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Introduction to the Toxins Special Issue on Ergot Alkaloids

by Christopher L. Schardl

Toxins 2015, 7(10), 4232-4237; https://doi.org/10.3390/toxins7104232 - 20 Oct 2015

Cited by 18 | Viewed by 6084

Abstract

Ergot alkaloids are among the most relevant natural products in the history of toxins and pharmaceuticals. Until the late 20th century, human and livestock exposure to ergot alkaloids was primarily through ingestion of “ergots,” which are spur-shaped or seed-like resting structures (sclerotia) of [...] Read more.

Ergot alkaloids are among the most relevant natural products in the history of toxins and pharmaceuticals. Until the late 20th century, human and livestock exposure to ergot alkaloids was primarily through ingestion of “ergots,” which are spur-shaped or seed-like resting structures (sclerotia) of ergot fungi, the Claviceps species. Because ergots have similar density to grains, traditional threshing techniques generally failed to remove them, and outbreaks of ergot typically led to mass poisonings. [...] Full article

(This article belongs to the Special Issue Ergot Alkaloids: Chemistry, Biology and Toxicology)

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Research

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Ergot Alkaloids in Feed for Pekin Ducks: Toxic Effects, Metabolism and Carry Over into Edible Tissues

by Sven Dänicke

Toxins 2015, 7(6), 2006-2023; https://doi.org/10.3390/toxins7062006 - 2 Jun 2015

Cited by 15 | Viewed by 6025

Abstract

Hardened sclerotia (ergots) of Claviceps purpurea contaminate cereal grains and contain toxic ergot alkaloids (EA). Information on EA toxicity in ducks is scarce. Therefore, the aim of the growth experiment (Day 0–49, n = 54/group) was to titrate the lowest observed adverse effect [...] Read more.

Hardened sclerotia (ergots) of Claviceps purpurea contaminate cereal grains and contain toxic ergot alkaloids (EA). Information on EA toxicity in ducks is scarce. Therefore, the aim of the growth experiment (Day 0–49, n = 54/group) was to titrate the lowest observed adverse effect level (LOAEL) for total ergot alkaloids (TEA). A control diet was prepared without ergots, and the diets designated Ergot 1 to 4 contained 1, 10, 15 and 20 g ergot per kg diet, respectively, corresponding to TEA contents of 0.0, 0.6, 7.0, 11.4 and 16.4 mg/kg. Sensitivity of ducks to EA was most pronounced at the beginning of the experiment when feed intake decreased significantly by 9%, 28%, 41% and 47% in groups Ergot 1 to 4, respectively, compared to the control group. The experiment was terminated after two weeks for ducks exposed to Ergot 3 and 4 due to significant growth retardation. Ergot alkaloid residues in edible tissues were lower than 5 ng/g. Bile was tested positive for ergonovine (=ergometrine = ergobasine) with a mean concentration of 40 ng/g. Overall, the LOAEL amounted to 0.6 mg TA/kg diet suggesting that ducks are not protected by current European Union legislation (1 g ergot/kg unground cereal grains). Full article

(This article belongs to the Special Issue Ergot Alkaloids: Chemistry, Biology and Toxicology)

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Links between Genetic Groups, Indole Alkaloid Profiles and Ecology within the Grass-Parasitic Claviceps purpurea Species Complex

by Mariell Negård, Silvio Uhlig, Håvard Kauserud, Tom Andersen, Klaus Høiland and Trude Vrålstad

Toxins 2015, 7(5), 1431-1456; https://doi.org/10.3390/toxins7051431 - 28 Apr 2015

Cited by 32 | Viewed by 8025

Abstract

The grass parasitic fungus Claviceps purpurea sensu lato produces sclerotia with toxic indole alkaloids. It constitutes several genetic groups with divergent habitat preferences that recently were delimited into separate proposed species. We aimed to 1) analyze genetic variation of C. purpurea sensu lato [...] Read more.

