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PubMed1978

Historical view on ergot alkaloids.

A short survey of the history of ergot, of the original and, for a long time, only source of ergot alkaloids, is given. Once a dreaded poison, ergot has changed its role over the centuries to become a rich treasure house of valuable pharmaceuticals. In the Middle Ages it was the cause of epidemics of ergotism, which cost tens of thousands of people their lives. Ergot was first mentioned by the German physician Lonitzer in 1582 as a remedy used by midwives for quickening childbirth. The isolation of pharmacologically useful alkaloids started in 1906 with the discovery of ergotoxine and its adrenolytic activity by Barger, Carr and Dale. In 1918, Stoll isolated ergotamine, the first chemically pure ergot alkaloid, which found widespread therapeutic use in obstetrics and internal medicine. In 1935 the specific oxytocic principle of ergot, ergonovine, was discovered simultaneously in four separate laboratories. Since then, worldwide investigations on ergot alkaloids resulted in the elucidation of their structures and total syntheses and preparation of valuable therapeutics such as Methergine, Hydergine, Dihydergot, and others.

Chemistry↗
PubMed2002

Reproductive toxicity of ergot alkaloids in mink.

Ergot alkaloids are-synthesized by fungi of the Claviceps family that infect rye as well as other cereals and grains. Since a portion of the ranch mink diet is cereal, mink are at a risk of being exposed to ergot alkaloids. This study was performed to determine the reproductive toxicity of ergot alkaloids derived from ergot-contaminated oats in mink. Four groups of 12 female mink each were fed diets containing 0, 3, 6 or 12 ppm ergot alkaloids from 2w prior to the breeding season until the kits were approximately 33-d old (133 d). Females were mated with untreated males. Ergo talkaloids caused a transient decrease in feed consumption, but body weights were unaffected. The gestation period of the mink in the 6 ppm group was longer compared to controls. The number of mink whelping varied significantly with 9 mink whelping each in the control and 3 ppm groups compared to 4 mink in the 6 ppm group and 1 in the 12 ppm group. Ergot alkaloids had a significant effect on kit survivabilitywith no kits surviving in the 12 ppm group. Serum prolactin was significantly depressed in the 3 ergot alkaloid groups compared to the control group. This study indicated that ingestion of ergot alkaloids at 3 ppm or higher resulted in reproductive toxicity in mink.

Animals↗
PubMed2005

Claviceps cyperi, a new cause of severe ergotism in dairy cattle consuming maize silage and teff hay contaminated with ergotised Cyperus esculentus (nut sedge) on the Highveld of South Africa.

During December/January 1996/97 typical summer syndrome (hyperthermia and a 30% drop in milk yield) occurred in succession in two Holstein dairy herds (n=240 and n=150 milking cows, respectively) on the South African Highveld. These farms are situated in the midst of the prime maize and dairy farming areas of South Africa where this condition had never been diagnosed before. The individual components of the concentrate on both farms were negative for ergot alkaloids. Endophytic fungi and/or ergot infestation of teff and other grasses fed to the cows were then suspected of being involved, but neither endophytes nor ergot alkaloids could be implicated from these sources. By measuring the serum prolactin levels of groups of sheep (n=5) fed the first farm's total mixed ration (TMR) or its three individual fibre components for a period of 11 days, the source of the ergot alkaloids was identified. A statistically significant decrease in the level of this hormone occurred only in the group on maize silage (which constituted 28% on dry matter base of the TMR). The involvement of the maize silage was further chemically confirmed by the high levels of total ergot alkaloids, predominantly ergocryptine, found by LC-MS in the silage as well as in the TMR (115-975 ppb and 65-300 ppb, respectively). The ergot alkaloid content (mainly ergocryptine) of the maize silage on the second affected farm was 875 ppb. Withdrawal of contaminated silage resulted in gradual recovery of stock on both farms. Nut sedge (Cyperus esculentus and Cyperus rotundus of the family Cyperaceae) has a world-wide distribution and is a common weed in annual crops, and can be parasitized by Claviceps cyperi. Careful examination of the maize silage from both farms revealed that it was heavily contaminated with nut sedge and that it contained minute sclerotia, identified as those of Claviceps cyperi, originating from the latter. Nut sedge was abundant on both farms and it is believed that late seasonal rain had resulted in mature, heavily ergotised nut sedge being cut with the silage. Claviceps cyperi sclerotia, collected on the affected fields in the following autumn contained 3600-4000 ppm ergocryptine. That the dominant alkaloid produced by this particular fungus was indeed ergocryptine, was confirmed by negative ion chemical ionization MS/MS. In one further outbreak in another Holstein herd, teff hay contaminated with ergotised nut sedge and containing 1200 ppb alkaloids, was incriminated as the cause of the condition. This is the first report of bovine ergotism not associated with the Poaceae infected with Claviceps purpureum or endophytes but with the family Cyperaceae and this particular fungal phytopathogen.

