Skip to main content
Log in

Study on formation of nitrated polycyclic aromatic hydrocarbons from different roasting condition in coffee

  • Original Article
  • Published:
Journal of Food Science and Technology Aims and scope Submit manuscript

Abstract

Nitrated polycyclic aromatic hydrocarbons (nitro-PAHs) are organic, carcinogenic and mutagenic compounds that originate from the reaction of PAHs with NOx and OH radicals. In this study, an analytical method was developed, for the determination of seven nitro-PAHs and the method was applied to quantify the nitro-PAHs, in coffee model systems, prepared with coffee beans produced from three distinct locations and under various roasting conditions. Also, experiments were performed to study the effect of adding various amino acids on the formation of nitro-PAHs. The free radicals produced, were quantified by electron spin resonance (ESR), to assess their correlation with the formed nitro-PAHs. After extraction and cleanup, the nitro-PAHs in coffee were analyzed by gas chromatography/mass selective detection. In all heated coffee model systems, the addition of the amino acids, significantly increased the nitro-PAHs compared to the control. The ESR results were consistent with previous outcomes on the formation of nitro-PAHs.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2

Similar content being viewed by others

References

  • Arisseto AP, de Figueiredo Toledo MC, Govaert Y, van Loco J, Fraselle S, Degroodt J-M (2008) A modified sample preparation for acrylamide determination in cocoa and coffee products. Food Anal Methods 1:49–55

    Article  Google Scholar 

  • Arvidsson P, Boekel M, Skog K, Solyakov A, Jägerstad M (1999) Formation of heterocyclic amines in a meat juice model system. J Food Sci 64:216–221

    Article  CAS  Google Scholar 

  • Atkinson R, Arey J (1994) Atmospheric chemistry of gas-phase polycyclic aromatic hydrocarbons: formation of atmospheric mutagens. Environ Health Perspect 102:117

    CAS  PubMed  PubMed Central  Google Scholar 

  • Atkinson BJ, Heath AW (1990) The limits of explanation and evaluation. Fam Process 29:164–167

    Article  Google Scholar 

  • Becidan M, Skreiberg Ø, Hustad JE (2007) NOx and N2O precursors (NH3 and HCN) in pyrolysis of biomass residues. Energy Fuels 21:1173–1180

    Article  CAS  Google Scholar 

  • Campa C, Doulbeau S, Dussert S, Hamon S, Noirot M (2005) Qualitative relationship between caffeine and chlorogenic acid contents among wild Coffea species. Food Chem 93:135–139

    Article  CAS  Google Scholar 

  • Collins J, Brown J, Alexeeff G, Salmon A (1998) Potency equivalency factors for some polycyclic aromatic hydrocarbons and polycyclic aromatic hydrocarbon derivatives. Regul Toxicol Pharmacol 28:45–54

    Article  CAS  PubMed  Google Scholar 

  • Dafflon O, Scheurer L, Koch H, Bosset JO (2000) Le dosage des hydrocarbures aromatiques polycycliques nitrés dans le poisson, les produits carnés et le fromage par chromatographie liquide à haute performance. Mitteilungen aus Lebensmitteluntersuchung und Hygiene 91:158–171

    CAS  Google Scholar 

  • De Vos R, Van Dokkum W, Schouten A, de Jong-Berkhout P (1990) Polycyclic aromatic hydrocarbons in Dutch total diet samples (1984–1986). Food Chem Toxicol 28:263–268

    Article  PubMed  Google Scholar 

  • Dennis M, Massey R, McWeeny D, Knowles M (1984) Estimation of nitropolycyclic aromatic hydrocarbons in foods. Food Addit Contam 1:29–37

    Article  CAS  PubMed  Google Scholar 

  • Dias RC, Benassi MdT (2015) Discrimination between arabica and robusta coffees using hydrosoluble compounds: is the efficiency of the parameters dependent on the roast degree? Beverages 1:127–139

    Article  CAS  Google Scholar 

  • Dušek B, Hajšlová J, Kocourek V (2002) Determination of nitrated polycyclic aromatic hydrocarbons and their precursors in biotic matrices. J Chromatogr A 982:127–143

    Article  PubMed  Google Scholar 

  • Elschner B (1983) Ch. P. Poole, jr.: Electron-Spin-Resonance, A Comprehensive Treatise on Experimental Techniques, John Wiley and Sons, New York, Chichester, Brisbane, Toronto, Singapore 1983. 780 Seiten, Preis:£ 61. Berichte der Bunsengesellschaft für physikalische Chemie 87:1230

    Article  Google Scholar 

  • Grosovsky AJ, Sasaki JC, Arey J, Eastmond D, Parks K, Atkinson R (1999) Evaluation of the potential health effects of the atmospheric reaction products of polycyclic aromatic hydrocarbons research report. Health Effects Institute. https://www.healtheffects.org/publication/evaluation-potential-health-effects-atmospheric-reaction-products-polycyclic-aromatic

  • Hansson K-M, Samuelsson J, Tullin C, Åmand L-E (2004) Formation of HNCO, HCN, and NH3 from the pyrolysis of bark and nitrogen-containing model compounds. Combust Flame 137:265–277

    Article  CAS  Google Scholar 

  • IARC M (1989a) IARC monographs on the evaluation of carcinogenic risk to humans, vol 46. International Agency for Research on Cancer, Lyon