The grass parasitic fungus Claviceps purpurea sensu lato produces sclerotia with toxic indole alkaloids. It constitutes several genetic groups with divergent habitat preferences that recently were delimited into separate proposed species. We aimed to 1) analyze genetic variation of C. purpurea sensu lato in Norway, 2) characterize the associated indole alkaloid profiles, and 3) explore relationships between genetics, alkaloid chemistry and ecology. Approximately 600 sclerotia from 14 different grass species were subjected to various analyses including DNA sequencing and HPLC-MS. Molecular results, supported by chemical and ecological data, revealed one new genetic group (G4) in addition to two of the three known; G1 (C. purpurea sensu stricto) and G2 (C. humidiphila). G3 (C. spartinae) was not found. G4, which was apparently con-specific with the recently described C. arundinis sp. nov, was predominantly found in very wet habitats on Molinia caerulea and infrequently in saline habitats on Leymus arenarius. Its indole-diterpene profile resembled G2, while its ergot alkaloid profile differed from G2 in high amounts of ergosedmam. In contrast to G1, indole-diterpenes were consistently present in G2 and G4. Our study supports and complements the newly proposed species delimitation of the C. purpurea complex, but challenges some species characteristics including host spectrum, habitat preferences and sclerotial floating ability. Full article

(This article belongs to the Special Issue Ergot Alkaloids: Chemistry, Biology and Toxicology)

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Open AccessArticle

The Key Role of Peltate Glandular Trichomes in Symbiota Comprising Clavicipitaceous Fungi of the Genus Periglandula and Their Host Plants

by Ulrike Steiner, Sabine Hellwig née Kucht, Mahalia A. Ahimsa-Müller, Nicola Grundmann, Shu-Ming Li, Christel Drewke and Eckhard Leistner

Toxins 2015, 7(4), 1355-1373; https://doi.org/10.3390/toxins7041355 - 16 Apr 2015

Cited by 11 | Viewed by 8277

Abstract

Clavicipitaceous fungi producing ergot alkaloids were recently discovered to be epibiotically associated with peltate glandular trichomes of Ipomoea asarifolia and Turbina corymbosa, dicotyledonous plants of the family Convolvulaceae. Mediators of the close association between fungi and trichomes may be sesquiterpenes, main components [...] Read more.

Clavicipitaceous fungi producing ergot alkaloids were recently discovered to be epibiotically associated with peltate glandular trichomes of Ipomoea asarifolia and Turbina corymbosa, dicotyledonous plants of the family Convolvulaceae. Mediators of the close association between fungi and trichomes may be sesquiterpenes, main components in the volatile oil of different convolvulaceous plants. Molecular biological studies and microscopic investigations led to the observation that the trichomes do not only secrete sesquiterpenes and palmitic acid but also seem to absorb ergot alkaloids from the epibiotic fungal species of the genus Periglandula. Thus, the trichomes are likely to have a dual and key function in a metabolic dialogue between fungus and host plant. Full article

(This article belongs to the Special Issue Ergot Alkaloids: Chemistry, Biology and Toxicology)

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Review

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Open AccessReview

Activities and Effects of Ergot Alkaloids on Livestock Physiology and Production

by James L. Klotz

Toxins 2015, 7(8), 2801-2821; https://doi.org/10.3390/toxins7082801 - 27 Jul 2015

Cited by 129 | Viewed by 11046

Abstract

Consumption of feedstuffs contaminated with ergot alkaloids has a broad impact on many different physiological mechanisms that alters the homeostasis of livestock. This change in homeostasis causes an increased sensitivity in livestock to perturbations in the ambient environment, resulting in an increased sensitivity [...] Read more.

Consumption of feedstuffs contaminated with ergot alkaloids has a broad impact on many different physiological mechanisms that alters the homeostasis of livestock. This change in homeostasis causes an increased sensitivity in livestock to perturbations in the ambient environment, resulting in an increased sensitivity to such stressors. This ultimately results in large financial losses in the form of production losses to livestock producers around the world. This review will focus on the underlying physiological mechanisms that are affected by ergot alkaloids that lead to decreases in livestock production. Full article

(This article belongs to the Special Issue Ergot Alkaloids: Chemistry, Biology and Toxicology)

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Analysis of Ergot Alkaloids

by Colin Crews

Toxins 2015, 7(6), 2024-2050; https://doi.org/10.3390/toxins7062024 - 3 Jun 2015

Cited by 68 | Viewed by 15113

Abstract

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. The major procedures [...] Read more.

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. The major procedures for ergot alkaloid analysis comprise liquid chromatography with tandem mass spectrometry (LC-MS/MS) and liquid chromatography with fluorescence detection (LC-FLD). Other methods based on immunoassays are under development and variations of these and minor techniques are available for specific purposes. Full article

(This article belongs to the Special Issue Ergot Alkaloids: Chemistry, Biology and Toxicology)

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Genetics, Genomics and Evolution of Ergot Alkaloid Diversity

by Carolyn A. Young, Christopher L. Schardl, Daniel G. Panaccione, Simona Florea, Johanna E. Takach, Nikki D. Charlton, Neil Moore, Jennifer S. Webb and Jolanta Jaromczyk

Toxins 2015, 7(4), 1273-1302; https://doi.org/10.3390/toxins7041273 - 14 Apr 2015

Cited by 82 | Viewed by 10010

Abstract

The ergot alkaloid biosynthesis system has become an excellent model to study evolutionary diversification of specialized (secondary) metabolites. This is a very diverse class of alkaloids with various neurotropic activities, produced by fungi in several orders of the phylum Ascomycota, including plant pathogens [...] Read more.

