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Analysis of ergot alkaloids — a review

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Abstract

Methods for detection and determination of ergot alkaloids in grains, grasses, feeds and grain foods are reviewed. They incorporate simple detection procedures - colorimetry, thin layer chromatography and enzyme-linked immunosorbent assay - or instrumental procedures such as liquid chromatography with fluorescence, mass spectrometric (MS) or MS/MS detection, capillary zone electrophoresis, and direct MS/MS.

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References

  1. Lorenz K (1979) Ergot on cereal grains. CRC Crit Rev Food Sci Nutr 11: 311–354

    Article  PubMed  CAS  Google Scholar 

  2. Kobel H, Sanglier J-J ( 1986) Ergot alkaloids. In: Rehm H-J, Reed G (eds) Biotechnology (4). VCH Verlagsgesellschaft, Weinheim, 569–609

    Google Scholar 

  3. Řeháček Z, Sajdl P (1990) Ergot Alkaloids - Chemistry, Biological Effects, Biotechnology. Elsevier, Amsterdam

  4. Flieger M, Wurst M, Shelby R (1997) Ergot alkaloids — sources, structures and analytical methods. Folia Microbiol 42: 3–30

    Article  CAS  Google Scholar 

  5. Powell RG, Petroski RJ (1992) Alkaloid toxins in endophyte-infected grasses. Natural Tox 1: 163–170

    Article  CAS  Google Scholar 

  6. Bhat RV, Roy DN, Tulpule PG (1976) The nature of alkaloids of ergoty pearl millet or bajra and its comparison with alkaloids of ergoty rye and ergoty wheat. Toxicol Appl Pharmacol 36: 11–17

    Article  PubMed  CAS  Google Scholar 

  7. Krishnamachari KAVR, Bhat RV (1976) Poisoning by ergoty bajra (pearl millet) in man. Indian J Med Res 64: 1624–1628

    PubMed  CAS  Google Scholar 

  8. Demeke T, Kidane Y, Wuhib E ( 1979) Ergotism - a report on an epidemic, 1977–78. Ethiopian J Med 17: 107–113

    CAS  Google Scholar 

  9. Hogg RA (1991) Poisoning of cattle fed ergotised silage. Vet Rec 129: 313–314

    PubMed  CAS  Google Scholar 

  10. Porter JK (1995) Analysis of endophyte toxins: fescue and other grasses toxic to livestock. J Anim Sci 73: 871–880

    PubMed  CAS  Google Scholar 

  11. Miles CO, Lane GA, di Menna ME, Garthwaite I, Piper EL, Ball OJ-P, Latch GCM, Allen JM, Hunt MB, Bush LP, Min FK, Fletcher I, Harris PS (1996) High levels of ergonovine and lysergic acid amide in toxicAchnatherum inebrians accompanying infection by anAcremonium-like endophytic fungus. J Agric Food Chem 44: 1285–1290

    Article  CAS  Google Scholar 

  12. Griffith RW, Grauwiler J, Hodel, C, Leist KH, Matter B (1978) Toxicologie considerations. In: Berde B, Schild HO (eds) Ergot Alkaloids and Related Compounds. Springer Verlag, Berlin, 805–851

    Google Scholar 

  13. Canadian Grain Commission (2004) Official Grain Grading Guide, Canadian Grain Commission, Winnipeg, Manitoba http://www.grainscanada.gc.ca/Pubs/GGG/ggg-e.htm

  14. Robbers JE, Krupinski VM, Sheriat HS, Huber DM (1975) A method for the detection of ergot contamination in ground triticale grain. Phytopathology 65: 455–457

    CAS  Google Scholar 

  15. Young JC (1981) Variability in the content and composition of alkaloids found in Canadian ergot. I. Rye. J Environ Sci Health 16: 83–111

    Article  CAS  Google Scholar 

  16. Young JC (1981) Variability in the content and composition of alkaloids found in Canadian ergot. II. Wheat. J Environ Sci Health 16: 381–393

    CAS  Google Scholar 

  17. Young JC, Chen Z (1982) Variability in the content and composition of alkaloids found in Canadian ergot. III. Triticale and barley. J Environ Sci Health 17: 93–107

    CAS  Google Scholar 

  18. Ware GM, Carman AS, Francis OJ Jr, Kuan SS (1986) Liquid Chromatographie determination of ergot alkaloids in wheat. J Assoc Off Anal Chem 69: 697–699

