About 50, including: Claviceps africana Claviceps fusiformis Claviceps paspali Claviceps purpurea Claviceps sorghi Claviceps zizaniae Claviceps lutea. Ergot pron. The most prominent member of this group is Claviceps purpurea "rye ergot fungus". This fungus grows on rye and related plants, and produces alkaloids that can cause ergotism in humans and other mammals who consume grains contaminated with its fruiting structure called ergot sclerotium.

Claviceps includes about 50 known species, mostly in the tropical regions. Economically significant species include C.

It affects oats only rarely. An ergot kernel, called a sclerotiumdevelops when a spore of fungal species of the genus Claviceps infects a floret of flowering grass or cereal. The infection process mimics a pollen grain growing into an ovary during fertilization.

ergot structure

Infection requires that the fungal spore have access to the stigma ; consequently, plants infected by Claviceps are mainly outcrossing species with open flowerssuch as rye Secale cereale and ryegrasses genus Lolium. The proliferating fungal mycelium then destroys the plant ovary and connects with the vascular bundle originally intended for seed nutrition.

The first stage of ergot infection manifests itself as a white soft tissue known as sphacelia producing sugary honeydew, which often drops out of the infected grass florets. This honeydew contains millions of asexual spores conidiawhich insects disperse to other florets. Later, the sphacelia convert into a hard dry sclerotium inside the husk of the floret. At this stage, alkaloids and lipids accumulate in the sclerotium.

Claviceps species from tropic and subtropic regions produce macro- and microconidia in their honeydew. Macroconidia are able to produce secondary conidia. A germ tube emerges from a macroconidium through the surface of a honeydew drop and a secondary conidium of an oval to pearlike shape is formed, to which the contents of the original macroconidium migrates. Secondary conidia form a white, frost-like surface on honeydew drops and spread via the wind.

No such process occurs in Claviceps purpureaClaviceps grohiiClaviceps nigricansand Claviceps zizaniaeall from northern temperate regions. When a mature sclerotium drops to the ground, the fungus remains dormant until proper conditions such as the onset of spring or a rain period trigger its fruiting phase. It germinates, forming one or several fruiting bodies with heads and stipesvariously coloured resembling a tiny mushroom. In the head, threadlike sexual spores form, which are ejected simultaneously when suitable grass hosts are flowering.

Ergot infection causes a reduction in the yield and quality of grain and hay, and if livestock eat infected grain or hay it may cause a disease called ergotism.

Black and protruding sclerotia of C. However, many tropical ergots have brown or greyish sclerotia, mimicking the shape of the host seed.

For this reason, the infection is often overlooked. Insects, including flies and moths, carry conidia of Claviceps species, but it is unknown whether insects play a role in spreading the fungus from infected to healthy plants. The evolution of plant parasitism in the Clavicipitaceae dates back at least million years, to the early-mid Cretaceous.

Ergometrine

An amber fossil discovered in preserves a grass spikelet and an ergot-like parasitic fungus. The fossil shows that the original hosts of the Clavicipitaceae could have been grasses. The discovery also establishes a minimum time for the conceivable presence of psychotropic compounds in fungi.

Ergotism is the name for sometimes severe pathological syndromes affecting humans or other animals that have ingested plant material containing ergot alkaloid, such as ergot-contaminated grains. The Hospital Brothers of St. Anthonyan order of monks established inspecialized in treating ergotism victims [14] with balms containing tranquilizing and circulation-stimulating plant extracts. The common name for ergotism is "St.Ergotamine is an ergopeptine and part of the ergot family of alkaloids ; it is structurally and biochemically closely related to ergoline.

It possesses structural similarity to several neurotransmittersand has biological activity as a vasoconstrictor.

Analysis of Ergot Alkaloids

It is used medicinally for treatment of acute migraine attacks sometimes in combination with caffeine.

Medicinal usage of ergot fungus began in the 16th century to induce childbirthyet dosage uncertainties discouraged the use.

It has been used to prevent post-partum hemorrhage bleeding after childbirth. It was first isolated from the ergot fungus by Arthur Stoll at Sandoz in and marketed as Gynergen in Ergotamine, dihydroergotamine, and methysergide, as well as the "triptan" sumatriptan, are all agonists for these receptors.