Animal Feed↗
PubMed1989

Ergotism: a possible etiology for puerperal psychosis.

Some reports in the medical literature have mentioned the occurrence of psychotic reactions in response to the use of certain ergot alkaloids in therapeutic doses. Prompted by these observations, we undertook a search for cases of "pure" puerperal psychosis (ie, typical manifestations 3-14 days postpartum) in order to evaluate the clinical background of this phenomenon. Special attention was paid to the medications that the patients had received peripartum. In the last 10 years, out of eight perinatal centers, we found only three cases that fulfilled the criteria of the quoted entity. In all instances, the manifestations of puerperal psychosis had been preceded by the administration of ergot derivatives. Based on the presented data, we hypothesize that typical postpartum psychosis may represent an idiosyncratic reaction to potent vasoactive drugs including ergot derivatives. The similarities between the clinical manifestations of ergotism and puerperal psychosis, and some of the epidemiologic features of the latter condition, appear to implicate ergot alkaloids as potential causative agents. Although the validity of the suggested interpretation requires further evaluation, we believe that the currently available data warrant caution with regard to the administration of ergot derivatives postpartum. These drugs should not be used in the absence of clear indication or in unnecessarily high doses. We suggest that ergotism be included in the differential diagnosis in cases of pure puerperal psychosis.

Adolescent↗
PubMed1983

Alkaloids in ergot found on different Gramineae in The Netherlands.

The alkaloid content and the composition of the alkaloid complex of thirteen samples of ergot sclerotia from different gramineous host species collected in The Netherlands were investigated. Two samples collected in France were also examined. Ergot of Glyceria fluitans (L.) R.Br. did not contain alkaloids. The total alkaloid content of ergot found on the other wild grasses was more than 0.2%. The ratio between the contents of water soluble and water insoluble alkaloids of the investigated ergot sclerotia varies between 1:10 and 1:20. The composition of the alkaloid complex in the sclerotia was studied by quantitative thin-layer chromatography. The sclerotia could be grouped into three main categories: --sclerotia of Lolium perenne L., Festuca arundinacea Schreb. and Arrhenatherum elatius (L.) P.B. ex J. et C. Presl, containing predominantly ergocornine, alpha- and beta-ergokryptine and ergosine; --sclerotia of Dactylis glomerata L., Phalaris arundinacea L., Alopecurus geniculatus L. and Holcus mollis L., containing predominantly ergosine, ergocristine and ergotamine; --sclerotia of Molinia caerulea (L.) Moench, containing predominantly ergocristine, ergosine and ergometrine. A great similarity was found between the composition of the alkaloid complex in ergot of Lolium perenne L. from different locations and also in ergot of Molinia caerulea (L.) Moench from different locations. This similarity was less in ergot of Dactylis glomerata L. collected from different locations.

Chromatography, Thin Layer↗
PubMed2006

Effects of ergot alkaloids on food preference and satiety in rabbits, as assessed with gene-knockout endophytes in perennial ryegrass (Lolium perenne).