    PubMed  CAS  Google Scholar 

  19. Shelby RA, Kelley VC (1990) An immunoassay for ergotamine and related alkaloids. J. Agric Food Chem 38: 1130–1134

    Article  CAS  Google Scholar 

  20. Shelby RA, Kelley VC (1991) Detection of ergot alkaloids in tall fescue by competitive immunoassay with a monoclonal antibody. Food Agric Immunol 3: 169–177

    Article  CAS  Google Scholar 

  21. Shelby RA, Kelley VC (1992) Detection of ergot alkaloids fromClaviceps species in agricultural products by competitive ELISA using a monoclonal antibody. J Agric Food Chem 40: 1090–1092

    Article  CAS  Google Scholar 

  22. Scott PM, Lawrence GA (1980) Analysis of ergot alkaloids in flour. J Agric Food Chem 28: 1258–1261

    Article  PubMed  CAS  Google Scholar 

  23. Scott PM, Lawrence GA (1982) Losses of ergot alkaloids during making of bread and pancakes. J Agric Food Chem 30: 445–450

    Article  PubMed  CAS  Google Scholar 

  24. Scott PM, Lombaert GA, Pellaers P, Bacler S, Lappi J (1992) Ergot alkaloids in grain foods sold in Canada. J AOAC Int 75: 773–779

    CAS  Google Scholar 

  25. Fajardo JE, Dexter JE, Roscoe MM, Nowicki TW (1995) Retention of ergot alkaloids in wheat during processing. Cereal Chem 72: 291–298

    CAS  Google Scholar 

  26. Ware GM, Price G, Carter L Jr, Eitenmiller RR (2000) Liquid Chromatographie preparative method for isolating ergot alkaloids, using a particle-loaded membrane extracting disc. J AOAC Int 83: 1395–1399

    PubMed  CAS  Google Scholar 

  27. Baumann U, Hunziker HR, Zimmerli B (1985) Mutterkoraalkaloide in schweizerischen Getreideprodukten. Mitt Gebiete Lebensm Hyg 76: 609–630

    CAS  Google Scholar 

  28. Lauber U, Schnaufer R, Gredziak M, Kiess-wetter Y (2005) Analysis of rye grains and rye meals for ergot alkaloids. Mycotoxin Research 21: 258–262

    CAS  Google Scholar 

  29. Rottinghaus GE, Schultz LM, Ross FP, Hill NS (1993) An HPLC method for the detection of ergot in ground and pelleted feeds. J Vet Diagn Invest 5: 242–247

    PubMed  CAS  Google Scholar 

  30. Rottinghaus GE, Garner GB, Cornell CM, Ellis JL (1991) HPLC method for quantitating ergovaline in endophyte-infested tall fescue: seasonal variation of ergovaline levels in stems with leaf sheaths, leaf blades, and seed heads. J Agric Food Chem 39: 112–115

    Article  CAS  Google Scholar 

  31. Yates SG Powell RG (1988) Analysis of ergopeptine alkaloids in endophyte-infected tall fescue. J Agric Food Chem 36: 337–340

    Article  CAS  Google Scholar 

  32. Stoll A, Schlientz W (1955) Über Belichtungsprodukte von Mutterkornalkaloide. Helv Chim Acta 38: 585–594

    Article  CAS  Google Scholar 

  33. Smith DJ, Shappell NW (2002) Technical note: Epimerization of ergopeptine alkaloids in organic and aqueous solvents. J Anim Sci 80: 1616–1622

    PubMed  CAS  Google Scholar 

  34. Hofmann A (1964) Die Mutterkornalkaloide. Ferdinand Erike Verlag, Stuttgart

    Google Scholar 

  35. Pakhomova S, Ondráček J, Hušák M, Kratochvíl B, Jegorov A, Stuchlík J (1995) Ergotamine tartrate bis(ethanol) solvate. Acta Cryst C51: 308–311

    CAS  Google Scholar 

  36. Lombaert GA (2001) Liquid Chromatographie method for the determination of ergot alkaloids in cereal grains. In: Trucksess MW, Pohland AE (eds) Mycotoxin Protocols. Humana Press, Totowa, NJ, 215–224

    Google Scholar 

  37. Michelon LE, Kelleher WJ (1963) A spectrophotometric determination of ergot alkaloids. A modified procedure employing paradimethylaminobenzaldehyde. Lloydia 26: 192–201

    CAS  Google Scholar 

  38. Zakhari NA, Hassan SM, El-Shabrawy Y (1991) Spectrophotometric determination of ergot alkaloids with ninhydrin. Acta Pharm Nord 3: 151–154

