Biosynthesis of the ergot alkaloids

2014 ◽  
Vol 31 (10) ◽  
pp. 1328-1338 ◽  
Author(s):  
Dorota Jakubczyk ◽  
Johnathan Z. Cheng ◽  
Sarah E. O'Connor
Keyword(s):  
Ergot Alkaloid ◽  
Ergot Alkaloids ◽  
Alkaloid Biosynthesis ◽  
New Developments

An update on new developments in the field of ergot alkaloid biosynthesis since 2011 is highlighted.

scholarly journals Towards the elimination of ergot alkaloid biosynthesis genes in Neotyphodium Coenophialum

2007 ◽  
Vol 13 ◽  
pp. 477-479
Author(s):  
S. Florea ◽  
C. Machado ◽  
D. Zhang ◽  
D.G. Panaccione ◽  
C.L. Schardl
Keyword(s):  
Tall Fescue ◽  
Ergot Alkaloid ◽  
Festuca Arundinacea ◽  
Ergot Alkaloids ◽  
Loxp Site ◽  
Alkaloid Biosynthesis ◽  
Neotyphodium Coenophialum ◽  
Type Locus ◽  
Dimethylallyltryptophan Synthase ◽  
Recombination System

Neotyphodium coenophialum strain e19 from tall fescue cv. Kentucky 31 carries dmaW1 and dmaW2, two gene homologues that encode dimethylallyltryptophan synthase, the enzyme for the first step in ergot-alkaloid biosynthesis. In our effort to disrupt both homologues and ultimately obtain marker-free mutants, we are using a marker-exchange strategy employing the Cre/ loxP site-specific recombination system. Of 1522 transformants obtained and screened, three were likely dmaW2 disruptants because they gave no PCR product from the wild-type locus, but yielded the larger PCR fragment from the disruption construct. The putative dmaW2-knockouts were also transformed with pKAES186, a plasmid with a cassette containing the cre and ble genes in between loxP sequences. The transformants obtained were screened for the presence of hph, cre and ble genes. The preliminary results indicate a loop-out of the hph gene. The transformants inoculated into endophyte-free tall fescue preserved their compatibility with the plant. The fungus grown from these plants will be further analysed for the presence of hph, cre and ble genes. Keywords: Cre/LoxP, dimethylallyltryptophan synthase, dmaW, Epichloë, ergot alkaloids, Festuca arundinacea, gene knockouts, Lolium arundinaceum, Neotyphodium coenophialum, tall fescue

Ergot alkaloid biosynthesis by isolates of Balansia epichloë and B. henningsiana

1981 ◽  
Vol 59 (12) ◽  
pp. 2534-2538 ◽  
Author(s):  
Charles W. Bacon ◽  
James K. Porter ◽  
Joe D. Robbins
Keyword(s):  
Ergot Alkaloid ◽  
Sampling Site ◽  
Total Yield ◽  
Ergot Alkaloids ◽  
Chemical Species ◽  
Alkaloid Biosynthesis ◽  
Andropogon Virginicus ◽  
Clavicipitaceous Fungi

Two endophytic clavicipitaceous fungi, Balansia epichloë and B. henningsiana, were isolated from several grasses, cultured on laboratory media, and assessed for their ability to produce the major ergot alkaloids agroclavine, chanoclavine (I), ergonovine, and ergonovinine. Data indicated that the ability of these two species of fungi to biosynthesize ergot alkaloids was host related. All isolates of B. epichloë from smut-grass (Sporobolus poiretii) and 59% of the isolates of B. henningsiana from broom-sedge (Andropogon virginicus) produced the major alkaloids in culture. All isolates of B. epichloë from Eragrostis secundiflora and E. hirsuta, and all isolates of B. henningsiana from Panicum tenerum failed to produce alkaloids. The total yield and chemical species of individual alkaloids varied among isolates from a sampling site.

scholarly journals Ergot Alkaloids of the Family Clavicipitaceae

2017 ◽  
Vol 107 (5) ◽  
pp. 504-518 ◽  
Author(s):  
Simona Florea ◽  
Daniel G. Panaccione ◽  
Christopher L. Schardl
Keyword(s):  
Ergot Alkaloid ◽  
Gene Loss ◽  
Ergot Alkaloids ◽  
Gene Clusters ◽  
Lysergic Acid ◽  
Forage Grasses ◽  
Alkaloid Biosynthesis ◽  
The Family ◽  
Gene Recruitment ◽  
Alkaloid Profiles

