Endophyte-associated ergot alkaloids

AccessScience ◽  
2015 ◽  
Keyword(s):  
Crop Science ◽  
2002 ◽  
Vol 42 (2) ◽  
pp. 518 ◽  
Author(s):  
N. S. Hill ◽  
J. H. Bouton ◽  
F. N. Thompson ◽  
L. Hawkins ◽  
C. S. Hoveland ◽  
...  
Keyword(s):  

1982 ◽  
Vol 47 (12) ◽  
pp. 3312-3317 ◽  
Author(s):  
Josef Stuchlík ◽  
Alois Krajíček ◽  
Ladislav Cvak ◽  
Jiří Spáčil ◽  
Petr Sedmera ◽  
...  

Two new alkaloids were isolated from the field ergot. Their structures, N-(D-lysergyl-L-valyl)cyclo(L-valyl-D-prolyl) (IV) and N-(D-lysergyl-L-valyl)cyclo(L-leucyl-D-prolyl) (V), were assigned by mass, 1H and 13C NMR spectroscopy.


2020 ◽  
Vol 113 (5) ◽  
pp. 2079-2085
Author(s):  
Navneet Kaur ◽  
W Rodney Cooper ◽  
Jennifer M Duringer ◽  
Arash Rashed ◽  
Ismael E Badillo-Vargas ◽  
...  

Abstract Our previous study provided correlative evidence that morning glory species harboring endophytic fungi (Periglandula) are resistant to potato psyllid [Bactericera cockerelli (Šulc)], whereas species free of fungi often allowed psyllid development. In this study, we manipulated levels of ergot alkaloids in host tissues by inoculating clippings from potato plants with extracts from morning glories that harbor Periglandula [Ipomoea leptophylla Torrey, Ipomoea imperati (Vahl) Grisebach, Ipomoea tricolor Cavanilles, Ipomoea pandurata (L.) G. F. Meyer, and Turbina corymbosa (L.)] and one species (Ipomoea alba L.) that does not harbor the endophyte. Ergot alkaloids (clavines, lysergic acid amides, and ergopeptines) were detected in potato clippings, thus confirming that leaves had taken up compounds from solutions of crude extracts. Psyllid mortality rates on inoculated clippings ranged between 53 and 93% in treatments producing biochemically detectable levels of alkaloids, when compared with 15% mortality in water controls or the alkaloid-free I. alba. We then tested synthetic analogs from each of the three alkaloid classes that had been detected in the crude extracts. Each compound was assayed by inoculating clippings of two host species (potato and tomato) at increasing concentrations (0, 1, 10, and 100 µg/ml in solution). Psyllids exhibited a large and significant increase in mortality rate beginning at the lowest two concentrations, indicating that even very small quantities of these chemicals led to mortality. Feeding by nymphs on artificial diets containing synthetic compounds resulted in 100% mortality within 48 h, irrespective of compound. Further testing of ergot alkaloids to characterize the mode of action that leads to psyllid mortality is warranted.


2020 ◽  
Vol 98 (Supplement_2) ◽  
pp. 31-31
Author(s):  
Kevin R Meng ◽  
Eric Bailey ◽  
Josh Zeltwanger ◽  
Hannah Allen ◽  
Mikaela Adams ◽  
...  

Abstract Chemical seed-head suppression of endophyte infected tall fescue (Lolium arundinaceum) improves stocker cattle performance but may decrease forage yield. Spring nitrogen application increases tall fescue growth with a concomitant increase in ergot alkaloids, produced by the symbiotic endophyte Epichloë coenophiala. We hypothesized that greater amounts of nitrogen applied to tall fescue would increase forage yield and offset losses in forage production from chemical suppression of seed-heads with metsulfuron without effect on alkaloid concentration. Ninety-six steers (270 ± 20 kg) were randomly assigned to one of sixteen paddocks (1.8 ha) on April 18 and continuously grazed for 57 d. Paddocks were blocked by previous use (n = 4) and randomly assigned to one of four treatments; no metsulfuron, no nitrogen (NEGCON), metsulfuron with 0 (MET0), 67 (MET67), or 134 (MET134) kg/ha of ammonium nitrate, applied March 11. Steers grazing MET0 paddocks were removed 17 d early due to insufficient forage availability. Steer weight, forage yield, forage nutritive value and ergot alkaloids in forage samples were measured monthly. Seed-head frequency and species composition were determined in June. Metsulfuron application reduced (P < 0.01) tall fescue seed-heads by 80%. Metsulfuron decreased (P = 0.03) ergovaline but ergovaline increased (P < 0.01) at each monthly sampling across treatments. Nitrogen had no impact on ergovaline concentration (P = 0.50). Forage yield tended to be least (P = 0.07) for MET0, intermediate for NEGCON and MET67, and tended to be greatest for MET134 (P = 0.08). Steer ADG was not affected by treatment (P < 0.80). Metsulfuron decreased NDF (P=0.02) regardless of fertilization rate. Forage CP increased with fertilization (P < 0.01) and no differences were detected between NEGCON and MET0 (P = 0.45). Species composition was not impacted (P >0.07) by treatment. Metsulfuron decreased seed-head growth and ergovaline concentration in tall fescue. Additional nitrogen fertilizer ameliorated forage yield lost to metsulfuron application but did not impact steer gain.