    CAS  Google Scholar 

  39. Zakhari NA, Hassan SM, El-Shabrawy Y (1989) Diazotised 4-nitroaniline as a chromogenic reagent for the determination of indole derivatives in certain pharmaceutical preparetions. Anal Lett 22: 3011–3024

    CAS  Google Scholar 

  40. Agurell S (1965) Thin-layer Chromatographie and thin-layer electrophoretic analysis of ergot alkaloids. Relations between structure, RM value and electrophoretic mobility in the clavine series. Acta Pharm Suecica 2: 357–374

    CAS  Google Scholar 

  41. Reichelt J, Kudrnáč S (1973) Analytical studies on ergot alkaloids and their derivatives. I. Separation of ergot alkaloids of the ergotoxine and ergotamine groups by thin-layer chromatography. J Chromatogr 87: 433–436

    Article  PubMed  CAS  Google Scholar 

  42. Eich E, Schunach W (1975) Direct quantitative evaluation of thin-layer chromatograms by remission- and fluorescence measurements. Part 4: Determination of ergot alkaloids from medicaments and ergot by fluorescence measurement. Planta Med 27: 58–64

    PubMed  CAS  Google Scholar 

  43. Prošek M, Kučan E, Katié M, Bano M (1976) Quantitative fluorodensitometric determination of ergot alkaloids. Chromatographia 9: 273–276

    Article  Google Scholar 

  44. Prošek M, Kučan E, Katié M, Bano M, Medja A (1978) Quantitative fluorodensitometric determination of ergot alkaloids. IV. Simultaneous measurement of fluorescence. Chromatographia 11: 578–580

    Article  Google Scholar 

  45. Hassan SM (1978) A simple thin-layer chromatography method for separating the ergot alkaloids. Pharmazie 33: 237

    PubMed  CAS  Google Scholar 

  46. Keipert S, Voigt R (1972) Quantitative Dünnschichtchromatographie von Mutterkornalkaloiden. J Chromatogr 64: 327–340

    Article  PubMed  CAS  Google Scholar 

  47. Szepesi G, Molnár J, Nyiredy S (1979) Separation and determination of ergotoxine and dihydroergotoxine alkaloids by a TLC method. Fresenius Z Anal Chem 294: 47–48

    Article  CAS  Google Scholar 

  48. Vanhaelen M, Vanhaelen-Fastré R (1972) Dosage photodensitométrique in situ des alcaloïdes dansSeeale cornutum. J Chromatogr 72: 139–144

    Article  PubMed  CAS  Google Scholar 

  49. Puech A, Dura Jacob M (1974) Identification d’alcaloïdes indoliques par Chromatographie en couches minces. Utilisation d’un révélateur à l’acide glyoxylique. J Pharm Belg 29: 126–132

    PubMed  CAS  Google Scholar 

  50. Rücker G, Taha A (1977) The use of πceptors for detection of alkaloids on thin layers. J Chromatogr 132: 165–177

    Article  PubMed  Google Scholar 

  51. Güven KC, Güneri T (1975) Thin-layer Chromatographie identification of ergot alkaloids and LSD. Eczacilik Bülteni 17: 46–48

    Google Scholar 

  52. Güven KC, Güneri T (1977) Identification of LSD and ergot alkaloids by thin-layer chromatography. Z Anal Chem 283: 32

    Article  Google Scholar 

  53. Röder E, Mutschier E, Rochelmeyer H (1969) Über die Verwendung von homogenen azeotropen Gemischen in der Dünnschicht-Chromatographie. III. Trennung von Mutterkornalkaloiden. Z Anal Chem 244: 46–47

    Google Scholar 

  54. Fowler R, Gomm PJ, Patterson DA (1972) Thin-layer chromatography of lysergide and other ergot alkaloids. J Chromatogr 72: 351–357

    Article  PubMed  CAS  Google Scholar 

  55. Lobo AM, Prabhakar S, Benito-Rodriguez AM (1981) The alkaloids of Portuguese ergot. Rev Port Quim 23: 1–6

    CAS  Google Scholar 

  56. Sallam LAR, Nairn N, El-Refai AH (1977) Thin-layer chromatography of some ergot alkaloids. Z Anal Chem 284: 47–48

    Article  CAS  Google Scholar 

  57. Hill NS, Agee CS (1994) Detection of ergoline alkaloids in endophyte-infected tall fescue by immunoassay. Crop Sci 34: 530–534

