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ERGOT

Claviceps purpurea

Ergot Family [Clavicipitaceae]

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16th Aug 2011, field, Ballykeeroge, Campile, Co. Wexford, Eire. Photo: © Paula O'Meara
A toxic fungal infection which affects grasses and cereal crops such as Rye, Wheat, Barley and rarely Oat. Here infecting Cock's-foot (Dactylis glomerata), a grass.


16th Aug 2011, field, Ballykeeroge, Campile, Co. Wexford, Eire. Photo: © Paula O'Meara
It is deep-purple coloured and grows long thin extensions to the grain. Since Ergot is carried on fungal spores which infects the ovary of grasses by mimicking fertilization by pollen grains, it must have open access to the stigma.


9th Aug 2014, Hightown, Sefton Coast. Photo: © RWD
Here infecting Couch Grass (Elymus repens).


Uniquely identifiable characteristics : a purple elongated extension from the grain of grasses and cereals.

Distinguishing Feature :

Cereal grain contaminated by the ascomycete fungus Claviceps purpurea (commonly called Ergot)are the bane of farmers around the World. The sclerotia eventually fall to the ground in the autumn remaining dormant until the following spring when they re-awkaken developing fruiting bodes. The fruiting bodies produce spores which re-infect the next seasons crop of flowers in the cereal or grass. The flowers of the grass are destroyed by the fungus before producing another crop of sclerotia. If bread made from wheat (or rye) containing just a few sclerotia contaminating the grains is consumed, then a medical condition called Ergotism can result. Since the toxic ergot alkaloids it contains have a vasoconstrictive effect, circulation of blood is restricted and gangrene of the extremities (fingers and toes) can result. This condition is called ergotoxicosis (aka Ergot poisoning or 'St. Anthony's Fire'). Other effects include bodily convulsions and spasms, diarrhoea, paraesthesia (pins and needles or a burning sensation of the skin), nausea, headaches, vomiting and psychic effects such as mania and psychosis.

In cattle it can cause 'paspalum staggers'.

The infected grain can be eliminated from non-infected grains by putting the grain in water; the infected grains will float where they can be skimmed off whilst the good grain will sink.

ERGOLINE (ERGOT) ALKALOIDS


Ergotamine is an ergot alkaloid or more specifically an ergopeptine which is synthesized within the Ergot fungus and which consists of two main parts. The moiety on the left in black is based upon Lysergic Acid with an amine group replacing the hydroxyl group by which means it is joined to the moiety in blue. The blue part consists of an amalgamation of three amino acids: L-Alanine, L-PhenylAlanine and L-Proline. It is the main alkaloid produced by the fungus Ergot.

The action on the body of Ergotamine and its derivatives is manifold. Possessing a similar structure to the neurotransmitters Serotonin (aka 5-HT), Dopamine and Adrenaline (aka Epinephrine) it is able to bind to the receptors for those neurotransmitters blocking them; thus acting as agonists of those neurotransmitters.

Ergotamine is one of several similar ergopeptine alkaloids synthesized within Ergot, such as Ergokryptine (aka Ergocryptine) and Ergochristine, but they may be of less importance than Ergotamine even though their pharmacological effects are probably similar.


Lysergic Acid Diethylamide (aka LSD-25 or just LSD) is the only substance shown on this page which is NOT produced by Ergot. LSD is depicted below Ergocryptine and Ergochristine to show its greater relationship with those two substances, since both have an amine nitrogen atom upper-right. It is much more psychoactive than any substance produced by Ergot and was first synthesized in 1938 by Albert Hofmann who later, in 1943, accidentally discovered its hallucinogenic properties. It is exceedingly potent requiring an oral dose of just 20 to 30 µ-gram of the substance before any psychic effects are discernible. There are four possible stereo-isomers of LSD, but only the (+)-isomer is psychoactive.

LSD-25 was manufactured commercially as a drug for use in psychiatry but in the 1960's recreational use of the drug began. So potent were the effects that several partakers fell to their deaths in high-rise buildings believing that they could fly! It was subsequently banned, but underground use of the drug continued. And, before you ask or think, your Author has never tried any recreational drugs; they are dangerous and can have permanent effects on personality and well-being. All drugs can be dangerous without medical supervision, and there are some drugs that are life-threatening even with intense medical supervision: think of drug-testing on paid but willing and previously healthy subjects!

Like crystals of sucrose (sugar) (when crushed) crystals of LSD are triboluminescent, emitting faint flashes of light when shaken which are visible only in the dark. Unlike sucrose, LSD is also strongly fluorescent glowing blue when illuminated by UV light.




Lysergic Acid is also found in Ergot, as is Ergoline from which it is derived. Lysergic Acid is also a psychoactive substance, but it is not as potent as the diethylamide, LSD. Like LSD-25, possessing two chiral centres, it too has 4 stereoisomers. Found also in Morning Glory (Ipomoea tricolor) and several other plants not native to the UK.

Ergoline is another of several ergot alkaloids found within Ergot. Like Ergotamine it is used pharmaceutically as a vasoconstrictor since it is a Serotonin (aka 5-HT) agonist like Ergotamine and can alleviate migraines (when used with coffee) and treat some symptoms of Parkinson's disease. Synthetic derivatives of these compounds are also used to treat these ailments, with a view to reducing any un-wanted side effects that these natural substances may possess.

A STEROIDAL COMPOUND


Ergot also produces the steroidal compound Ergosterol which is also synthesized in several other fungal species, but this is not an alkaloid. It performs similar functions within Fungi and Protozoa that Cholesterol does in animals. Ergosterol is the pro-vitamin form of Vitamin D2 (aka Ergocalciferol) - simply exposing it to ultraviolet light will convert it to Vitamin D2. Vitamin D2 (but not Ergosterol) can be given to patients as a Vitamin D) supplement.

Vitamin D comes in 5 forms (vitamers): Vitamin D1 to Vitamin D5, all of which are slightly different secosteroids where one of the bonds in the steroidal rings is broken.


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ERGOT

Claviceps purpurea

Ergot Family [Clavicipitaceae]