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Original Articles

An epimer of deoxynivalenol: purification and structure identification of 3-epi-deoxynivalenol

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Pages 1523-1530 | Received 07 May 2015, Accepted 07 Jul 2015, Published online: 06 Aug 2015

References

  • Bennett GA, Peterson RE, Plattner RD, Shotwell OL. 1981. Isolation and purification of deoxynivalenol and a new trichothecene by high pressure liquid chromatography. J Am Oil Chem Soc. 58:A1002–1005.
  • Berthiller F, Crews C, Dall’Asta C, Saeger SD, Haesaert G, Karlovsky P, Oswald IP, Seefelder W, Speijers G, Stroka J. 2013. Masked mycotoxins: a review. Mol Nutr Food Res. 57:165–186.
  • Clifford LJ, Jia QS, Pestka JJ. 2003. An improved method for the purification of the trichothecene deoxynivalenol (vomitoxin) from Fusarium graminearum culture. J Agr Food Chem. 51:521–523.
  • Cole RJ, Cox RH. 1981. Handbook of Toxic Fungal Metabolites. New York (NY): Academic Press; p. 152–263.
  • Donovan JI, Luthria DL, Stremple P, Waterhouse AL. 1999. Analysis of (+)-catechin, (–)-epicatechin and their 3´- and 4´-O-methylated analogs – a comparison of sensitive methods. J Chromatogr B. 726:277–283.
  • Eriksen GS, Pettersson H, Lundh T. 2004. Comparative cytotoxicity of deoxynivalenol, nivalenol, their acetylated derivatives and de-epoxy metabolites. Food Chem Toxicol. 42:619–624.
  • Forsell JH, Jensen R, Tai J-H, Witt M, Lin WS, Pestka JJ. 1987. Comparison of acute toxicities of deoxynivalenol (vomitoxin) and 15-acetyldeoxynivalenol in the B6C3F1 mouse. Food Chem Toxicol. 25:155–162.
  • Greenhalgh R, Gilbert J, King RR, Blackwell BA, Startin JR, Shepherd MJ. 1984. Synthesis, characterization, and occurrence in bread and cereal products of an isomer of 4-deoxynivalenol (vomitoxin). J Agr Food Chem. 32:1416–1420.
  • Harada M, Kan Y, Naoki H, Fukui Y, Kageyama N, Nakai M, Miki W, Kiso Y. 1999. Identification of the major antioxidative metabolites in biological fluids of the rat with ingested (+)-catechin and (–)-epicatechin. Biosci Biotech Bioch. 63:973–977.
  • He J. 2015. Detoxification of Deoxynivalenol by a Soil Bacterium Devosia mutans 17-2-E-8 [ Doctor of Philosophy thesis]. Guelph: School of Environmental Sciences, University of Guelph; p. 130.
  • He J, Tsao R, Yang R, Zhou T. 2009. Purification of patulin from Penicillium expansum culture: high-speed counter-current chromatography versus preparative high performance liquid chromatography. Food Addit Contam: Part A. 26:101–107.
  • He J, Yang R, Zhou T, Tsao R, Young JC, Zhu H, Li X-Z, Boland GJ. 2007. Purification of deoxynivalenol from Fusarium graminearum rice culture and mouldy corn by high-speed counter-current chromatography. J Chromatogr A. 1151:187–192.
  • He J, Zhou T, Young JC, Boland GJ, Scott PM. 2010. Chemical and biological transformations for detoxification of trichothecene mycotoxins in human and animal food chains: A review. Trends Food Sci Tech. 21:67–76.
  • Ikunaga Y, Sato I, Grond S, Numajiri N, Yoshida S, Yamaya H, Hiradate S, Hasegawa M, Toshima H, Koitabashi M, et al. 2011. Nocardioides sp. Strain WSN05-2, isolated from a wheat field, degrades deoxynivalenol, producing the novel intermediate 3-epi-deoxynivalenol. Appl Microbiol Biot. 89:419–427.
  • Ito Y. 2005. Golden rules and pitfalls in selecting optimum conditions for high-speed counter-current chromatography. J Chromatogr A. 1065:145–168.