Neotyphodium species are fungal endophytes best known for their protection of grass hosts and production of bioactive metabolites including ergot alkaloids. Perennial ryegrass-Neotyphodium sp. Lp1 symbiota that have altered ergot alkaloid profiles (resulting from knockouts in two different endophyte genes) were fed, along with controls, to rabbits to test the effects of ergot alkaloids on food preference and satiety. Interestingly, rabbits dramatically preferred plants that were endophyte-infected but free of ergot alkaloids over endophyte-free plants (P = 0.01). Accumulation of ergot alkaloids of the clavine class counteracted the added appeal of endophyte-infected plants. In satiety tests, consumption of ergovaline (the ultimate ergot pathway product in wild-type endophyte), but not of several other ergot alkaloids, during an initial meal had a negative effect on subsequent rabbit chow consumption (P < 0.05). The data indicate that clavines were sufficient to reduce the appeal of endophyte-infected grasses, whereas only ergovaline reduced appetite.

Animals↗
PubMed2000

Sorghum ergot (Claviceps africana) associated with agalactia and feed refusal in pigs and dairy cattle.

OBJECTIVE: To establish the aetiology and define the main clinical features of a syndrome characterised by severe feed refusal, death of piglets and reduced milk production in pigs and dairy cattle. DESIGN: Clinical, pathological, toxicological and epidemiological examination of clinical cases in 10 piggeries and 4 dairies, located between 50 and 150 km south-west of Rockhampton. RESULTS: All cases were associated with the feeding of sorghum grain infected with sorghum ergot (Claviceps africana). There was mild to severe feed refusal when the sorghum was first offered. Sows fed ergot before farrowing had shrunken udders, produced no colostrum, and displayed signs of oestrus. All of their piglets died, apparently from starvation: necropsy of a few piglets showed that they were born alive and walked, but had ingested no milk. Sows fed the grain after farrowing had severe reductions in milk production despite aggressive sucking by piglets, leading to very poor growth of piglets. There were no signs of infectious disease. Ergot in sorghum samples ranged from 1 to 31% ergot sclerotes by weight. Total alkaloid concentrations in mixed feeds ranged from 5 to 40 mg/kg, with dihydroergosine accounting for approximately 90%. At the same time, in the same districts, there were reports of feed refusal and reduced milk production from 4 dairy farms. Grain samples from these farms contained up to 17% C africana ergot sclerotia. CONCLUSION: Agalactia and feed refusal are classical signs of poisoning by rye ergot (C purpurea), but this is the first time that sorghum ergot has been associated with a similar syndrome.

Animal Feed↗
PubMedDate not supplied

Liquid chromatographic preparative method for isolating ergot alkaloids, using a particle-loaded membrane extracting disk.

A liquid chromatographic method is described for the determination of ergot alkaloids in wheat. Ergonovine, ergotamine, ergocornine, alpha-ergocryptine, and ergocristine are extracted from wheat with methanol-0.25% concentrated H3PO4 (40 + 60) pH 2.2, cleaned up by using a solid-phase extraction (SPE) disk, and separated by reversed-phase liquid chromatography with fluorescence detection. Ergot alkaloids are basic compounds that form water-soluble salts in acidic aqueous solution. Because ergot alkaloid salts are positively charged, they can be easily and selectively trapped on a negatively charged strong cation-exchange SPE disk. A strong wash solvent, methanol-0.25% concentrated H3PO4 (40 + 60) was used to remove matrix interferences not bonded by ionic interactions with the cation-exchange column. The ergot alkaloids were eluted from the ion-exchange column by adjusting the pH of the elution solvents to slightly basic conditions (pH 9). The SPE disk concentrated and cleanly separated the ergot alkaloids from matrix interferences. Standard calibration curves for ergot alkaloids for the concentration range 0.1-2.0 microg/mL were linear. The SPE disk had a column capacity equivalent to about 1 g extracted wheat. At spiking levels of 2.3-46 ng/g for ergonovine and 20-400 ng/g for ergotamine, ergocornine, alpha-ergocryptine, and ergocristine, the mean recovery was 88.1% with a coefficient of variation (CV) of 5.33%. The recovery data ranged from 79.1 to 95.9%. Ergonovine had the lowest overall recovery and the largest CV. The method has an estimated reliable limit of detection and limit of quantitation of <5 and <20 ng/g, respectively, for each ergot alkaloid tested.

