Cleavage of zearalenone by trichosporon mycotoxinivorans to a novel nonestrogenic metabolite7

Applied and Environmental Microbiology

Volumn 76, Issue 7, 2010, Pages 2353-2359

  Vekiru, Elisavet ^a   Hametner, Christian ^b   Mitterbauer, Rudolf ^a,e   Rechthaler, Justyna ^c   Adam, Gerhard ^a   Schatzmayr, Gerd ^d   Krska, Rudolf ^a   Schuhmacher, Rainer ^a  

^a UNIVERSITY OF NATURAL RESOURCES AND LIFE SCIENCES   (Austria)

^b VIENNA UNIVERSITY OF TECHNOLOGY   (Austria)

^c UNIVERSITY OF APPLIED SCIENCES WIENER NEUSTADT   (Austria)

^d BIOMIN RESEARCH CENTER   (Austria)

^e NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ANIMAL FEED; ANIMAL PRODUCTION; BIO-ETHANOL PRODUCTION; COMPETITIVE BINDING ASSAY; DIODE ARRAY DETECTORS; ESTROGENIC ACTIVITIES; ESTROGENIC MYCOTOXIN; FUSARIUM SPECIES; HEXANOIC ACIDS; HUMAN ESTROGEN RECEPTORS; IN-VITRO; KETONE GROUP; LC-MS/MS; LIQUID CHROMATOGRAPHY-TANDEM MASS SPECTROMETRY; MACROCYCLIC RINGS; MOLECULAR FORMULA; PLANT MATERIAL; TIME-OF-FLIGHT MS; TRANSFORMATION PRODUCTS; TRICHOSPORON; YEAST BIOASSAY; ZEARALENONE;

ANIMALS; BIOASSAY; BIOETHANOL; BIOMOLECULES; DETOXIFICATION; ETHANOL; FATTY ACIDS; KETONES; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; METABOLITES; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; RESONANCE; YEAST;

CHEMICAL CONTAMINATION;

STEROID; ZEARALENONE;

BIOASSAY; BIOFUEL; BIOTRANSFORMATION; DETOXIFICATION; FUNGUS; LIQUID CHROMATOGRAPHY; MAIZE; MASS SPECTROMETRY; METABOLITE; MICROBIAL ACTIVITY; NUCLEAR MAGNETIC RESONANCE; TOXIN; YEAST;

ARTICLE; BIOTRANSFORMATION; CHEMISTRY; DRUG ANTAGONISM; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; METABOLISM; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TANDEM MASS SPECTROMETRY; TRICHOSPORON;

BIOTRANSFORMATION; CHROMATOGRAPHY, LIQUID; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR WEIGHT; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; STEROIDS; TANDEM MASS SPECTROMETRY; TRICHOSPORON; ZEARALENONE;

ANIMALIA; FUSARIUM; TRICHOSPORON MYCOTOXINIVORANS; ZEA MAYS;

EID: 77950262737     PISSN: 00992240     EISSN: 10985336     Source Type: Journal    
DOI: 10.1128/AEM.01438-09     Document Type: Article

References (38)

