Цинатрин Б

Description

Cinatrin B (CAS 136266-34-7) is a natural lactone, one of the members of the cinatrine family, inhibitors of the phospholipase A2 enzyme. Chemical formula C18H28O8.

Basic Attributes

• CAS No: 136266-34-7
• Chemical formula: C18H28O8
• Molecular Weight: 372.411
• Exact mass: 372.17841785 g/mol
• PSA: 130 Ų

Substance class

Spiro-gamma-dilactone (or gamma-lactone), a derivative of polyhydroxypentadecane-1,2,3-tricarboxylic acids. Belongs to the cinatrine family (cinatrines A, B, C1, C2, C3) - a group of structurally similar lactones of microbial origin, differing from each other in the degree and position of hydroxylation of the original pentadecane chain.

Source of receipt

Isolated from the fermentation broth of the fungus Circinotrichum falcatisporum RF-641 during targeted screening of producers of phospholipase A2 inhibitors, carried out while studying the taxonomy and cultivation conditions of this strain.

Mechanism of action and biological activity

Cynatrine B inhibits phospholipase A2 isolated from rat platelets in a dose-dependent manner, and also inhibits the activity of porcine pancreatic phospholipase A2 and cobra venom phospholipase A2 (Naja naja). Inhibition of this enzyme stops the release of arachidonic acid from membrane phospholipids, a key step in the inflammatory cascade prior to the synthesis of prostaglandins and leukotrienes, which explains the research interest in cinnatrines as potential anti-inflammatory agents.

Implications for chemical synthesis

The complex spirolactone structure of the molecule made cynathrin B the object of enantiospecific total synthesis: (-)-cynathrin B is obtained from D-arabinose, while the spirolactone system was formed by the Ireland-Claisen rearrangement followed by hydrolysis and stereoselective iodolactonization - this confirms the absolute configuration of the natural compound and opens the way to the preparation of its derivatives and analogues for structural-activity research.

Scope of application

Used in pharmacological research as a biochemical tool to study the regulation of phospholipase A2 and associated inflammatory processes, as well as a reference compound in the development of new inhibitors of this enzyme and in comparing activity within the cinatrine family.

Storage and transportation

The substance is stored dry at a low temperature, in a sealed container protected from light, as is customary for labile natural lactones that are prone to hydrolysis of the lactone cycle upon contact with moisture. Information about UN transport codes, hazard classes and GHS phrases for this compound was not found in available sources; they are not given in order to avoid unreliable data.

Comparison within a family

Among the five known cinatrines (A, B, C1, C2, C3), cinatrine C3 is considered the most potent inhibitor of phospholipase A2 in published data, while cinatrine A and cinatrine B exhibit comparable but less pronounced activity. Comparison of structures - the number and position of hydroxyl groups on the pentadecane chain, as well as the type of lactone ring (spiro-dilactone versus monocyclic gamma-lactone) - provides the basis for establishing the structure dependence of activity within this family of natural inhibitors isolated from the same producer.