Ergot structure

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Ergot structure

Ergometrinealso known as ergonovineis a medication used to cause contractions of the uterus to treat heavy vaginal bleeding after childbirth.

ergot structure

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. 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. 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.

ergot structure

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.

Claviceps purpurea

Serotonin receptor modulators. Antagonists: Atypical antipsychotics e. Antagonists: AR-A Beta blockers e. Agonists: BRL Ergolines e.Use NCBI link to find]. NCBI: [1]. The fungus Claviceps purpurea is responsible for causing the fungal disease ergot of rye. Claviceps is capable of replacing the seeds of many forage grasses and cereal grains with alkaloid containing sclerotia. These sclerotia, which are purplish-brown masses of hardened mycelia, can cause human poisoning, called ergotism, when consumed.

It is hypothesized that ergotism caused "bewitchment," the strange behavior reported during the Salem Witch Trials 3. Symptoms documented included hallucinations, vomiting, psychosis, and delirium. Of the approximate 40 species of Claviceps described, C. Ascospores are dispersed by wind and land on plant stigma alongside pollen grains.

These spores infect the ovary and hyphae begin to develop. Following hyphal development, conidia are formed and dispersed with the help of insects who are attracted to a sticky honeydew created by a combination of fungal conidia and sap from the host plant.

The infected plant ovary is then replaced by sclerotia, or ergot, which consists of hardened mycelia used for protection, dormancy, and survival. When the crop is harvested, the sclerotia is harvested along with the grain, leading to contamination. Contamination comes from alkaloids present in the sclerotia, which are categorized into three groups: clavines, ergopeptines, and amides of lysergic acid, the latter being a derivative used to produce LSD 4.

Organism: Claviceps purpures Strain: In historical accounts ergotism caused hallucinations, fever, convulsions, loss of fertility, miscarriage, and loss of limbs in humans. Due to modern management strategies, the risk of exposure to ergotism today is low in comparison to historical times 1. Today, compounds isolated from Claviceps have been used to create medicines to treat migraine headaches, heavy menstrual bleeding, bleeding after child-birth, and neurological and cardiovascular disorders.

Schumann, G. Ergot of rye. The Plant Health Instructor.A brief discussion of the hallucinogenic properties of lysergic acid diethylamide is also featured.

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Students at the University of Pittsburgh receive an introduction to pharmacognosy and natural products during their first-professional year in an introductory course in Drug Development. The role of natural products as both historical and continuing sources of drugs, as well as sources of precursors for semisynthetic modification and sources of probes for yet undiscovered drug moieties, is emphasized. In addition, students are continually exposed to the concept that complex natural products are a result of secondary metabolism, and as such are produced via the unique combination of a relatively limited number of structurally unsophisticated primary metabolites.

As a consequence, secondary metabolites have a more limited distribution in nature, and their occurrence is an expression of the individuality of the parent species. Although it has been speculated that the 4,year old Eleusinian Mysteries of ancient Greece were connected with ergot-induced hallucinations, the earliest authenticated reports of the effects of ergot occurred in Chinese writings in approximately BC, when the substance was used in obstetrics.

Analysis of Ergot Alkaloids

A magic spell found in a small temple in Mesopotamia dating to BC referred to abnormally infested grain as mehruwhile Sumerian clay tablets of the same period described the reddening of damp grain as samona. In BC the Hearst Papyrus of Egypt described a particular preparation in which a mixture of ergot, oil, and honey was recommended as a treatment for hair growth.

In BC Hippocrates furnished a description of corn blight and subsequently described ergot as melanthionnoting its use to halt postpartum hemorrhage. Around BC the Greeks concluded that barley was more susceptible than wheat to rust infections, and that windy fields had less rust than damp, shady low-lying ones. The first documented epidemic of ergotism likely occurred in AD, when some 20, people of the Aquitane region of France about half of the population died of the effects of ergot poisoning.

Finally, inergot was recognized as a fungus by von Munchhausen. Epidemics of ergot poisoning, often termed ergotismcontinued to ravage continental Europe through the Middle Ages and outbreaks of ergotism occurred in Germany in, and These epidemics were due, in part, to the fact that rye was grown in larger quantities in medieval times, and many people particularly those less wealthy ingested contaminated rye flour. These outbreaks were characterized by the production of 2 distinct forms of toxic reactions, with these reactions now being understood to be attributable to the effects of the alkaloids produced by the parasitic ergot fungus which was contained within the ergot fungal body sclerotium.

The fungus-contaminated grain crops along with their fungal metabolites ergot alkaloids were ingested with flour prepared from the grain. Hands, feet, and whole limbs would swell, producing a violent, burning pain that ultimately culminated in the separation of a dry gangrenous limb usually a foot at a joint, without pain or loss of blood. Anthony's Fire was so named because the Order of St. The second form of ergotism, also known as the convulsive form Ergotismus convulsivuswas particularly common in Germany and was typically characterized by the development of delirium and hallucinations, accompanied by rigid, extremely painful flexed limbs, muscle spasms, convulsions, and severe diarrhea.