    Google Scholar 

  • IARC M (1989b) IARC monographs on the evaluation of carcinogenic risk to humans, vol 46. World Health Organization, International Agency for Research on Cancer, Geneva

    Google Scholar 

  • Kato T, Harashima T, Moriya N, Kikugawa K, Hiramoto K (1996) Formation of the mutagenic/carcinogenic imidazoquinoxaline-type heterocyclic amines through the unstable free radical Maillard intermediates and its inhibition by phenolic antioxidants. Carcinogenesis 17:2469–2476

    Article  CAS  PubMed  Google Scholar 

  • Larsson BK, Pyysalo H, Sauri M (1988) Class separation of mutagenic polycyclic organic material in grilled and smoked foodsAbtrennung mutagenen polycyclischen organischen Materials in gegrillten und geräucherten Lebensmitteln Zeitschrift für Lebensmittel-Untersuchung und. Forschung 187:546–551

    CAS  Google Scholar 

  • Mendes LC, de Menezes HC, Aparecida M, Da Silva A (2001) Optimization of the roasting of robusta coffee (C. canephora conillon) using acceptability tests and RSM. Food Qual Prefer 12:153–162

    Article  Google Scholar 

  • Miller J, Sandin R, Miller E, Rusch H (1955) The carcinogenicity of compounds related to 2-acetylaminofluorene: II. Variations in the bridges and the 2-substituent. Can Res 15:188–198

    CAS  Google Scholar 

  • Pederson T, Siak JS (1981) The role of nitroaromatic compounds in the direct-acting mutagenicity of diesel particle extracts. J Appl Toxicol 1:54–60

    Article  CAS  PubMed  Google Scholar 

  • Pitts JN Jr, Harger W, Lokensgard DM, Fitz DR, Scorziell GM, Mejia V (1982) Diurnal variations in the mutagenicity of airborne particulate organic matter in California’s south coast air basin. Mutat Res Lett 104:35–41

    Article  CAS  Google Scholar 

  • Ren Q, Zhao C, Chen X, Duan L, Li Y, Ma C (2011) NOx and N2O precursors (NH3 and HCN) from biomass pyrolysis: Co-pyrolysis of amino acids and cellulose, hemicellulose and lignin. Proc Combust Inst 33:1715–1722

    Article  CAS  Google Scholar 

  • Rosenkranz HS, Mermelstein R (1985) The genotoxicity, metabolism and carcinogenicity of nitrated polycyclic aromatic hydrocarbons. J Environ Sci Health C 3:221–272

    Google Scholar 

  • Schlemitz S, Pfannhauser W (1996) Monitoring of nitropolycyclic aromatic hydrocarbons in food using gas chromatography Zeitschrift für Lebensmittel-Untersuchung und. Forschung 203:61–64

    CAS  Google Scholar 

  • Siegmund B, Weiss R, Pfannhauser W (2003) Sensitive method for the determination of nitrated polycyclic aromatic hydrocarbons in the human diet. Anal Bioanal Chem 375:175–181

    Article  CAS  PubMed  Google Scholar 

  • Tian F-J, Yu J, McKenzie LJ, J-i Hayashi, Li C-Z (2007) Conversion of fuel-N into HCN and NH3 during the pyrolysis and gasification in steam: a comparative study of coal and biomass. Energy Fuels 21:517–521

    Article  CAS  Google Scholar 

  • Tokiwa H, Nakagawa R, Ohnishi Y (1981) Mutagenic assay of aromatic nitro compounds with Salmonella typhimurium. Mutat Res Lett 91:321–325

    Article  CAS  Google Scholar 

  • Turrio-Baldassarri L, Didomenico A, Rocca CL, Iacovella N, Rodriguez F (1996) Polycyclic aromatic hydrocarbons in Italian national and regional diets. Polycycl Aromat Compd 10:343–349

    Article  CAS  Google Scholar 

  • Vignoli JA, Viegas MC, Bassoli DG, de Toledo Benassi M (2014) Roasting process affects differently the bioactive compounds and the antioxidant activity of arabica and robusta coffees. Food Res Int 61:279–285

    Article  CAS  Google Scholar 

  • Ziegler W, Garcia Penalver L, Preiss U, Wallnoefer P (1999) Fate of nitropolycyclic aromatic hydrocarbons in artificially contaminated fruits and vegetables during food processing. Adv Food Sci 21:54–57

    CAS  Google Scholar 

  • Zimmermann K, Atkinson R, Arey J (2012) Effect of NO2 concentration on dimethylnitronaphthalene yields and isomer distribution patterns from the gas-phase OH radical-initiated reactions of selected dimethylnaphthalenes. Environ Sci Technol 46:7535–7542

    Article  CAS  PubMed  Google Scholar 

Download references

Acknowledgements

This work was supported by the Dongguk University Research Fund of 2017 (S-2017-G0001-0001) and funded by Korea Environmental Industry & Technology Institute (A117-00197-0703-0).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Han-Seung Shin.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ko, JH., Das, G., Kim, JE. et al. Study on formation of nitrated polycyclic aromatic hydrocarbons from different roasting condition in coffee. J Food Sci Technol 55, 3991–4000 (2018). https://doi.org/10.1007/s13197-018-3324-6

Download citation

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13197-018-3324-6

Keywords

Navigation