Reactions of Citrinin with Amino Compounds Modelling Thermal Food Processing

Overview

Journal Mycotoxin Res

Specialty Microbiology

Date 2024 Sep 19

PMID 39298071

Authors

Lea Bruckner

Benedikt Cramer

Hans-Ulrich Humpf

Affiliations

Soon will be listed here.

Abstract

Citrinin (CIT) is a nephrotoxic mycotoxin, produced by several species of Penicillium, Aspergillus, and Monascus. The foodstuffs most frequently contaminated with CIT include cereals, cereal products, and red yeast rice. Studies on the occurrence of CIT in food have shown that the CIT concentrations in processed cereal-based products are generally lower than in unprocessed industry cereal samples. One possible explanation is the reaction of CIT with major food components such as carbohydrates or proteins to form modified CIT. Such modified forms of CIT are then hidden from conventional analyses, but it is possible that they are converted back into the parent mycotoxin during digestion. The aim of this study is therefore to investigate reactions of CIT with food matrix during thermal processes and to gain a deeper understanding of the degradation of CIT during food processing. In this study, we could demonstrate that CIT reacts with amino compounds such as proteins, under typical food processing conditions, leading to modified forms of CIT.

Citing Articles

Thermal Stability and Matrix Binding of Citrinin in the Thermal Processing of Starch-Rich Foods.

Bruckner L, Neuendorff F, Hadenfeldt K, Behrens M, Cramer B, Humpf H Toxins (Basel). 2025; 17(2).

PMID: 39998103 PMC: 11860567. DOI: 10.3390/toxins17020086.

References

Seefelder W, Knecht A, Humpf H . Bound fumonisin B1: analysis of fumonisin-B1 glyco and amino acid conjugates by liquid chromatography-electrospray ionization-tandem mass spectrometry. J Agric Food Chem. 2003; 51(18):5567-73. DOI: 10.1021/jf0344338. View

Jaus A, Rhyn P, Haldimann M, Bruschweiler B, Fragniere Rime C, Jenny-Burri J . Biomonitoring of ochratoxin A, 2'R-ochratoxin A and citrinin in human blood serum from Switzerland. Mycotoxin Res. 2022; 38(2):147-161. PMC: 9038883. DOI: 10.1007/s12550-022-00456-0. View

Silva L, Pereira A, Pena A, Lino C . Citrinin in Foods and Supplements: A Review of Occurrence and Analytical Methodologies. Foods. 2020; 10(1). PMC: 7822436. DOI: 10.3390/foods10010014. View

Bretz M, Beyer M, Cramer B, Knecht A, Humpf H . Thermal degradation of the Fusarium mycotoxin deoxynivalenol. J Agric Food Chem. 2006; 54(17):6445-51. DOI: 10.1021/jf061008g. View

Hagelberg S, Hult K, Fuchs R . Toxicokinetics of ochratoxin A in several species and its plasma-binding properties. J Appl Toxicol. 1989; 9(2):91-6. DOI: 10.1002/jat.2550090204. View

Fliege R, Metzler M . The mycotoxin patulin induces intra- and intermolecular protein crosslinks in vitro involving cysteine, lysine, and histidine side chains, and alpha-amino groups. Chem Biol Interact. 1999; 123(2):85-103. DOI: 10.1016/s0009-2797(99)00123-4. View

Biesiekierski J . What is gluten?. J Gastroenterol Hepatol. 2017; 32 Suppl 1:78-81. DOI: 10.1111/jgh.13703. View

Sokalingam S, Raghunathan G, Soundrarajan N, Lee S . A study on the effect of surface lysine to arginine mutagenesis on protein stability and structure using green fluorescent protein. PLoS One. 2012; 7(7):e40410. PMC: 3392243. DOI: 10.1371/journal.pone.0040410. View

Bergmann D, Hubner F, Wibbeling B, Daniliuc C, Cramer B, Humpf H . Large-scale total synthesis of C-labeled citrinin and its metabolite dihydrocitrinone. Mycotoxin Res. 2018; 34(2):141-150. DOI: 10.1007/s12550-018-0308-3. View

10.

Vrabcheva T, Usleber E, Dietrich R, Martlbauer E . Co-occurrence of ochratoxin A and citrinin in cereals from Bulgarian villages with a history of Balkan endemic nephropathy. J Agric Food Chem. 2000; 48(6):2483-8. DOI: 10.1021/jf990891y. View

11.

Beyer M, Ferse I, Mulac D, Wurthwein E, Humpf H . Structural elucidation of T-2 toxin thermal degradation products and investigations toward their occurrence in retail food. J Agric Food Chem. 2009; 57(5):1867-75. DOI: 10.1021/jf803516s. View

12.

von Bargen C, Hubner F, Cramer B, Rzeppa S, Humpf H . Systematic approach for structure elucidation of polyphenolic compounds using a bottom-up approach combining ion trap experiments and accurate mass measurements. J Agric Food Chem. 2012; 60(45):11274-82. DOI: 10.1021/jf3030369. View

13.

Degen G, Reinders J, Kraft M, Volkel W, Gerull F, Burghardt R . Citrinin Exposure in Germany: Urine Biomarker Analysis in Children and Adults. Toxins (Basel). 2023; 15(1). PMC: 9862099. DOI: 10.3390/toxins15010026. View

14.

Sueck F, Poor M, Faisal Z, Gertzen C, Cramer B, Lemli B . Interaction of Ochratoxin A and Its Thermal Degradation Product 2'-Ochratoxin A with Human Serum Albumin. Toxins (Basel). 2018; 10(7). PMC: 6070976. DOI: 10.3390/toxins10070256. View

15.

El Adlouni C, Tozlovanu M, Naman F, Faid M, Pfohl-Leszkowicz A . Preliminary data on the presence of mycotoxins (ochratoxin A, citrinin and aflatoxin B1) in black table olives "Greek style" of Moroccan origin. Mol Nutr Food Res. 2006; 50(6):507-12. DOI: 10.1002/mnfr.200600055. View

16.

Hirota M, Mehta A, Yoneyama K, Kitabatake N, Menta Alka B . A major decomposition product, citrinin H2, from citrinin on heating with moisture. Biosci Biotechnol Biochem. 2002; 66(1):206-10. DOI: 10.1271/bbb.66.206. View

17.

Neely W, Ellis S, Davis N, Diener U . Spectroanalytical parameters of fungal metabolites. I. Citrinin. J Assoc Off Anal Chem. 1972; 55(5):1122-7. View

18.

Bittner A, Cramer B, Humpf H . Matrix binding of ochratoxin A during roasting. J Agric Food Chem. 2013; 61(51):12737-43. DOI: 10.1021/jf403984x. View

19.

Kuchenbuch H, Cramer B, Humpf H . Matrix binding of T-2 toxin: structure elucidation of reaction products and indications on the fate of a relevant food-borne toxin during heating. Mycotoxin Res. 2019; 35(3):261-270. DOI: 10.1007/s12550-019-00350-2. View

20.

Knecht A, Schwerdt G, Gekle M, Humpf H . Combinatory effects of citrinin and ochratoxin A in immortalized human proximal tubule cells. Mycotoxin Res. 2013; 21(3):176-81. DOI: 10.1007/BF02959258. View