Ergotamine and DHE were originally developed as sympatholytics, but it was later concluded that their therapeutic efficacy was probably mediated by vasoconstriction of cranial blood vessels. As expected from this pharmacologic profile, their most important pharmacologic effect is arterial constriction. Ergotamine is a secondary metabolite natural product and the principal alkaloid produced by the ergot fungus, Claviceps purpureaand related fungi in the family Clavicipitaceae.

These precursor compounds are the substrates for the enzyme, tryptophan dimethylallyltransferasecatalyzing the first step in ergot alkaloid biosynthesis, i.

Further reactions, involving methyltransferase and oxygenase enzymes, yield the ergolinelysergic acid. Lysergic acid LA is the substrate of lysergyl peptide synthetasea nonribosomal peptide synthetasewhich covalently links LA to the amino acids, L - alanineL - prolineand L - phenylalanine. Ergotamine continues to be prescribed for migraines and cluster headaches. Contraindications include: atherosclerosisBuerger's syndromecoronary artery diseasehepatic disease, pregnancy, pruritusRaynaud's syndromeand renal disease.

In the United States, ergotamine is available as a suppository, a sublingual tablet, and a tablet, sometimes in combination with caffeine. For the best results, dosage should start at the first sign of an attack. Side effects of ergotamine include nausea and vomiting. At higher doses, it can cause raised arterial blood pressurevasoconstriction including coronary vasospasm and bradycardia or tachycardia.

Severe vasoconstriction may cause symptoms of intermittent claudication. Ergotamine is a controlled substance in the United States as it is a commonly used precursor for the production of LSD. From Wikipedia, the free encyclopedia. IUPAC name. Interactive image.Ergoline derivatives comprise a diverse group of chemical compounds whose structural skeleton is the alkaloid ergoline. Ergoline derivatives are used clinically for the purpose of vasoconstriction 5-HT 1 receptor agonists— ergotamine and in the treatment and alleviation of migraines used with caffeine and Parkinson's disease.

Some ergoline alkaloids found in ergot fungi are implicated in the condition ergotismwhich causes convulsive and gangrenous symptoms. Others are psychedelic substances, including LSD and some alkaloids in Argyreia nervosaIpomoea tricolor and related species. In addition to the naturally occurring ergonovine used as an oxytocic and ergotamine a vasoconstrictor used to control migrainesynthetic derivatives of importance are the oxytocic metherginethe anti-migraine drugs dihydroergotamine and methysergidehydergine a mixture of dihydroergotoxine mesylates, INN : ergoline mesylatesand bromocriptineused 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 is the psychedelic drug LSD. Ergolines can pass into breast milk and should not be used during breastfeeding. Ergoline alkaloids are found in lower fungi [4] and some species of flowering plants : the Mexican species Turbina corymbosa and Ipomoea tricolor of the Convolvulaceae morning glory family, the seeds of which were identified as the psychedelic plant drugs known as "ololiuhqui" and "tlitliltzin", respectively.

The Hawaiian species Argyreia nervosa includes similar alkaloids. It is possible, though not proven, that ergine or isoergine are responsible for the psychedelic effects. There may be a fungal origin of the ergoline alkaloids also in the Convolvulaceae. Like the ergot alkaloids in some monocot plants, the ergoline alkaloids found in the plant Ipomoea asarifolia Convolvulaceae are produced by a seed-transmitted endophytic clavicipitaceous fungus.

Ergoline alkaloids were first isolated from ergota fungus that infects grain and causes the disease ergotism. Ergot also has a long history of medicinal use, which led to attempts to characterize its activity chemically.

This began in with the isolation by G. Barger and F. Carr of ergotoxine, so-named since it appeared to exhibit more of the toxicity of ergot than its therapeutic qualities. The isolation of ergotamine in by Arthur Stoll made possible the first therapeutic use of isolated ergoline alkaloids. With the determination of the basic chemical structure of the ergot alkaloids in the early s, an era of intensive exploration of synthetic derivatives began. There are 3 main classes of ergoline derivatives, the water-soluble amides of lysergic acidthe water-insoluble ergopeptines i.

The relationship between these compounds is summarized in the following structural formula and table of substitutions. Peptide ergot alkaloids or ergopeptines also known as ergopeptides are ergoline derivatives that contain a tri peptide structure attached to the basic ergoline ring in the same location as the amide group of the lysergic acid derivatives.