Chromatography, Liquid↗
PubMed1976

Some consequences of the ingestion by young and growing pigs of feed contaminated with ergot.

Growing pigs were fed freshly milled ergot sclerotia (Claviceps purpurea Fr (Tul)) from North American wheat containing 0-31 per cent of total alkaloids of which 30 per cent was ergotoxine, 30 per cent ergosine, 20 per cent ergotamine and 20 per cent other ergot alkaloids. Pigs were induced to ingest a diet heavily contaminated with ergot (10 per cent w/w). The presence of ergot reduced feed intake and growth of the pigs, but there was no evidence of peripheral necrosis, of internal or external haemorrhage, or of changes in haemotological characteristics. Balance experiments in which the diet was contaminated with 4 per cent (w/w) of ergot showed that 90 per cent of the alkaloids were absorbed by the pigs, but none could be detected in tissues or urine. The ingestion of ergot did not affect the digestibility of the diet, but the urinary excretion of nitrogen was increased and the retention of nitrogen reduced. The presence of ricinoleic acid was shown to be a useful diagnostic feature of ergot contamination of diets, digesta and faeces; it was not found in body tissues.

Animal Feed↗
PubMed2002

The effect of topical natural ergot alkaloids on the intraocular pressure and aqueous humor dynamics in rabbits with alpha-chymotrypsin-induced ocular hypertension.

BACKGROUND: We previously reported that topical natural ergot alkaloids ergocristine, alpha-ergocryptine and ergocornine dose-dependently reduce intraocular pressure in ocular normotensive rabbits, most likely by decreasing aqueous humor inflow. In the present study, the effects of these compounds on intraocular pressure and aqueous humor dynamics in a rabbit model for ocular hypertension were assessed. METHODS: Experiments were conducted in albino rabbits made ocular hypertensive by intracameral injection of alpha-chymotrypsin. Intraocular pressure responses to drug vehicle and seven different doses of topical natural ergot alkaloids were examined in order to obtain dose-response relationships for comparing the intraocular pressure-lowering effect and potency of these drugs. Tonographies were also performed to ascertain the actions of natural ergot alkaloids on aqueous humor dynamics in alpha-chymotrypsin-induced ocular hypertensive rabbits. RESULTS: Topical application of the natural ergot alkaloids ergocristine, alpha-ergocryptine and ergocornine lowered intraocular pressure in alpha-chymotrypsin-induced ocular hypertensive rabbits in a dose-related fashion, with ergocristine displaying the greatest intraocular pressure-lowering effect. Tonographic studies revealed a decrease in the tonographic outflow facility following topical application of natural ergot alkaloids, although only the effects of both ergocristine and alpha-ergocryptine reached statistical significance. All natural ergot alkaloids tested significantly reduced the calculated aqueous humor inflow. CONCLUSION: This study suggests that the natural ergot alkaloids ergocristine, alpha-ergocryptine and ergocornine effectively decrease intraocular pressure in the alpha-chymotrypsin-induced model of ocular hypertension. Since these compounds reduce the tonographic aqueous humor outflow facility, their final ocular antihypertensive effect appears to result from a remarkable reduction of the aqueous humor inflow.

Administration, Topical↗
PubMed1988

Ergot alkaloids block neurogenic extravasation in dura mater: proposed action in vascular headaches.

Although the ergot alkaloids (ergots) are useful drugs for the acute treatment of migraine headaches, their mechanism of action remains obscure. When administered to rats in clinically relevant doses, ergots blocked the development of neurogenic plasma extravasation in dura mater. Plasma extravasation was induced by depolarization of perivascular axons following capsaicin injection or unilateral electrical stimulation of the trigeminal nerve. The ergot action could not be accounted for by vasoconstriction alone because neurogenic plasma leakage was not blocked by angiotensin or phenylephrine. Furthermore, ergots did not block plasma extravasation induced by administering sensory neuropeptides that mediate enhanced permeability. We propose that the therapeutic effects of ergots in vascular headaches may result from peripheral blockade of small fiber (C or A-delta)-dependent neurogenic inflammation within the dura mater.