Ergot alkaloids are highly diverse in structure, exhibit diverse effects on animals, and are produced by diverse fungi in the phylum Ascomycota, including pathogens and mutualistic symbionts of plants. These mycotoxins are best known from the fungal family Clavicipitaceae and are named for the ergot fungi that, through millennia, have contaminated grains and caused mass poisonings, with effects ranging from dry gangrene to convulsions and death. However, they are also useful sources of pharmaceuticals for a variety of medical purposes. More than a half-century of research has brought us extensive knowledge of ergot-alkaloid biosynthetic pathways from common early steps to several taxon-specific branches. Furthermore, a recent flurry of genome sequencing has revealed the genomic processes underlying ergot-alkaloid diversification. In this review, we discuss the evolution of ergot-alkaloid biosynthesis genes and gene clusters, including roles of gene recruitment, duplication and neofunctionalization, as well as gene loss, in diversifying structures of clavines, lysergic acid amides, and complex ergopeptines. Also reviewed are prospects for manipulating ergot-alkaloid profiles to enhance suitability of endophytes for forage grasses.

scholarly journals Assessment of ergot (Claviceps purpurea) exposure in pregnant and postpartum beef cows

2018 ◽  
Vol 98 (4) ◽  
pp. 688-700 ◽  
Author(s):  
T. Grusie ◽  
V. Cowan ◽  
J. Singh ◽  
J. McKinnon ◽  
B. Blakley
Keyword(s):  
Ergot Alkaloid ◽  
Post Partum ◽  
Ergot Alkaloids ◽  
Maximum Size ◽  
Beef Cows ◽  
Plasma Prolactin ◽  
Claviceps Purpurea ◽  
Ambient Temperatures ◽  
Beef Cow ◽  
The Impact

Cows were fed ration for 9 wk containing 5, 48, 201, and 822 μg kg−1 ergot alkaloids. The objective was to evaluate the impact of ergot consumption in beef cow–calf operations. Ergot alkaloids up to 822 μg kg−1 did not alter the weight of peripartum and postpartum beef cows (P = 0.93) or nursing calves (P = 0.08), rectal temperature (P = 0.16), or plasma prolactin concentrations (P = 0.30) at moderate ambient temperatures. Ergot did not influence the time (>1 ng mL−1; P = 0.79) or the progesterone concentration (P = 0.38) at the time of first postpartum rise or the size of the first (14 ± 0.6 mm; P = 0.40) and second (13 ± 0.5 mm; P = 0.41) follicles to ovulate. The maximum size of the first postpartum corpus luteum (CL) was 4 mm larger in the 822 μg kg−1 ergot group compared with the control (P = 0.03) for the first ovulation post partum, but not for the second (P = 0.11). There was no effect of ergot exposure on the number of days until the appearance of the first (43 ± 4 d; P = 0.95) or second (52 ± 4 d; P = 0.98) CL post partum. Ergot alkaloid concentrations up to 822 μg kg−1 did not affect pregnancy rates (X2 = 0.36). In conclusion, ergot alkaloid exposure for 9 wk to concentrations as high as 822 μg kg−1 did not alter performance in pregnant and postpartum beef cattle at moderate ambient temperatures.

Isolation of ergovaline, ergoptine, and ergonine, new alkaloids of the peptide type, from ergot sclerotia

1979 ◽  
Vol 57 (13) ◽  
pp. 1638-1641 ◽  
Author(s):  
Rudolf Brunner ◽  
Peter Leopold Stütz ◽  
Hans Tscherter ◽  
Paul Albert Stadler
Keyword(s):  
Total Synthesis ◽  
Ergot Alkaloid ◽  
Ergot Alkaloids ◽  
Extraction Processes

The isolation of three new ergot alkaloids of the peptide type from sclerotia of Clavicepspurpurea and from mother liquors of rye ergot alkaloid extraction processes is described. The constitution of the new alkaloids ergovaline, ergoptine, and ergonine has been established by comparison with compounds previously obtained by total synthesis.

scholarly journals Influence of Prolonged Serotonin and Ergovaline Pre-Exposure on Vasoconstriction Ex Vivo