A variety of modifications to the basic ergoline are seen in nature, for example agroclavineelymoclavinelysergol. Those deriving from dimethylergoline are referred to as clavines.Ergoline derivatives comprise a diverse group of chemical compounds whose structural skeleton is the alkaloid ergoline. Ergoline derivatives are used clinically for the purpose of vasoconstriction 5-HT 1 receptor agonists— ergotamine and in the treatment and alleviation of migraines used with caffeine and Parkinson's disease.

Some ergoline alkaloids found in ergot fungi are implicated in the condition ergotismwhich causes convulsive and gangrenous symptoms. Others are psychedelic substances, including LSD and some alkaloids in Argyreia nervosaIpomoea tricolor and related species. In addition to the naturally occurring ergonovine used as an oxytocic and ergotamine a vasoconstrictor used to control migrainesynthetic derivatives of importance are the oxytocic metherginethe anti-migraine drugs dihydroergotamine and methysergidehydergine a mixture of dihydroergotoxine mesylates, INN : ergoline mesylatesand bromocriptineused 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 is the psychedelic drug LSD. Ergolines can pass into breast milk and should not be used during breastfeeding.

Ergoline alkaloids are found in lower fungi [4] and some species of flowering plants : the Mexican species Turbina corymbosa and Ipomoea tricolor of the Convolvulaceae morning glory family, the seeds of which were identified as the psychedelic plant drugs known as "ololiuhqui" and "tlitliltzin", respectively. The Hawaiian species Argyreia nervosa includes similar alkaloids.

It is possible, though not proven, that ergine or isoergine are responsible for the psychedelic effects. There may be a fungal origin of the ergoline alkaloids also in the Convolvulaceae. Like the ergot alkaloids in some monocot plants, the ergoline alkaloids found in the plant Ipomoea asarifolia Convolvulaceae are produced by a seed-transmitted endophytic clavicipitaceous fungus.

Ergoline alkaloids were first isolated from ergota fungus that infects grain and causes the disease ergotism. Ergot also has a long history of medicinal use, which led to attempts to characterize its activity chemically. This began in with the isolation by G. Barger and F. Carr of ergotoxine, so-named since it appeared to exhibit more of the toxicity of ergot than its therapeutic qualities. The isolation of ergotamine in by Arthur Stoll made possible the first therapeutic use of isolated ergoline alkaloids.

With the determination of the basic chemical structure of the ergot alkaloids in the early s, an era of intensive exploration of synthetic derivatives began.

There are 3 main classes of ergoline derivatives, the water-soluble amides of lysergic acidthe water-insoluble ergopeptines i. The relationship between these compounds is summarized in the following structural formula and table of substitutions. Peptide ergot alkaloids or ergopeptines also known as ergopeptides are ergoline derivatives that contain a tri peptide structure attached to the basic ergoline ring in the same location as the amide group of the lysergic acid derivatives.

A variety of modifications to the basic ergoline are seen in nature, for example agroclavineelymoclavinelysergol. Those deriving from dimethylergoline are referred to as clavines. Examples of clavines, include festuclavinefumigaclavine Afumigaclavine B and fumigaclavine C. Some synthetic ergoline derivatives do not fall easily into any of the above groups. Some examples are:. From Wikipedia, the free encyclopedia.

Redirected from Ergot alkaloid.Ergot of Rye - I: Introduction and History. Ergot of Rye is a plant disease that is caused by the fungus Claviceps purpurea. The so-called ergot that replaces the grain of the rye is a dark, purplish sclerotium Figs. The sexual stage consists of stroma in which the asci and ascospores are produced. Although the ergot is far different in appearance than the true grain, its occurrence was so common that it was thought to be part of the rye plant, until the 's, when the true nature of the ergot was understood.

Although the common name indicates that this fungus is a disease of rye, it also can infect several other grains, with rye being the most common host for this species. It is the ergot stage of the fungus that contains a storehouse of various compounds that have been useful as pharmaceutical drugs as well as mycotoxins that can be fatal when consumed.

The proportion of the compounds produced will vary within the species. Thus, the victim that has lived through ergot poisoning once may experience different symptoms if they were unfortunate enough to consume ergot for a second time. This species was also the original source from which LSD was first isolated.

It is believed that symptoms of ergotism have been recorded since the middle ages and possibly even as far back as ancient Greece.