The term ignis sacer holy fire was commonly employed for epidemics of ergotism, but numerous other terms, mainly of Latin derivation, were coined, including: Ignis judicalis, Ignis occultus, Morbus hic tabificus, Mortifer ardor, Pestilens ille morbus, Pestis ignaria, Plaga ignis, Plaga illa, and Plaga invisibilis.

Other terms for ergotism included names of regions Mal de Cologne and of saints to whom an appeal for help was made St. Anthony, St. Martin, St. In scientists at Marburg University observed that signs of ergotism often appeared after blighted rye grains were consumed, and that blight was promoted by cold, damp growing seasons. In it was observed that feeding of blighted grain to animals produced an illness similar to human ergotism and by the end of the 18th century poisoning was demonstrated in animals.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.

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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.

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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.

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. 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.A related genus, Clavicepsincludes C.

Earth tongue is the common name for the more than 80 Geoglossum species of the order Helotiales. They produce black to brown, club-shaped fruiting structures on soil or on decaying….


The disease decreases the production of viable grains by infected plants and can contaminate harvests. Ergot is commonly associated with rye infected by C. For example, ergot of…. Hallucinations also can be induced by input overload produced mechanically, such as bombarding several sensory systems with intense stimuli simultaneously e.

ergot structure

During the 19th century it was recognized that molds are responsible for such diseases as yellow-rice toxicoses in Japan and alimentary toxic aleukia in Russia. The eruption of so-called turkey X disease in…. LSD is usually prepared by chemical synthesis in a laboratory. Its basic chemical structure is similar to that of the ergot alkaloids, and it is structurally related to several other drugs e.

Certain plant families are particularly rich in alkaloids; all plants of the poppy family Papaveraceae are thought to contain them, for example. The Ranunculaceae buttercupsSolanaceae nightshadesand Amaryllidaceae amaryllis are other prominent alkaloid-containing. Ergot fungus. Article Media.

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Ergot fungus fungus species.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.

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.

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The Headaches. New York: Raven Press.The principles and application of established and newer methods for the quantitative and semi-quantitative determination of ergot alkaloids in food, feed, plant materials and animal tissues are reviewed.

The techniques of sampling, extraction, clean-up, detection, quantification and validation are described. Other methods based on immunoassays are under development and variations of these and minor techniques are available for specific purposes. The analysis of ergot alkaloids EA is of considerable importance, and a substantial topic because the alkaloids are encountered in many different situations that affect humans and animals, and they are found in many different matrices.

The earliest interest was in the analysis of grain crops contaminated by the sclerotia ergots of Claviceps species and was based on the physical counting of the sclerotia in grain samples. Investigations led to the development of pharmaceutical forms of EA and subsequently the need for medicinal analysis, and in other cases, of forensic application.

Developments in instrumental techniques have given us the ability to separate and measure individual ergot compounds and their isomers, and this in turn has allowed the possibility of monitoring and regulating the contamination of cereal based foods. There is a requirement therefore to measure EA in ergot sclerotia, infected cereals, forage grasses, processed foods, pharmaceutical preparations, illicit preparations, and body fluids and organs.

Chemical analysis today usually follows a distinct pathway of careful sampling and homogenisation, extraction of the analyte, separation of the analyte from co-extracted materials clean-updetection and quantification.

ergot structure

Examples of these procedure are provided in the following paragraphs. Once a procedure has been developed its performance is characterised by repeated testing within a laboratory and then in ideal circumstances by a collaborative trial involving the participation of a suitable number of laboratories.

Measurements can be qualitative i. Several techniques are applicable to different matrices with some modification. There is a growing demand for rapid testing methods, and those that can be deployed in the field or on the production line. Claviceps purpurea produces lactam ergot alkaloids ergopeptams containing isoleucine as a second amino acid, which have been found to predominate in some infected wild grasses from Norway [ 1 ]. Methods for the determination of EA in cereals and their products were reviewed in by Komarova and Tolkachev [ 2 ] and again in by Krska and Crews [ 3 ].

Chromatographic and mass spectrometric methods to determine lysergic acid diethylamide LSD and related compounds in body fluids have been reviewed by Reuschel et al. Structures of representative types of some major EA are given in Figure 1.

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Lysergic acid amides include ergonovine ergometrine, or ergobasinelysergic acid amide, lysergic acid diethylamide, lysergic acid 2-hydroxyethylamide, methylergonovine and methysergide. Most of these compounds are pharmacologically active. Lysergic acid is a chiral compound with two stereocenters. The isomer with inverted configuration at C-8 close to the carboxyl group is called iso -lysergic acid.

The EA found in Claviceps sclerotia are the ergopeptines ergometrine, ergotamine, ergosine, ergocristine, ergocryptine and ergocornine. These alkaloids have a double bond at C9—C10 which allows epimerisation to take place at the C8 position as shown in Figure 2. Epimerisation forms C8- R isomers with left-hand rotation, which are known as ergopeptines, and C8- S isomers with right-hand rotation, which are known as ergopeptinines, and are less toxic.

The N6 nitrogen gives the protonated EA pKa values of 5. The driving forces for the conversion between epimeric forms are complex and not fully understood [ 5 ]. Ergovaline is a major ergot alkaloid found in tall fescue grass Fescue arundinacea Schreb.



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