  • Kilcoyne J, Mccarron P, Twiner MJ, Nulty C, Crain S, Quilliam MA, Rise F, Wilkins AL, Miles CO. 2014. Epimers of azaspiracids: isolation, structural elucidation, relative LC-MS response, and in vitro toxicity of 37-epi-azaspiracid-1. Chem Res Toxicol. 27:587–600.
  • King RR, Greenhalgh R. 1985. Chemical deoxygenation of the epoxide moiety in deoxynivalenol (vomitoxin). Can J Chem. 63:1089–1092.
  • King RR, Greenhalgh R. 1987. Structural elucidation of a novel deoxynivalenol analog. J Org Chem. 52:1605–1606.
  • Miller JD, Taylor A, Greenhalgh R. 1983. Production of deoxynivalenol and related compounds in liquid culture by Fusarium graminearum. Can J Microbiol. 29:1171–1178.
  • [NTP] National Toxicology Program. 2009. Chemical Information Review Document for Deoxynivalenol [CAS No. 51481-10-8]. [Internet]. [cited 2014 Mar 16]. Available from: http://ntp.niehs.nih.gov/ntp/noms/support_docs/deoxynivalenol060809.pdf
  • Pestka J, Lin WS, Miller ER. 1987. Emetic activity of the trichothecene 15-acetyldeoxynivalenol in swine. Food Chem Toxicol. 25:855–858.
  • Pestka JJ, Lin WS, Forsell JH. 1986. Decreased feed consumption and body-weight gain in the B6C3F1 mouse after dietary exposure to 15-acetyldeoxynivalenol. Food Chem Toxicol. 24:1309–1313.
  • Ran R, Wang C, Han Z, Wu A, Zhang D, Shi J. 2013. Determination of deoxynivalenol (DON) and its derivatives: current status of analytical methods. Food Control. 34:138–148.
  • Sato I, Ito M, Ishizaka M, Ikunaga Y, Sato Y, Yoshida S, Koitabashi M, Tsushima S. 2012. Thirteen novel deoxynivalenol-degrading bacteria are classified within two genera with distinct degradation mechanisms. FEMS Microbiol Lett. 327:110–117.
  • Scott PM, Lawrence GA, Telli A, Iyengar JR. 1984. Preparation of deoxynivalenol (vomitoxin) from field-inoculated corn. J Assoc Off Anal Chem. 67:32–34.
  • Shima J, Takase S, Takahashi Y, Iwai Y, Fujimoto H, Yamazaki M, Ochi K. 1997. Novel detoxification of the trichothecene mycotoxin deoxynivalenol by a soil bacterium isolated by enrichment culture. Appl Environ Microbiol. 63:3825–3830.
  • Szekeres A, Lorántfy L, Bencsik O, Kecskeméti A, Szécsi Á, Mesterházy Á, Vágvölgyi C. 2013. Rapid purification method for fumonisin B1 using centrifugal partition chromatography. Food Addit Contam: Part A. 30:147–155.
  • Witt MF, Hart LP, Pestka JJ. 1985. Purification of deoxynivalenol (vomitoxin) by water-saturated silica-gel chromatography. J Agr Food Chem. 33:745–748.
  • Wu X, Murphy P, Cunnick J, Hendrich S. 2007. Synthesis and characterization of deoxynivalenol glucuronide: its comparative immunotoxicity with deoxynivalenol. Food Chem Toxicol. 45:1846–1855.
  • Yoshizawa T, Morooka N. 1974. Studies on the toxic substances in infected cereals (III). Acute toxicities of new trichothecene mycotoxins: deoxynivalenol and its monoacetate (Japanese). J Food Hyg Soc Jpn. 15:261–269.
  • Zhou T, He J. 2009 Oct 6. Bacterial isolate, methods of isolating bacterial isolates and methods for detoxification of trichothecene mycotoxins. United States Provisional Patent Application No. 61/249,023.
  • Zhou T, He J. 2010 Oct 6. Bacterial isolate, methods of isolating bacterial isolates and methods for detoxification of trichothecene mycotoxins. Patent Cooperation Treaty Application No. 61/249,023 (international).

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