Ergovaline

12' -hydroxy -2' -methyl- 5'α -(1- methylethyl) ergotaman -3 ', 6' ,18 -trione

Fixed

207-208 ° C ( with decomposition)

Template: Infobox chemical / molecular formula search available

Ergovaline is a naturally occurring chemical compound from the group of ergot alkaloids. It is produced as a main alkaloid of the symbiotic in and on various grasses Epichloë and Neotyphodium fungal genera.

History

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

Occurrence

The presence of ergovaline was detected in various grasses. But not the grasses, but living with them in a symbiotic community fungi of the genera Epichloë and Neotyphodium are responsible for the production of the alkaloid. With a share of 4 percent in the alkaloid ergovaline can moreover be regarded as an alkaloid of the Purple Brown ergot fungus.

Properties

Chemical and physical properties

Ergovalin are the typical test reactions to ergot alkaloids, including the Van Urk reaction. In its physicochemical properties it is similar to other ergot alkaloids, particularly ergosine.

Stereochemistry

Ergovaline is a chiral natural product with six asymmetric centers. In aqueous solution Ergovalin tends to C8 epimerization to Ergovalinin.

Biological Significance

The presence of ergovaline in pasture grasses that are colonized with endophytic fungi of the genera Epichloë and Neotyphodium is regarded as the main cause of fescue poisoning in cattle. In his symptoms, fescue poisoning similar to ergotism in animals. Symptoms may include in particular increased body temperature, decreased weight gain, gangrene, decreased prolactin levels and decreased reproductive performance.

In its pharmacology is similar to the ergot alkaloid ergovaline, ergotamine. At the molecular level Ergovalin enabled, among other things, the serotonin receptors 5 - HT1B and 5- HT2A, dopamine D2 receptor and α1 -adrenoceptors.