Брейниионозид А

Description

Breinionoside A is a megastigman glycoside, a natural compound isolated from plants of the genus Breynia (Breynia officinalis, Breynia scabra), used in traditional herbal medicine in Southeast Asia. CAS 823182-23-6, chemical formula C19H32O9.

Basic Attributes

• Chemical formula: C19H32O9
• Molecular Weight: 404.45198
• Exact weight: 404.205
• PSA Specs: 157
• XLogP3: -1.8

According to primary source data: 404.45198; 404.205; -1.8.

Chemical structure

According to the IUPAC nomenclature - (4S,5R)-4-[(1E)-3-(beta-D-glucopyranosyloxy)-4-hydroxy-1-buten-1-yl]-4-hydroxy-3,3,5-trimethylcyclohexanone. The molecule belongs to the class of megastigmanes - carotenoid derivatives with a cyclohexanone core, linked to glucose through a glycosidic bond; the structure includes a butenyl linker with two hydroxyl groups and a trimethyl-substituted cyclohexanone ring, typical of this group of norisoprenoid glycosides, widely found in the plant world as products of the oxidative cleavage of carotenoids.

Biological activity

According to published research data, the compound exhibits antioxidant, anti-inflammatory and antitumor activity. The XLogP3 value of -1.8 indicates the pronounced hydrophilicity of the molecule due to the glycosidic fragment, which is consistent with the high PSA value (157) - the compound is highly soluble in polar media, which is typical for natural glycosides involved in the water transport of secondary metabolites in plant tissues. This combination of properties is characteristic of a whole class of megastigman glycosides, which are being studied as promising sources of biologically active molecules of plant origin.

Scope of application

Analytical standard for HPLC and reference material for phytochemical and pharmacological studies of extracts of plants of the genus Breynia. It is not a registered medicinal product; is used exclusively for research purposes as a marker compound for quantitative analysis of plant raw materials and as an object for studying the structure-activity relationships in the series of megastigman glycosides, as well as for standardizing herbal remedies based on Breynia officinalis, used in traditional medicine of the growing region.

Storage and transportation

As an analytical standard of natural origin, it is stored in a place protected from light and moisture at a low temperature (a refrigerator is recommended), in a sealed original container to avoid hydrolysis of the glycosidic bond and oxidation of the butenyl fragment of the molecule. Transportation of samples to analytical laboratories is carried out under the maintenance of a cold chain, which is typical for unstable natural glycosides.

Identification

Full set of reference properties: molecular formula C19H32O9, molecular weight 404.45198, exact mass 404.205, CAS 823182-23-6. The coincidence of these parameters with independent databases confirms the correct identification of megastigman glycoside isolated from plants of the genus Breynia. Additional confirmation of the structure is provided by the stereochemical designation (4S,5R) and configuration (1E) of the double bond of the butenyl linker, determined by NMR spectroscopy during the initial isolation of the compound.