and the release of nitric oxide in the J774.A1 macrophage line stimulated by lipopolysaccharide
• skin irritant effects were assessed in cell cultures and on reconstructed human epidermis
• the genotoxicity of verminoside and verbascoside on human lymphocytes was studied with the participation of PARP-1 and p53 proteins

Scope of application

• analytical standard for the analysis of iridoid glycosides from plant extracts
• reference compound in phytochemistry of Bignoniaceae and Scrophulariaceae
• object of research on anti-inflammatory activity and safety of plant extracts

Storage and handling

There are no hazard classifications or transport codes in the product card, and the melting point is not indicated. Store in a tightly closed container, away from light and moisture, in a cool place; glycosides with a caffeoyl moiety are sensitive to oxidation and hydrolysis. Wear gloves and safety glasses. Taking into account the published data on genotoxicity, contact with the substance should be minimized and sample selection should be carried out without dusting.