    CAS  Google Scholar 

  58. Schnitzius JM, Hill NS, Thompson CS, Craig AM (2001) Semiquantitative determination of ergot alkaloids in seed, straw, and digesta samples using a competitive enzyme-linked immunosorbent assay. J Vet Diagn Invest 13: 230–237

    PubMed  CAS  Google Scholar 

  59. Molloy JB, Moore CJ, Bruyeres AG, Murray S, Blaney BJ (2003) Determination of dihydroergosine in sorghum ergot using an immunoassay. J Agric Food Chem 51: 3916–3919

    Article  PubMed  CAS  Google Scholar 

  60. Heacock RA, Langille KR, MacNeil JD, Frei RW (1973) A preliminary investigation of the high-speed liquid chromatography of some ergot alkaloids. J Chromatogr 77: 425–430

    Article  PubMed  CAS  Google Scholar 

  61. Szepesy L, Fehér I, Szepesi G, Gazdag M (1978) High-performance liquid chromatography of ergot alkaloids. J Chromatogr 149: 271–280

    Article  CAS  Google Scholar 

  62. Wurst M, Flieger M, Řeháček Z (1978) Analysis of ergot alkaloids by high-performance liquid chromatography. I. Clavines and simple derivatives of lysergic acid. J Chromatogr 150: 477–483

    Article  CAS  Google Scholar 

  63. Yoshida A, Yamazaki S, Sakai T (1979) Étude par Chromatographie liquide à haute pression des alcaloïdes de l’ergot. J Chromatogr 170: 399–404

    Article  CAS  Google Scholar 

  64. Wurst M, Flieger M, Řeháček Z (1979) Analysis of ergot alkaloids by high-performance liquid chromatography. II. Cyclol alkaloids (ergopeptines). J Chromatogr 174: 401–407

    Article  CAS  Google Scholar 

  65. Lin LA (1993) Detection of alkaloids in foods with a multi-detector high performance liquid Chromatographie system. J Chromatogr 632: 69–78

    Article  PubMed  CAS  Google Scholar 

  66. Klug C, Baltes W, Krönert W, Weber R (1984) Mutterkornalkaloide in Cerealien — eine Methodenbeschreibung. Z Lebensm Unters Forsch 179: 245–246

    Article  PubMed  CAS  Google Scholar 

  67. Shelby RA, Olsovska J, Havlicek V, Flieger M (1997) Analysis of ergot alkaloids in endophyte-infected tall fescue by liquid chromatography/electrospray ionization mass spectrometry. J Agric Food Chem 45: 4674–4679

    Article  CAS  Google Scholar 

  68. Müller C, Klaffke HS, Krauthause W, Wittkowski R (2006) Determination of ergot alkaloids in rye and rye flour. Mycotoxin Research 22: 197–200

    Article  Google Scholar 

  69. Lombaert GA, Pellaers P, Roscoe V, Mankotia M, Neil R, Scott PM (2003) Mycotoxins in infant cereal foods from the Canadian market. Food Addit Contam 20: 494–504

    Article  PubMed  CAS  Google Scholar 

  70. Hatinguais P, Beziat D, Negol P, Tarroux R (1978) Contribution au dosage des alcaloïdes peptidiques duClaviceps purpurea. Trav Soc Pharm Montpellier 38: 329–342

    CAS  Google Scholar 

  71. Fankel R, Slad I (1980) Rasche und quantitative HPLC-Methode zur Bestimmung der Mutterkornhauptalkaloide. Fresenius Z Anal Chem 303: 208

    Article  CAS  Google Scholar 

  72. Magg H, Ballschmiter K (1985) Retention indices of some ergopeptines in reversed-phase high-performance liquid chromatography. J Chromatogr 331: 245–251

    Article  CAS  Google Scholar 

  73. Mohamed R, Gremaud E, Richoz-Payot J, Tabet JC, Guy PA (2006) Quantitative determination of five ergot alkaloids in rye flour by liquid chromatography-electrospray ionisation tandem mass spectrometry. J Chromatogr A 1114: 62–72

    Article  PubMed  CAS  Google Scholar 

  74. Bürk G, Höbel W, Rieht A (2006) Ergot alkaloids in cereal products: results from the Bavarian Health and Food Safety Authority. Mol Nutr Food Res 50: 437–442

    Article  PubMed  CAS  Google Scholar 

  75. Favretto D, Frison G, Vogliardi S, Ferrara SD (2007) Highly specific quantification of ergotamine in urine, blood, and hair samples by liquid chromatography-tandem mass spectrometry. Ther Drug Monit 29: 325–332