The ergot alkaloid biosynthesis system has become an excellent model to study evolutionary diversification of specialized (secondary) metabolites. This is a very diverse class of alkaloids with various neurotropic activities, produced by fungi in several orders of the phylum Ascomycota, including plant pathogens and protective plant symbionts in the family Clavicipitaceae. Results of comparative genomics and phylogenomic analyses reveal multiple examples of three evolutionary processes that have generated ergot-alkaloid diversity: gene gains, gene losses, and gene sequence changes that have led to altered substrates or product specificities of the enzymes that they encode (neofunctionalization). The chromosome ends appear to be particularly effective engines for gene gains, losses and rearrangements, but not necessarily for neofunctionalization. Changes in gene expression could lead to accumulation of various pathway intermediates and affect levels of different ergot alkaloids. Genetic alterations associated with interspecific hybrids of Epichloë species suggest that such variation is also selectively favored. The huge structural diversity of ergot alkaloids probably represents adaptations to a wide variety of ecological situations by affecting the biological spectra and mechanisms of defense against herbivores, as evidenced by the diverse pharmacological effects of ergot alkaloids used in medicine. Full article

(This article belongs to the Special Issue Ergot Alkaloids: Chemistry, Biology and Toxicology)

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Ergot Alkaloids Produced by Endophytic Fungi of the Genus Epichloë

by Philippe Guerre

Toxins 2015, 7(3), 773-790; https://doi.org/10.3390/toxins7030773 - 6 Mar 2015

Cited by 72 | Viewed by 11668

Abstract

The development of fungal endophytes of the genus Epichloë in grasses results in the production of different groups of alkaloids, whose mechanism and biological spectrum of toxicity can differ considerably. Ergot alkaloids, when present in endophyte-infected tall fescue, are responsible for “fescue toxicosis” [...] Read more.

The development of fungal endophytes of the genus Epichloë in grasses results in the production of different groups of alkaloids, whose mechanism and biological spectrum of toxicity can differ considerably. Ergot alkaloids, when present in endophyte-infected tall fescue, are responsible for “fescue toxicosis” in livestock, whereas indole-diterpene alkaloids, when present in endophyte-infected ryegrass, are responsible for “ryegrass staggers”. In contrast, peramine and loline alkaloids are deterrent and/or toxic to insects. Other toxic effects in livestock associated with the consumption of endophyte-infected grass that contain ergot alkaloids include the “sleepy grass” and “drunken horse grass” diseases. Although ergovaline is the main ergopeptine alkaloid produced in endophyte-infected tall fescue and is recognized as responsible for fescue toxicosis, a number of questions still exist concerning the profile of alkaloid production in tall fescue and the worldwide distribution of tall fescue toxicosis. The purpose of this review is to present ergot alkaloids produced in endophyte-infected grass, the factors of variation of their level in plants, and the diseases observed in the mammalian species as relate to the profiles of alkaloid production. In the final section, interactions between ergot alkaloids and drug-metabolizing enzymes are presented as mechanisms that could contribute to toxicity. Full article

(This article belongs to the Special Issue Ergot Alkaloids: Chemistry, Biology and Toxicology)

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Biology, Genetics, and Management of Ergot (Claviceps spp.) in Rye, Sorghum, and Pearl Millet

by Thomas Miedaner and Hartwig H. Geiger

Toxins 2015, 7(3), 659-678; https://doi.org/10.3390/toxins7030659 - 25 Feb 2015

Cited by 111 | Viewed by 20659

Abstract

Ergot is a disease of cereals and grasses caused by fungi in the genus Claviceps. Of particular concern are Claviceps purpurea in temperate regions, C. africana in sorghum (worldwide), and C. fusiformis in pearl millet (Africa, Asia). The fungi infect young, usually [...] Read more.

