Recent Advances in Analytical Methodology for Cyclopiazonic Acid

  • Joe W. Dorner
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 504)


Cyclopiazonic acid (CPA) is a toxic indole tetramic acid that has been isolated from numerous speciesofAspergillusandPenicillium.It has been found as a natural contaminant of cheese, corn, peanuts and various feedstuffs. Historically, thin-layer chromatography has been the most widely used method for quantitative determination of CPA in fungal cultures and agricultural commodities. Several liquid chromatographic (LC) and spectrophotometric methods have also been used, but these require extensive, time-consuming cleanup procedures to achieve accurate quantitation. More recently, enzyme-linked immunosorbent assays (ELISA) have been developed for quantification of CPA, and an immunoaffinity column (IAC) has been developed for cleanup of sample extracts prior to quantification by ELISA or LC. In applying the IAC to the cleanup of peanut extracts, recovery of CPA from spiked samples ranged from 83.7% to 90.8%, and the method was successfully applied to the analysis of peanuts that were naturally contaminated with CPA.


High Performance Liquid Chromatographic High Performance Liquid Chromatographic System Mixed Feed Cyclopiazonic Acid Immunoaffinity Column 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. Balachandran, C., and Parthasarathy, K.R., 1996, Occurrence of cyclopiazonic acid in feeds and feedstuffs in Tamil Nadu, IndiaMycopathologia133:159.CrossRefGoogle Scholar
  2. Bradbum, N., Coker, R.D., and Blunden, G., 1994, The aetiology of turkey ‘X’ diseasePhytochemistry35:817.CrossRefGoogle Scholar
  3. Bryden, W.L., 1991, Occurrence and biological effects of cyclopiazonic acid, in: Emerging Food Safety Problems Resulting from Microbial Contamination, K. Mise, and J.L. Richard, ed., Toxic Microorganisms Panel of the UJNR, Tokyo.Google Scholar
  4. Burdock, G.A., and Flamm, W G, 2000, Review article: safety assessment of the mycotoxin cyclopiazonic acidInt. J. Toxicol.19:195.CrossRefGoogle Scholar
  5. Chang-Yen, I., and Bidasee, K., 1990, Improved spectrophotometric determination of cyclopiazonic acid in poultry feed and cornJ. Assoc. Off. Anal. Chem.73:257.Google Scholar
  6. Cole, R.J., 1986, Etiology of turkey “X” disease in retrospect: A case for the involvement of cyclopiazonic acidMycotoxin Res.2:3.CrossRefGoogle Scholar
  7. de Jesus, A.E., Steyn, P.S., Vleggaar, R., Kirby, G.W., Varley, M.I., and Ferreira, N.P., 1981, Biosynthesis of a-cyclopiazonic acid. Steric course of proton removal during the cyclisation of l-cyclopiazonic acid inPenicillium griseofulvum J. Chem. Soc. Perkin Trans.I 3292. CrossRefGoogle Scholar
  8. Dorner, J.W., 1983, Production of cyclopiazonic acid byAspergillus tamarii Kita Appl. Environ. Microbiol. 46:1435.Google Scholar
  9. Dourer, J.W., Cole, R.J., Erlington, D.J., Suksupath, S., McDowell, G.H., and Bryden, W.L., 1994, Cyclopiazonic acid residues in milk and eggsJ. Agric. Food Chem.42:1516.CrossRefGoogle Scholar
  10. Dorner, J.W., Cole, R.J., and Lomax, L.G., 1985, The toxicity of cyclopiazonic acid, in:Trichothecenes and Other MycotoxinsJ. Lacey, ed., John Wiley & Sons, Ltd., Chichester.Google Scholar
  11. Dorner, J.W., Cole, R.J., Lomax, L.G., Gosser, H.S., and Diener, U.L., 1983, Cyclopiazonic acid production byAspergillus flavusand its effects on broiler chickens,Appl. Environ. Microbiol.46:698.Google Scholar
  12. Dorner, J.W., Sobolev, V.S., Yu, W., and Chu, F.S., 2000, Immunochemical method for cyclopiazonic acid, in:Mycotoxin ProtocolsM.W. Trucksess, and A.E. Pohland, ed., Humana Press, Totowa, New Jersey.Google Scholar
  13. Gallagher, R.T, Richard, J.L., Stahr, H.M., and Cole, R.J., 1978, Cyclopiazonic acid production by aflatoxigenic and non-aflatoxigenic strains ofAspergillus flavus Mycopathologia 66:31.CrossRefGoogle Scholar