1999 ◽  
Vol 23 (2) ◽  
pp. 94-95
Author(s):  
Mark A. E. Bowman ◽  
Ralph E. Bowman

Reaction of the N-formyl enol-lactone 4 and the corresponding N-acetyl 10 and N-methoxycarbonyl 11 derivatives with bis(trimethylsilyl)potassiomalonate in THF at 60°C followed by treatment with aqueous sodium hydrogen carbonate and cyclisation as above, yielded the 4-formyl-, 4-acetyl- and 4-methoxycarbonyl-tricyclic ketones 7, 13 and 14 in yields of 31, 35 and 36%, respectively.


1936 ◽  
Vol 113 (3) ◽  
pp. 767-778
Author(s):  
Walter A. Jacobs ◽  
Lyman C. Craig
Keyword(s):  

1938 ◽  
Vol 122 (2) ◽  
pp. 419-423
Author(s):  
Walter A. Jacobs ◽  
Lyman C. Craig
Keyword(s):  

Toxins ◽  
2021 ◽  
Vol 13 (4) ◽  
pp. 291
Author(s):  
Rossalin Yonpiam ◽  
Jair Gobbet ◽  
Ashok Jadhav ◽  
Kaushik Desai ◽  
Barry Blakley ◽  
...  

Ergotism is a common and increasing problem in Saskatchewan’s livestock. Chronic exposure to low concentrations of ergot alkaloids is known to cause severe arterial vasoconstriction and gangrene through the activation of adrenergic and serotonergic receptors on vascular smooth muscles. The acute vascular effects of a single oral dose with high-level exposure to ergot alkaloids remain unknown and are examined in this study. This study had two main objectives; the first was to evaluate the role of α1-adrenergic receptors in mediating the acute vasocontractile response after single-dose exposure in sheep. The second was to examine whether terazosin (TE) could abolish the vascular contractile effects of ergot alkaloids. Twelve adult female sheep were randomly placed into control and exposure groups (n = 6/group). Ergot sclerotia were collected and finely ground. The concentrations of six ergot alkaloids (ergocornine, ergocristine, ergocryptine, ergometrine, ergosine, and ergotamine) were determined using HPLC/MS at Prairie Diagnostic Services Inc., (Saskatoon, SK, Canada). Each ewe within the treatment group received a single oral treatment of ground ergot sclerotia at a dose of 600 µg/kg BW (total ergot) while each ewe in the control group received water. Animals were euthanized 12 h after the treatment, and the pedal artery (dorsal metatarsal III artery) from the left hind limb from each animal was carefully dissected and mounted in an isolated tissue bath. The vascular contractile response to phenylephrine (PE) (α1-adrenergic agonist) was compared between the two groups before and after TE (α1-adrenergic antagonist) treatment. Acute exposure to ergot alkaloids resulted in a 38% increase in vascular sensitivity to PE compared to control (Ctl EC50 = 1.74 × 10−6 M; Exp EC50 = 1.079 × 10−6 M, p = 0.046). TE treatment resulted in a significant dose-dependent increase in EC50 in both exposure and control groups (p < 0.05 for all treatments). Surprisingly, TE effect was significantly more pronounced in the ergot exposed group compared to the control group at two of the three concentrations of TE (TE 30 nM, p = 0.36; TE 100 nM, p < 0.001; TE 300 nM, p < 0.001). Similar to chronic exposure, acute exposure to ergot alkaloids results in increased vascular sensitivity to PE. TE is a more potent dose-dependent antagonist for the PE contractile response in sheep exposed to ergot compared to the control group. This study may indicate that the dry gangrene seen in sheep, and likely other species, might be related to the activation of α1-adrenergic receptor. This effect may be reversed using TE, especially at early stages of the disease before cell death occurs. This study may also indicate that acute-single dose exposure scenario may be useful in the study of vascular effects of ergot alkaloids.


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