1. Bauer, J., K. Heinritzi, M. Gareis, and B. Gedek. 1987. Veränderungen am Genitaltrakt des weiblichen Schweines nach Verfütterung praxisrelevanter Zearalenonmengen. Tierärztl. Praxis 15:33-36.
2. Berthiller, F., R. Schuhmacher, G. Adam, and R. Krska. 2009. Formation, determination and significance of masked mycotoxins. Anal. Bioanal. Chem. 395:1243-1252.
3. Binder, E. M. 2007. Managing the risk of mycotoxins in modern feed production. Anim. Feed Sci. Tech. 133:149-166.
4. Bloomquist, C., J. N. Davidson, and E. G. Pearson. 1982. Zearalenone toxicosis in prepubertal daily heifers. J. Am. Vet. Med. Assoc. 180:164-165.
5. EFSA J. 2004. Opinion of the scientific panel on contaminants in the food chain on a request from the commission related to zearalenone as undesirable substance in animal feed. EFSA J. 89:1-35.
6. Ehrlich, K. C., B. Montalbano, S. M. Boue, and D. Bhatnagar. 2005. An aflatoxin biosynthesis cluster gene encodes a novel oxidase required for conversion of versicolors A to sterigmatocystin. Appl. Environ. Microbiol. 71: 8963-8965.
7. El-Sharkaway, S. H., M. I. Selim, M. S. Afifi, and F. T. Halaweish. 1991. Microbial transformation of zearalenone to a zearalenone sulfate. Appl. Environ. Microbiol. 57:549-552.
8. El-Sharkawy, S. H. 1989. Microbial transformation of zearalenone. 111. Formation of zearalenone-2-4-0-ß-diglucoside. Acta Pharm. Jugosl. 39:303-310.
9. El-Sharkawy, S. H., and Y. Abul-Hajj. 1988. Microbial cleavage of zearalenone. Xenobiotica 18:365-371.
10. El-Sharkawy, S. H., and Y. Abul-Hajj. 1988. Microbial transformation of zearalenone. II. Reduction, hydroxylation, and methylation products. J. Org. Chem. 53:515-519.
11. Gareis, M., J. Bauer, J. Thiem, G. Plank, S. Grabley, and B. Gedek. 1990. Cleavage of zearalenone-glycoside, a "masked" mycotoxin, during digestion in swine. Zentralbl. Veterinarmed. B 37:236-240.
12. Gromadzka, K, A. Waékiewicz, J. Chetkowski, and P. Goliúski. 2008. Zearalenone and its metabolites: occurrence, detection, toxicity and guidelines. World Mycotoxin J. 1:209-220.
13. Hagler, W. M., C. J. Mirocha, S. V. Pathre, and J. C. Behrens. 1979. Identification of the naturally occurring isomer of zearalenol produced by Fusarium roseum 'Gibbosum' in rice culture. Appl. Environ. Microbiol. 37: 849-853.
14. Hurd, R. N. 1977. Structure activity relationships in zearalenones, p. 379-391. In J. V. Rodricks, C. W. Hesseltine, and M. A. Mehlman, (ed.), Mycotoxins in human and animal health. Fathotox Publishers, Park Forest South, IL.
15. Hussein, H. S., and J. M. Brasel. 2001. Toxicity, metabolism and impact of mycotoxins on humans and animals. Toxicology 167:101-134.
16. Kakeya, H., N. Takahashi-Ando, M. Kimura, R. Onose, I. Yamaguchi, and H. Osada. 2002. Biotransformation of the mycotoxin zearalenone to a nonestrogenic compound by a fungal strain Clonostachys sp. Biosci. Biotechnol. Biochem. 66:2723-2726.
17. Kakimura, H. 1986. Conversion of zearalenone to zearalenone glycoside by Rhizopus sp. Appl. Environ. Microbiol. 52:515-519.
18. Kataoka, M., K. Honda, K. Sakamoto, and S. Shimizu. 2007. Microbial enzymes involved in lactone compound metabolism and their biotechnological applications. Appl. Microbiol. Biotechnol. 75:257-266.
19. Kim, T. W., J. Y. Hwang, Y. S. Kim, S. H. Joo, S. C. Chang, J. S. Lee, S. Takatsuto, and S. K. Kim. 2005. Arabidopsis CYF85A2, a cytochrome P450, mediates the Baeyer-Villiger oxidation of castasterone to brassinolide in brassinosteroid biosynthesis. Plant Cell 17:2397-2412.
20. Kuiper, G. G., J. G. Lemmen, B. Carlsson, J. C. Corton, S. H. Safe, P. T. Van der Saag, B. Van der Burg, and J. A. Gustafsson. 1998. Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Endocrinology 139:4252-4263.
21. Mitterbauer, R., H. Weindorfer, N. Safaie, R. Krska, M. Lemmens, P. Ruckenbauer, K. Kuchler, and G. Adam. 2003. A sensitive and inexpensive yeast bioassay for the mycotoxin zearalenone and other compounds with estrogenic activity. Appl. Environ. Microbiol. 69:805-811.