  14. Gorst-Allman, C.P., and Steyn, P.S., 1979, Screening methods for the detection of thirteen common mycotoxins, JChromatogr.175:325.CrossRefGoogle Scholar
  15. Goto, T., Shinshi, E., Tanaka, K., and Manabe, M., 1987, Analysis of cyclopiazonic acid by normal phase high-performance liquid chromatographyAgric. Biol. Chem.51:2581.CrossRefGoogle Scholar
  16. Hahnau, S., and Weiler, E.W., 1991, Determination of the mycotoxin cyclopiazonic acid by enzyme immunoassayJ. Agrie. Food Chem.39:1887.CrossRefGoogle Scholar
  17. Hahnau, S., and Weiler, E.W., 1993, Monoclonal antibodies for the enzyme immunoassay of the mycotoxin cyclopiazonic acidJ. Agric. Food Chem.41:1076.CrossRefGoogle Scholar
  18. Holzapfel, C.W., 1968, The isolation and structure of cyclopiazonic acid, a toxic metabolite ofPenicillium cyclopiumWestling,Tetrahedron24:2101.CrossRefGoogle Scholar
  19. Huang, X., and Chu, F.S., 1993, Production and characterization of monoclonal and polyclonal antibodies against the mycotoxin cyclopiazonic acidJ. Agric. Food Chem.41:329.CrossRefGoogle Scholar
  20. Huang, X., Darner, J.W., and Chu, F.S., 1994, Production of aflatoxin and cyclopiazonic acid by various Aspergilli: an ELISA analysisMycotoxin Res.10:101.CrossRefGoogle Scholar
  21. Lansden, J.A., 1984, Liquid chromatographic analysis system for cyclopiazonic acid in peanutsJ. Assoc. Off. Anal. Chem.67:728.Google Scholar
  22. Lansden, J.A., 1986, Determination of cyclopiazonic acid in peanuts and corn by thin layer chromatographyJ. Assoc. Off. Anal. Chem.69:965.Google Scholar
  23. Lansden, J.A., and Davidson, J.I., 1983, Occurrence of cyclopiazonic acid in peanutsAppl. Environ. Microbiol.45:766.Google Scholar
  24. Le Bars, J., 1979, Cyclopiazonic acid production byPenicillium camembertiThom and natural occurrence of this mycotoxin in cheese,Appl. Environ. Microbiol.38:1052.Google Scholar
  25. Le Bars, J., 1990, Detection and occurrence of cyclopiazonic acid in cheesesJ. Environ. Pathol. Toxicol. Oncol.10:136.Google Scholar
  26. Lee, Y.J., and Hagler, W.M., Jr., 1991, Aflatoxin and cyclopiazonic acid production byAspergillus flavusisolated from contaminated maize,J. Food Sci.56:871.CrossRefGoogle Scholar
  27. Luk, K.C., Kobbe, B., and Townsend, J.M., 1977, Production of cyclopiazonic acid byAspergillus flavus Link, Appl.Environ. Microbiol. 33:211Google Scholar
  28. Lund, F., 1995, Diagnostic characteriazation ofPenicillium palitans P. commune andP. solitum Lett. Appl. Microbiol. 21:60.CrossRefGoogle Scholar
  29. Malik, R.K., Engel, G., and Teuber, M., 1986, Effect of some nutrients on the production of cyclopiazonic acid byPenicillium verrucosumvar.cyclopium,Appl. Microbio!. Biotechnol.24:71.Google Scholar
  30. Matsudo, T., and Sasaki, M., 1995, Simple determination of cyclopiazonic acidBiosci. Biotech. Biochem.59:355.CrossRefGoogle Scholar
  31. Nishie, K., Cole, R.J., Dorner, J.W., 1985, Toxicity and neuropharmacology of cyclopiazonic acidFood Chem. Toxicol.23:831.CrossRefGoogle Scholar
  32. Norred, W.P., Cole, R.J., Dorner, J.W., and Lansden, J.A., 1987, Liquid chromatographic determination of cyclopiazonic acid in poultry meatJ. Assoc. Off Anal. Chem.70:121.Google Scholar
  33. Norred, W.P., Porter, J.K., Dourer, J.W., and Cole, R.J., 1988, Occurrence of the mycotoxin cyclopiazonic acid in meat after oral administration to chickensJ. Agric. Food Chem.36:113.CrossRefGoogle Scholar
  34. Ohmomo, S., Sugita, M., and Abe, M., 1973, Isolation of cyclopiazonic acid, cyclopiazonic acid imine and bissecodehydrocyclopiazonic acid from the cultures ofAspergillus versicolor(Vuill.) Tiraboschi,J Agr. Chem. Soc. Japan47:83.Google Scholar
  35. Orth, R., 1977, Mycotoxins ofAspergillus oryzaestrains for use in the food industry as starters and enzyme producing molds,Ann. Nutr. Alim.31:617.Google Scholar
