Каулилексин С

Description

Caulilexin C is a phytoalexin from the cruciferous family (Brassicaceae) with antifungal activity. It is formed in the plant in response to infection by fungal pathogens Rhizoctonia solani and Sclerotinia sclerotiorum from metabolites of methoxyglucobrassicin.

Basic Attributes

• CAS No.: 30536-48-2
• Chemical formula: C11H10N2O
• Molecular weight: 186.2099
• Accurate weight: 186.21
• PSA Specifications: 38
• XLogP3: 2.25

Physico-chemical characteristics

• Density: 1.1±0.1 g/cm3
• Boiling point: 350.7±34.0 °C at 760 mmHg.
• Flash point: 165.9±25.7°C
• Refractive index: 1.580

Chemical structure

The systematic name is 1-methoxy-1H-indol-3-acetonitrile (2-(1-methoxy-1H-indol-3-yl)acetonitrile). The molecule is an indole derivative with an N-methoxy group on the nitrogen atom of the indole ring and an acetonitrile substituent in the 3-position.

Biosynthesis and biological activity

It is formed from desulfo derivatives of methoxyglucobrassicin - cruciferous glucosinolate - under the action of enzymes of fungal pathogens that attack the plant. Causes complete inhibition of the growth of Rhizoctonia solani at a concentration of 0.5 mM and has less effect on Leptosphaeria maculans (77% inhibition), exhibiting slightly more pronounced antifungal activity than the related phytoalexin arvelexin. Additionally inhibits the human acyl-CoA cholesterol transferase enzymes hACAT1 and hACAT2 at a concentration of 100 μg/ml.

Scope of application

It is used as an object for studying the mechanisms of induced defense of plants of the Brassicaceae family against fungal pathogens and as a reference compound in screening inhibitors of cholesterol metabolism (ACAT).

Glucosinolate defense pathway

Cruciferous plants store biologically inert glucosinolates in undamaged tissues—sulfur-containing secondary metabolites that are hydrolyzed by the enzyme myrosinase when the cell is damaged. Methoxyglucobrassicin is one of the indole glucosinolates in this pathway; Its desulfo derivatives, under the action of enzymes of pathogenic fungi, are converted into active phytoalexins, including caulilexin C and structurally similar camalexin, which makes this group of compounds a key element in the chemical immune defense of plants against phytopathogenic microorganisms.

Storage and transportation conditions

Store in an airtight container, in a dry, cool place, protected from light, away from heat sources - a flash point of 165.9 ± 25.7 ° C classifies the substance as flammable liquids and solid materials of moderate fire hazard. Wear gloves and safety glasses and avoid dust formation. The substance has not been assigned UN transport codes.

Dual biological significance

The combination of antifungal activity and inhibitory effect on ACAT enzymes in one molecule is relatively uncharacteristic of plant phytoalexins and makes caulilexin C an interesting object for parallel studies of plant defense chemistry and the pharmacology of cholesterol metabolism; Such “dual-functional” natural compounds often serve as a starting point for the development of highly specialized synthetic analogues optimized for one of the activities.