Detection and Quantitative Analysis of the Non-cytotoxic allo-Tenuazonic Acid in Tomato Products by Stable Isotope Dilution HPLC-MS/MS

Journal of Agricultural and Food Chemistry

Volumn 63, Issue 50, 2015, Pages 10879-10884

  Hickert, Sebastian ^a   Krug, Isabel ^a   Cramer, Benedikt ^a   Humpf, Hans Ulrich ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

alternaria; cytotoxicity; liquid chromatography; mass spectrometry; mycotoxin; stable isotope dilution assay

Indexed keywords

AGRICULTURAL PRODUCTS; CYTOTOXICITY; FRUITS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMERS; ISOTOPES; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PLANTS (BOTANY);

ALTERNARIA; ALTERNARIA ALTERNATA; ANALYTICAL METHOD; CHROMATOGRAPHIC SEPARATIONS; CYTOTOXIC EFFECTS; MYCOTOXIN; STABLE ISOTOPE DILUTION; STABLE ISOTOPE DILUTION ASSAY;

CHROMATOGRAPHY;

TENUAZONIC ACID;

ANALYSIS; CELL SURVIVAL; CHEMISTRY; DRUG EFFECTS; FOOD CONTAMINATION; FOOD HANDLING; FRUIT; GERMANY; HEAT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HT 29 CELL LINE; HUMAN; INDICATOR DILUTION CURVE; ISOLATION AND PURIFICATION; ISOMERISM; LIMIT OF DETECTION; PROCEDURES; TANDEM MASS SPECTROMETRY; TOMATO;

CELL SURVIVAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FOOD CONTAMINATION; FOOD HANDLING; FRUIT; GERMANY; HOT TEMPERATURE; HT29 CELLS; HUMANS; INDICATOR DILUTION TECHNIQUES; ISOMERISM; LIMIT OF DETECTION; LYCOPERSICON ESCULENTUM; TANDEM MASS SPECTROMETRY; TENUAZONIC ACID;

EID: 84952359876     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/acs.jafc.5b04812     Document Type: Article

References (28)

