Пектолинаригенин

Description

Pectolinarigenin is a flavone aglycone, 5,7-dihydroxy-6,4'-dimethoxyflavone. Another form of writing of the same structure: scutellarein 4',6-dimethyl ether, 6-methoxyacacetin, hydrangea. It is an aglycone of the glycoside pectolinarin: during acidic or enzymatic hydrolysis of the latter, the carbohydrate part is split off and pectolinarinin remains.

Basic Attributes

• CAS No.: 520-12-7
• Chemical formula: C17H14O6
• Molecular weight: 314.29
• Class of compounds: flavones (methoxylated derivatives of scutellarein)
• Substituent positions: hydroxyls at C-5 and C-7, methoxy groups at C-6 and C-4'

Plant sources

The main objects of isolation are species of the thistle genus: Cirsium japonicum and Cirsium chanroenicum. In the latter, the compound is described as an anti-inflammatory agent together with the glycoside pectolinarin.

Activity studied

• Anti-inflammatory effect: dual inhibition of cyclooxygenase-2 (COX-2) and 5-lipoxygenase (5-LOX), that is, simultaneous interference with the prostaglandin and leukotriene pathways
• In vitro cancer models: inhibition of hepatoma cell growth by SK-HEP-1 with an IC50 of approximately 10 µM
• Antioxidant effect: in HepG2 cells, a concentration of 10 μM reduced the accumulation of reactive oxygen species over 24 hours and increased the expression of NQO-1 and AKR1B10 proteins
• Pigmentation: in melan-a cells, a concentration of 30 µM suppressed melanin biosynthesis without signs of cytotoxicity
• Kidney fibrosis: a weakening of the process through inhibition of the TGFβ/SMAD3 and JAK2/STAT3 signaling pathways has been described

Scope of application

Analytical standard for standardization of raw materials and extracts of thistle, including control of the pectolinarin/pectolinarigenin ratio. Reference compound in pharmacological screening: test systems for COX-2 and 5-LOX, cellular models of oxidative stress, melanogenesis, fibrosis. Material for structural and functional studies of methoxylated flavones.

Storage and handling

The crystalline powder is stored in a tightly closed dark glass container in the refrigerator, limiting contact with air and light: free phenolic hydroxyls at C-5 and C-7 are oxidized. Stock solutions are usually prepared in DMSO and used fresh. Protective equipment when working: gloves, safety glasses, hanging under the hood. Suppliers do not provide a separate harmonized GHS classification for the substance.