Advertisement

European Food Research and Technology

, Volume 218, Issue 2, pp 147–151 | Cite as

Studies on the occurrence and formation of 1,2-dicarbonyls in honey

  • Kai U. Weigel
  • Tommy Opitz
  • Thomas HenleEmail author
Original Paper

Abstract

The 1,2-dicarbonyl compounds 3-deoxyglucosulose (3-DG), methylglyoxal (MGO) and glyoxal (GO) were measured for the first time in 21 honey samples as the corresponding quinoxalines after derivatization with orthophenylenediamine using RP-HPLC and UV-detection. Compared to 5-hydroxymethylfural (HMF), which was also quantified, and ranged between 0.6 and 44 mg/kg, up to 100-fold higher amounts of 3-DG were found, ranging from 79 to 1,266 mg/kg. During storage of honey at 35 °C and 45 °C, a linear increase of 3-DG was observed. Values for GO and MGO were in the ranges 0.2–2.7 mg/kg and 0.4–5.4 mg/kg respectively, and were not affected by storage. Using semi-preparative RP-HPLC, glucosone, a 1,2-dicarbonyl compound previously unknown to occur in foods was isolated from a honey sample and characterized by LC-MS and NMR spectroscopy.

Keywords

Honey 3-Deoxyglucosulose Glyoxal Methylglyoxal 5-Hydroxymethylfurfural 

Notes

Acknowledgements

We thank Dr. Uwe Schwarzenbolz, Institute of Food Chemistry, Technical University of Dresden, for performing the LC-MS analysis and we are grateful to Annett Rudolf, Institute of Organic Chemistry, Technical University of Dresden, for recording the NMR spectra.

References

  1. 1.
    Ledl F, Schleicher E (1990) Angew Chem 102:597–734Google Scholar
  2. 2.
    Rodrigues JA, Barros A, Rodrigues PG (1999) J Agric Food Chem 47:3219–3222CrossRefPubMedGoogle Scholar
  3. 3.
    De Revel G, Pripis-Nicolau L, Barbe J-C, Bertrand A (2000) J Sci Food Agr 80:102–108CrossRefGoogle Scholar
  4. 4.
    Barros A, Rodrigues JA, Almeida PJ, Oliva-Teles MT (1999) J Liq Chrom 22:2061–2069CrossRefGoogle Scholar
  5. 5.
    Vlassara H, Palace MR (2002) J Int Med 251:57–101Google Scholar
  6. 6.
    Odani H, Shinzato T, Matsumoto Y, Usami J, Meada K (1999) Biochem Biophys Res Commun 256:89–93CrossRefPubMedGoogle Scholar
  7. 7.
    Niwa T (1999) J Chrom B 731:23–36CrossRefGoogle Scholar
  8. 8.
    Wieslander A (1996) Nephrol Dial Transplant 11:958–959PubMedGoogle Scholar
  9. 9.
    Wieslander A, Deppisch R, Svensson E, Forsbäck G, Speidel R, Rippe B (1995) Perit Dial Int 15:158–164PubMedGoogle Scholar
  10. 10.
    White JW (1978) Adv Food Res 287–364Google Scholar
  11. 11.
    Honig-Verordnung vom 13.12.1976, in der Fassung vom 6.08.2002Google Scholar
  12. 12.
    Henle T, Bachmann A (1996) Z Lebensm Unters Forsch 202:72–74PubMedGoogle Scholar
  13. 13.
    Nilsson-Thorell C, Muscalu N, Andrén A, Kjellstrand P, Wieslander A (1993) Perit Dial Int 13:208–213PubMedGoogle Scholar
  14. 14.
    Adams R (1974) J Chromatogr 95:189–212CrossRefPubMedGoogle Scholar
  15. 15.
    Henle T, Walter H, Krause I, Klostermeyer H (1991) Int Dairy J 1:125–135Google Scholar
  16. 16.
    Matissek R, Schnepel F M, Steiner G (1992) Lebensmitteanalytik, 2nd edn. Springer, Berlin Heidelberg New YorkGoogle Scholar
  17. 17.
    Hofmann T (1999) Eur Food Res Technol 209:113–121CrossRefGoogle Scholar
  18. 18.
    Villamiel M, del Castillo MD, Corzo N, Olano A (2001) J Sci Food Agric 81:790–793CrossRefGoogle Scholar
  19. 19.
    Schalkwijk C, Posthuma N, ten Brink H, ter Wee P, Teerlink T (1999) Perit Dial Int 19:325–333PubMedGoogle Scholar
  20. 20.
    Weenen H (1998) Food Chem 62:393–401CrossRefGoogle Scholar
  21. 21.
    Wells-Knecht KJ, Zyzak DV, Litchfield JE, Thorpe SR, Baynes JW (1995) Biochem 34:3702–3709PubMedGoogle Scholar
  22. 22.
    Wolff SP, Dean RT (1987) Biochem J 245:243–250PubMedGoogle Scholar
  23. 23.
    Cheng R, Kawakishi S (1994) J Agr Food Chem 42:700–7003Google Scholar

Copyright information

© Springer-Verlag 2004

Authors and Affiliations

  1. 1.Institute of Food ChemistryTechnical University of DresdenDresdenGermany

Personalised recommendations