Эрисубин А

Description

Erysubin A is a natural flavonoid isolated from the stem bark of Erythrina caffra Thunb. (erythrina cape, legume family). Structurally, it belongs to furochromenones, prenylated isoflavonoids characteristic of the genus Erythrina. Full systematic name according to IUPAC: 4-hydroxy-6-(4-hydroxyphenyl)-2-(2-hydroxypropan-2-yl)furo[3,2-g]chromen-5-one, in Russian-language sources it appears as 4-Hydroxy-2-(1-hydroxy-1-methylethyl)-6-(4-hydroxyphenyl)-5H-furo[3,2-g][1]benzopyran-5-one.

Basic Attributes

• CAS No.: 221150-18-1
• Chemical formula: C20H16O6
• Molecular Weight: 352.33744
• Exact weight: 352.095
• PSA specification: 100
• XLogP3: 3.2

Chemical class and structure

Erisubin A is a furanochromen-4-one with an isopropyl hydroxylated substituent and a free phenolic group on the side aromatic ring. This structure is typical of secondary metabolites of the genus Erythrina - plants that accumulate prenylated and furanated isoflavonoids in the bark and roots as an element of chemical defense. A PSA value of 100 indicates several oxygen sites capable of hydrogen bonding (three hydroxyl groups and a carbonyl group), and an XLogP3 of 3.2 indicates a moderate lipophilicity of the molecule.

Biological activity

According to studies of the phytochemistry of the genus Erythrina, erysubin A exhibits cytotoxic activity against tumor cells of the HL-60 line (promyelocytic leukemia), with half-maximal inhibition rates in the range of 4.3–18.0 μM, depending on the experimental conditions. Related prenylated isoflavones from the same structural family (notably from Cudrania tricuspidata) exhibit a similar spectrum of activity, suggesting a common pharmacophore role for the furanochromenone core.

Scope of application

Like most rare isoflavonoids of the genus Erythrina, erisubin A is supplied as an analytical standard for pharmacological and phytochemical studies - used as a reference marker in the identification and quantification of isoflavonoids by HPLC and LC-MS methods, as well as as a research object in screening the antitumor activity of natural compounds. The relationship with other isoflavonoids of Erythrina (erisubin B and related structures of the same series) makes the substance a convenient reference compound when constructing databases of mass spectral fragmentation of furanochromenones.

Storage and handling

The substance is stored in powder form in an airtight container, in a cool, dry place, protected from direct light - the phenolic and furan fragments of the molecule are sensitive to oxidation and photodestruction. The work is carried out using standard personal protective equipment for laboratory assistants - gloves, safety glasses, no contact with skin and mucous membranes, since detailed toxicological data on the pure substance have not been published. Refrigerated storage is recommended for long-term stability of the reference sample.