Андрографидин Е

Substance identification

Andrographidine E is a flavone glycoside from the Andrographis paniculata plant, 5-(beta-D-glucopyranosyloxy)-7,8-dimethoxy-2-(2-methoxyphenyl)-4H-1-benzopyran-4-one. CAS number 113963-41-0, formula C24H26O11.

Physico-chemical characteristics

• Molecular weight: 490.5
• Exact weight: 490.147522
• PSA Specifications: 157.28
• XLogP3: 0.22
• Density: 1.449±0.06 g/cm3 (predicted)
• Melting point: 126–130 °C (solvent: methanol, CAS 67-56-1)
• Boiling point: 779.5±60.0 °C (predicted)
• Flash point: 267.4±26.4°C
• Refractive index: 1.627

Plant source and substance class

Andrographidin E was isolated from the root of Andrographis paniculata (Acanthaceae family) and was first described along with andrographidin A (flavanone glycoside) and andrographidines B, C, D, F (flavone glycosides) in a phytochemical study in 1987. Belongs to the class of flavone glycosides - methoxylated flavone, glycosylated with glucose at position 5.

Biological significance

Flavone glycosides of andrographis root, including andrographidin E, are considered as phytochemical markers of the authenticity of Andrographis paniculata plant materials, widely used in traditional medicine in the treatment of infectious diseases, along with the main active ingredient of the plant, andrographolide.

Traditional uses of the plant

Andrographis paniculata is known in traditional medicine of India and Southeast Asia as the “king of bitters” and is used as an antipyretic and anti-cold remedy; standardized extracts of the plant are used in over-the-counter medications against the symptoms of acute respiratory viral infections. Although the main active ingredient of andrographis is the diterpene lactone andrographolide, the flavone glycosides of the root, including andrographidin E, serve as additional phytochemical markers of the quality and authenticity of the raw material.

Biosynthesis of the flavonoid skeleton

The flavone skeleton of andrographidin E is biosynthesized in plants from phenylpropanoid and polyketide precursors through a chalcone step, followed by cyclization to flavan, oxidation to flavone, and methoxylation of aromatic rings; glycosylation with a glucose residue at position 5 completes the biosynthesis, increasing the water solubility of the final compound.

Structural feature

A distinctive feature of andrographidin E among natural flavonoids is the presence of an ortho-methoxyphenyl substituent (2-methoxyphenyl) at position 2 of the flavan ring instead of the more common para-substituted phenyl fragment characteristic of most flavones; This substitution is atypical for plant flavonoids and distinguishes the andrographidine series from structurally related glycosides of other species.

Application and storage

Used as an analytical standard for phytochemical standardization of Andrographis paniculata root raw materials. Store in a sealed container protected from light at a low temperature.