    Article  PubMed  CAS  Google Scholar 

  76. Lehner AF, Craig M, Fannin N, Bush L, Tobin, T. (2005) Electrospray[+] tandem quadrapole mass spectrometry in the elucidation of ergot alkaloids chromatographed by HPLC: screening of grass or forage samples for novel toxic compounds. J Mass Spectrom 40: 1484–1502

    Article  PubMed  CAS  Google Scholar 

  77. Sulyok M, Berthiller F, Krska R, Schuhmacher R (2006) Development and validation of a liquid chromatography/tandem mass spectrometric method for the determination of 39 mycotoxins in wheat and maize. Rapid Commun Mass Spectrom 20: 2649–2659

    Article  PubMed  CAS  Google Scholar 

  78. Eckers C, Games DE, Mallen DNB, Swann BP (1982) Studies of ergot alkaloids using highperformance liquid chromatography-mass spectrometry and B/E linked scans. Biomed Mass Spectrom 9: 162–173

    Article  CAS  Google Scholar 

  79. Fanali S, Flieger M, Steinerova N, Nardi A (1992) Use of cyclodextrins for the enantioselective separation of ergot alkaloids by capillary zone electrophoresis. Electrophoresis 13: 39–43

    Article  PubMed  CAS  Google Scholar 

  80. Frach K, Blaschke G (1998) Separation of ergot alkaloids and their epimers and determination in sclerotia by capillary electrophoresis. J Chromatogr A 808: 247–252

    Article  PubMed  CAS  Google Scholar 

  81. Berry AJ, Games DE, Perkins JR (1986) Supercritical fluid Chromatographie and supercritical fluid-mass spectrometric studies of some polar compounds. J Chromatogr 363: 147–158

    Article  CAS  Google Scholar 

  82. Scott PM (1993) Gas chromatography of mycotoxins. In: Betina V (ed) Chromatography of Mycotoxins. Techniques and Applications. Elsevier, Amsterdam, 373–425

    Google Scholar 

  83. Klug C, Baltes W, Kronert W, Weber R (1988) A method for the determination of ergot alkaloids in food. Z Lebensm Unters Forsch 186: 108–113

    Article  PubMed  CAS  Google Scholar 

  84. Agurell S, Ohlsson A (1971) Gas chromatography of ergot alkaloids. J Chromatogr 61, 339–342

    Article  PubMed  CAS  Google Scholar 

  85. Plattner RD, Yates SG, Porter JK (1983) Quadrupole mass spectrometry/mass spectrometry of ergot cyclol alkaloids. J Agric Food Chem 31: 785–789

    Article  CAS  Google Scholar 

  86. Yates SG, Plattner RD, Garner GB (1985) Detection of ergopeptine alkaloids in endophyte infected toxic Ky-31 tall fescue by mass spectrometry/mass spectrometry. J Agric Food Chem 33: 719–722

    Article  CAS  Google Scholar 

  87. Rowan DD, Shaw GJ (1987) Detection of ergopeptine alkaloids in endophyte-infected perennial ryegrass by tandem mass spectrometry. New Zealand Vet J 35: 197–198

    CAS  Google Scholar 

  88. Mohamed R, Gremaud E, Tabet JC, Guy PA (2006) Mass spectral characterization of ergot alkaloids by electrospray ionization, hydrogen/ deuterium exchange, and multiple stage mass spectrometry: Usefulness of precursor ion scan experiments. Rapid Commun Mass Spectrom 20: 2787–2799.

    Article  PubMed  CAS  Google Scholar 

  89. Uhlig S, Vikoren T, Ivanova L, Handeland K (2007) Ergot alkaloids in Norwegian wild grasses: a mass spectrometric approach. Rapid Commun Mass Spectrom 21: 1651–1660

    Article  PubMed  CAS  Google Scholar 

  90. Porter JK, Betowski D (1981) Chemical ionizetion mass spectrometry of ergot cyclol alkaloids. J Agric Food Chem 29: 650–653

    Article  CAS  Google Scholar 

  91. Roberts CA, Benedict HR, Hill NS, Kallenbach RL, Rottinghaus GE (2005) Determination of ergot alkaloid content in tall fescue by nearinfrared spectroscopy. Crop Sci 45: 778–783

    CAS  Google Scholar 

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Scott, P.M. Analysis of ergot alkaloids — a review. Mycotox Res 23, 113–121 (2007). https://doi.org/10.1007/BF02951506

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