Ergovalin

Structural formula
General
Surname	Ergovalin
other names	12'-Hydroxy-2'-methyl-5'α- (1-methylethyl) -ergotaman-3 ', 6', 18-trione
Molecular formula	C 29 H 35 N 5 O 5
External identifiers / databases
CAS number 2873-38-3 PubChem 104843 ChemSpider 94635 Wikidata Q5385834
properties
Molar mass	533.6 g mol −1
Physical state	firmly
Melting point	207–208 ° C (with decomposition)
safety instructions
GHS hazard labeling no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Ergovalin is a naturally occurring chemical compound from the group of ergot alkaloids . It is produced as a main alkaloid by the fungi of the genera Epichloë and Neotyphodium that live symbiotically in and on various sweet grasses .

history

Ergovalin was first described in 1964 by Albert Hofmann and co-workers as a pure synthetic product without a natural correlate known at the time. In field trials with the purple-brown ergot fungus ( Claviceps purpurea ) in 1967, ergovalin was identified as a naturally occurring alkaloid. It took over a decade to the occurrence of this alkaloid in with grass-nuclear mushroom ( Epichloë typhina ) infected grasses evidence and its importance as a major cause of fescue poisoning ( Fescue toxicosis was detected) in cattle.

Occurrence

The occurrence of Ergovalin has been proven in various sweet grasses. However, it is not the grasses that are responsible for the production of the alkaloid, but rather the fungi of the genera Epichloë and Neotyphodium that live with them in a symbiotic community . With a share of 4 percent in the alkaloid fraction, Ergovalin can also be regarded as a minor alkaloid of the purple-brown ergot fungus.

properties

Chemical and physical properties

Ergovalin gives the typical detection reactions to ergot alkaloids including the Van Urk reaction . In its physicochemical properties, it is similar to other ergot alkaloids, especially ergosine .

Stereochemistry

Ergovaline is a chiral natural product with six centers of asymmetry . In aqueous solution ergovalin tends to epimerize C8 to ergovalinine .

Biological importance

The occurrence of ergovaline in pasture grasses that are colonized with endophytic fungi of the genera Epichloë and Neotyphodium is considered to be the main cause of fescue poisoning in grazing cattle. In its symptoms, fescue poisoning is similar to ergotism in animals. In particular, the symptoms include increased body temperature, decreased weight gain, gangrene , decreased prolactin levels and decreased reproductivity.

In its pharmacology , ergovalin is similar to the ergot alkaloid ergotamine . At the molecular level, ergovalin activates the serotonin receptors 5-HT _1B and 5-HT _2A , the dopamine receptor D ₂ and α ₁ -adrenoceptors .

Individual evidence

1. ↑ ^{a b c d e} Rudolf Brunner, Peter Leopold Stütz, Hans Tscherter, Paul Albert Stadler: Isolation of ergovaline, ergoptine, and ergonine, new alkaloids of the peptide type, from ergot sclerotia . In: Canadian Journal of Chemistry . 57 (13), 1979, pp. 1638-1641, doi : 10.1139 / v79-263 .
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. ↑ PA Stadler, AJ Frey, H. Ott, A. Hofmann: The synthesis of ergosine and the valine analog of the ergotamine group. 61. Communication on ergot alkaloids . In: Helvetica Chimica Acta . 47, No. 7, 1964, pp. 1911-1921. doi : 10.1002 / hlca.19640470731 .
4. ^ Shelly G. Yates and Richard G. Powell, Analysis of ergopeptine alkaloids in endophyte-infected tall fescue . In: Journal of Agricultural and Food Chemistry . 36, No. 2, 1988, pp. 337-340. doi : 10.1021 / jf00080a023 .
5. ↑ James K. Porter, Charles W. Bacon, Joe D. Robbins, Don Betowski: Ergot alkaloid identification in clavicipitaceae systemic fungi of pasture grasses . In: J. Agric. Food Chem . 29, No. 3, 1981, pp. 653-657. doi : 10.1021 / jf00105a055 .
6. ↑ JF White Jr., G. Morgan-Jones, AC Morrow, AC: Taxonomy, life cycle, reproduction, and detection of Acremonium endophytes. . In: Agric. Ecosystems and Environ . 44, No. 13-37, 1993.
7. ↑ JR Strickland, JW Oliver, DL Cross: Fescue toxicosis and its impact on animal agriculture . In: Vet Hum Toxicol . 35, No. 5, 1993, pp. 454-464. PMID 8249272 .
8. ↑ BT Larson, DL Harmon, EL Piper, LM Griffis, LP Bush: Alkaloid binding and activation of D2 dopamine receptors in cell culture . In: J. Anim. Sci. . 77, No. 4, 1999, pp. 942-947. PMID 10328360 .
9. ↑ DC Dyer: Evidence that ergovaline acts on serotonin receptors . In: Life Sci. . 53, No. 14, 1993, pp. PL223-PL228. PMID 8371626 .
10. ↑ C. Schöning, M. Flieger, HH Pertz: Complex interaction of ergovaline with 5-HT2A, 5-HT1B / 1D, and alpha1 receptors in isolated arteries of rat and guinea pig . In: J. Anim. Sci . 79, No. 8, 2001, pp. 2202-2209. PMID 11518230 .