Advertisement

European Food Research and Technology

, Volume 225, Issue 5–6, pp 857–863 | Cite as

Quantification of 3-aminopropionamide in cocoa, coffee and cereal products

Correlation with acrylamide concentrations determined by an improved clean-up method for complex matrices
  • Michael Granvogl
  • Peter SchieberleEmail author
Original Paper

Abstract

Based on recent results confirming 3-aminopropionamide (3-APA) as a very effective precursor of acrylamide in the absence of further “catalysts”, this compound was quantified for the first time in cocoa masses, cocoa beans, coffee and cereal products by LC–MS–MS after derivatisation with dansyl chloride. Cocoa masses contained >3000 μg/kg of 3-APA, but varied significantly in its concentration. For the quantification of acrylamide (AA) in cocoa and coffee, an improved isolation procedure using charcoal was developed. In various samples of unroasted and roasted cocoa beans, the concentrations of AA were by a factor of >5 lower than those of 3-APA, but the concentrations of 3-APA and AA were more closely correlated as compared to the concentrations of AA and Asparagine. Experiments on authentic cocoa beans from Ghana and Sulawesi indicated that the thermal generation of 3-APA during roasting was much more pronounced as compared to its biochemical formation. By administering fermented cocoa beans with [13C4 15N2]-asparagine before roasting, 3-APA was confirmed as transient intermediate in AA formation during cocoa roasting. Among the cereal products analysed, in particular popcorn contained quite high amounts of 3-APA, which were also well correlated with the AA concentration. Contrary, in coffee products, 3-APA was always lower than AA.

Keywords

Cocoa Coffee Cereals 3-Aminopropionamide Acrylamide Labelling studies 

Notes

Acknowledgments

The authors gratefully acknowledge the skillful assistance by Jörg Stein and S. Kaviani-Nejad. Thanks are also to Ines Otte for performing the LC-MS-MS measurements and Käthe Schiesser for performing the amino acid analyses.

References

  1. 1.
    Tareke E, Rydberg P, Karlsson P, Eriksson S, Törnqvist M (2002) J Agric Food Chem 50:4998–5006CrossRefGoogle Scholar
  2. 2.
    Rosén J, Hellenäs K-E (2002) Analyst 127:880–882CrossRefGoogle Scholar
  3. 3.
    Becalski A, Lau BP-Y, Lewis D, Seaman SW (2003) J Agric Food Chem 51:802–808CrossRefGoogle Scholar
  4. 4.
    Ono H, Chuda Y, Ohnishi-Kameyama M, Yada H, Ishizaka M, Kobayashi H, Yoshida M (2003) Food Addit Contam 20:215–220CrossRefGoogle Scholar
  5. 5.
    Ahn JS, Castle L, Clarke DB, Lloyd AS, Philo MR, Speck DR (2002) Food Addit Contam 19:1116–1124CrossRefGoogle Scholar
  6. 6.
    Weisshaar R (2004) Eur J Lipid Sci Technol 106:786–792CrossRefGoogle Scholar
  7. 7.
    Amrein TM, Schoenbaechler B, Escher F, Amado R (2004) J Agric Food Chem 52:4282–4288CrossRefGoogle Scholar
  8. 8.
    Jezussek M, Schieberle P (2003) J Agric Food Chem 51:7866–7871CrossRefGoogle Scholar
  9. 9.
    Amrein TM, Lukac H, Andres L, Perren R, Escher F, Amado R (2005) J Agric Food Chem 53:7819–7825CrossRefGoogle Scholar
  10. 10.
    Stadler RH, Blank I, Varga N, Robert F, Hau J, Guy PA, Robert M-C, Riediker S (2002) Nature 419:449–450CrossRefGoogle Scholar
  11. 11.
    Mottram DS, Wedzicha BL, Dodson AT (2002) Nature 419:448–449CrossRefGoogle Scholar
  12. 12.
    Schieberle P, Koehler P, Granvogl M (2005) New aspects on the formation and analysis of acrylamide. In: Friedman M, Mottram D (eds) Advances in experimental medicine and biology, vol 561. Springer Verlag, New York, pp 205–222Google Scholar
  13. 13.
    Zyzak DV, Sanders RA, Stojanovic M, Tallmadge DH, Eberhart BL, Ewald DK, Gruber DC, Morsch TR, Strothers MA, Rizzi GP, Villagran MD (2003) J Agric Food Chem 51:4782–4787CrossRefGoogle Scholar
  14. 14.
    Vass M, Amrein TM, Schönbächler B, Escher F, Amado R (2004) Czech J Food Sci 22:19–21Google Scholar
  15. 15.
    Levine RA, Smith RE (2005) J Agric Food Chem 53:4410–4416CrossRefGoogle Scholar
  16. 16.
    Surdyk N, Rosén J, Andersson R, Aman P (2004) J Agric Food Chem 52:2047–2051CrossRefGoogle Scholar
  17. 17.
    Mustafa A, Andersson R, Rosén J, Kamal-Eldin A, Aman P (2005) J Agric Food Chem 53:5985–5989CrossRefGoogle Scholar
  18. 18.
    Becalski A, Lau BP-Y, Lewis D, Seaman SW, Hayward S, Sahagian M, Ramesh M, Leclerc Y (2004) J Agric Food Chem 52:3801–3806CrossRefGoogle Scholar
  19. 19.
    Williams JSE (2005) Food Chem 90:875–881CrossRefGoogle Scholar
  20. 20.
    De Wilde T, De Meulenaer B, Mestdagh F, Govaert Y, Vandeburie S, Ooghe W, Fraselle S, Demeulemeester K, Van Peteghem C, Calus A, Degroodt J-M, Verhé R (2005) J Agric Food Chem 53:6550–6557CrossRefGoogle Scholar
  21. 21.
    Stadler RH, Robert F, Riediker S, Varga N, Davidek T, Devaud S, Goldmann T, Hau J, Blank I (2004) J Agric Food Chem 52:5550–5558CrossRefGoogle Scholar
  22. 22.
    Granvogl M, Jezussek M, Koehler P, Schieberle P (2004) J Agric Food Chem 52:4751–4757CrossRefGoogle Scholar
  23. 23.
    Granvogl M, Schieberle P (2006) J Agric Food Chem 54:5933–5938CrossRefGoogle Scholar
  24. 24.
    Granvogl M, Bugan S, Schieberle P (2006) J Agric Food Chem 54:1730–1739CrossRefGoogle Scholar
  25. 25.
    Riediker S, Stadler RH (2003) J Chromatogr A 1020:121–130CrossRefGoogle Scholar
  26. 26.
    Delatour T, Perisset A, Goldmann T, Riediker S, Stadler RH (2004) J Agric Food Chem 52:4625–4631CrossRefGoogle Scholar
  27. 27.
    Aguas PC, Fitzhenry MJ, Giannikopoulos G, Varelis P (2006) Anal Bioanal Chem 385:1526–1531CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 2006

Authors and Affiliations

  1. 1.Chair for Food ChemistryTechnical University of MunichGarchingGermany

Personalised recommendations