Ergovaline

Ergovaline is an ergopeptine and one of the ergot alkaloids. It is usually found in endophyte-infected species of grass like Tall fescue[1] or Perennial Ryegrass.[2] It is toxic to cattle feeding on infected grass, probably because it acts as a vasoconstrictor.[1][3]

Ergovaline
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC29H35N5O5
Molar mass533.629 g·mol−1
3D model (JSmol)
SMILES
  • O=C3N1CCC[C@H]1[C@]2(O)O[C@](C(=O)N2[C@H]3C(C)C)(NC(=O)[C@@H]7/C=C6/c4cccc5c4c(c[nH]5)C[C@H]6N(C)C7)C
InChI
  • InChI=1S/C29H35N5O5/c1-15(2)24-26(36)33-10-6-9-22(33)29(38)34(24)27(37)28(3,39-29)31-25(35)17-11-19-18-7-5-8-20-23(18)16(13-30-20)12-21(19)32(4)14-17/h5,7-8,11,13,15,17,21-22,24,30,38H,6,9-10,12,14H2,1-4H3,(H,31,35)/t17-,21-,22+,24+,28-,29+/m1/s1 N
  • Key:BGHDUTQZGWOQIA-VQSKNWBGSA-N N
 NY (what is this?)  (verify)

See also
  • Neotyphodium coenophialum

References
  1. Browning R (2003). "Tall Fescue Endophyte Toxicosis in Beef Cattle: Clinical Mode of Action and Potential Mitigation through Cattle Genetics" (PDF). Beef Improvement Federation. {{cite journal}}: Cite journal requires |journal= (help)
  2. Hovermale JT, Craig AM (July 2001). "Correlation of ergovaline and lolitrem B levels in endophyte-infected perennial ryegrass (Lolium perenne)". Journal of Veterinary Diagnostic Investigation. 13 (4): 323–7. doi:10.1177/104063870101300407. PMID 11478604.
  3. Schnitzius JM, Hill NS, Thompson CS, Craig AM (May 2001). "Semiquantitative determination of ergot alkaloids in seed, straw, and digesta samples using a competitive enzyme-linked immunosorbent assay". Journal of Veterinary Diagnostic Investigation. 13 (3): 230–7. doi:10.1177/104063870101300307. PMID 11482600.


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