Toxins ◽  
2021 ◽  
Vol 14 (1) ◽  
pp. 9
Author(s):  
Eriton E. L. Valente ◽  
David L. Harmon ◽  
James L. Klotz
Keyword(s):  
Blood Vessels ◽  
Ergot Alkaloid ◽  
Inhibitory Concentration ◽  
Contractile Response ◽  
Ex Vivo ◽  
Ergot Alkaloids ◽  
Exposure Period ◽  
Inhibitory Response ◽  
Previous Exposure ◽  
Ic50 Concentration

Ergot alkaloid mycotoxins interfere in many functions associated with serotonergic neurotransmitters. Therefore, the objective was to evaluate whether the association of serotonin (5-hydroxytryptamine, 5-HT) and ergot alkaloids during a 24 h pre-incubation could affect the vascular contractile response to ergot alkaloids. To evaluate the effects of 24 h exposure to 5-HT and ergot alkaloids (ergovaline, ERV), two assays were conducted. The first assay determined the half-maximal inhibitory concentration (IC50) following the 24 h pre-exposure period, while the second assay evaluated the effect of IC50 concentrations of 5-HT and ERV either individually or in combination. There was an interaction between previous exposure to 5-HT and ERV. Previous exposure to 5-HT at the IC50 concentration of 7.57 × 10−7 M reduced the contractile response by more than 50% of control, while the exposure to ERV at IC50 dose of 1.57 × 10−10 M tended to decrease (p = 0.081) vessel contractility with a response higher than 50% of control. The 24 h previous exposure to both 5-HT and ERV did not potentiate the inhibitory response of blood vessels in comparison with incubation with each compound alone. These results suggest receptor competition between 5-HT and ERV. More studies are necessary to determine the potential of 5-HT to treat toxicosis caused by ergot alkaloids.

scholarly journals Differentially expressed genes in cotyledon of ewes fed mycotoxins

BMC Genomics ◽  
2020 ◽  
Vol 21 (1) ◽  
Author(s):  
J. L. Britt ◽  
R. E. Noorai ◽  
S. K. Duckett
Keyword(s):  
Wound Healing ◽  
Differentially Expressed Genes ◽  
Ergot Alkaloid ◽  
Ergot Alkaloids ◽  
Late Gestation ◽  
Fetal Weight ◽  
Differentially Expressed ◽  
Coagulation Cascade ◽  
Peroxisome Proliferator ◽  
Metabolism Regulation

Abstract Background Ergot alkaloids (E+) are mycotoxins produced by the endophytic fungus, Epichloë coenophiala, in tall fescue that are associated with ergotism in animals. Exposure to ergot alkaloids during gestation reduces fetal weight and placental mass in sheep. These reductions are related to vasoconstrictive effects of ergot alkaloids and potential alterations in nutrient transport to the fetus. Cotyledon samples were obtained from eight ewes that were fed E+ (n = 4; E+/E+) or E- (endophyte-free without ergot alkaloids; n = 4; E−/E-) seed during both mid (d 35 to 85) and late (d 85–133) gestation to assess differentially expressed genes associated with ergot alkaloid induced reductions in placental mass and fetal weight, and discover potential adaptive mechanisms to alter nutrient supply to fetus. Results Ewes fed E+/E+ fescue seed during both mid and late gestation had 20% reduction in fetal body weight and 33% reduction in cotyledon mass compared to controls (E−/E-). Over 13,000 genes were identified with 110 upregulated and 33 downregulated. Four genes had a |log2FC| > 5 for ewes consuming E+/E+ treatment compared to controls: LECT2, SLC22A9, APOC3, and MBL2. REViGO revealed clusters of upregulated genes associated glucose, carbohydrates, lipid, protein, macromolecular and cellular metabolism, regulation of wound healing and response to starvation. For downregulated genes, no clusters were present, but all enriched GO terms were associated with anion and monocarboxylic acid transport. The complement and coagulation cascade and the peroxisome proliferator-activated receptor signaling pathway were found to be enriched for ewes consuming E+/E+ treatment. Conclusions Consumption of ergot alkaloids during gestation altered the cotyledonary transcriptome specifically related to macronutrient metabolism, wound healing and starvation. These results show that ergot alkaloid exposure upregulates genes involved in nutrient metabolism to supply the fetus with additional substrates in attempts to rescue fetal growth.

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