Identification of six new Alternaria sulfoconjugated metabolites by high-resolution neutral loss filtering

Rapid Communications in Mass Spectrometry

Volumn 29, Issue 19, 2015, Pages 1805-1810

  Kelman, Megan J ^a,b   Renaud, Justin B ^a   Seifert, Keith A ^c   MacK, Jonathan ^c   Sivagnanam, Kumaran ^d   Yeung, Ken K C ^b   Sumarah, Mark W ^a,b  

^a AGRICULTURE AND AGRI FOOD CANADA   (Canada)

^b UNIVERSITY OF WESTERN ONTARIO   (Canada)

^c OTTAWA RESEARCH AND DEVELOPMENT CENTRE   (Canada)

^d GRAIN RESEARCH LABORATORY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ALGAE; BIOMOLECULES; CROPS; ELECTROSPRAY IONIZATION; GRAIN (AGRICULTURAL PRODUCT); LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; POLYSACCHARIDES; STRAIN;

AGRICULTURAL CROPS; ALTERNARIA; ALTERNARIA SPP; HIGH RESOLUTION; NEUTRAL LOSS; ORBITRAP; Q EXACTIVE; SCREENING METHODS; SECONDARY METABOLITES; SMALL GRAINS;

METABOLITES;

SULFUR DERIVATIVE;

ALTERNARIA; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; FOOD GRAIN; ISOLATION AND PURIFICATION; LIQUID CHROMATOGRAPHY; METABOLISM; METABOLOME; MICROBIOLOGY; PROCEDURES;

ALTERNARIA; CHROMATOGRAPHY, LIQUID; EDIBLE GRAIN; METABOLOME; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SULFUR COMPOUNDS;

EID: 84940644941     PISSN: 09514198     EISSN: 10970231     Source Type: Journal    
DOI: 10.1002/rcm.7286     Document Type: Article

References (33)