Animals↗
PubMed2004

Fragmentation patterns of selected ergot alkaloids by electrospray ionization tandem quadrupole mass spectrometry.

Tall fescue toxicosis and other maladies in livestock result from the ingestion of vasoconstrictive ergot alkaloids produced by fungal endophytes associated symbiotically with the grass. In order to facilitate future analyses of grass extracts considered responsible for outbreak of related livestock diseases, we examined the electrospray ionization mass spectra of specific ergot alkaloids under conditions that permit protonation. Our purposes were both to record the spectra with interpretation of mechanisms of fragmentation and to derive commonalities that would allow the prediction of mass spectra of related compounds for which standards were not readily available. With [M + H](+) values in parentheses, water-insoluble lysergic acid peptide ergot derivatives ergovaline (m/z 534), ergotamine (m/z 582), ergocornine (m/z 562), ergocryptine (m/z 576) and ergocrystine (m/z 610) exhibited a consistent loss of water (-18 u) from the C-12' alpha-hydroxy functionality. Of this group, ergovaline and ergotamine generated an m/z 320 fragment deriving from cleavage of ring E amide and ether functions with retention of the peptide ring system methyl group. Ergocornine, ergocryptine and ergocrystine similarly formed an m/z 348 fragment with retention of isopropyl. These assignments were supported by the lack of similar fragments from the water-soluble ergot ergonovine, which lacks a peptide ring system. Clavine-type ergot alkaloids lysergic acid and lysergol lack any substituents beyond simple ones directly on the C-8 position and, similarly to ergonovine, lack significant fragments at m/z 268, 251 and 225 shared by the peptide ergot alkaloids.

Animal Feed↗
PubMed2006

Valvular heart disease in Parkinson's disease treated with ergot derivative dopamine agonists.

Valvular heart disease, associated with ergot derivative dopamine agonists, has been reported in patients with Parkinson's disease (PD). There are few comparative studies on the frequency, severity, and dose dependency of valvular disease associated with ergot derivatives. We analyzed these factors in 58 PD patients who were taking ergot derivatives (22 were taking bromocriptine and 36 were taking pergolide) and compared them with 20 age-matched controls based on the two-dimensional echocardiographic findings. Aortic, mitral, and tricuspid valvular thicknesses, as well as tenting areas and tenting distance of the mitral valve were measured. We also assessed the correlation between the cumulative or daily doses of ergot derivatives and each valvular parameter. There was no significant increase in the frequency of valvulopathy in the PD patients taking bromocriptine or pergolide. We identified a positive correlation between the daily dose of pergolide and the tenting area of the mitral valve (r = 0.385; P = 0.020). However, other valvular parameters were not found to correlate with the age, disease duration, treatment duration, or dosage of medication. Our study failed to uncover definitive harmful effects of ergot derivative dopamine agonists on cardiac valves; this is considering the relatively lower daily doses than other reported cases. To establish a dosage dependency with valvulopathy, a more detailed study with higher doses of ergot derivatives for longer duration of treatment may be needed.

Adult↗
PubMed1983

Interaction of ergot alkaloids and their combination (co-dergocrine) with alpha-adrenoceptors in the CNS.

Co-dergocrine (Hydergine), composed of four dihydrogenated peptide ergot alkaloids (dihydroergocornine, dihydroergocristine, dihydro-alpha-ergokryptine and dihydro-beta-ergokryptine), has been reported to interact with alpha-adrenoceptors. The effect of the combination and its individual components on alpha-adrenoceptors subtypes in the rat brain was investigated in the present study. All five ergot drugs displaced [3H]rauwolscine, [3H]clonidine and [3H]WB 4101 from specific binding sites in membrane preparations from rat and bovine brain at nanomolar concentrations. In rat cerebral occipital cortex slices, the ergot drugs inhibited 1-noradrenaline-stimulated cyclic AMP formation (alpha 1-adrenoceptor test) and facilitated electrically evoked noradrenaline release (alpha 2-adrenoceptor test) at nanomolar concentrations. The results from the functional tests suggest that the ergot drugs have a slightly higher affinity to alpha 2-adrenoceptors which are antagonised in a competitive manner. The alpha 1-adrenoceptors are antagonised by the ergot drugs in a non-competitive manner. The relative order of potency at both receptor types was similar in that dihydroergocornine, dihydro-alpha-ergokryptine and dihydro-beta-ergokryptine were equipotent, whereas dihydroergocristine was less potent. The effect of the combination of the ergot alkaloids at both alpha-adrenoceptors appears to reflect the summation of the contributions of its components. The differences seen in the functional tests were less pronounced in the binding tests.

