Цинатрин А

Description

Cinatrin A (CAS 136266-33-6) is a natural lactone of the cinatrine family, phospholipase A2 inhibitors, chemical formula C18H26O8.

Basic Attributes

• CAS No: 136266-33-6
• Chemical formula: C18H26O8
• Molecular Weight: 370.395
• Exact mass: 370.16276778 g/mol
• PSA: 130 Ų

Substance class

Spiro-gamma-dilactone (gamma-lactone), a derivative of 1,2,3,5-tetra- or 1,2,3(1,2,4)-trihydroxypentadecane-1,2,3-tricarboxylic acids. One of five members of the cynathrine family - A, B, C1, C2, C3, differing from each other in the degree of hydroxylation and the type of lactone cycle.

Source of receipt

Isolated from the fermentation broth of the fungus Circinotrichum falcatisporum RF-641 along with other cynatrines during targeted screening of producers of phospholipase A2 inhibitors and subsequent study of the taxonomy and cultivation conditions of the producing strain.

Mechanism of action and biological activity

Cinathrine A, along with cynathrine B and C3, dose-dependently inhibits phospholipase A2 isolated from rat platelets. The action is associated with blocking the hydrolysis of cell membrane phospholipids by this enzyme, which stops the release of arachidonic acid, a precursor of pro-inflammatory eicosanoids (prostaglandins, leukotrienes), which play a role in the development of inflammatory reactions.

Implications for Research

Like other cynatrines, the compound is considered as a model inhibitor of phospholipase A2 in the study of the molecular mechanisms of inflammation and in the search for new anti-inflammatory substances based on lactone structures of microbial origin. Comparison of the activity of cynathrine A with other members of the family (cynathrines B, C1, C2, C3) allows researchers to establish the dependence of biological activity on the structure of the molecule.

Scope of application

It is used in biochemical and pharmacological studies as a reference inhibitor of phospholipase A2, as well as as an object for studying structure-activity relationships within the cinatrine family.

Storage and transportation

Store dry, at a low temperature, in a sealed container protected from light - as is customary for unstable microbial lactones that are sensitive to hydrolysis of the lactone cycle upon contact with moisture. Data on UN transport codes, hazard class and GHS phrases for cynathrine A are not available in available sources and are not provided.

Comparison within a family

Cinathrine A differs from cinatrine B by one hydroxyl group in the pentadecane chain (C18H26O8 versus C18H28O8), which is reflected in the molecular weight (370.395 versus 372.411) and, according to published data, in the degree of phospholipase A2 inhibition. A side-by-side comparison of cinatrines A, B, C1, C2, and C3 reveals how small changes in parent chain hydroxylation alter biological activity within the same structural family.