1. J. D. Miller, S. N. Richardson,. Mycotoxins in Canada: A perspective for 2013. The Regulatory Governance Initiative 2013.
2. V. Ostry,. Alternaria mycotoxins: an overview of chemical characterization, producers, toxicity, analysis and occurrence in foodstuffs. World Mycotoxin J. 2008, 1, 175.
3. R. M. Clear, S. K. Patrick, D. Gaba, D. Abramson, D. M. Smith,. Prevalence of fungi and fusariotoxins on hard red spring and amber durum wheat seed from western Canada, 2000 to 2002. Can. J. Plant Pathol. 2005, 27, 528.
4. S. Marin, A. J. Ramos, G. Cano-Sancho, V. Sanchis,. Mycotoxins: Occurrence, toxicology, and exposure assessment. Food Chem. Toxicol. 2013, 60, 218.
5. C. Dall'Asta, M. Cirlini, C. Falavigna,. Mycotoxins from Alternaria: Toxicological implications. Adv. Mol. Toxicol. 2014, 8, 107.
6. S. Takaoka, M. Kurata, Y. Harimoto, R. Hatta, M. Yamamoto, K. Akimitsu, T. Tsuge,. Complex regulation of secondary metabolism controlling pathogenicity in the phytopathogenic fungus Alternaria alternata. New Phytol. 2014, 202, 1297.
7. T. Tsuge, Y. Harimoto, K. Akimitsu, K. Ohtani, M. Kodama, Y. Akagi, M. Egusa, M. Yamamoto, H. Otani,. Host-selective toxins produced by the plant pathogenic fungus Alternaria alternata. FEMS Microbiol Rev. 2013, 37, 44.
8. H. Raistrick, C. E. Stickings, R. Thomas,. Studies in the biochemistry of micro-organisms. 90. Alternariol and alternariol monomethyl ether, metabolic products of Alternaria tenuis. Biochem. J. 1953, 55, 421.
9. P. M. Scott,. 17-Other mycotoxins, in Mycotoxins in Food, (Eds:, N. Magan, M. Olsen,). Woodhead Publishing, 2004, pp. 406-440.
10. E. M. Brugger, J. Wagner, D. M. Schumacher, K. Koch, J. Podlech, M. Metzler, L. Lehmann,. Mutagenicity of the mycotoxin alternariol in cultured mammalian cells. Toxicol Lett. 2006, 14, 221.
11. T. J. Schrader, W. Cherry, K. Soper, I. Langlois, H. M. Vijay,. Examination of Alternaria alternata mutagenicity and effects of nitrosylation using the Ames Salmonella test. Teratog. Carcinog. Mutagen. 2001, 21, 261.
12. EFSA Panel on Contaminants in the Food Chain (CONTAM). 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), 2407 [97 pp.], December 3, 2014. DOI: 10.2903/j.efsa.2011.2407.
13. A. T. Bottini, J. R. Bowen, D. G. Gilchrist,. Phytotoxins. II. Characterization of a phytotoxic fraction from Alternaria alternata f. sp. lycopersici. Tetrahedron Lett. 1981, 22, 2723.
14. 2 and Alternaria alternata f. sp. lycopersici toxin (AAL) in cultured mammalian cells. Mycopathologica 1991, 116, 97.
15. A. De Girolamo, M. Solfrizzo, C. Vitti, A. Visconti,. Occurrence of 6-methoxymellein in fresh and processed carrots and relevant effect of storage and processing. J. Agric. Food Chem. 2004, 52, 6478.
16. M. Solfrizzo, C. Vitti, A. De Girolamo, A. Visconti, A. Logrieco, P. Fanizzi,. Radicinols and radicinin phytotoxins produced by Alternaria radicina on carrots. J. Agric. Food Chem. 2004, 52, 3655.
17. E. Van de Perre, N. Deschuyffeleer, L. Jacxens, F. Vekeman, W. Van der Hauwaert, S. Asam, M. Rychlik, F. Devlieghere, B. De Meulenaer,. Screening of moulds and mycotoxins in tomatoes, bell peppers, onions, soft red fruits and derived tomato products. Food Control 2014, 37, 165.
18. B. P. Lau, P. M. Scott, D. A. Lewis, S. R. Kanhere, C. Cléroux, V. A. Roscoe,. Liquid chromatography-mass spectrometry and liquid chromatography-tandem mass spectrometry of the Alternaria mycotoxins alternariol and alternariol monomethyl ether in fruit juices and beverages. J. Chromatogr. A 2003, 998, 119.
19. P. M. Scott, W. Zhao, S. Feng, B. P. Lau,. Alternaria toxins alternariol and alternariol monomethyl ether in grain foods in Canada. Mycotoxin Res. 2012, 28, 261.
20. A. H. Aly, R. Edrada-Ebel, I. D. Indriani, V. Wray, W. E. G. Müller, F. Totzke, U. Zirrgiebel, C. Schächtele, M. H. G. Kubbutat, W. H. Lin, P. Proksch, R. Ebel,. Cytotoxic metabolites from the fungal endophyte Alternaria sp. and their subsequent detection in its host plant Polygonum senegalense. J. Nat. Prod. 2008, 71, 972.
21. H. Mikula, P. Skrinjar, B. Sohr, D. Ellmer, C. Hametner, J. Frohlich,. Total synthesis of masked Alternaria mycotoxins-sulfates and glycosides of alternariol (AOH) and alternariol-9-methyl ether (AME). Tetrahedron 2013, 69, 10322.
22. R. M. Pope, C. S. Raska, S. C. Thorp, J. Liu,. Analysis of heparan sulfate oligosaccharides by nano-electrospray ionization mass spectrometry. Glycobiology 2001, 11, 505.
23. D. Q. Liu, Y. Xia, R. Bakhtiar,. Use of a liquid chromatography/ion trap mass spectrometry/triple quadrupole mass spectrometry system for metabolite identification. Rapid Commun. Mass Spectrom. 2002, 16, 1330.
24. A. Lafaye, C. Junot, B. Ramounet-Le Gall, P. Fritsch, E. Ezan, J. Tabet,. Profiling of sulfoconjugates in urine by using precursor ion and neutral loss scans in tandem mass spectrometry. Application to the investigation of heavy metal toxicity in rats. J. Mass Spectrom. 2004, 39, 655.
25. Q. Ruan, S. Peterman, M. A. Szewc, L. Ma, D. Cui, W. G. Humphreys, M. Zhu,. An integrated method for metabolite detection and identification using a linear ion trap/Orbitrap mass spectrometer and multiple data processing techniques: application to indinavir metabolite detection. J. Mass Spectrom. 2008, 43, 251.
26. 2 production by Aspergillus niger. J. Agric. Food Chem. 2007, 55, 9727.
27. B. Andersen, A. Dongo, B. Pryor,. Secondary metabolite profiling of Alternaria dauci, A. porri, A. solani, and A. tomatophila. Mycol. Res. 2008, 112, 241.
28. S. N. Richardson, A. K. Walker, T. K. Nsiama, J. McFarlane, M. W. Sumarah, A. Ibrahim, J. D. Miller,. Griseofulvin-producing Xylaria endophytes of Pinus strobus and Vaccinium angustifolium: evidence for a conifer-understory species endophyte ecology. Fungal Ecol. 2014, 11, 107.
29. B. Wang, J. You, J. B. King, S. Cai, E. Park, D. R. Powell, R. H. Cichewicz,. Polyketide glycosides from Bionectria ochroleuca inhibit Candida albicans biofilm formation. J. Nat. Prod. 2014, 77, 2273.
30. T. Pluskal, S. Castillo, A. Villar-Briones, M. Orešič,. MZmine 2: Modular framework for processing, visualizing, and analyzing mass spectrometry-based molecular profile data. BMC Bioinformatics 2010, 11, 395.
31. S. Ojanpera, A. Pelander, M. Pelzing, I. Krebs, E. Vuori, I. Ojanpera,. Isotopic pattern and accurate mass determination in urine drug screening by liquid chromatography/time-of-flight mass spectrometry. Rapid Commun. Mass Spectrom. 2006, 20, 1161.
32. A. Kaufmann,. Strategy for the elucidation of elemental compositions of trace analytes based on a mass resolution of 100 000 full width at half maximum. Rapid Commun. Mass Spectrom. 2010, 24, 2035.
33. B. Andersen, K. F. Nielsen, V. Fernandez Pinto, A. Patriarca,. Characterization of Alternaria strains from Argentinean blueberry, tomato, walnut and wheat. Int. J. Food Microbiol. 2015, 196, 1.