Festuclavin

from Wikipedia, the free encyclopedia
Structural formula
Festuclavin structural formula
General
Surname Festuclavin
other names
  • Dihydroagroclavine
  • 6.8 β- dimethylergoline
  • (6a R , 9 R , 10a R ) -7,9-dimethyl-6,6a, 8,9,10,10a-hexahydro-4 H -indolo [4,3- fg ] quinoline
Molecular formula C 16 H 20 N 2
External identifiers / databases
CAS number 569-26-6
PubChem 332915
Wikidata Q15113508
properties
Molar mass 240.3 g mol −1
Melting point

approx. 242 ° C

solubility
safety instructions
GHS hazard labeling
no classification available
Toxicological data

45 mg kg −1 ( LD 50 ,  mouse ,  ip )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Festuclavin is a naturally occurring chemical compound . It is an alkaloid belonging to the group of clavins , which is produced by numerous ergot fungi and other sac fungi that parasitize on sweet grasses . Its name is derived from its occurrence in Festuca rubra (common red fescue), which is infected with ergot fungi.

Occurrence

Due to its key position in the biosynthesis of ergot alkaloids of the dihydroclavin type, Festuclavin is quite widespread within the group of organisms that produce ergot alkaloids. Originally festuclavine was in ergot and in infected grasses of the genera of Phalaris ( Phalaris ) and the comb couch grass ( Agropyron found). In addition to various ergot fungi of the genera Claviceps and Epichloë , the phylogenetically more distant representatives of the Trichocomaceae family , in particular from the genera Aspergillus and Penicillium , are considered producers of this clavin.

The occurrence of festuclavin and other clavins in bindweed plants is particularly noticeable . Here they are both part of their toxic principle and the psychotropic effect of the ritually used bindweed herbs ololiuqui (especially from Turbina corymbosa ) and tlitliltzin ( Ipomoea violacea and other Ipomoea species). An infestation with ergot fungi of the genus Periglandula is held responsible for the occurrence of festuclavin in bindweed plants .

biosynthesis

The biosynthesis of festuclavine is by a series of enzymes , the so-called by a cluster EAS - Gene ( ergot alkaloid synthesis genes are encoded = Mutterkornalkaloidsynthesegene), catalyzed.

In a first reaction step, the amino acid tryptophan is prenylated to dimethylallyltryptophan with dimethylallylpyrophosphate with the participation of the gene product of dmaW , dimethylallyltryptophan synthase . A methyl transferase catalyzes the N -methylation to N -methyldimethylallyltryptophan. The C-ring closes to form chanoclavin -I with catalysis by chanoclavin synthase. Oxidation of chanoclavin-I leads to chanoclavin-I-aldehyde, which is cyclized to festuclavin with the participation of the chanoclavin cyclase encoded by the easA gene, with closure of the D ring and reduction of the double bond.

Festuclavin is also the starting point for the biosynthesis of numerous other alkaloids. The fumigaclavins from Aspergillus fumigatus and other species as well as the dihydromutter corn alkaloids, for example produced by Claviceps africana , are derived from festuclavin. In this way, Festuclavin takes a key position in the biosynthesis of the dihydroclavins.

properties

Chemical and physical properties

Festuclavin is easily soluble in chloroform , ethyl acetate , acetone , methanol , ethanol , pyridine , dilute acids . However, its solubility in benzene , toluene and diethyl ether is limited. Festuclavin is insoluble in petroleum ether.

Festuclavin gives the typical detection reactions to ergot alkaloids. These include, in particular, the Van Urk reaction and detection with Keller's reagent .

Stereochemistry

Costaclavin

Festuclavin is a chiral natural product with three centers of asymmetry . Festuclavin has an All- R configuration. The other diastereomers of Festuclavin are its C-8 epimer pyroclavin and its C-10 epimer costaclavin . In contrast, the C-5 epimer is of no importance.

pharmacology

Festuclavin is an antagonist of α 1 -adrenoceptors and 5-HT 2 -receptors . In higher doses, Festuclavin has an antimicrobial and cytostatic effect.

Individual evidence

  1. ↑ a b c d e f Abe M, Yamatodani S: Isolation of two further water-soluble ergot alkaloid . In: J. Agr. Chem. Soc. (Japan) . 24, 1954, p. 501.
  2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
  3. ↑ Drug Research . Vol. 35, pp. 1760, 1985.
  4. ↑ Entry on Festuclavin in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  5. ↑ Anatoly G. Kozlovsky: Producers of ergot alkaloids out of the Claviceps genus . In: Vladimir Kren, Ladislav Cvak (eds.): Ergot: The Genus Claviceps. Medicinal and Aromatic Plants - Industrial Profiles . CRC Press, 2004, ISBN 0-203-30419-5 , pp. 479-499.
  6. ↑ Eckart Eich: Tryptophan-derived alkaloid . In: Solanaceae and convolvulaceae - secondary metabolites: biosynthesis, chemotaxonomy, biological and economic significance . Springer, 2008, ISBN 3-540-74540-8 , pp. 213-260.
  7. ↑ Steiner U, Leibner S, Schardl CL, Leuchtmann A, Leistner E: Periglandula, a new fungal genus within the Clavicipitaceae and its association with Convolvulaceae . In: Mycologia . 103, No. 5, 2011, pp. 1133-1145. doi : 10.3852 / 11-031 . PMID 21558502 .
  8. ↑ Tudzynski P Hölter K, Correia T, Arntz C, N Grammel, cellar U: Evidence for ergot alkaloid of gene cluster in Claviceps purpurea . In: Mol Gen Genet . 261, No. 1, 1999, pp. 133-141. PMID 10071219 .
  9. ↑ Panaccione DG: Origins and significance of ergot alkaloid diversity in fungi . In: FEMS Microbiol Lett . 251, No. 1, 2005, pp. 9-17. PMID 16112823 .
  10. ↑ Cheng JZ, Coyle CM, Panaccione DG, O'Connor SE: Controlling a structural branch point in ergot alkaloid biosynthesis . In: J Am Chem Soc . 132, No. 37, 2010, pp. 12835-12837. doi : 10.1021 / ja105785p . PMID 20735127 .
  11. ↑ Pertz H: Naturally occurring clavines: antagonism / partial agonism at 5-HT2A receptors and antagonism at alpha 1-adrenoceptors in blood vessels . In: Planta Med . 62, No. 5, 1996, pp. 387-392. PMID 8923801 .
  12. ↑ Eich E, Eichberg D: On the antibacterial effect of clavine alkaloids and their partially synthetic derivatives . In: Planta Med . 45, No. 7, 1982, pp. 146-147. PMID 17396846 .
  13. ↑ Glatt H, Pertz H, Kasper R, Eich E: Clavine alkaloids and derivatives as mutagens detected in the Ames test . In: Anticancer Drugs . 3, No. 6, 1992, pp. 609-614. PMID 1288732 .