Minor mycotoxins 221 Ergot alkaloids

The first documented epidemic of ergotism likely occurred in 944-945 AD, when some 20,000 people of the Aquitane region of France (about half of the population) died of the effects of ergot poisoning. Ergoline or ergot alkaloids were first isolated from ergot, a black tuber-like non-endophytic fungus that infects grains and causes the disease known as ergotism. More specifically, the ergot alkaloids are produced by several species of Claviceps, a genus of fungi that invades the female portion of the host plant and replaces the ovary with a mass of fungal tissue called sclerotium. The isolation by G. Barger and F.H. Carrin of ergotoxine, so named since it appeared to have more toxic effects than the therapeutic properties of ergot, was the starting point, followed by the isolation of ergotamine, the first ergot alkaloid used in therapeutic, in 1918 by A. Stoll. With the determination of the basic chemical structure of the ergot alkaloids in the early 1930s, an era of intensive exploration of synthetic derivatives began. The ergot alkaloids are indole compounds that are biosynthetically derived from L-tryptophan and represent the largest group of nitrogenous fungal metabolites found in nature. Over 80 different ergot alkaloids have been isolated, mainly from various Claviceps species (over 70 alkaloids), but also from other fungi and higher plants. In addition to the naturally occurring ergonovine (used as an oxytocic) and ergotamine (an analgesic used to control migraine), synthetic derivatives of continuing importance today are the oxytocic methergine, the antimigraine drugs dihydroergotamine and methysergide, the anti-senility nootropic (smart drug) Hydergine™ and bromocriptine, used for numerous purposes including treatment of Parkinson's disease. Newer synthetic ergolines used for Parkinson's disease include pergolide and lisuride. Perhaps the most famous ergoline derivative of all is the psychedelic drug lysergide (LSD). To sum up, the ergot alkaloids comprise the largest group of nitrogen-containing fungal compounds and are generally divided into four major groups based on their chemical similarities: (1) the clavines (agroclavine, elymoclavine and lysergol), (2) the lysergic acids, (3) the lysergic acid amides (ergine, ergonovine, methergine, methysergide and LSD and (4) the ergopeptines (ergotamine, ergovaline, a-ergosine and a-ergocryptine) [27]. Selected members of these groups of compounds are involved in either nervous or gangrenous syndromes in humans and animals that consume grains or grain products contaminated with the sclerotia of the fungus.

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