Аглен Б

Description

Aglaine B is a cyclopenta[b]benzofuran alkaloid, CAS 177262-32-7, isolated from plants of the genus Aglaia (family Meliaceae). Chemical formula C36H42N2O8, molecular weight 630.72700, exact mass 630.29411630.

Basic Attributes

• CAS No: 177262-32-7
• Chemical formula: C36H42N2O8
• Molecular Weight: 630.72700
• Exact weight: 630.29411630

Physico-chemical characteristics

• PSA Specifications: 126.79000
• XLogP3: 4.40200

Connection class

Like Aglen C, the compound belongs to the Aglaia cyclopenta[b]benzofuran lignans, a structural class that includes natural lactones with a five-membered cyclopentane ring fused to a benzofuran moiety. The name “aglen” reflects the origin of the substance from plants of the genus Aglaia. The molecular formula of aglene B is identical to the formula of aglene C (C36H42N2O8), and the difference between the two compounds lies in the spatial arrangement of substituents and stereocenters with similar masses (630.72700 for both).

Biological activity class

Aglaia cyclopenta[b]benzofurans are the subject of active study as a source of natural leads with antitumor, insecticidal and antifungal activity, in particular against the rice blast pathogen Pyricularia grisea/oryzae. For representatives of the class that have been most studied in this regard (didesmethyl rocaglamide), suppression of cell proliferation has been demonstrated at the level of action of vinblastine sulfate; The structural element determining the activity is the hydroxyl group at C8b - its methylation eliminates the effect. Separately, antibacterial, antiviral and neuroprotective properties are described for compounds of this series.

Class action mechanism

Rockaglamide-like compounds of Aglaia, to which aglene B belongs, bind to the eukaryotic translation initiation factor eIF4A and “lock” its RNA helicase activity on messenger RNA, stopping the initiation of protein synthesis. This mechanism of action distinguishes the class from classical antitumor drugs acting on DNA or the spindle, and makes compounds of this series an object of study in molecular translational biology.

Scope of application

Aglen B is used as a phytochemical reference standard in studying the composition of Aglaia species, as well as as an object for screening the antitumor and antifungal activity of cyclopent[b]benzofuran alkaloids.

Storage and handling

The substance 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. Work with the powder using gloves and respiratory protection, excluding the formation of dust and contact with skin, and store separately from food products.

Sample preparation

Solutions for quantitative and qualitative analysis are prepared immediately before measurement: long-term storage of the solution increases the risk of hydrolysis of the lactone fragment of the molecule and racemization of its chiral centers, which distorts the results of chromatographic determination.