Тараксастерол

Description

Taraxasterol is a pentacyclic triterpene alcohol, one of the main triterpenoids of the dandelion Taraxacum officinale. The systematic designation is urs-20(30)-en-3β-ol with the 18α,19α configuration; The exocyclic double bond at C-20 distinguishes the taraxatane series from the ursane series. The historical names lactucerol, α-lactucerol, isolactucerol and saussureol reflect the isolation of the substance from lettuce and saussurea.

Identification

• CAS No.: 1059-14-9 (additional registration numbers 1392-12-7, 1400-18-6)
• Chemical formula: C30H50O
• UNII: 64SK2ERN9P
• English name: Taraxasterol
• Synonyms: (+)-taraxasterol; urs-20(30)-en-3-ol, (3β,18α,19α)-; 18α,19βH-urs-20(30)-en-3β-ol; 4-taraxasterol; isolactucerol; saussurol; α-lactucerol; lactucerol
• Section: terpenes

Basic Attributes

• Molecular Weight: 426.73
• Exact weight: 426.72
• PSA specifications: 20.23
• XLogP3: 11.06
• Density: 1.00 ± 0.1 g/cm³ (predicted)
• Melting point: 221–222 °C
• Boiling point: 488.2 ± 14.0 °C (predicted)
• Flash point: 217.0 ± 12.4 °C
• Refractive index: 1.534
• Specific rotation: D +96.3° (CHCl3)

Specific rotation of +96.3° in chloroform is a mandatory indicator for incoming control: taraxasterol is optically active, and the angle confirms the authenticity and stereochemical purity of the batch, along with a melting point of 221–222 °C.

Mechanism of anti-inflammatory action

The compound interferes with the NF-κB and MAPK signaling cascades. In RAW 264.7 macrophages stimulated with lipopolysaccharide, taraxasterol dose-dependently reduces the production of nitric oxide, prostaglandin E2, tumor necrosis factor α, interleukin 1β and interleukin 6, and also suppresses the expression of inducible NO synthase (iNOS) and cyclooxygenase 2 (COX-2). In BV2 microglia, inhibition of the inflammatory response to lipopolysaccharide through activation of the nuclear receptor LXRα has been described. In experiments on mice, the substance protected against acute lung injury and endotoxic shock caused by lipopolysaccharide.

Scope of application

• reagent in models of inflammation, neuroinflammation and endotoxic shock
• tool for studying NF-κB, MAPK and LXRα receptor pathways
• object of research on hepatoprotection, antioxidant and antitumor effects
• standard sample for determining triterpenes in dandelion raw materials using HPLC and GC-MS methods
• marker of authenticity of medicinal plant raw materials Taraxacum

Storage and handling

Store in a closed container, in a dry and dark place. Dissolution: DMSO for cell experiments, chloroform and dichloromethane for analytics; the substance does not dissolve in water. Hanging in a fume hood, gloves.