Ergot is a disease of cereals and grasses caused by fungi in the genus Claviceps. Of particular concern are Claviceps purpurea in temperate regions, C. africana in sorghum (worldwide), and C. fusiformis in pearl millet (Africa, Asia). The fungi infect young, usually unfertilized ovaries, replacing the seeds by dark mycelial masses known as sclerotia. The percentage of sclerotia in marketable grain is strictly regulated in many countries. In winter rye, ergot has been known in Europe since the early Middle Ages. The alkaloids produced by the fungus severely affect the health of humans and warm-blooded animals. In sorghum and pearl millet, ergot became a problem when growers adopted hybrid technology, which increased host susceptibility. Plant traits reducing ergot infection include immediate pollination of receptive stigmas, closed flowering (cleistogamy), and physiological resistance. Genetic, nonpollen-mediated variation in ergot susceptibility could be demonstrated in all three affected cereals. Fungicides have limited efficacy and application is weather dependent. Sorting out the sclerotia from the harvest by photocells is expensive and time consuming. In conclusion, molecular-based hybrid rye breeding could improve pollen fertility by introgressing effective restorer genes thus bringing down the ergot infection level to that of conventional population cultivars. A further reduction might be feasible in the future by selecting more resistant germplasm. Full article

(This article belongs to the Special Issue Ergot Alkaloids: Chemistry, Biology and Toxicology)

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Diversification of Ergot Alkaloids in Natural and Modified Fungi

by Sarah L. Robinson and Daniel G. Panaccione

Toxins 2015, 7(1), 201-218; https://doi.org/10.3390/toxins7010201 - 20 Jan 2015

Cited by 47 | Viewed by 9680

Abstract

Several fungi in two different families––the Clavicipitaceae and the Trichocomaceae––produce different profiles of ergot alkaloids, many of which are important in agriculture and medicine. All ergot alkaloid producers share early steps before their pathways diverge to produce different end products. EasA, an oxidoreductase [...] Read more.

Several fungi in two different families––the Clavicipitaceae and the Trichocomaceae––produce different profiles of ergot alkaloids, many of which are important in agriculture and medicine. All ergot alkaloid producers share early steps before their pathways diverge to produce different end products. EasA, an oxidoreductase of the old yellow enzyme class, has alternate activities in different fungi resulting in branching of the pathway. Enzymes beyond the branch point differ among lineages. In the Clavicipitaceae, diversity is generated by the presence or absence and activities of lysergyl peptide synthetases, which interact to make lysergic acid amides and ergopeptines. The range of ergopeptines in a fungus may be controlled by the presence of multiple peptide synthetases as well as by the specificity of individual peptide synthetase domains. In the Trichocomaceae, diversity is generated by the presence or absence of the prenyl transferase encoded by easL (also called fgaPT1). Moreover, relaxed specificity of EasL appears to contribute to ergot alkaloid diversification. The profile of ergot alkaloids observed within a fungus also is affected by a delayed flux of intermediates through the pathway, which results in an accumulation of intermediates or early pathway byproducts to concentrations comparable to that of the pathway end product. Full article

(This article belongs to the Special Issue Ergot Alkaloids: Chemistry, Biology and Toxicology)

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Biosynthetic Pathways of Ergot Alkaloids

by Nina Gerhards, Lisa Neubauer, Paul Tudzynski and Shu-Ming Li

Toxins 2014, 6(12), 3281-3295; https://doi.org/10.3390/toxins6123281 - 10 Dec 2014

Cited by 94 | Viewed by 14678

Abstract

Ergot alkaloids are nitrogen-containing natural products belonging to indole alkaloids. The best known producers are fungi of the phylum Ascomycota, e.g., Claviceps, Epichloë, Penicillium and Aspergillus species. According to their structures, ergot alkaloids can be divided into three groups: clavines, lysergic [...] Read more.

Ergot alkaloids are nitrogen-containing natural products belonging to indole alkaloids. The best known producers are fungi of the phylum Ascomycota, e.g., Claviceps, Epichloë, Penicillium and Aspergillus species. According to their structures, ergot alkaloids can be divided into three groups: clavines, lysergic acid amides and peptides (ergopeptines). All of them share the first biosynthetic steps, which lead to the formation of the tetracyclic ergoline ring system (except the simplest, tricyclic compound: chanoclavine). Different modifications on the ergoline ring by specific enzymes result in an abundance of bioactive natural products, which are used as pharmaceutical drugs or precursors thereof. From the 1950s through to recent years, most of the biosynthetic pathways have been elucidated. Gene clusters from several ergot alkaloid producers have been identified by genome mining and the functions of many of those genes have been demonstrated by knock-out experiments or biochemical investigations of the overproduced enzymes. Full article

(This article belongs to the Special Issue Ergot Alkaloids: Chemistry, Biology and Toxicology)

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