Animals↗
PubMed2000

Chronic ergot toxicity: A rare cause of lower extremity ischemia.

Chronic ergot toxicity is a rare cause of lower extremity ischemia. The cornerstone of therapy in ergot toxicity is to discontinue the use of caffeine, cigarettes, and all ergot-containing medications. Although multiple different therapies have been recommended for acute toxicity, no specific treatment is uniformly recommended in chronic toxicity. We present a case of long-term ergot use for migraine headaches in a woman who had severe chronic lower extremity claudication. This case demonstrates the unique features associated with the diagnosis and management of chronic ergot toxicity. We recommend a conservative approach consisting of observation, antiplatelet agents, and the discontinuance of ergots. If symptoms progress to rest pain or gangrene, surgical treatment should be considered.

Adult↗
PubMed2003

Ergotism associated with HIV antiviral protease inhibitor therapy.

Ergotism is a rare condition of acute vasospasm found classically in young and middle-aged women taking ergot alkaloid agents to treat migraine headache. We report the case of a young man with human immunodeficiency virus (HIV) positivity and describe the drug interaction between protease inhibitors and ergot alkaloid agents, which most likely predisposed to development of ergot toxicity. The HIV-positive population receiving antiviral therapy may be an under-recognized group at risk for ergotism through decreased hepatic metabolism of ergot preparations.

Adult↗
PubMed1988

Procedure for isolating the endophyte from tall fescue and screening isolates for ergot alkaloids.

A procedure was developed to isolate and determine ergot alkaloid production by Acremonium coenophialum, the endophytic fungus of tall fescue. The procedure established that macerated leaf sheath or pith from inflorescence stem placed either in a liquid medium or on a corn meal-malt extract agar medium produced isolated mycelium and characteristic conidia within a 3- to 3.5-week period. Once isolated, each fungus was placed in another liquid medium, M104T, where competent strains produced total ergot alkaloids ranging from 38 to 797 mg/liter. Several isolates were negative for ergot alkaloid synthesis. The production of ergot alkaloids by individual isolates was unstable; isolates rapidly degenerated in their ability to produce ergot alkaloids during subculture. However, the procedure as presented allows the assessment of an isolate for ergot alkaloid synthesis during its initial isolation.

Acremonium↗
PubMed1978

Binding interactions of ergot alkaloids with monoaminergic receptors in the brain.

The interactions of ergot alkaloids and of other drugs with dopamine (DA) and alpha-adrenergic receptors were investigated. The tested ergot alkaloids inhibit synaptosomal tyrosine hydroxylase activity and reverse the apomorphine-elicited inhibition of synaptosomal tyrosine hydroxylase activity. Thus, ergot alkaloids interact as both agonists and antagonists with the presynaptic DA receptors. Ergot alkaloids also compete effectively for the binding of 3H-DA and 3H-haloperidol to bovine striatal membranes. These results show that these drugs are mixed agonist-antagonists with respect to the postsynaptic DA receptors. To determine the effects of ergot alkaloids and of neuroleptics on the alpha-adrenergic receptors in the CNS, we have measured their effects on the binding of 3H-dihydroergocryptine and 3H-WB-4101 to cerebral cortical membranes. The displacing potencies of the tested ergot alkaloids and of the neuroleptics indicated that they have a high affinity for the alpha-adrenoreceptors in the CNS. The mechanisms underlying the therapeutic efficacy of mixed agonist-antigonists of DA and alpha-adrenergic receptors in Parkinson's disease and in geriatric disorders were considered.

Animals↗