Лейкомизин

Description

Leukomysin (leukodin, desacetoxymatricarin) is a sesquiterpene lactone of the Guianan series from plants of the genus Artemisia. The skeleton is azuleno[4,5-b]furan-2,7-dione with three methyl groups; configuration (3S,3aS,9aS,9bS), lactone ring at 6α,7β position. The reaction center of the molecule is a cyclopentenone, capable of attaching thiol groups to proteins; the biological activity of the substance is associated with this. Known as an anti-inflammatory and angioprotective compound.

Basic Attributes

• CAS No: 17946-87-1
• Chemical formula: C15H18O3
• Molecular Weight: 246.304
• Exact weight: 246.30
• UNII: 1G2W00IRUI
• DSSTox ID: DTXSID20170810
• PSA specifications: 43.4
• XLogP3: 1.6

Physico-chemical characteristics

• Melting point: 202–203 °C
• Specific rotation: D24 +52.5° (c = 1 in chloroform)
• Impact cross-section: 154.2 Ų [M+H]⁺ (CCS type: TW, method - polyalanine and drug standards calibrated)

Biological activity

• suppression of cyclooxygenase COX-2, IC50 129 μg/ml
• suppression of inducible NO synthase, IC50 160 μg/ml
• moderate antioxidant and antimicrobial activity (isolated, among other things, from Artemisia iwayomogi)
• angioprotective effect

Scope of application

• standard sample for the analysis of sesquiterpene lactones in wormwood raw materials using HPLC and LC-MS methods
• studies of anti-inflammatory mechanisms, regulation of inflammatory gene expression
• starting material in the preparation of dehydroleucodine and other semisynthetic derivatives

Storage and handling

Sesquiterpene lactones alkylate thiols, so skin sensitization is possible: wear gloves, avoid contact with skin and inhalation of dust. Keep the container closed, protect from heat and light.