Аглен С

Description

Aglaine C is a cyclopenta[b]benzofuran alkaloid, CAS 177468-85-8, isolated from plants of the genus Aglaia (family Meliaceae). Chemical formula C36H42N2O8, molecular weight 630.72700.

Basic Attributes

• CAS No.: 177468-85-8
• Chemical formula: C36H42N2O8
• Molecular Weight: 630.72700

Physico-chemical characteristics

• PSA Specifications: 126.79000
• XLogP3: 4.40200

Connection class

Cyclopenta[b]benzofuran lignans are a group of natural substances from the genus Aglaia, attracting attention as a source of promising leads with antitumor and insecticidal activity, as well as a pronounced antifungal effect against the pathogen of rice blast (Pyricularia grisea/oryzae). The name “aglen” (Aglaine) directly indicates the generic affiliation of the plant source - Aglaia; aglene C is one of the members of this structural family, along with the related compound aglene B, which differs in the position of substituents with a similar molecular formula.

Biological activity class

Representatives of the cyclopenta[b]benzofuran series of Aglaia (for example, didesmethylrocaglamide) have been described to inhibit cell proliferation at concentrations comparable to the effect of vinblastine sulfate. Structural and functional analysis shows that the hydroxyl group at C8b is necessary for antiproliferative activity—its methylation completely eliminates the inhibitory effect. In addition to the antitumor effect, compounds of this class have been noted to have antibacterial, antiviral and neuroprotective properties.

Class action mechanism

For rocaglamide-like compounds of Aglaia, to which aglene C structurally belongs, binding has been established with the eukaryotic translation initiation factor eIF4A: the molecule “locks” the RNA helicase on the messenger RNA and blocks the initiation of protein synthesis. This mechanism is fundamentally different from the action of classical cytostatics on DNA or the spindle and explains the interest in this class as a source of molecular probes for studying translation regulation.

Scope of application

Aglen C is used as a reference standard for phytochemical analysis of Aglaia species and as an object for screening the biological activity of cyclopenta[b]benzofuran lignans in studies of natural antitumor and antifungal compounds.

Storage and handling

The substance, like other representatives of this structural class, is stored in the form of a dry powder in a tightly closed, light-proof container at a low temperature (2–8 °C), protected from moisture, heat and direct light due to the presence of functional groups sensitive to hydrolysis and racemization. When working, use gloves and respiratory protection, prevent the formation of dust, store separately from food products and in places inaccessible to unauthorized persons.

Related connection

The closest structural analogue of aglene C is aglene B, isolated from the same plant source and having an identical gross formula C36H42N2O8 with a similar molecular weight; the difference comes down to the spatial arrangement of the substituents.