Тайваньгомофлавон А

Description

Taiwan homoflavone A is a biflavonoid isolated from Wilson's capitate Cephalotaxus wilsoniana. The molecule is a dimer formed by the combination of two flavonoid units: 7,4'-dimethoxy-5-hydroxy-6-methylflavone and 5,7,4'-trihydroxyflavone (apigenin). The bond between them is formed between the C-3' atom of the methoxyphenyl ring of the first unit and the C-8 atom of the chromene ring of the second. According to the structural classification, the compound belongs simultaneously to hydroxyflavones, methoxyflavones, biflavonoids and biaryls; the presence of a methyl group on the carbon atom of the ring makes it a C-methylated biflavone. Exhibits cytotoxic activity.

Basic Attributes

• CAS No: 265120-00-1
• Chemical formula: C33H24O10
• Molecular weight: 580.53766
• Exact weight: 580.137
• PSA Specifications: 152
• XLogP3: 6.1

Structure and its features

The compound is built from two different flavonoid blocks, rather than two identical ones. The first block is a flavone with two methoxy groups (at positions 7 and 4'), a hydroxyl at position 5, and a methyl group at C-6. The second block is apigenin, a flavone with three free hydroxyls at positions 5, 7 and 4'. The blocks are connected through a C-3'-C-8 biaryl bond, that is, directly between the carbon atoms of two aromatic systems, without an oxygen bridge. This bond rigidly fixes the relative positions of the halves of the molecule.

Biological activity

• cytotoxic activity - a property established by isolating a compound from Cephalotaxus wilsoniana
• Classification roles: metabolite and antitumor agent

Scope of application

• reference substance in the phytochemical study of biflavonoids of the genus Cephalotaxus
• standard for chromatographic methods for determining biflavones in plant materials
• object of preclinical studies of antitumor activity

What follows from the molecular characteristics

The lipophilicity of XLogP3 is 6.1 with a polar surface of 152, a profile characteristic of dimeric polyphenols with partially methylated hydroxyls. Methylation of two of the five possible hydroxyl positions increases lipophilicity compared to fully hydroxylated biflavones of the same series: the structurally similar taiwanhomoflavone B has an XLogP3 value of 5.7 with the same polar surface. The practical consequence is the same for both compounds - poor solubility in water; the working medium is dimethyl sulfoxide or water-alcohol mixtures.

Storage and handling

The card contains only molecular characteristics. Melting point, solubility, density, refractive index, GHS classification, labels, transport codes and toxicity data are not available - they are taken from the safety data sheet and certificate of analysis of the batch. Polyphenols are oxidized by atmospheric oxygen and destroyed by light, so the product should be stored in a dark glass container, tightly closed, in a cool place; Prepare solutions before use. Weigh and dissolve under a hood, wearing gloves and safety glasses; Taking into account cytotoxic activity, access is limited, waste is collected separately.