There are approximately 35 species of Clavicepswith most occurring on grasses. All species form the sclerotium that is described above, and will form the same types of compounds. Although some research have been carried out in these other species, the bulk of our knowledge and most of our research has been concerned with Ergot of Rye.

how to grow ergot

Today, we will go over the consequences of consumption of the ergot stage of Claviceps purpurea and describe some of the impact that it has had. Poisoning attributed to Ergot of Rye is referred to as ergotism.

ergot structure

Although this fungus is recognized as one species, there are two sets of symptoms that can be found in cases where serious poisoning as occurred: convulsive and gangrenous ergotism. Convulsive ergotism is characterized by nervous dysfunction, where the victim is twisting and contorting their body in pain, trembling and shaking, and wryneck, a more or less fixed twisting of the neck, which seems to simulate convulsions or fits.

In some cases, this is accompanied by muscle spasms, confusions, delusions and hallucinations, as well as a number of other symptoms. In gangrenous ergotism, the victim may lose parts of their extremities, such as toes, fingers, ear lobes or in more serious cases, arms and legs may be lost.

This type of ergotism causes gangrene to occur by constricting the blood vessels leading to the extremities. Because of the decrease in blood flow, infections occur in the extremities, accompanied by burning pain. Once gangrene has occurred, the fingers, toes, etc. If the infected extremities are not removed, infection can spread further up the extremity that has been infected. Gangrenous ergotism is common in grazing, farm animals.

This link shows pictures of a cow in which the gangrenous ergotism has occurred in the ear and hooves. Today, we will cover some examples of gangrenous and convulsive ergotism and the impact that it has had in different places and times.

Discovering The Cause of Ergotism. The occurrence of Claviceps purpurea must have began with the cultivation of rye since it was far more common on that host than in other grains. Rye was a weed grain and occurred wherever wheat was cultivated. Often it became the dominant plant when wheat fields were abandoned. Thus, in a way, where ever civilization became established, rye would follow it there. However, it was not cultivated for food until some time, in the early Middle Ages around the 5th.

Centuryin what is now eastern Europe and western Russia. It was in the Rhine Valley, in A. It was at this time that the symptoms but not the knowledge of what caused the symptoms from consumption of ergot was called Holy Fire.Ergotism pron.

It is also known as ergotoxicosisergot poisoningand Saint Anthony's Fire. The symptoms can be roughly divided into convulsive symptoms and gangrenous symptoms. Convulsive symptoms include painful seizures and spasmsdiarrheaparesthesiasitching, mental effects including mania or psychosisheadaches, nausea and vomiting.

Usually the gastrointestinal effects precede central nervous system effects. The dry gangrene is a result of vasoconstriction induced by the ergotamine - ergocristine alkaloids of the fungus. It affects the more poorly vascularized distal structures, such as the fingers and toes. Symptoms include desquamation or peeling, weak peripheral pulsesloss of peripheral sensation, edema and ultimately the death and loss of affected tissues.

Vasoconstriction is treated with vasodilators. Historically, eating grain products, particularly rye, contaminated with the fungus Claviceps purpurea was the cause of ergotism. The toxic ergoline derivatives are found in ergot-based drugs such as methylergometrineergotamine or, previously, ergotoxine. The deleterious side-effects occur either under high dose or when moderate doses interact with potentiators such as erythromycin.

The alkaloids can pass through lactation from mother to child, causing ergotism in infants. Dark-purple or black grain kernels, known as ergot bodies, can be identifiable in the heads of cereal or grass just before harvest. In most plants the ergot bodies are larger than normal grain kernels, but can be smaller if the grain is a type of wheat.

A larger separation between the bodies and the grain kernels show the removal of ergot bodies during grain cleaning. Removal of ergot bodies is done by placing the yield in a brine solution; the ergot bodies float while the healthy grains sink. Rotating crops using non-susceptible plants helps reduce infestations since ergot spores only live one year. Crop rotation and deep tillage, such as deep moldboard ploughingare important components in managing ergot, as many cereal crops in the 21st century are sown with a "no-till" practice new crops are seeded directly into the stubble from the previous crop to reduce soil erosion.

Chemical controls can also be used, but are not considered economical especially in commercial operations, and germination of ergot spores can still occur under favorable conditions even with the use of such controls. Epidemics of the disease were identified throughout history, though the references in classical writings are inconclusive.

