Ergovaline

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Ergovaline

Ergovaline is an ergopeptine and one of the ergot alkaloids. It is found in ergot-infected cereal grains, especially rye, and in the endophyte-infected grasses. Ergovaline is a potent vasoconstrictor, and its presence in endophyte-infected grasses can cause a variety of diseases in grazing animals, collectively known as ergotism.

Chemistry

Ergovaline is a member of the ergopeptine group of ergot alkaloids, which are derived from the amino acid tryptophan. It is a complex molecule with a unique structure that includes a tripeptide moiety and a tetracyclic ergoline ring system. The ergoline ring system is responsible for the biological activity of ergovaline and other ergot alkaloids.

Biosynthesis

The biosynthesis of ergovaline involves several steps and is carried out by the fungus Claviceps purpurea, which infects cereal grains and grasses. The process begins with the conversion of tryptophan to chanoclavine by the enzyme dimethylallyltryptophan synthase. Chanoclavine is then converted to agroclavine, which is further converted to elymoclavine. Elymoclavine is finally converted to ergovaline by a series of enzymatic reactions.

Toxicity

Ergovaline is a potent vasoconstrictor, meaning it can constrict blood vessels and reduce blood flow. This can lead to a variety of health problems in animals that consume ergovaline-contaminated feed, including gangrene of the extremities, abortion, reduced milk production, and loss of weight. The condition caused by ergovaline and other ergot alkaloids is known as ergotism.

Detection and Control

Ergovaline can be detected in feed samples using various analytical methods, including high-performance liquid chromatography (HPLC) and liquid chromatography-mass spectrometry (LC-MS). Control of ergovaline contamination involves managing the growth of endophyte-infected grasses and the use of ergot-free cereal grains in animal feed.

See Also

• Ergotamine
• Ergocryptine
• Ergotism
• Ergoline