Ergovaline

Ergovaline

Clinical data
Pregnancy category	US: 4 months
Identifiers
CAS Number	2873-38-3
PubChem (CID)	104843
ChemSpider	94635
Chemical and physical data
Formula	C29H35N5O5
Molar mass	533.619 g/mol
3D model (Jmol)	Interactive image
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(cn5)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 Key:BGHDUTQZGWOQIA-VQSKNWBGSA-N
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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]

See also

• Neotyphodium coenophialum

References

1. Richard Browning (2003). "Tall Fescue Endophyte Toxicosis in Beef Cattle: Clinical Mode of Action and Potential Mitigation through Cattle Genetics" (PDF). Beef Improvement Federation.
2. Hovermale, J. T.; Craig, A. M. (2001). "Correlation of Ergovaline and Lolitrem B Levels in Endophyte-Infected Perennial Ryegrass (Lolium Perenne)". Journal of Veterinary Diagnostic Investigation. 13 (4): 323–327. doi:10.1177/104063870101300407. PMID 11478604.
3. Schnitzius, J. M.; Hill, N. S.; Thompson, C. S.; Craig, A. M. (2001). "Semiquantitative determination of ergot alkaloids in seed, straw, and digesta samples using a competitive enzyme-linked immunosorbent assay". Journal of veterinary diagnostic investigation : official publication of the American Association of Veterinary Laboratory Diagnosticians, Inc. 13 (3): 230–237. PMID 11482600.