  36. Pitt, J.I., Cruickshank, R.H., and Leistner, L., 1986Penicillium commune P. camembertiithe origin of white cheese moulds, and the production of cyclopiazonic acidFood Microbiol. 3:363.CrossRefGoogle Scholar
  37. Prasongsidh, B.C., Kailasapathy, K., Skurray, G.R., and Bryden, W.L., 1998, Analysis of cyclopiazonic acid I milk by capillary electrophoresisFood Chem.61:515.CrossRefGoogle Scholar
  38. Purchase, I.F.H., 1971, The acute toxicity of the mycotoxin cyclopiazonic acid to ratsToxicol. Appl. Pharmacol.18:114.CrossRefGoogle Scholar
  39. Rao, L.B., and Husain, A., 1985, Presence of cyclopiazonic acid in kodo millet(Paspalum scrobiculatum)causing ‘kodua poisoning’ in man and its production by associated fungi,Mycopathologia89:177.CrossRefGoogle Scholar
  40. Rao, B.L., and Husain, A., 1987, A simple colorimetric method for screening cyclopiazonic acid in agricultural commoditiesMycopathologia97:89.CrossRefGoogle Scholar
  41. Rathinavelu, A., and Shanmugasundaram, E.R.B., 1984, Simple calorimetric estimation of cyclopiazonic acid in contaminated food and feedsJ. Assoc. Off Anal. Chem.67:38.Google Scholar
  42. Ross, P.F., Rice, L.G., Casper, H., Crenshaw, J.D., and Richard, J.L., 1991, Novel occurrence of cyclopiazonic acid in sunflower seedsVet. Hum. Toxicol.33:284.Google Scholar
  43. Sargeant, K., Sheridan, A., O’Kelly, J., and Carnaghan, R.B.A., 1951, Toxicity associated with certain samples of groundnutsNature192:1096.CrossRefGoogle Scholar
  44. Scott, P.M., 1995, Natural toxins, in:Official Methods of Analysis of AOAC InternationalP.A. Cunniff, ed., AOAC International, Arlington, VA.Google Scholar
  45. Simúnek, J., Bfezina, P., Matousková, J., Badová, L., Stétina, J., and Jezová, J., 1992, Determination of cyclopiazonic acid in dairy productsScripta Medica65:419.Google Scholar
  46. Sobolev, V.S., Horn, B.W., Dorner, J.W., and Cole, R.J., 1998, Liquid chromatographic determination of major secondary metabolites produced byAspergillusspecies from sectionFlavi,J. AOAC Int.81:57.Google Scholar
  47. Steyn, P.S., 1969, The separation and detection of several mycotoxins by thin-layer chromatographyJ. Chromatogr.45:473.CrossRefGoogle Scholar
  48. Still, P., Eckardt, C., and Leistner, L., 1978, Bildung von cyclopiazonsäure durchPenicillium camembertiIsolate von Käse,Fleischwirtschaft58:876.Google Scholar
  49. Stoltz, D.R., Widiastuti, R., Maryam, R., Tri Akoso, B., Amang, and Unruh, D., 1988, Suspected cyclopiazonic acid mycotoxicosis of quail in IndonesiaToxicon26:39.Google Scholar
  50. Urano, T., Trucksess, M.W., Beaver, R.W., Wilson, D.M., Dorner, J.W., and Dowell, F.E., 1992a, Co-occurrence of cyclopiazonic acid and aflatoxins in cona and peanutsJ. AOAC Int.75:838.Google Scholar
  51. Urano, T., Trucksess, M.W., Matusik, J., and Dorner, J.W., 1992b, Liquid chromatographic determination of cyclopiazonic acid in corn and peanutsJ. AOAC Int. 75:319. Google Scholar
  52. Widiastuti, R., Maryam, R., Blaney, B.J., Stoltz, S., and Stoltz, D.R., 1988, Cyclopiazonic acid in combination with aflatoxins, zearalenone and ochratoxin A in Indonesian cornMycopathologia104:153.CrossRefGoogle Scholar
  53. Wilson, M.E., Hagler, W.M., Jr., Ort, J.F., Brake, J.T., Cullen, J.M., Cole, R.J., 1986, Acute and subacute effects of cyclopiazonic acid in broiler chickensPoultry Sci.65 (Suppl. I):145.Google Scholar
  54. Yu, W., and Chu, F.S., 1998, Improved direct competitive enzyme-linked immunosorbent assay for cyclopiazonic acid in corn, peanuts, and mixed feedJ Agric. Food Chem.46:1012.CrossRefGoogle Scholar
  55. Yu, W., Dorner, J.W., and Chu, F.S., 1998, Immunoaffmity column as cleanup tool for a direct competitive enzyme-linked inununosorbent assay of cyclopiazonic acid in corn, peanuts, and mixed feedJ. AOAC Int.81:1169.Google Scholar

Copyright information

© Springer Science+Business Media New York 2002

Authors and Affiliations

  • Joe W. Dorner
    • 1
  1. 1.National Peanut Research LaboratoryUSDA, ARSSE Dawson

Personalised recommendations