22. Moinar, O., G. Schatzmayr, E. Fuchs, and H. Prillinger. 2004. Trichosporon mycotoxinivorans sp. nov., a new yeast species useful in biological detoxification of various mycotoxins. Syst. Appl. Microbiol. 27:661-671.
23. Plasencia, J., and C. J. Mirocha. 1991. Isolation and characterization of zearalenone sulfate produced by Fusarium spp. Appl. Environ. Microbiol. 57:146-150.
24. Politis, I., K. Fegeros, S. Nitsch, G. Schatzmayr, and D. Kanatas. 2005. Use of Trichosporon mycotoxinivorans to suppress the effects of ochratoxicosis on the immune system of broiler chicks. Br. Poultry Sci. 46:1-8.
25. Poppenberger, B., F. Berthiller, H. Bachmann, D. Lucyshyn, C. Peterbauer, R. Mitterbauer, R. Schuhmacher, R. Krska, J. Glössl, and G. Adam. 2006. Heterologous expression of Arabidopsis UDP-glucosyltransferases in Saccharomyces cerevisiae for production of zearalenone-4-O-glucoside. Appl. Environ. Microbiol. 72:4404-4410.
26. Schatzmayr, G., D. Heidler, E. Fuchs. M. Mohnl, M. Täubel, A. P. Loibner, R. Braun, and E. M. Binder. 2003. Investigation of different yeast strains for the detoxification of ochratoxin A. Mycotoxin Res. 19:124-128.
27. Schatzmayr, G., F. Zehner, M. Täubel, D. Schatzmayr, A. Klimitsch, A. P. Loibner, and E. M. Binder. 2006. Microbiological for deactivating mycotoxins. MbI. Nutr. Food Res. 50:543-551.
28. Schug, K. A. 2002. Pseudo-molecular ion formation by aromatic acids in negative ionization mode electrospray ionization mass spectrometry. Ph.D. dissertation. Virginia Polytechnic Institute and State University, Blacksburg, VA.
29. Schuh, M., and W. Baumgartner. 1988. Mikrobiologisch und mykotoxikologisch kontaminierte Futtermittel als Krankheitsursache bei Rindern. Wien Tierärztl. Mschr. 75:329-332.
30. Shin, B. S., S. H. Hong, S. W. Hwang, H. J. Kim, J. B. Lee, H. S. Yoon, D. J. Kim, and S. D. Yoo. 2009. Determination of zearalenone by liquid chroma\tography/tandem mass spectrometry and application to a pharmacokinetic study. Biomed. Chromatogr. 23:1014-1021.
31. Takahashi-Ando, N., M. Kimura, H. Kakeya, H. Osada, and I. Yamagu-chi. 2002. A novel lactonohydrolase responsible for the detoxification of zearalenone: enzyme purification and gene cloning. Biochem. J. 365:1-6.
32. Takahashi-Ando, N., S. Ohsato, T. Shibata, H. Hamamoto, I. Yamaguchi, and M. Kimura. 2004. Metabolism of zearalenone by genetically modified organisms expressing the detoxification gene from Clonostachys rosea. Appl. Environ. Microbiol. 70:3239-3245.
33. Takahashi-Ando, N., T. Tokai, H. Hamamoto, I. Yamaguchi, and M. Kimura. 2005. Efficient decontamination of zearalenone, the mycotoxin of cereal pathogen, by transgenic yeasts through the expression of a synthetic lactonohydrolase gene. Appl. Microbiol. Biotechnol. 67:838-844.
34. ten Brink, G. J., I. W. C. E. Arends, and R. A. Sheldon. 2004. The BaeyerVilliger reaction: new developments toward greener procedures. Chem. Rev. 104: 4105-4124.
35. Torres Pazmiño, D. E., and M. W. Fraaije. 2007. Discovery, redesign and applications of Baeyer-Villiger monooxygenases, p. 107-127. In T. Matsuda (ed.), Future directions in biocatalysis. Elsevier, Amsterdam, Netherlands.
36. Torres Pazmiño, D. E., R. Snajdrova, B. J. Baas, M. Ghobrial, M. D. Mihovilovic, and M. W. Fraaije. 2008. Self-sufficient Baeyer-Villiger monooxygenases: effective coenzyme regeneration for biooxygenation by fusion engineering. Angew. Chem. Int. Ed. Engl. 47:2275-2278.
37. Vekiru, E. 2009. Towards the development of a novel biological feed additive for mycotoxin degradation: isolation, structural elucidation and quantification of biotransformation-products of the estrogenic zearalenone. Ph.D. thesis. Vienna University of Technology, Vienna, Austria.
38. Zinedine, A., J. M. Soriano, J. C. Moltó, and J. Maňes. 2007. Review on the toxicity, occurrence, metabolism, detoxification, regulations and intake of zearalenone: an oestrogenic mycotoxin. Food Chem. Toxicol. 45:1-18.