Rye, the main vector route for transmitting ergotism, was not grown much around the Mediterranean. When Fuchs in separated references to ergotism from erysipelas and other afflictions, he found the earliest reference to ergotism in the Annales Xantenses for the year "a great plague of swollen blisters consumed the people by a loathsome rot, so that their limbs were loosened and fell off before death.

In the Middle Ages, the gangrenous poisoning was known as "holy fire" or "Saint Anthony's fire", named after monks of the Order of St. Anthony who were particularly successful at treating this ailment. The 12th century chronicler Geoffroy du Breuil of Vigeois recorded the mysterious outbreaks in the Limousin region of France, where the gangrenous form of ergotism was associated with the local Saint Martial.

Likewise, an outbreak in Paris ca. The blight, named cockspur [5] due to the appearance of infected grains, was identified and named by Denis Dodartwho reported the relation between ergotized rye and bread poisoning in a letter to the French Royal Academy of Sciences in John Ray mentioned ergot for the first time in English the next year.

Notable epidemics of ergotism occurred up into the 19th century. Fewer outbreaks have occurred since then due to rye being carefully monitored in developed countries. However, a severe outbreak of something akin to ergot poisoning occurred in the French village of Pont-Saint-Esprit inresulting in five deaths. There is evidence [8] of ergot poisoning serving a ritual purpose in the ritual killing of certain bog bodies.

When milled, the ergot is reduced to a red powder, [10] obvious in lighter grasses but easy to miss in dark rye flour.Ergometrinealso known as ergonovineis a medication used to cause contractions of the uterus to treat heavy vaginal bleeding after childbirth. Common side effect include high blood pressurevomiting, seizuresheadache, and low blood pressure.

Ergometrine was discovered in It has a medical use in obstetrics to facilitate delivery of the placenta and to prevent bleeding after childbirth by causing smooth muscle tissue in the blood vessel walls to narrow, thereby reducing blood flow. It is usually combined with oxytocin Syntocinon as syntometrine. It can induce spasm of the coronary arteries.

ergot structure

Possible side effects include nauseavomitingabdominal pain, diarrheaheadachedizzinesstinnituschest painpalpitationbradycardiatransient hypertension and other cardiac arrhythmiasdyspnearashesand shock. Anthony's fire": prolonged vasospasm resulting in gangrene and amputations; hallucinations and dementia; and abortions.

ergot structure

Gastrointestinal disturbances such as diarrhea, nausea, and vomiting, are common. While it acts at alpha-adrenergicdopaminergicand serotonin receptors the 5-HT 2 receptorit exerts on the uterus and other smooth muscles a powerful stimulant effect not clearly associated with a specific receptor type. The pharmacological properties of ergot were known and had been utilised by midwives for centuries, but were not thoroughly researched and publicised until the early 20th century. However, its abortifacient effects and the danger of ergotism meant that it was only prescribed cautiously, as in the treatment of postpartum haemorrhage.

From Wikipedia, the free encyclopedia. IUPAC name. Interactive image. Archived from the original on Retrieved 1 December Weinheim: Wiley-VCH. Chichester: Wiley. World Health Organization model list of essential medicines: 21st list Geneva: World Health Organization.

International Drug Price Indicator Guide. Retrieved 25 December Jpn Heart J. Cochrane Database Syst Rev. Acetergamine Ergometrine Syntometrine Methylergometrine. Oxytocin Carbetocin Demoxytocin. Diphenidine Ephenidine Fluorolintane Methoxphenidine. Dextrallorphan Dextromethorphan Dextrorphan Racemethorphan Racemorphan. Apomorphine Aporphine Bromocriptine Cabergoline Lisuride Memantine Nuciferine Pergolide Phenethylamine Piribedil Pramipexole Ropinirole Rotigotine Salvinorin A Also indirect D 2 agonists, such as dopamine reuptake inhibitors cocainemethylphenidatereleasing agents amphetaminemethamphetamineand precursors levodopa.

Glaucine Isoaminile Noscapine Pukateine. Serotonin receptor modulators. Antagonists: Atypical antipsychotics e. Antagonists: AR-A Beta blockers e. Agonists: BRL Ergolines e. Antagonists: Metitepine methiothepin. Antagonists: Mianserin Metitepine methiothepin. Agonists: 4-Methylaminorex Aminorex Amphetamines e. Antagonists: Agomelatine Atypical antipsychotics e. Agonists: 2Cs e.