1. Rosett, T.; Sankhala, R. H.; Stickings, C. E.; Taylor, M. E. U.; Thomas, R. Metabolites of Alternaria tenuis auct.: culture filtrate products Biochem. J. 1957, 67, 390-400 10.1042/bj0670390
2. Stickings, C. E. Metabolites of Alternaria tenuis auct.: the structure of tenuazonic acid Biochem. J. 1959, 72, 332-340 10.1042/bj0720332
3. Ostry, V. Alternaria mycotoxins: an overview of chemical characterization, producers, toxicity, analysis and occurrence in foodstuffs World Mycotoxin J. 2008, 1, 175-188 10.3920/WMJ2008.x013
4. European Food Safety Authority (EFSA) Scientific Opinion on the risks for animal and public health related to the presence of Alternaria toxins in feed and food, EFSA J. 2011, 9 (10), 1-97.
5. Pero, R. W.; Posner, H.; Blois, M.; Harvan, D.; Spalding, J. W. Toxicity of metabolites produced by the "Alternaria" Environ. Health Perspect. 1973, 4, 87-94 10.1289/ehp.730487
6. Griffin, G. F.; Chu, S. S. Toxicity of the Alternaria metabolites alternariol, alternariol methyl ether, altenuene, and tenuazonic acid in the chicken embryo assay Appl. Environ. Microbiol. 1983, 46, 1420-1422
7. Youngner, J. S. Influence of inhibitors of protein synthesis on interferon formation in mice Virology 1970, 40, 335-343 10.1016/0042-6822(70)90410-1
8. Smith, E. R.; Fredrickson, T. N.; Hadidian, Z. Toxic effects of the sodium and the N,N′-dibenzylethylenediamine salts of tenuazonic acid (NSC-525816 and NSC-82260) Cancer Chemother. Rep. 1968, 52, 579-585
9. Joshi, A.; Min, Z.; Brumley, W. C.; Dreifuss, P. A.; Yang, G. C.; Sphon, J. A. Mass spectrometry of the copper salt of tenuazonic acid Biomed. Mass Spectrom. 1984, 11, 101-105 10.1002/bms.1200110302
10. Shephard, G. S.; Thiel, P. G.; Sydenham, E. W.; Vleggaar, R.; Marasas, W. F. O. Reversed-phase high-performance liquid chromatography of tenuazonic acid and related tetramic acids J. Chromatogr., Biomed. Appl. 1991, 566, 195-205 10.1016/0378-4347(91)80124-U
11. Gallardo, G. L.; Pena, N. I.; Chacana, P.; Terzolo, H. R.; Cabrera, G. M. l -Tenuazonic acid, a new inhibitor of Paenibacillus larvae World J. Microbiol. Biotechnol. 2004, 20, 609-612 10.1023/B:WIBI.0000043175.23621.8c
12. Siegel, D.; Merkel, S.; Bremser, W.; Koch, M.; Nehls, I. Degradation kinetics of the Alternaria mycotoxin tenuazonic acid in aqueous solutions Anal. Bioanal. Chem. 2010, 397, 453-462 10.1007/s00216-009-3288-5
13. Lebrun, M. H.; Nicolas, L.; Boutar, M.; Gaudemer, F.; Ranomenjanahary, S.; Gaudemer, A. Relationships between the structure and the phytotoxicity of the fungal toxin tenuazonic acid Phytochemistry 1988, 27, 77-84 10.1016/0031-9422(88)80594-6
14. B-site of Chlamydomonas reinhardtii, Biochim Biochim. Biophys. Acta, Bioenerg. 2007, 1767, 306-318 10.1016/j.bbabio.2007.02.007
15. Gitterman, C. O. Antitumor, cytotoxic and antibacterial activities of tenuazonic acid and congeneric tetramic acids J. Med. Chem. 1965, 8, 483-486 10.1021/jm00328a015
16. 2-tenuazonic acid and development of a rapid HPLC-MS/MS method for the analysis of tenuazonic acid in tomato and pepper products J. Agric. Food Chem. 2013, 61, 114-120 10.1021/jf305138k
17. Asam, S.; Liu, Y.; Konitzer, K.; Rychlik, M. Development of a stable isotope dilution assay for tenuazonic acid J. Agric. Food Chem. 2011, 59, 2980-2987 10.1021/jf104270e
18. Gross, M.; Curtui, V.; Ackermann, Y.; Latif, H.; Usleber, E. Enzyme immunoassay for tenuazonic acid in apple and tomato products J. Agric. Food Chem. 2011, 59, 12317-12322 10.1021/jf203540y
19. Siegel, D.; Rasenko, T.; Koch, M.; Nehls, I. Determination of the Alternaria mycotoxin tenuazonic acid in cereals by high-performance liquid chromatography-electrospray ionization ion-trap multistage mass spectrometry after derivatization with 2,4-dinitrophenylhydrazine J. Chromatogr. A 2009, 1216, 4582-4588 10.1016/j.chroma.2009.03.063
20. Lebrun, M. H.; Gaudemer, F.; Boutar, M.; Nicolas, L.; Gaudemer, A. Ion-pair, anion-exchange and ligand-exchange high-performance liquid chromatography of tenuazonic acid and 3-acetyl 5-substituted pyrrolidine-2,4-diones J. Chromatogr. A 1991, 464, 307-322 10.1016/S0021-9673(00)94249-3
21. Scott, P. M.; Kanhere, S. R. Liquid chromatographic determination of tenuazonic acids in tomato paste J.-Assoc. Off. Anal. Chem. 1980, 63, 612-621
22. Tölgyesi, á.; Stroka, J.; Tamosiunas, V.; Zwickel, T. Simultaneous analysis of Alternaria toxins and citrinin in tomato: an optimized method using liquid chromatography-tandem mass spectrometry Food Addit. Contam., Part A 2015, 32, 1512-1522 10.1080/19440049.2015.1072644
23. Hickert, S.; Bergmann, M.; Ersen, S.; Cramer, B.; Humpf, H.-U. Survey of Alternaria toxin contamination in food from the German market, using a rapid HPLC-MS/MS approach. Mycotoxin Res. 2015, 10.1007/s12550-015-0233-7
24. Zanoni, B.; Pagliarini, E.; Giovanelli, G.; Lavelli, V. Modelling the effects of thermal sterilization on the quality of tomato puree J. Food Eng. 2003, 56, 203-206 10.1016/S0260-8774(02)00251-0
25. Ishiyama, M.; Miyazono, Y.; Sasamoto, K.; Ohkura, Y.; Ueno, K. A highly water-soluble disulfonated tetrazolium salt as a chromogenic indicator for NADH as well as cell viability Talanta 1997, 44, 1299-1305 10.1016/S0039-9140(97)00017-9
26. Tominaga, H.; Ishiyama, M.; Ohseto, F.; Sasamoto, K.; Hamamoto, T.; Suzuki, K.; Watanabe, M. A water soluble tetrazolium salt useful for colorimetric cell viability assay Anal. Commun. 1999, 36, 47-50 10.1039/a809656b
27. Mulac, D.; Humpf, H.-U. Cytotoxicity and accumulation of ergot alkaloids in human primary cells Toxicology 2011, 282, 112-121 10.1016/j.tox.2011.01.019
28. Annesley, T. M. Ion suppression in mass spectrometry Clin. Chem. 2003, 49, 1041-1044 10.1373/49.7.1041