Lactam ergot alkaloids (ergopeptams) as predominant alkaloids in sclerotia of Claviceps purpurea from Norwegian wild grasses

Toxicon

Volumn 52, Issue 1, 2008, Pages 175-185

  Uhlig, Silvio ^a   Petersen, Dirk ^b  

^a NORWEGIAN VETERINARY INSTITUTE   (Norway)

^b UNIVERSITY OF OSLO   (Norway)

Author keywords

Clavicipitaceae; Ergot; Indole alkaloids; Ion trap MS; NMR

Indexed keywords

ALPHA ERGOCRYPTAM; ERGOANNAM; ERGOCRISTAM; ERGOCRYPTAM; ERGOPEPTAM; ERGOT ALKALOID; LACTAM;

ARTICLE; CHEMICAL STRUCTURE; CLAVICEPS PURPUREA; CONTROLLED STUDY; GRASS; MASS SPECTROMETRY; NONHUMAN; NORWAY; PRIORITY JOURNAL;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CLAVICEPS; ERGOT ALKALOIDS; POACEAE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

CLAVICEPS PURPUREA; CLAVICIPITACEAE; POACEAE;

EID: 47849084274     PISSN: 00410101     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.toxicon.2008.05.002     Document Type: Article

References (19)

1. Bach N.J., Boaz H.E., Kornfeld E.C., Chang C.-J., Floss H.G., Hagaman E.W., and Wenkert E. Nuclear magnetic resonance spectral analysis of the ergot alkaloids. J. Org. Chem. 39 (1974) 1272-1276
2. Beran M., and Krepelka J. Současný stav výzkumu námelových alkaloidu. Česk. Farm. 34 (1985) 194-198
3. 1H-NMR spectroscopy. J. Pharm. Biomed. Anal. 12 (1994) 27-40
4. Černy A., Krajček A., Spáčil J., Beran M., Kakáč B., and Semonský M. Isolation of N-[N-(d-lysergyl)-l-valyl]-cyclo(l-phenylalanyl-d-prolyl) from the ergotoxine type of field ergot and some of its reactions. Collect. Czech. Chem. Commun. 41 (1976) 3415-3419
5. Flieger M., Sedmera P., Vokoun J., Řehaček Z., Stuchlik J., Malinka Z., Cvak L., and Harazim P. New alkaloids from a saprophytic culture of Claviceps purpurea. J. Nat. Prod. 47 (1984) 970-976
6. Flieger M., Wurst M., and Shelby R. Ergot alkaloids - sources, structures and analytical methods. Folia Microbiol. 42 (1997) 3-30
7. Flieger M., Wurst M., Stuchlik J., and Řehaček Z. Isolation and separation of new natural lactam alkaloids of ergot by high-performance liquid chromatography. J.Chromatogr. 207 (1981) 139-144
8. Floss H.G., Tcheng-Lin M., Kobel H., and Stadler P. On the biosynthesis of peptide ergot alkaloids. Experientia 30 (1974) 1369-1370
9. Komarova E.L., and Tolkachev N.O. Medicinal plants: the chemistry of peptide ergot alkaloids. Part 1. Classification and chemistry of ergot peptides. Pharm. Chem. J. 35 (2001) 504-513
10. Komarova E.L., Shain S.S., and Sheichenko V.I. Isolation of the ergot strain Claviceps purpurea (Fr.) Tul. VKM-F-366D producing the lactamic alkaloid ergocornam. Prikl. Biokhim. Mikrobiol. 38 (2002) 658-663
11. Mukherjee J., and Menge J. Progress and prospects of ergot alkaloid research. Adv. Biochem. Eng. Biotechnol. 68 (2000) 1-20
12. Pakhomova S., Ondráček J., Hušák M., Kratochvil B., Jegorov A., Cvak L., Sedmera P., and Havlicek V. Conformation of ergopeptam and ergopeptine alkaloids (ergocristam and ergocristine). Z. Kristall. 212 (1997) 593-600
13. Reynolds W.F., and Enriquez R.G. Choosing the best pulse sequences, acquisition parameters, postacquisition processing strategies, and probes for natural product structure elucidation by NMR spectroscopy. J. Nat. Prod. 65 (2002) 221-244
14. Schardl C.L., Panaccione D.G., and Tudzynski P. Ergot alkaloids - biology and molecular biology. Alkaloids Chem. Biol. 63 (2006) 45-86
15. Stadler P. Neuere Ergebnisse der Mutterkornalkaloid-Forschung (New results of ergot alkaloid research). Planta Med. 46 (1982) 131-144
16. Stuchlik J., Krajiček A., Cvak L., Spačil J., Sedmera P., Flieger M., Vokoun J., and Řehaček Z. Non-cyclol (lactame) ergot alkaloids. Collect. Czech. Chem. Commun. 47 (1982) 3312-3317
17. Stütz P., Brunner R., and Stadler P.A. Ein neues Alkaloid aus dem Mycel eine Claviceps purpurea- Stammes. Zur Biogenese von Ergocristin. Experientia 29 (1973) 936-937
18. Szántay Jr. C., Bihari M., Brlik J., Csehi A., Kassai A., and Aranyi A. Structural elucidation of two novel ergot alkaloid impurities in α-ergokryptine and bromokryptine. Acta Pharm. Hung. 64 (1994) 105-108
19. Uhlig S., Vikøren T., Ivanova I., and Handeland K. Ergot alkaloids in Norwegian wild grasses: a mass spectrometric approach. Rapid Commun. Mass Spectrom. 21 (2007) 1651-1660