Insights into the Mechanism and Enantioselectivity in the Biosynthesis of Ergot Alkaloid Cycloclavine Catalyzed by Aj_EasH from Aspergillus japonicus

2019 ◽  
Vol 58 (20) ◽  
pp. 13771-13781 ◽  
Author(s):  
Lijuan Yan ◽  
Yongjun Liu
Keyword(s):  
Ergot Alkaloid ◽  
Aspergillus Japonicus

scholarly journals Structural characterization of EasH (Aspergillus japonicus) – an oxidase involved in cycloclavine biosynthesis

2016 ◽  
Vol 52 (99) ◽  
pp. 14306-14309 ◽  
Author(s):  
Dorota Jakubczyk ◽  
Lorenzo Caputi ◽  
Clare E. M. Stevenson ◽  
David M. Lawson ◽  
Sarah E. O'Connor
Keyword(s):  
Structural Characterization ◽  
Ergot Alkaloid ◽  
Heme Iron ◽  
Ring Formation ◽  
Aspergillus Japonicus ◽  
Non Heme Iron

Aj_EasH is a non-heme iron- and α-keto-glutarate-dependent oxidase that is responsible for an unusual cyclopropyl ring formation in the biosynthesis of the fungal ergot alkaloid cycloclavine.

Crystal Forms of Semisynthetic Ergot Alkaloid Terguride

2002 ◽  
Vol 67 (4) ◽  
pp. 479-489 ◽  
Author(s):  
Michal Hušák ◽  
Bohumil Kratochvíl ◽  
Ivana Císařová ◽  
Ladislav Cvak ◽  
Alexandr Jegorov ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Ergot Alkaloid ◽  
Simplified Model ◽  
Quantum Mechanical ◽  
Quantum Mechanical Calculations ◽  
X Ray Diffraction ◽  
Torsion Angles ◽  
Crystal Forms ◽  
X Ray ◽  
Independent Molecules

Two new structures of semisynthetic ergot alkaloid terguride created by unusual number of symmetry-independent molecules were determined by X-ray diffraction methods at 150 K. Form A (monoclinic, P212121, Z = 12) contains three symmetry-independent terguride molecules and two molecules of water in the asymmetric part of the unit cell. The form CA (monoclinic, P21, Z = 8) is an anhydrate remarkable by the presence of four symmetry-independent molecules in the crystal structure. Conformations of twelve symmetry-independent molecules that were found in four already described terguride structures are compared with torsion angles obtained by ab initio quantum-mechanical calculations for the simplified model of N-cyclohexyl-N'-diethylurea.

Determining the Rate of Ergot-alkaloid Degradation in Toxic Endophyte-infected Tall Fescue Hay and Haylage During Long Term Storage

2021 ◽  
Vol 99 (Supplement_2) ◽  
pp. 22-22
Author(s):  
Charles A Zumbaugh ◽  
Susannah A Gonia ◽  
Kathryn M Payne ◽  
Thomas B Wilson
Keyword(s):  
Tall Fescue ◽  
Ergot Alkaloid ◽  
Fixed Effects ◽  
High Performance ◽  
Nutritive Value ◽  
Day Treatment ◽  
Random Effect ◽  
Storage Period ◽  
Neutral Detergent Fiber ◽  
Experimental Unit

Abstract The objectives of this experiment were to determine changes in the nutritive value and ergot alkaloid concentrations of endophyte-infected tall fescue hay and haylage during a 180-d storage period. Forage from a single field of Kentucky-31 tall fescue was cut for hay in late June and allowed to dry in the field. The dry matter (DM) of the windrow of cut forage was measured every 2 h after clipping. Forage was sampled from the windrow in 6 location blocks once forage DM reached target levels for haylage and hay treatments. Haylage and hay samples were taken when the DM of the windrow reached 50% and 80%, respectively. Seven subsamples of each treatment within block were chopped to 1.91 cm in length with a lettuce chopper and vacuum sealed in oxygen-excluding bags. Sample bags were stored indoors and opened at 30 d intervals over the 180-d storage period. Samples were analyzed for pH, nutritive value, and individual ergot alkaloid concentrations using high-performance liquid chromatography. Within each storage day, treatment within block was considered the experimental unit. Data were analyzed in SAS using the MIXED procedure with fixed effects of treatment, day, and the treatment by day interaction. Location block was considered a random effect. As expected, pH was decreased for haylage compared to hay at all time points (P < 0.01) and DM was greater (P < 0.01) for hay compared to haylage. Neutral detergent fiber values were greater (P < 0.01) for hay compared to haylage and declined during storage (P < 0.01). Total ergot alkaloid concentrations did not differ by treatment (P = 0.61), but ergovaline concentrations declined (P < 0.01) during storage. Collectively, these results indicate minimal differences in nutritive value and ergot alkaloid concentrations between hay and haylage during storage, and that ergovaline concentrations decline during storage.

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.

TOTAL SYNTHESIS OF ERGOT ALKALOID, (±)-6,7-SECOAGROCLAVINE

1981 ◽  
Vol 10 (5) ◽  
pp. 615-618 ◽  
Author(s):  
Masanori Somei ◽  
Fumio Yamada ◽  
Yoshio Karasawa ◽  
Chikara Kaneko
Keyword(s):  
Total Synthesis ◽  
Ergot Alkaloid

A gene cluster for ergovaline biosynthesis

2007 ◽  
Vol 13 ◽  
pp. 460-460
Author(s):  
D.J. Fleetwood ◽  
B. Scott ◽  
G.A. Lane ◽  
A. Tanaka ◽  
R.D. Johnson
Keyword(s):  
Gene Cluster ◽  
Ergot Alkaloid

Some strains of Epichloë and Neotyphodium endophytes produce the ergot alkaloid ergovaline, which is implicated in livestock toxicoses caused by ingestion of endophyte-infected grasses.

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