ESI-Mass spectrometric and HPLC elucidation of a new ergot alkaloid from perennial ryegrass hay silage associated with bovine reproductive problems

Andreas F. Lehner, Jennifer M. Duringer, Charles T. Estill, Thomas Tobin, A. Morrie Craig

Research output: Contribution to journalReview articlepeer-review

7 Scopus citations


This case report involves four dairies in the Willamette Valley, Oregon, which experienced reproductive problems associated with the presence of a large, previously unidentified, peak eluting at 5min in a standard ergovaline high-performance liquid chromatography assay of perennial ryegrass silage fed to those animals. Mycotoxin analysis of the silage was negative, as was serological screening of the herds for infectious bovine rhinotracheitis, bovine diarrhea virus and Leptospirosis, including culturing of urine for Leptospira hardjo hardjobovis. Prolactin concentrations were low in most cattle, consistent with ingestion of ergot alkaloids. We believe that this peak represents a novel ergot alkaloid-related compound due to its extractability with Ergosil, its detectability due to fluorescence, and its chromatographic retention between ergovaline (mw=533) and ergotamine (mw=581). Its molecular weight was calculated as 570 owing to the predominance of a m/z 593.5 ion in the full scan ESI(+)MS and its deduced tendency to complex with Na+ (as m/z 593) or K + (as m/z 609) ions. We offer rationales for elucidation of the structure of this compound, with the closest starting point comprising an m.w. of 566a fructofuranosyl-(2-1)-O-beta-D-fructofuranoside derivative of 6,7-secoergoline from Claviceps fusiformis. This m.w. requires modifications, such as reduction of two double bonds in the secoergoline component to give the target 570 m.w. Despite the lack of a definitive structure, the analysis herein provides a starting point for eventual elucidation of this apparently new ergot alkaloid, and to guide and encourage further investigation as to its association with endophyte toxicosis in livestock.

Original languageEnglish
Pages (from-to)606-621
Number of pages16
JournalToxicology Mechanisms and Methods
Issue number8
StatePublished - Oct 2011

Bibliographical note

Funding Information:
Funding for this project was provided in part by the Oregon Agricultural Experiment Station (project ORE00871) and the United States Department of Agriculture (USDA), Agricultural Research Service under cooperative agreement # 58–6227-8-044, Dale Bumpers Small Farms Research Center, Booneville AR. Any opinions, findings, conclusions, or recommendation expressed in this publication are those of the author(s) and do not necessarily reflect the view of the U.S. Department of Agriculture. Published as paper #396 from the Equine Pharmacology, Therapeutics and Toxicology Program at the Maxwell H. Gluck Equine Research Center and Department of Veterinary Science, University of Kentucky. Published as Kentucky Agricultural Experimental Station Article # 11–14-031 with the approval of the Dean and Director, College of Agriculture and The Kentucky Agricultural Experimental Station. This work was supported in part by ongoing research support from The National Horsemen’s Benevolent and Protective Association and the Alabama, Arizona, Arkansas, Canada, Charles Town (West Virginia), Florida, Iowa, Indiana, Kentucky, Louisiana, Michigan, Minnesota, Nebraska, Ohio, Oklahoma, Ontario (Canada), Oregon, Pennsylvania, Tampa Bay Downs (Florida), Texas, Washington State, and West Virginia Horsemen’s Benevolent and Protective Associations and the Florida Horsemen’s Charitable Foundation, the Oklahoma Quarter Horse Racing Association and the Neogen Corporation.


  • Dairy cows
  • Ergot alkaloids
  • Reproductive problems
  • Ryegrass
  • Silage

ASJC Scopus subject areas

  • Toxicology
  • Health, Toxicology and Mutagenesis


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