Festuclavine

• Dihydroagroclavin
• 6.8 β - Dimethylergolin

Approximately 242 ° C

• Insoluble in petroleum ether; slightly soluble in chloroform, ethyl acetate, acetone, methanol, ethanol, pyridine, dilute acids

45 mg · kg -1 ( LD50, mouse, ip)

Template: Infobox chemical / molecular formula search available

Festuclavine is a naturally occurring chemical compound. It is a scoring to the group of clavines alkaloid, which is produced by numerous parasitic on grasses ergot fungi and other filamentous fungi. Its name derives from its occurrence in infected with ergot fungus Festuca rubra ( red fescue Common ).

Occurrence

Festuclavine possesses due to its key role in the biosynthesis of ergot alkaloids from Dihydroclavin type a fairly wide distribution within the group of ergot alkaloids producing organisms. Originally festuclavine in ergot infested grasses of the genera as well as the gloss grasses ( Phalaris ) and the crest couch grass ( Agropyron ) was found. In addition to various ergot fungi of the genera Claviceps and Epichloë the phylogenetically more distant representatives of Trichocomaceae family, especially from the genera Aspergillus and Penicillium, as producers of this Clavins apply.

Particularly striking is the occurrence of festuclavine and other Clavinen in wind plants. Here they are both part of their toxic principle and the psychotropic effect of the ritual used Windengewächs Ololiuqui drugs (especially from Turbina corymbosa ) and Tlitliltzin (Ipomoea violacea and other Ipomoea species). For the occurrence of festuclavine in wind plants infested with ergot fungi of the genus Periglandula is blamed.

Biosynthesis

Biosynthesis festuclavine is a number of enzymes, by a so-called cluster EAS genes ( ergot alkaloid synthesis genes = Mutterkornalkaloidsynthesegene ) are coded catalyzed.

In a first reaction step, the amino acid tryptophan dimethylallyl with the involvement of the gene product of dmaw, the Dimethylallyltryptophansynthase, prenylated to Dimethylallyltryptophan. A methyltransferase catalyzes the N-methylation to N- Methyldimethylallyltryptophan. The ring closure of the C ring to chanoclavine -I is made under the catalysis of Chanoclavinsynthase. Oxidation of chanoclavine -I leads to chanoclavine -I -aldehyde, which is cyclized with the participation of the protein encoded by the gene EASA Chanoclavincyclase with ring closure of the D ring and reduction of the double bond to festuclavine.

Festuclavine is also the starting point for the biosynthesis of many other alkaloids. So pass the Fumigaclavine from Aspergillus fumigatus and other species and the Dihydromutterkornalkaloide that are produced by Claviceps africana, for example, on the festuclavine. In this way festuclavine occupies a key position in the biosynthesis of Dihydroclavine.

Properties

Chemical and physical properties

Festuclavine is readily soluble in chloroform, ethyl acetate, acetone, methanol, ethanol, pyridine, dilute acids. Its solubility in benzene, toluene and diethyl ether, however, is limited. Petroleum ether festuclavine is insoluble.

Festuclavine are the typical test reactions to ergot alkaloids. These include in particular the Van Urk reaction and detection with Keller's reagent.

Stereochemistry

Festuclavine is a chiral natural product with three asymmetric centers. Festuclavine has an all- R configuration. As a further diastereomers of Festuclavins its C -8 epimer Pyroclavin and its C-10 epimer Costaclavin in nature occur. Without meaning, however, is the C- 5 epimer.

Pharmacology

Festuclavine is an antagonist at α1 -adrenoceptors and 5- HT2 receptors. In higher doses festuclavine has antimicrobial and cytostatic.